10 Hotels Near Douglas Park Chicago

Hotels Near Douglas Park Chicago on map

We have researched the closest and highest-reviewed hotels within walking distance of Douglas Park and have compiled this list of the ten best options for your stay in Chicago.

1. The Shamrock

Located only 2.5 miles (4.8 km) away from Douglas Park, you can take a bus for a short ride from Roosevelt & Cicero to Roosevelt & Albany on route 12, or take a 45-minute walk along Roosevelt Rd.

The most affordable room is 110 USD per night. Free cancellation.
You can cancel later, so lock in this great price today.

Phone number: +17084774450

Hotel website: www.theshamrockcicero.com

One of the 5-star reviews: “A freshly remodeled hotel inside and out. The receptionist was very friendly and welcoming. A gas station right next door. We felt safe and had a well-lighted parking lot.” Source: Google.com

Lowest rating review: “The location and the cleanliness definitely are not ideal. I found food stains on the table, smeared lipstick on chair, urine on toilet seat. Lastly there was strong odor of cigarettes along with burns/ stains all over the floor of the room and bathroom.” Source: Google.com

Pets are not allowed/Service animals only

2. Hyatt House Chicago Medical/University District

Hyatt House Chicago Medical/University District

Stars: 3

Located only 2.6 miles (4.3 km) away from Douglas Park, you can walk there in under 30 minutes or take the 12-route bus from Taylor & Damen to Roosevelt & California.

You can stay here for 209 USD per night at the lowest. No prepayment is needed – pay at the property.

Hotel phone number: +13124920000

Visit hotel website: https://www.hyatt.com/en-US/hotel/illinois/hyatt-house-chicago-west-loop-fulton-market/chixl

Best review: “Very happy with our 4 night stay here! It was perfect for Pitchfork music fest which was a 1/2 mile walk. Kitchen suite was spacious, staff was very friendly, and morning breakfast was nice. Room was very quiet too. Would definitely stay here again. Tons of great restaurants & bars in walking distance.” Source: Booking.com

Worst review: “It is too expensive for what you get. The area was up and coming before covid. Now it is a bit stuck in-between. The Room is very basic. A/C old system and super noisy. Hotel staff not alway helpful. Definitely there are better locations in town.” Source: Booking.com

Pets are allowed

3. Chicago Marriott at Medical District/UIC

Chicago Marriott at Medical District/UIC

Located only 2 miles (3.2 km) away from Douglas Park, you can easily get there by bus or on foot. Route 12 will take you directly to the edge of the park via Roosevelt Rd.

The cheapest room is 180 USD per night. No prepayment is needed.

The hotel has 3 stars.

Call the hotel directly: +13124911234

Official website: https://www.marriott.com/en-us/hotels/chidm-chicago-marriott-at-medical-district-uic/overview/?scid=f2ae0541-1279-4f24-b197-a979c79310b0

5-star review: “The staff was so pleasant and accommodating! They really made this tourist feel welcome. Rooms were as good as can be, and the shower was especially luxurious. Real easy to get to the United Center from here.” Source: Google.com

1-star review: “I wish I did not stay here. There is no room service? No restaurant. The bar sucks as their choice of drinks are limited and serves no food. No maid service due to pandemic, unless you reserve it the night before(did not tell me when I checked in). M lounge only has junk food like chips and cookies. Hotel is run down and would not stay here again.” Source: Google.com

Pets are not allowed

4. The Publishing House Bed and Breakfast

The Publishing House Bed and Breakfast

Located only 2 miles (3.2 km) away from Douglas Park. You can take a bus or the blue line subway from Racine to Kedzie-Homan station.

The smallest room is 249 USD per night, you can book directly on the hotel website. This is a luxury boutique hotel.

Phone number: +13125545857

Official website: https://publishinghousebnb.com

Best review: “The Publishing House is a quaint, beautiful building. The room was spectacular and peaceful! The breakfast was amazing! The staff is so personable and I loved it here!” Source: Hotels.com

The rare bad review: “The sound insulation of our room” “Harvey” “really left something to be desired. We hear a lot of noise from the street. Fortunately, there are earplugs offered on the nightstand.” Source: Hotels.com

Pets are not allowed

5. Hotel Chicago West Loop

Hotel Chicago West Loop

Located only 2.2 miles (3.6 km) away from Douglas Park, there are many bus routes and a nearby subway station to easily get around.

This hotel has 2 stars.

