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Best Things to Do in Chicago Today

Updated: December 21, 2023
 By Mel

This post has information on the most fun things to do in Chicago today, tonight, tomorrow, or anytime.

We include nighttime, free, as well as family-friendly events and activities. Let's get started!


Planning a visit to Chicago can be overwhelming with the sheer number of world-class attractions.

Our suggestions for the top fun things to do in Chicago are listed below.

For more ideas on top popular attractions, check out our comparison guide on tourist discount passes, which could help you save money on entry fees. 

1. Watch a Pro Sports Game

Chicago has multiple well-loved professional sports teams, which means that no matter when you come to the city there will most likely be a game happening somewhere. 

Click here to see all the matches in Chicago.

Many of these teams will play evening games during their regular seasons, so this could be an excellent activity to enjoy after dark.

For more things to do in the evening, please read our nighttime activities section.

2. Learn about Chicago Architecture

One of the top things Chicago is known for is the diverse and impressive architecture you’ll find around the city.

Learn about the different styles and time periods on a guided Architecture Tour of Chicago.

Just as there are many diverse bridges, buildings, and structures, there are diverse ways of seeing it all and learning about the architects.

Architecture tours come in multiple forms like river tours, which give an interesting perspective, as well as free walking tours.

The biggest architecture enthusiasts will enjoy the Chicago Architecture Foundation’s over 3-hour bus tour

3. Attend a Concert

There is an abundance of great venues where you can find live music in Chicago.

The city has a wealth of local bands and also frequently attracts big-name artists.

If you’re interested in going to a concert, make sure to check and see what’s on at the following venues:

Click here to find all the concerts in the city. No matter the genre you’re into, we’re sure you’ll find it!  

4. Take a Sightseeing Tour

The best introduction to Chicago is to take a tour.

Free Tours by Foot offers walking tours of Chicago of various neighborhoods, including the Loop, the Riverwalk, and specialty tours like an evening Chicago Ghost Tour.