The cheapest room is 185 USD per night. There is no need to prepay, free cancellation available.

Phone number: +13122432900

Hotel website: https://www.hotelchicagowestloop.com//?utm_source=google&utm_medium=organic&utm_campaign=business-listing

Best review: “Helpfulness of staff, reasonable price by big city standards. Very convenient location for visiting the city by public transport(bus), which is also very cheap. Artwork on the walls is a bonus. Room is basic but clean and comfortable. Felt safe in the location.” Source: Booking.com

Worst review: “The carpets in the halls were dirty and clearly hadn’t been vacuumed in several days. When I arrived and asked for the $25 parking that is advertised and that I have used here before, I was told it was a $45 valet that evening only, despite being a Thursday evening. The valet staff was aggressive, rude, and unhelpful, leading to us circling the block looking for other parking. was able to find a SpotHero reservation just a few blocks away.” Source: Booking.com

Pets are allowed

6. Nobu Hotel Chicago

Nobu Hotel Chicago

Located only 3 miles (4.7 km) away from Douglas Park, you can get there by taking the Pink subway line from Morgan to California station.

The lowest price for 1 night’s stay is 413 USD. Free cancellation NOT available.

Nobu is a 5-star luxury hotel.

Phone number: +13127798888

Official website: https://chicago.nobuhotels.com/

Top review: “Every possible detail about my stay here was impeccable. Truly one of the most interesting hotels I have ever been in. I would have stayed longer if I could have! The rooms are extremely well-decorated and the rainfall shower head cured me of all ailments. You won’t regret it here!” Source: Google.com

Critical review: “Honestly, for the price we paid to stay in the Yubune King room, it was disappointing to see that the bathroom was not cleaned since we stayed there for two nights. We had the wooden bathtub in our room, which we loved and paid extra for, they couldn’t replenish the small scrub and bath salts for it. When we came back, you can see that the salt line in the tub was still there. I was expecting much more from Nobu and this really isn’t the great standard I was expecting. They also did not take all of the dirty towels away that was there either.” Source: Google.com

Pets are allowed

7. Crowne Plaza – Chicago West Loop, an IHG Hotel

Crowne Plaza - Chicago West Loop, an IHG Hotel

Located 3.5 miles (5.6 km) away from Douglas Park and within walking distance of Morgan metro station. You can take the Pink line train to California station to get to the park easily from this hotel.

The cheapest room is 250 USD per night. The hotel has 4 stars.

Phone number: +13128295000

Official website: https://www.ihg.com/crowneplaza/hotels/us/en/chicago/chish/hoteldetail?cm_mmc=GoogleMaps--CP--US-_-CHISH

Best review: “We had a great stay at Crown plaza!! The hotel staff was very friendly and helpful Vernell, Brandon, and Mary Ann made our stay excellent. We were always greeted with a smile and good laughs. The room was very clean and the beds were very comfortable. It was also a great location, close to anything you could need. Highly recommend!” Source: Google.com

Worst review: “No microwave, Room was not clean, Poor quality bed, mattress, uncomfortable and congested room. Smelly bed covers, sheets, pillows, and quilts. I would give less than zero if there is a negative rating system for this hotel. I do not recommend anyone.” Source: Google.com

Pets are allowed

8. The Hoxton, Chicago

The Hoxton, Chicago

Located 3.8 miles (6.2 km) away from Douglas Park, easily accessible via the pink line metro train, from Morgan to California station.

The most affordable room is 404 USD per night. Booking is non-refundable.

The Hoxton is a 4-star hotel.

Phone number: +13127611700

Official website: https://thehoxton.com/chicago/?utm_source=google&utm_medium=local&utm_campaign=hotel-thehoxtonchicago

Best review: “Packs a lot of nice features into a small room footprint. One of the best showers I’ve had in a hotel. Great location with plenty of things around. The staff was excellent and overall this location lives up to the high standards of other Hoxton locations around the world.” Source: expedia.com

Worst review: “Horrible Manager. The room was noisy, I was able to hear the train every 10 minutes, and I requested another room, but they did not want to give me another room. I requested a refund and after calling my credit card company they accepted to give me a “partial” refund, they are charging one night for no service. Also, the pool closes at 3 pm. Horrible timing to close the pool, especially in summer. The price that they charge for the night, with this kind of service, is not worth it.” Source: expedia.com

Pets are allowed

9. Chicago Parthenon Hostel

Located 3.2 miles (5.2 km) away from Douglas Park and within walking distance of the UIC-Halsted metro station. You can easily get to Douglas park via the blue line train to
Kedzie-Homan station.

You can stay here for 80 USD per night. It is classified as a 2-star hotel.

Phone number: +13122581399

Hostel website: http://chicagoparthenonhostel.com/

Best review: “The hostel is located a short walk from Union Station (Amtrak, Metra) in an interesting part of town. A lot of shops, cafes, parks & coffee shops within walking distance. Walgreens nearby. Several buses and the blue line are nearby. You get a clean bed in a shared, same-gender room. There’s a shared bathroom and common room with vending machines and free tea & coffee. you can store your bag or rent a towel for a small fee. The staff is nice but often busy.” Source: Google.com

Worst review: “Dilapidated and dirty rooms, shower walls full of mold, clogged toilets. We were charged $3 per bag just for a few hours on the last day to put them in an open, unguarded room. We had never seen that in our lives, the only positive point of the establishment is the location. To flee!” Source: Google.com

Pets are not allowed

10. Holiday Inn & Suites Chicago-Downtown

Located 3.5 miles (5.6 km) away from Douglas Park, you can take the Blue line from Clinton to the Western station – just 4 stops – and then take a short walk to get there.

The cheapest room is 310 USD per night

It’s a 3-star hotel.

Phone number: +13129579100

Visit official website: https://www.ihg.com/holidayinn/hotels/us/en/chicago/chiwh/hoteldetail?cm_mmc=GoogleMaps--HI--US-_-CHIWH

Best review: “The room was nice and very clean. The bed was comfortable and the toiletries were super! Everything you could need was thought of. Breakfast is extra but conveniently there is a first floor restaurant.” Source: booking.com

Worst review: “This hotel is absolutely not worth the price. You could pay the same amount or just slightly more per night and stay at a hotel that is 5x better quality. The bathroom is tiny and extremely old.” Source: booking.com

Pets are not allowed

About Douglass Park

Douglass (Anna and Frederick) Park is 161.85 acres in size and is located in North Lawndale and sections of Pilsen.

Douglass Park is a historic regional park that provides visitors with a variety of recreational and cultural possibilities. Two gymnasiums, an auditorium, a computer lab, a fitness facility, a kitchen, a grand ballroom, and conference rooms are among the fieldhouse’s amenities.

Tennis courts, a game day football stadium, an outdoor pool, water spray features, basketball courts, an artificial turf soccer field, a pavilion, baseball fields, and a small golf putting range are all available in the park.

Three newly rebuilt playgrounds are also available at Douglass Park. A playground on the park’s west end was refurbished and renamed Sunshine Daydream Playground in honor of a Grateful Dead song in the summer of 2016. This new playground features an interactive water fountain as well as music-themed play equipment for kids of all ages and abilities.

Park Events

Douglass Park has teamed with a number of community organizations to provide extra facilities to visitors. The park offers a computer learning center to the community’s youth thanks to a partnership with the Chicago Bulls basketball team. The park holds a series of summer concerts and the annual Junta Hispana festival in July in collaboration with Ravinia.

Young park visitors can participate in seasonal sports or cultural programs such as dance, art, performing arts, and theater. Youth attend day camps and speciality arts camps during the summer. Adults at Douglas Park participate in a variety of activities, such as working out at the fitness center or taking aerobics and conditioning classes. Families can also take part in the free monthly “Bring the Family to the Table” nutritional lunch, which is sponsored by the Greater Chicago Food Depository.

Douglass Park also organizes entertaining special events for the whole family throughout the year, such as dance and theater performances, Movies in the Park screenings, and other Night Out in the Parks activities.

Park Name

The Chicago Park District Board of Commissioners voted on September 9, 2020, to officially take Stephen Douglas’s name off the park. The Board will officially name the park after Anna and Frederick Douglass on November 18, 2020. This is in response to a request from the community.

Frederick Augustus Washington Bailey, who was of mixed race, was born a slave on the eastern shore of Maryland in 1818. After Douglass taught himself to read and write, he went to Baltimore and got a job at the docks. There, he met Anna Murray, a free black woman. She was born free, to parents who had been slaves in the past. Ms. Murray worked as a housekeeper and a laundress to earn enough money to be financially stable on her own. She gave Frederick money, which he used to dress up as a sailor and get away from being a slave. Ms. Murray moved to New York with Frederick, where they got married and started a family. Later, when they moved to New Bedford, Massachusetts, he dropped his middle name and they changed their last name to Douglass to hide who he was. During their 44-year marriage, Anna helped Frederick with his growing career as a speaker and abolitionist. She also kept the house running and raised their five children.