Free Tours by Foot - ChicagoExcellentFree Tours by Foot - Chicago4.9 Based on 265 reviews fromSee all reviews review us onJane T.Jane T. ★★★★★ Michael was very informative, knowledgeable and enthusiastic. We had a fantastic couple of hours , we only wish it had been the first thing we did when we arrived in Chicago.Joy H.Joy H. ★★★★★ We had Michael D. for the Winter Loop Tour. Michael had so much interesting information. He was lively yet casual -- it was easy to ask questions. He was so knowledgeable about various topics. We will definitely sign up for other tours.Genoveva G.Genoveva G. ★★★★★ Michael was our tour guide for the Architecture Tour. He was awesome. Very punctual and knowledgeable of the history of the buildings as well as the different eras. Even though the weather wasn't the greatest, he was patient and answered all our questions. I definitely recommend him and will take future tours with him. Thank you, Michael!!Ma Esther H.Ma Esther H. ★★★★★ Tomamos el tour de arquitectura con Michael y nos encantó, muy bien informado, muy interesante y super professional, lo recomiendo muy ampliamente.Marina G.Marina G. ★★★★★ We had the architecture tour with Michael and it was amazing and super interesting. We had a great time walking around the riverwalk even if it was in the 30s, he had great history stories. Highly recommend the tour. From TexasDoraBDoraB ★★★★★ I had the architecture tour with China and it was amazing! I had a great time walking around the Loop learning the fascinating stories of the seemingly similar, but otherwise completely different buildings from such a knowledgeable person!I also took the crime tour around Lincoln Park with Bruce and got to know a lot more about gangsters in the early 1900s.Highly recommend!Wandy C.Wandy C. ★★★★★ LOVED the architecture tour with China! a genuine & captivating storyteller with a sense of humour, everything I look for in a tour guide. thoroughly enjoyed the 2 hours spent & would highly recommend her tour when you find yourself in chicagoDENIS V.DENIS V. ★★★★★ Chicago, the Windy City, deserves a solid 5-star rating! It's simply magnificent with its breathtaking skyline, beautiful lakefront, and a vibrant cultural scene. The city's charm is irresistible, making you want to come back again and again. From its iconic architecture to the friendly locals, Chicago never disappoints. A must-visit destination!" ⭐️⭐️⭐️⭐️⭐️gal M. ★★★★★ אחלי סיור, עם china המדריכה. היה מעולהA Z (.A Z (. ★★★★★ Had a great tour listening to the rise of skyscraper architecture with China! Highly recommend booking a tour and exploring the city in this easy and accessible way!Massimo S.Massimo S. ★★★★☆ Veramente comoda da girare a piedi!Vanessa BVanessa B ★★★★★ What a fantastic organization! Did a night time haunted/history tour with Kelly on a Sunday night. Got some great stories, photos, and exercise! Pay what you feel the tour is worth at the end. Definitely worth it!Christjanna M.Christjanna M. ★★★★★ I was traveling by myself and this was a great way to get my trip started. Learned some history, saw cool buildings/art, walked a lot and got some good recommendations for what to do with the rest of my day. Highly recommend any tour with Aram!Su R cSu R c ★★★★★ To experience the real Chicago that too in an inexpensive fashion join their walking tours.They have different tours offered by them to suit your taste.I did their loop tour and architecture tour.Both were super informative.The guides were jolly and cracking jokes at the right moment.TIP: Book at least 3-7 days in advance to get confirmation from them before joining the tourLisa S.Lisa S. ★★★★★ Really enjoyed Aram's walking tour of Chicago🏙️Great guide with the perfect pace and voice!Lots of interesting facts and pointed out so many things you might not notice on your own and told you the history behind them!Thanks for a Great Tour Aram!Mitchell C.Mitchell C. ★★★★★ Great tour this morning with Aram! Highly recommend.Filipe W.Filipe W. ★★★★★ Sally B.Sally B. ★★★★★ We loved our Loop tour with Andy. He was so knowledgeable and interesting. He gave great advice about where to eat. Would definitely recommend.EricEric ★★★★★ J’ai fait deux tours à Chicago et ils étaient tous deux excellents. Les guides Aram et Bruce étaient fantastiques, chacun amène son expérience et sa personnalité et rendent la promenade enrichissante et chaleureuse. Des 7 free tours auxquels j’ai participé durant ces 15 jours aux États Unis, ceux de Chicago ont été de loin les meilleurs. Chaudement recommandé !CynthiaCynthia ★★★★★ I did the Loop tour with Aram. He shared a lot of info and recommendations. He’s an excellent speaker and easy to understand. I recommend his tours to anyone.Тагирова М.Тагирова М. ★★★★★ In March 2023 I took 2 tours by this company at Chicago: Lincoln Park & Gangster Tour (guide Bruce) and Loop and Millennium Park Tour (guide Mike). Both tours were wonderful and super informative. Every time I travel I try to go to a tour by Free Tours by Foot. Highly recommend!Francy LFrancy L ★★★★★ Excellent way to know more about ChicagoMarilia HMarilia H ★★★★★ Bruce was our amazing guide! Well versed in everything Chicago, he knew by heart every single address, dates and details of history. So impressive! Tour was very pleasant and didn't feel rushed. Great for a cold day.liron K.liron K. ★★★★★ Carolina Ríos T.Carolina Ríos T. ★★★★★ My guide was Mike, an extremely kind person who seems to enjoy a lot telling people the fun facts and history of Chicago. Very recommended 👌🏻Hiromi S.Hiromi S. ★★★★★ An amazing tour. Love this company. So informative and learned tons about Chicago history. Scott was amazing! Highly recommended.Brianna S.Brianna S. ★★★★★ Scott is greatEmily A.Emily A. ★★★★★ I’ve done two tours with them now and loved every minute. Guided were engaging and knowledge. I can’t recommend this tour enough. It’s nice to get up close to the buildings as they talk and point out details and tell stories. Their tours are a must do in Chicago!Carol C.Carol C. ★★★★★ I just did a haunted tour with Andy today and it was incredible. Despite not being a Chicago native himself, the guy know knows his Chicago history more than the typical Chicago local. He has done his homework and seems like the guy who is always improving to give the best tours possible. He explains the dark side of Chicago. It isn't just rainbows. Chicago is the home to several serial killers and his knowledge about that is beyond informative. Aside he is very friendly, funny and kind. He seems to have a genuine passion about Chicago. The good and the ugly. Behind the buildings, there is a lot of haunted and dark history with some twisted corruption. I totally recommend a tour with Andy and I am sure the rest of the team is great as well.fabiola C.fabiola C. ★★★★☆ Adriana fue extraordinaria super recomendaciones que nos dio y en español 🙂 Solamente los spots en donde nos paramos casi no hay para sentarseMaría Cecilia V.María Cecilia V. ★★★★★ alejandra estrada G.alejandra estrada G. ★★★★★ I did the Riverwalk & Historical Tour with Aram and hd a great time! Our guide Aran was awesome, very knowledgeable and and entertainer, so he kept things interesting and fun the whole time. I highly recommend doing this tour, and if possible the other ones they offer! Next time I come to Chicago, I’m definitely booking another tour with them!Tamara M.Tamara M. ★★★★★ Aram is a fantastic guide. He’s knowledgeable about the city, it’s architecture and it’s history. He’s also very personable and entertaining. This is a great tour for tourists and locals alike! As a lifelong resident, I learned a few things that I did not know about my city. If you’re wondering if you should do the Chicago Riverwalk tour, do it!Meghan H.Meghan H. ★★★★★ Our tour was absolutely incredible. Mitch was our guide for the haunted history tour and he was phenomenal. He was very sweet and friendly, made sure we were all safe and happy, and was an excellent guide. He knew so much about everything, is a wonderful storyteller, and even added humor to it, but he was also very careful to be sensitive about the tragedies we were discussing. Overall it was an absolutely amazing experience, and I really appreciated allowing us to pay what we could. I was only in town for one night for business, and my budget wasn't huge. Thank you for giving us an amazing experience anyway! I've been on a lot of ghost tours in a lot of places, and this was definitely one of my favorites!Laila Dalla T.Laila Dalla T. ★★★★★ I did a tour with Andy today and he was one of the best guides ever: funny, knowledgeable, individual, giving first hand insights and much more! Guides like Andy make cities appear like hidden gems!Karen S.Karen S. ★★★★★ 👌👌👌YvonneYvonne ★★★★★ GermanBrother113GermanBrother113 ★★★★★ Went on the Millennium Park and Loop Tour with Sean, and had a great time. Very knowledgeable guide, fun stories and good pace throughout the tour.Definitely recommend it when you get to Chicago and don’t have to much time, he shows that part of town very well!Rosaria D.Rosaria D. ★★★★★ We went on 3 of these tours in Chicago. Our guide was Arhem for 2 of them and Mitchell for the mob tour. They were absolutely outstanding. I had my 2 teenage sons with me and they loved it too. The tour felt like someone telling you a story of the city. I’m very well travelled and this was excellent!!!Marie-Noelle G.Marie-Noelle G. ★★★★★ The walking tour was fantastic thanks to Aaron knowledge of the city. You can see that he is really passionate about Chicago.Will be back for more!Carmel G.Carmel G. ★★★★☆ Hugh M.Hugh M. ★★★★★ I did the downtown tour with Aram and it was well worth it. A lot of places and things I wouldn’t have known or discovered by myselfLexa S.Lexa S. ★★★★★ Aram was such an engaging tour guide and the information he shared on The Birth of a Skyscraper tour was fascinating, educational and entertaining! Thoroughly enjoyed this tour and would strongly recommend it!Harman B.Harman B. ★★★★★ Yvonne R.Yvonne R. ★★★★★ Brian is a knowledgeable, humorous,pleasant guide. Most of the tour centers around the architecture of Chicago buildings. Not much walking.Ellen G.Ellen G. ★★★★★ We did the 2 hour walking tour Aram - a highlight of out time in Chicago and would highly recommend! We have done lots of these tours but this was by far our favourite. We saw and appreciated things we would have otherwise missed. Aram was an excellent guide.Fiorella P.Fiorella P. ★★★★★ I went in a walking tour today and Andy was our guide. I loved it! It was the perfect length and combination of topics and places. Andy was very nice, funny and gave us great advice (which I followed, and it’s the best advice). I would recommend this tour to anyone visiting or living in the city.Su Lynn L.Su Lynn L. ★★★★★ Joined the loop and millenium park tour. Had Aram as our guide and he was really great- he shared lots of interesting facts about the city along with amusing anecdotes, and showed us a few hidden sights. Highly recommend this tour!js_loader