Douglass started reading the abolitionist newspaper The Liberator and started going to abolitionist meetings. The Anti-Slavery Society then hired Douglass to give talks for money. This was his first time speaking in public. He would go on to become one of the most well-known speakers of his time. He worked hard to end slavery and to help people of color become better morally and intellectually. He also fought for women’s rights. Frederick Douglass also wrote three books about himself.

Douglass knew that the Emancipation Proclamation was a groundbreaking piece of writing. Douglass went to Lincoln’s second inaugural speech in 1865 and often used quotes from it. Douglass was said to have felt that Lincoln’s death was both a personal and national tragedy when he heard about it.

3 Day Chicago Itinerary

If you want to go to the Windy City for a long weekend but don’t know what to do, keep reading for our epic 3 days in Chicago itinerary!

Even though Chicago is the third-largest city in the US, people who fly to one of the coasts often skip it.

I think that Chicago is the best city in the United States. New York and Los Angeles are great, but I’d rather live in Chicago with its friendly Midwestern vibe.

The Chicago skyline is one of the most beautiful in the world. It is right on Lake Michigan. After all, the first skyscraper was built right here in 1885!

There’s so much to do here that you could spend your whole life there and never get bored.

If you have a good plan for your time in Chicago, you can see the best of the city in 3 days. Let’s get to it!

Best Time to Visit Chicago

Planning when you’ll go to Chicago is the first step in figuring out what you’ll do there for 3 days.

In the winter, Chicago can be very cold, which can make your trip less fun. If you don’t like cold weather and wind that bites, you should avoid December through March.

The best time to go to Chicago is from May to October. In the summer, it’s hot and crowded, but there’s so much going on that it’s worth it to deal with these small problems.

CityPASS for Chicago

Before you go to Chicago, another big tip I have is to buy a Chicago CityPASS.

This is basically just a multi-use ticket that saves you a lot of money (50 percent to be exact!) on a lot of great Chicago attractions.

You can visit the Shedd Aquarium, Skydeck Chicago, the Field Museum’s Adler Planetarium, the Art Institute of Chicago’s 360 CHICAGO Observation Deck, or the Museum of Science and Industry with the pass, which costs USD$109.

Best of all, most of these entrances come with express or premium tickets that are part of the CityPASS. This saves you both time and money.

We really think you should get one if you want to make the most of your time in Chicago and use our itinerary.

How to Move Around in Chicago

The CTA’s network of train and bus lines makes it easy to get around Chicago. The “L” is what people in Chicago call the train because it mostly runs on “el-evated tracks.”

If you’re going to be in Chicago for 3 days, you should just get a CTA pass that lets you ride anywhere. These are added to a Ventra card for $20.

You can get a Ventra card from a vending machine for $5, and when you register the card, the $5 will be put back into your account. On the CTA website, you can find out how to get around Chicago.

You can count on the CTA to get you from Lincoln Park in the north to the Museum of Science and Industry in the south.

Or, you could hop on and off the open-top bus, which will take you everywhere in the city.

In the middle of the city, a lot of Chicago’s best sights are all within walking distance.

Now that some of the details have been taken care of, let’s get started with your 3-day Chicago itinerary!

Morning of Day 1

If you want to get the most out of your first day in Chicago, you’ll need to get going right away.

Get up early, eat a big breakfast and a cup of coffee, and then get ready to rock.

Loop Walking Tour

Taking a walking tour of the Loop is the best way to start your trip to Chicago. The majority of Chicago’s attractions are in this part of downtown.

You can explore the Loop in a number of ways. If you like meeting new people and hearing what a local guide has to say, you can sign up for one of Free Tours by Foot’s many tours.

If this is your first time in Chicago, I recommend going on their tour of the Loop and Millennium Park at 10 a.m. Or, if you’re really interested in architecture, you can go on their 10:30 tour called “The Birth of the Skyscraper.” Both are great choices!

MetroWalkz has a lot of self-guided tours of Chicago that people who like to do things on their own can check out. This Architecture/Loop tour is a great way to get to know the city, and it’s not too hard to follow.