If you’re looking for something a bit more exciting than walking, there are many ways to explore the city:

Foodies can get excited about Chicago’s culinary culture on food tours, as well.

You can sample your way through different neighborhoods with these self-guided food tours:

5. Go to the Theater

Chicago’s theatre scene is a close second to New York’s Broadway (well, we think so!). Find all the theatrical performances in Chicago here

We also recommend taking a tour of the Chicago Theatre before or after catching a show.

The crowd-pleasing Blue Man Group has year-round shows in Chicago.

If you book soon enough, you could get seats in the Splash Zone and end up covered in colorful paint! 

Comedy fans will love seeing a performance at Second City or Annoyance Theater, which all offer extremely affordable tickets! 

The best way to see a show on a budget is during Chicago’s Theatre Week.

6. Visit Chicago’s Navy Pier

One of the most well-known attractions in Chicago is the Navy Pier.

It is a highlight of visitors’ visits to the Lake Michigan shore at any time of year, thanks to Winter Wonderland when it's cold out and fireworks in the summer. 

Here you’ll find boat tours (it’s an actual pier), the Chicago Children’s Museum, restaurants, and entertainment.

Find out more about how you can spend a few hours at the pier with our post about things to do at the Navy Pier.  

7. Find an Observation Deck

Chicago has an impressive skyline day or night.

You can see it all from a birds-eye view and marvel at the architecture from one of the city’s observation decks.

The main Observation Decks in Chicago are:

Each is included for free on at least a few of the tourist attraction discount passes.

8. Enjoy a Dinner or Boat Cruise

From Chicago river cruises to the waters of Lake Michigan, there are multiple boat tours available to take

One of the most popular options is to have an enjoyable lunch or dinner on the water to relax and have fun with your travel buddies or family.

These lunch and dinner cruises usually last 2 to 3 hours. 

From interesting architecture and museums to public art and sports stadiums, Chicago has plenty of popular attractions to see. 

Some of the Popular Attractions Include: 

For a list of even more fun attractions take a look at the section below.

10. Save Money with a Tourist Discount Pass

Visitors can save up to 50% on retail admission prices with a Chicago tourist pass.

These services provide heavy discounts at some of the most popular attractions in the city.

Here are a few of the sites you can visit with various discount passes, which include great year-round activities such as:

If you plan to visit even a few of these attractions, you could easily save quite a few dollars as well as time, since select attractions on these cards have skip-the-line passes.

To find out which city pass will save you the most, read our full post

11. Honorable Mention: Take a Food Tour

If you want help finding the best dishes in Chicago, consider taking a Secret Food Tour.

This outing includes tastings at 6 different locations, giving you a good sense of the most popular meals in the city.

Guests can expect to enjoy samples of deep-dish pizza, Italian beef sandwiches, pierogis, multiple chocolates, and more.

In addition to all the great food, you can also get an upgraded drink package if you're interested in having a few good brews along the way.

For even more great options, check our post covering Chicago food tours.


Chicago has some exciting nightlife and entertainment to enjoy, from tours to live music and open-late attractions.

Most of these activities are fun things to do in Chicago for adults.

See our full post on things to do in Chicago at night for more ideas on what to do.

12. Try to Escape from The Escape Game

From an art heist to a prison break to special ops, you get an hour to go through this real-life puzzle.

The Escape Game Chicago has over 2300 5-star reviews - and don't worry if you don't make it, you'll get a discount to try again!

The Escape Game Chicago is fun for all ages.

13. Take a Chicago Ghost Tour

Discover the spooky history of Chicago and hear tales of the supernatural on a professionally guided ghost tour of the city.

Chicago Ghost Tours

In addition to learning about creepy myths and legends that were born in the area, you’ll also likely hear a lot about the more disturbing criminal history of Chi-town.

14. See a Live Performance in the Theatre District

No matter when you choose to visit Chicago, chances are you’ll have several opportunities to see a musical or other theatrical performance.

Chicago Theatre Lobby

For more information about the best theatres in the windy city and excellent opportunities to save money on tickets, check our post covering the Chicago Theatre District.

15. Enjoy the City Lights From an Observation Deck

There are two really great observation decks in Chicago, and both of them are open after dark, giving you the opportunity to see the city as it lights up at night.

The Skydeck is open until 10 pm in the summer and 8 pm in the winter, while 360 Chicago is open until 11 pm on weekends.

16. Watch the Blue Man Group

This troupe has set up a semi-permanent residence in Chicago, which means that you can reasonably expect them to be performing whenever you choose to visit the windy city.

In addition to being an excellent nighttime activity, the Blue Man Group is also appropriate for kids and teens, which makes it a good choice for families as well.

17. Cheer on Your Favorite Team

As we mentioned in the top 10, there are a lot of great sports teams in Chi-town.

Many of them host games after dark, making this an excellent activity to enjoy at night.

Check this list of sporting events in Chicago to find a game that begins in the evening.

18. Go to a Chicago Symphony Orchestra Concert

This city tends to attract a lot of popular musicians throughout the year.

But, if you’re a fan of classical music, the Chicago Symphony Orchestra offers one of the best experiences in the area.

In addition to performing the works of beloved composers such as Mozart, Chopin, and more, this group also hosts movie concert events in which the music from the film is performed by the orchestra.

19. Go to a Museum After Dark

Some of the museums in Chicago offer fun activities in the evening.

The MCA has a summer jazz series called Tuesdays on the Terrace which typically starts at 5:30 pm and lasts about an hour.

It’s also worth noting that the Art Institute of Chicago is open until 8 pm on Thursday and Friday.

20. Savor a Chicago-Style Sausage

No jaunt to Chicago is complete without savoring a Chicago-style sausage and hot dog. These are no ordinary sausages—they're a culinary delight adorned with toppings like pickled cucumbers, tomato slices, and tangy mustard.

Roam the city and partake in a sausage journey, sampling offerings from various stands to find the best in town.

21. Enjoy a Chicago-Style Deep Dish Pizza

This is the only city in the world where you can order an authentic deep-dish pizza, so why not make this popular dish part of your dinner plans?

If you want some help finding the best slice in town, make sure to read our post covering where you can find some delicious Chicago-style deep-dish pizza.

22. See a Comedy Show at Second City

The Second City Theatre is one of the best comedy clubs in Chicago, and they host several great comedy shows throughout the year.

Many notable comedians like Chris Farley, Tina Fey, and Bill Murray have graced the stage here, making it a hallmark of Chicago's comedy scene.

Check this list of stand-up comedy shows to see who is performing in Chicago.

23. Take a Walk on the Chicago Riverwalk

If you’re looking for an affordable activity after dark, one of the best things to do is just down the Chicago Riverwalk.

This is a great location to enjoy watching the city light up as the sun goes down, and it’s also one of the best spots to either begin or end a romantic date.

24. Visit to the John Hancock Center

The John Hancock Monument stands as more than a lofty edifice—it's a beacon in Chicago's sky tapestry. As evening falls, this location gifts visitors with jaw-dropping panoramas of city glow and neighboring Lake Michigan.

The observatory remains open into the night, positioning it as a dreamlike venue for after-dark activities. Grab a signature cocktail from the on-site tavern and let yourself become enveloped in the vast urban vista for a memorable evening.

For thrill-seekers, don't miss the Tilt experience on the observatory floor, offering a unique and vertigo-inducing view of the Tribune Tower and beyond.

For more details, take a look at our full post on things to do in Chicago at night.


There are plenty of things to see and do while visiting Chicago on a budget!

Read our full free things to do in Chicago post for more details. Listed in this section are our top 10 free activities in Chicago:

25. Take a Free Walking Tour

There are a lot of interesting things to see in this city, and many of them are included in free walking tours.

We have pay-what-you-wish services covering a variety of subjects such as the architecture of the city, the Chicago Riverwalk, the Magnificent Mile, Millennium Park, and even a Ghost tour!

Check this list of free Chicago walking tours to find one you’ll enjoy.

26. Go to a Free Concert or Festival

During the summer months, there are often several free festivals held at various public squares and parks throughout the windy city.

Many of these events will also include free concerts, allowing you to enjoy some live music without worrying about ticket prices!

Check our monthly TTD posts to see what’s on the schedule when you plan to visit Chicago.

27. Explore a Free Museum

There are several museums in Chicago that offer free admission on either a daily basis or at least once a week.

No matter what you’re interested in learning about, chances are there is a museum you’ll enjoy exploring.