No matter which choice you make, you’ll get to see some of the city’s most famous spots in just a few hours. Some of the most interesting things are the historic beginning of Route 66 and the great Chicago Theatre.

Day 1 – Afternoon

At this point, what you do next depends on what kind of tour you chose. You can be flexible, since the next two stops are only a short walk apart.

Before we continue with the three-day plan for Chicago, it’s time for lunch! If you’re in the Loop and want to try a local favorite, you have a simple choice…

The Chicago Dog

In the Loop, there are a lot of restaurants to choose from, but you don’t want to go all the way to Chicago just to eat at an overrated chain or a tourist trap that charges too much.

Al’s is a well-known restaurant in the area that serves Chicago-style hot dogs and Italian beef sandwiches.

A Chicago dog is a hot dog made of all beef and served on a sesame seed bun. It comes with tomato, chopped onions, pickled peppers, relish, a pickle spear, and yellow mustard. It’s heaven on a bun, to put it simply.

I would be wrong not to also talk about Portillo’s. One of the best Chicago-style hot dogs is also made there.

Even though they’re not on today’s schedule, keep them in mind if you want another hot dog during your three days in Chicago (and trust me, you will).

Millennium Park

Millennium Park: City of Chicago. Downtown Chicago at Dusk. Illinois State USA. American Cities Collection

Even if you went to Millennium Park on your walking tour, it’s worth going back there to learn more.

There are a lot of interesting things to see here, like the Cloud Gate and the Crown Fountain.

The second one is often called “The Bean,” and it is one of the most popular places to take pictures in Chicago. Don’t forget to take that classic Chicago picture for Instagram, and then keep going.

You should also check out the Jay Pritzker Pavilion, the BP Pedestrian Bridge, the Chicago Cultural Center, and the Lurie Garden in Millennium Park.

On a nice day, it’s easy to spend two or three hours in Millennium Park.

If you want to keep walking, Buckingham Fountain and Grant Park are also in this area.

The Museum of Art in Chicago

Even though there is a lot of great public art in the Loop, the Art Institute of Chicago has the best pieces. People who like art will definitely want to add this to their 3 day plan for Chicago.

The Art Institute of Chicago is tucked away on Michigan Avenue at the south end of Millennium Park. It has a very impressive collection, and there are always new shows of modern and contemporary art.

Use your Chicago CityPASS to get into the Art Institute of Chicago quickly.

The museum is open every day from 10:30 a.m. to 5 p.m., and on Thursdays it stays open until 8 p.m.

Day 1 – Evening

Before the sun goes down, you should hurry to the next place on your 3-day Chicago itinerary. Try to plan it so that you get there about an hour before it gets dark. I’m telling you, it’s worth it!

The Willis Tower

Chicago, Illinois, USA downtown city skyline on Lake Michigan at dawn.

The Willis Tower should be your next stop, whether or not you go to the museum. This is one of the most well-known skyscrapers in Chicago, the city that first built them.

This building used to be called the Sears Tower. For 25 years, it was the tallest building in the world. It is the second-tallest building in the US. It is 442 meters (1,450 feet) tall.

If you only have 3 days to spend in Chicago, you should definitely visit the Willis Tower.

Visit the Skydeck Chicago by going to the 103rd floor and stepping out onto “The Ledge,” a glass balcony that lets you look straight down. You’ll want to see how beautiful the city looks from this spot.

Don’t forget that just before sunset is the best time to go to the Willis Tower. From March to September, it’s open until 10 p.m., and tickets cost $25 for adults and $17 for kids.

Still, you don’t have to pay extra for a ticket to the Skydeck Chicago because it’s included in your CityPASS.

Dinner and Drinks

Dinner and drinks are in order to celebrate getting through the busy first day of the Chicago trip. When it comes to where to eat and drink in the Loop, the world is your oyster.

After such a long day, you might want to go to bed (kind of) early. With this plan for 3 days in Chicago, we still have a lot to do! Yes, you can go out and get drunk if you want to.

Morning of Day 2

If breakfast isn’t included at your hotel, you should start the second day at Yolk’s South Loop location.

This is the best place to get a big breakfast and a cup of coffee before a busy day in the city. Go ahead and fill up on carbs, because you’ll be walking a lot today.

Museum Campus

Walk across the street after breakfast to see Agora, a sculpture made up of 106 figures without heads.