Some of the most notable examples include the Chicago Design Museum, the Museum of Contemporary Photography, the National Museum of Puerto Rican Arts and Culture, and many more.

28. Spend Some Time in Wicker Park

This is one of the trendiest areas in Chicago, and it’s full of interesting shops, restaurants, and even street art.

We currently offer a self-guided walking tour of Wicker Park which includes several popular stops, including the public park itself and its statue of Charles Wicker.

29. Discover the Architecture of Chicago

The windy city is home to some of the most impressive architectural feats of modern times, including a variety of notable skyscrapers.

We currently offer a free architectural walking tour of Chicago, and there are also self-guided tours covering locations such as Navy Pier, Millennium Park and the Downtown Chicago Theatre District.

30. Visit a Public Park

There are several excellent public parks in Chicago where you can enjoy a nice walk, perhaps go on a picnic, or even take your kids to a playground.

If you’re looking for help picking the best park to visit, check our post covering 6 of the best Chicago parks.

31. Enjoy Beautiful and Interesting Street Art

You’ll find a lot of unique artwork sprinkled across this city, including both planned-out sculptures and original graffiti work from street artists.

Consider using our guide to public art in Chicago to find some of the most well-known and high-quality artwork which is entirely free to experience.

32. Get Free Entry to Popular Attractions

Depending on which service you choose and how you use it, you could easily use a Chicago tourist pass for enough different activities that eventually anything else you used it for would be entirely free.


33. Take a Free Brewery Tour

There are several great places to great beer in the windy city and even some breweries that offer entirely free tours.

In addition to providing details about some of the best pubs and bars in the city, our guide to Chicago Craft Beer also includes information about local breweries and the (sometimes free) tours they offer.

34. Visit the Navy Pier

There are a lot of fun things to see and do at the Navy Pier, including a variety of notable sites like the Crystal Gardens, the Miller Lite Beer Garden, a Ferris Wheel, and more.

If you’re looking for help finding the best places to visit, check our self-guided tour of Navy Pier for guidance.

For more budget-friendly activities, check out our full free things to do in Chicago post.

35. Adventure to Cloud Gate (The Bean)

Misty Archway, informally dubbed "The Bean," is an essential city sculpture set in Millennium Park. The bonus—it's free of charge.

Its reflective surfaces create interesting opportunities for photography. The park itself is a frequent stage for no-cost artistic and communal events, serving as a core for creative spirits.

The park offers a unique view of the Chicago skyline, making it a contrast to the towering Willis Tower nearby.

36. Explore the Grant Park

Nicknamed "The People's Meadow," Grant Park delivers another complimentary experience. It showcases decorative floral arrangements, water art features, and relaxed pathways.

This is the optimal backdrop for casual strolls or alfresco dining with the family. In addition, the locale frequently serves as the setting for free community events such as musical fiestas and open-air films.

The park serves as a tranquil space for a stroll, offering a calming backdrop to the bustling Michigan Avenue.

37. Spend the Time at Lakeside Walkway (Lakefront Trail)

For those fond of walking or cycling, the Lakeside Walkway supplies miles of striking, free pathways.

Adjacent to Lake Michigan, this route presents captivating scenes and abundant options for outdoor fun. Beaches, gardens, and other natural highlights can be explored along this path without any financial commitment.

The trail offers vistas of Soldier Field and the 103rd floor of Willis Tower, adding another layer of interest to your outdoor experience.


Visiting Chicago with the kids?

Here are our top ten ideas for family-friendly Chicago activities that both children and their parents can enjoy.

Make sure you read our full post on things to do with kids in Chicago for more inspiration!

38. Take a Bike Tour of the City

With so many interesting things to see and do in Chicago, it can be difficult to get around and discover all the sites.

Thankfully, there are bike rental services that offer bicycles for both adults and children.

All bike rental companies provide helmets and other protective gear to keep everyone safe.

Kids love to ride bikes, so this is a fun way to explore the city and see some of the most notable landmarks as a family.

39. Visit the Chicago Children’s Museum

The Chicago Children’s Museum has a lot of fun, hands-on exhibits that are designed to help kids learn about the world around them.

If you’re looking for an activity that will engage the imaginations of your children, this is an excellent museum where they can go on a hunt for dinosaur bones, create art, play in a treehouse, and more.