To get to the Museum Campus, keep walking east toward Lake Michigan. The Field Museum, the Shedd Aquarium, and the Adler Planetarium are all in this area.

If you only have 3 days in Chicago, you might want to just go to one place. I’ve been to all three, and the Field Museum is my favorite.

There are always new and interesting things to see at the Field Museum.

Inside Ancient Egypt, Birds of America, and Brewing Up Chicago are some of the shows they have right now. Before you go, check their website to see what’s going on.

Simple admission to the Field Museum costs $26 for adults and $19 for children.

If you bought a CityPASS, you get into all three, unless you go to the Art Institute on the first day. You might as well go to the aquarium if you have the pass.

The aquarium is pretty cool, to be honest. Even if you don’t have the CityPASS, you should probably try to fit it in.

Adult tickets cost $40 and kids’ tickets cost $30, and you’ll get your money’s worth.

Day 2 – Afternoon

There are a few cafes and food stands on the campus of the museum, so feel free to grab a snack and a drink before getting started.

On days like this, it’s best to eat a big breakfast and dinner and just nibble throughout the day. When you have so many things to do in Chicago in 3 days, you have to stay on the move.

Grant Park

The southern part of Grant Park is where the museum is. This vast green space is known as “Chicago’s Front Yard.” It is like Central Park in New York City.

Walk through the park to see the Buckingham Fountain, the Rose Garden, and the Seated Lincoln Statue, among other places of interest. If you want to sit down and relax for a while, there are plenty of benches.

Some of the biggest events in the city, like the Taste of Chicago and Lollapalooza, take place in Grant Park.

Before you book your trip, check the calendar of events to see what’s going on. Some are free, and others can cost hundreds of dollars.

Riverwalk or Cruise on the River

Chicago River walk with Yacht running and traing running over the rail track, illinois, USA. Business Architecture and building with tourist concept

Stick close to the shoreline and walk north along Lake Michigan until you reach the Riverwalk. This beautiful path for pedestrians along the Chicago River is a great place to take a stroll.

If your feet are tired from all the walking, you can take this great river cruise to see the beautiful buildings in Chicago instead.

One of the best things to do in Chicago in 3 days is to walk along the Chicago River and look at the sights.

Wendella Boats has a river cruise that is a great way to see architecture. Make sure you have your camera with you for this one, because the views of the city are amazing.

Evening of Day 2

I’m sure you want to eat your hand off by now, but you have to keep going for a little while longer. Trust me, the wait will be worth it!

Magnificent Mile

The Magnificent Mile is a short section of Michigan Avenue in downtown Chicago that is on the other side of the Chicago River. This is the best shopping area in the city, with high-end stores, nice restaurants, and small hotels.

Along the Magnificent Mile, you can also see historic skyscrapers like the Wrigley Building, Tribune Tower, and Old Watertower.

The City Gallery, which has photography shows about Chicago, is in the second one. You can go there for free, so you might as well if you’re in the area.

Even if you’re not shopping, it’s still fun to take a short walk down Michigan Avenue. Because it will lead you to…

Chicago pizza with a deep dish

You had a hot dog on the first day, so now it’s time to eat some deep-dish pizza like they make in Chicago.

Since it is cooked in a deep pan, a Chicago-style deep dish pizza can have a lot of cheese on it. You can also add any other toppings you want, of course.

Now you understand why I’ve been making you walk around all day while you wait for dinner. This deep-dish pizza is really tasty and filling, so I made sure you could have at least a few slices.

There are a lot of places that make deep-dish pizza as they do in Chicago, but I brought you here because two of the best are close by.

When you get to the corner of Michigan and Superior, you have to make a big decision. If you turn left, you’ll end up at Giordano’s. Gino’s East will be on your right if you turn right.

Just flip a coin, because either way you’ll win. Both are famous for their deep-dish pizzas, so you can’t really go wrong.

Navy Pier

Navy Pier at Michigan lake, Chicago, illlinios, USA

Navy Pier is not too far from the Magnificent Mile. On a three-day weekend in Chicago, this is the best place to be on Saturday night.

The Centennial Ferris Wheel is the first thing you can do. Adult tickets cost $18 and children’s tickets cost $16, but you can save a few dollars if you buy them online.

Navy Pier also has fireworks shows every other week from the end of May to the end of August. On Wednesdays at 9:30 PM and Saturdays at 10:15 PM, these things happen.

Find a place to stand on the Navy Pier or sign up for an evening cruise to see the show. A great thing to do in Chicago is to take a cruise and watch the fireworks as you go.