Best of all, admission is free for children 15 and under on the first Sunday of every month, and they offer late hours every Thursday!

40. Cheer on a Chicago Sports Team

As we’ve mentioned before, Chicago is home to several great teams in multiple sports including baseball, basketball, hockey, and football.

No matter which sports your kids love, chances are you’ll have a chance to take them to a game during your trip to the windy city.

Check this list of sporting events in Chicago to find one that your children will enjoy.

41. Enjoy Family-Friendly Attractions For Less

There are a lot of popular kid-friendly activities and attractions that are included with Chicago tourist passes.

Depending on how you use these services, you could save anywhere from 20% - 50% off ticket prices.

If you plan to take your kids to locations such as Shedd Aquarium, 360 Chicago, Skydeck, LEGOLAND, Brookfield Zoo, Chicago Children’s Museum, or the Navy Pier, we recommend using a tourist pass to save money.


42) Explore the City Using Public Transportation

Chicago is well known for its public transportation system, which allows residents of the city to get around with ease.

Whether you want to hop on the train or take a bus, this is undoubtedly one of the most affordable ways to travel around Chi-town.

Check our post on the Chicago Public Transportation system for more information.

43. Spend Some Time on Lake Michigan

If you want a great view of the city skyline from the water, a cruise on Lake Michigan is an excellent and family-friendly activity.

There are several different Chicago cruises available, and there are also sailboat and kayak services you may want to consider.

44. Go to a Family-Friendly Comedy Show

Although most comedians tell jokes specifically for adult audiences, there are some comedy clubs and troupes that perform more family-friendly fare in Chicago.

CSZ offers excellent comedy shows aimed at all ages, and they also provide training for both adults and kids!

45. Take the Kids to Navy Pier

With its many family-friendly attractions and even amusement rides like a Ferris wheel and carousel, this is probably one of the most perfect locations in Chicago for children and their families.

In addition to all the traditional waterfront activities, there is also an IMAX Theatre, Funhouse Maze, the Chicago Children’s Museum, and more fun things to see and do at Navy Pier.

46. Winding Path at Maggie Daley Park

The Winding Path in Maggie Daley Park is a circuit designed explicitly for family amusement. During colder months, it transforms into a frozen skating loop, and in warm weather, it welcomes scooters and roller skates.

It offers an interactive and one-of-a-kind way for families to exercise in the great outdoors. This ribbon-like path is perfect for families, whether they prefer to ice skate in the winter or roller skate in the warmer months.

Mini-golfing located here has a certain whimsical charm, especially because the course is lined with miniature versions of well-known Chicago landmarks, such as the Picasso sculpture in Daley Plaza and the six-foot-tall Willis Tower.

47. Discover the Crown Fountain

Crown Fountain is more than just a water feature—it's an interactive marvel and a social gathering point. Nestled in Chicago's Millennium Park, this fountain stands out with its two glass-brick towers, each equipped with a large LED screen.

These screens project the faces of Chicago residents, making it a deeply communal and inclusive work of public art.

48. Discover the Tallest Buildings in Chicago

The windy city is home to some of the most historic skyscrapers in the world, and there are many different ways to see these landmarks.

Whether you’d rather save money with a self-guided tour, or you want to see these incredible buildings from the water on a cruise, there are several great Chicago architecture tours to choose from.

49. See a Live Magic Show

Give your kids the opportunity to be amazed at clever tricks and seemingly impossible feats performed by a live magician!

The Chicago Magic Lounge hosts a lot of great magic shows throughout the year, and these events are sure to be a hit with the family.

For more things to do with the kids, read our family-friendly activities in Chicago post.


Below is a list of many of the best things to see and places to visit in Chicago.

For in-depth information on how to visit these Chicago attractions, simply click on the site’s name and you will find ticket prices, tips on getting discounts, and what you can see while there. 

Top Chicago Attractions:

Things To Do in Chicago by Month


We think any time is the best time to visit Chicago. See our monthly posts to see what's happening when you are in town.

Winter Season (Nov, Dec, Jan, Feb)

Springtime (March, April, May)

Summer in the City (June July, Aug)

Fall (Sept, Oct)

Let Us do the Planning | Itineraries for Chicago

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