You decide what to do.

If you still have gas in your car after all the things to do at the Navy Pier, good for you! On day two, I just ran you ragged all over Chicago. Because of this, it’s time to pick your own adventure!

For most people, that will mean getting a drink from the hotel bar and going to bed. That’s all right. At my age, that sounds like a great way to spend a Saturday night.

Those of you who are young and hip probably can’t wait for a big night out on the town. You crazy kids, go for it!

Your options are endless. There are comedy clubs, live music venues, and just about every kind of bar you can think of.

In Chicago, you can find anything from a speakeasy with creative cocktails to a classy wine and jazz bar to a good old-fashioned dive.

Three Dots & a Dash is one of my favorite places in this part of town. This cool tiki bar has a great selection of drinks that will take you right to the Caribbean.

If you’re going to party hard one night, this is it! Most bars in Chicago close at 2:00 AM, but some stay open until 4:00 AM on the weekends. You’ve been warned…

Day 3 – Morning

How early the last day of your 3-day trip to Chicago starts depends on how late you were out the night before.

Those who already wish they hadn’t ordered that last round might need to sleep in and eat a greasy brunch, while the hard-working people who did sleep will be up and at ’em. People, life is all about choices!

No matter what you did the night before, get some food and caffeine in your system and get going to finish up this 3-day Chicago plan.

Your Choice of Museum

We start our third and last day in Chicago with a slow trip to a museum. You can choose from three great museums that are all within a few blocks of each other.

People who like art will be drawn to the Museum of Contemporary Art, which focuses on art made after World War II.

The Richard H. Driehaus Museum might be a good place to go if you are more interested in architecture and old things. It’s in a 19th-century mansion that has been fixed up and takes you back to the Gilded Age.

People in Chicago are very passionate about their teams, so the city is very much a sports town. Check out the Chicago Sports Museum, which has a lot of fun displays and memorabilia.

360 Chi-town

I sent you to the Willis Tower on the first day, but John Hancock’s 360 Chicago on Michigan Avenue is still worth a visit.

This observation deck on the 94th floor of the John Hancock Building gives you a different view of the city that you will definitely want to see.

Also, if you bought a CityPASS, you already have access to the John Hancock building. If you didn’t get the pass, an adult ticket costs $25 and a child’s ticket costs $15.

Those who are feeling brave (and not hungover) might want to go on Tilt, which is Chicago’s most exciting ride.

If you need something stronger, you can buy a ticket that comes with any adult drink you want. Sunday Funday!

If you don’t buy the Chicago CityPASS, you might want to buy this ticket to see the views from the John Hancock building’s 360 Chicago on the 94th floor.

Afternoon of Day 3

When you come down from the 360 Chicago observation deck in the John Hancock building, you have a lot of lunch options. There are Cuban, Vietnamese, Mediterranean, and the Chicago classic, deep dish pizza, all within a few blocks.

If you want to eat lunch with a view, you could go to The Kennison. This high-end bar and restaurant looks out over Lincoln Park. Modern American food is on the menu, and there are a lot of great cocktails and drinks to choose from.

The Lincoln Park

Lincoln Park is our next stop. You can take the bus, call an Uber, or walk there in 30 minutes.

This huge park on the shores of Lake Michigan has a lot to offer. At the south end of North Avenue Beach is a beach.

On a nice day in Chicago, lounging on the beach and swimming in the lake are hard to beat. If you want to do more, you can play beach volleyball or rent a SUP or bike.

The Lincoln Park Zoo, which you can visit for free, is in the middle. Costs add up when you go sightseeing, so this awesome free attraction is definitely one of the best things to do in Chicago.

After such a busy 3 days in Chicago, you should definitely just take it easy and enjoy everything Lincoln Park has to offer. You’ve done a lot in a short amount of time, so congratulations!

The evening of Day 3

At this point in the trip, you’ve had three perfect days in Chicago. Get a drink or two to celebrate, and enjoy your last night in the city!

What you do on your last night depends on when you’re there and what you’re interested in. That’s why it’s time once again to…

You decide what to do.

Bridge over Chicago River, Chicago, Illinois, United States

In a perfect world, the Chicago Cubs would be playing at night while you are there. You could head north to Wrigley Field, which is the second-oldest baseball park in the United States.

Between April and September, the Cubs have about 80 home games, so there’s a good chance they’ll be in town when you are. Even if you don’t like baseball, you should try to go to a game if you can.

Chicago has two Major League Baseball teams. But the White Sox stadium is a long way south of where you’ll be on day 3, and I don’t think it’s worth the trip.

If you visit Chicago between October and April, you might be able to catch a home game of the Bulls (NBA), Blackhawks (NHL), or Bears (NFL). Check their schedules to find out what’s going on in town while you’re there.

If you’d rather have a good laugh, you can go back to the south end of Lincoln Park. There are three of the best comedy clubs in the city just a block away: Second City, UP, and Zanies.

I almost always go to Chicago to see live music, so of course, I’ll mention that here.

The music scene in the city is great, and there’s always something going on. There’s a show for everyone, whether you like rock, hip-hop, jazz, electronic, blues, pop, or whatever else you crazy Millenials listen to these days.

I usually look at Jambase to find out what shows are on.


I hope this huge tour of Chicago was fun for you!

From Navy Pier to Millennium Park to the Chicago riverwalk to the city’s famous hot dogs and more, there is never a dull moment when you visit Chicago.

This 3-day plan for Chicago should have given you some ideas about what to do in the Windy City.

Itinerary Travel Guide for Chicago

Now that you know what to do on a long weekend in Chicago, I’ve put together a mini-guide to this great city to help you decide where to stay, where to eat, and of course where to drink!

Where to Live in Chicago

If this is your first time in Chicago, you might be wondering where to stay.

Most people who come to Chicago for the first time choose to stay in downtown, and for good reason. There are many places to stay, things to see, places to eat, and things to do at night.

As you might expect, it costs money to stay downtown. River North, Lincoln Park, Bucktown, and Wicker Park are also popular places to stay that are a bit cheaper.

Chicago has every kind of place to lay your head. There are 5-star hotels, cute B&Bs, dirty motels, fun hostels, and a lot of options on sites like Airbnb.

Here are some options for all price ranges:

HI is the best hostel in Chicago. Chicago Hostelling International is a well-known hostel for backpackers, and their location in downtown Chicago is the best hostel in Chicago.

There are a number of options for private rooms and dorm rooms. You can get a bunk for less than $40 a night here, which is a great deal for this great place. This includes a free breakfast and free walking tours and activities during the day and at night.

But that’s not all. They also have a big lounge with a ping-pong table and a TV room with a lot of movies. The best part is that this hostel is good for the environment. They have things in the kitchen that can be used again and places to recycle all over the building.

Congress Plaza is the best mid-range hotel.

This hotel in downtown Chicago is very old. It was built in 1893. Don’t worry, because it’s been updated many times over the years!

It’s hard to find a better spot than this one. I usually stay with friends in more quiet areas, but when I want to be in the middle of everything, I come here.

From here, Grant Park is just across the street. Many of the rooms even have a nice view of Lake Michigan. With rooms starting at only $115 a night, staying here is a great deal.

Check prices and stock levels.

Peninsula is the best high-end hotel.

US News & World Report recently named the 5-star Peninsula Chicago the second best hotel in the country. People, this place is fancy!

It’s right on the Magnificent Mile, which is full of expensive shops. This is for sure where the best people live.

The hotel has three different restaurants and a very nice fitness center, in addition to the very nice rooms.

It is on the top two floors of the building and has a 25-meter pool and a spa that has won a lot of awards. Here, rooms start at about $600 per night.

Where in Chicago to eat and drink

I’m lucky to have a good friend who is very active in the Chicago hospitality scene.

I asked him for a list that I could add to this guide. He has never given me bad advice about food and drinks, so you can count on these tips the next time you go to Chicago.


Dove’s Lunchroom


Joe’s Stone Crab is a steakhouse that is hard to get into at night, but it’s a great place to go for a boozy brunch.

Parson’s Chicken & Fish doesn’t really serve brunch, but their patio is a great place to watch people.

Big Star: A classic Chicago taco place with a patio that is always busy

3 Arts Club


Bavette’s Bar and Boeuf Giant

The Roister with Smoked Meats from Green Street: Below is a great BBQ place and High Five Ramen.

RPM Steak Boeufhaus

Ash and Maple

Nico Osteri Drinks

Billy Sunday Bird House (try to get down to the office)

Violet Hour

Start with Scofflaw and move to Best Intentions.

Longman & Eagle

The California Clipper: It’s been around since before prohibition!

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