35 Free Things to Do in Chicago

35 Free Things to Do in Chicago

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35 Free Things to Do in Chicago35 Free Things to Do in Chicago25 Free Things to Do in Chicago 25 Free Things to Do in Chicago

25 Free Things to Do in Chicago 25 Free Things to Do in Chicago

35 Free Things to Do in Chicago 35 Free Things to Do in Chicago

As one of the largest cities in one of the most expensive countries in the world, Chicago is probably not the first city that comes to mind when planning a budget trip. However, if you know where to go, there’s a lot you can see and do without spending a penny. From cultural museums to beautiful parks, Chicago has something fun for everyone. Here are 35 fun and free things to do in Chicago.

25 Free Things to Do in Chicago

1. Take a free tour of the city with Chicago Greeter or Free Tours by Foot

My favorite way to start a trip to a new city is by taking a free walking tour. While free walking tours aren’t as popular in the United States as they are in Europe, you have a couple of options for free walking tours in Chicago. The first is to check out a new neighborhood or get an overview of the city from a Chicago local through Chicago Greeter. You will be matched with a local greeter who will take you on a 2-4 hour tour of the city for free. Groups must not be more than six people, and you are required to book a reservation at least 10 days in advance. Alternatively, if you have less time or are looking for more flexibility, you can hire an instagreeter for only one hour, and no reservation is needed. The best part about booking a tour through Chicago Greeter is that your itinerary is completely personalized. If you have a particular interest in Chicago history but less of an interest in Chicago sports, your tour guide can personalize your tour to see and talk primarily about Chicago history while skipping information on Chicago sports. As is the case with free walking tours in Europe, you’ll want to tip your tour guide for volunteering his or her time to show you around the city.

The other option is to book a tour through Free Tours by Foot. These tours are more structured and offer less personalization. Some options for tours through Free Tours by Foot include the North Loop and Millennium Park tour, the Riverwalk and History Tour, the Blues and Gangster Tour, the Chicago Ghost Tour, and the Architecture Tour. Most tours last approximately two hours, and you can see a complete list and detailed information for the tours here. As always, you will want to tip your tour guide at the end of your tour.

2. Go ice skating at one of the many public ice rinks

There are numerous outdoor ice skating rinks scattered throughout Chicago. The two most popular free rinks in the city center are the Maggie Daley ribbon and the ice rink at Millennium Park. If you have your own skates, you can enter the rink and use it for as long as you want for free. If you do not have your own skates, you can rent skates for $12 at Millennium Park and $12 on weekdays at Maggie Daley or $14 on weekends. The Maggie Daley ice skating ribbon is one of the newest additions to the city and looks similar to some of the courses on Mario Kart, with winding paths and even a few small hills. In the summer months, there is an outdoor rock climbing wall and playground for the whole family to enjoy. The rink at Millennium Park is a traditional rink that offers excellent views of the city and of the Bean (Cloud Gate), discussed more below.

3. Laugh at your own reflection in the Bean (Cloud Gate)

The Bean is one of the most iconic sculptures in Chicago. It is referred to as “the bean” because of how it is shaped like a big bean. Tourists and locals alike love looking at their own reflections through the bean, and it is common to find people in weird poses and positions there trying to get a unique looking photo.

25 Free Things to Do in Chicago

4. Attend a concert at the Grant Park Music Festival in the summer

Grant Park Music Festival is a 10-week classical music series that runs from June to August each year and features the Grant Park Symphony Orchestra and Grant Park Chorus, along with featured guests. It takes place at the outdoor ampitheatre in Grant Park and is completely free to the public. Bring a picnic and enjoy the entire concert, or stop by and have a quick listen while visiting the Bean or Art Institute. Hanging around Grant Park is one of our favorite things to do in Chicago!

5. Take your date on a romantic walk through Lurie Garden in Millennium Park

Lurie Garden is a 2.5 acre garden on the south end of Millennium Park. There are walking paths that run through the gardens. Whether you’re a horticulture enthusiast or not, this is a great place for a romantic walk with your date or for some peaceful reflection time for yourself.

6. Window shop on the Magnificent Mile 

If you enjoy shopping, you will find your heaven on the Magnificent Mile, a mile long section of Michigan Avenue lined with high end shops. While you may not be able to afford much from these stores or may not wish to blow your entire travel budget on clothes, window shopping is always free! Check out the newest styles and trends on this street. Who knows, you might even spot someone famous!

7. Escape the crowds on Michigan Avenue and enjoy photography and art at the Museum of Contemporary Photography

The Museum of Contemporary Photography (MOCP) is one of my favorite museums in the city but remains unknown to most locals. It is located inside the Columbia College building on Michigan Avenue right across from Grant Park and the Buckingham Fountain. The MOCP was founded by Columbia College in 1976 and showcases photography from top photographers in Chicago, nationwide, and throughout the entire world. Despite its status as the leading photography museum in the Midwest, it is rarely crowded, so it’s a great way to escape the crowds on Michigan Avenue and enjoy art and photography in a peaceful setting.

READ MORE:  What We Loved, Hated, and Learned From Our 2016 Travels

25 Free Things to Do in Chicago

8. Say hi to the animals at Lincoln Park Zoo

Like most big cities, Chicago has a zoo called the Lincoln Park Zoo. Founded in 1868, it is one of the oldest zoos in North America, and it is one of the only zoos that offers free admission. The zoo occupies 35 acres in the heart of Chicago’s Lincoln Park neighborhood and is steps away from Lake Michigan. Be sure to stop by and check out the newest arctic tundra polar bear exhibit.

9. Stroll around Navy Pier

Navy Pier is a 3,300 foot long pier that juts out into Lake Michigan. The pier is lined with shops, restaurants, and even a movie theatre, and there are events taking place there daily. From daily cruises to yoga classes to mini golf to the summer beer garden to performances by top musicians and artists, Navy Pier is always full of fun, energy, and excitement. While a lot of the activities cost money, it is free to walk around Navy Pier and take in the sights.

25 Free Things to Do in Chicago

10. Get the best view of the city from Promontory Point

Another structure that juts out into Lake Michigan, Promontory Point offers the best views of the full Chicago skyline. It is located directly east of Chicago’s Hyde Park neighborhood, home to the prestigious University of Chicago. In the summer, you’ll find sunbathers, swimmers, kayakers, and wind surfers in the water and on the nearby beach. Enjoy the lake breeze and the views here on your way to lunch at Hyde Park or an afternoon at the Museum of Science and Industry.

11. Get cultured at the National Museum of Mexican Art in Pilsen

The National Museum of Mexican Art is the first Mexican culture center/museum in the Midwest and the largest in the United States. It is located in Chicago’s Pilsen neighborhood, a largely hispanic neighborhood bustling with culture and some of the city’s best Mexican cuisine. It is open Tuesday thru Sunday from 10 AM to 5 PM and offers free admission to the public. It also offers free public tours on certain Saturdays each month. You can check the event calendar here prior to your visit.

12. Attend a free event at the DANK Haus German American Cultural Center in Lincoln Square

The DANK Hause is a German cultural center and language school in Chicago’s Lincoln Square neighborhood, a heavily German neighborhood. Be sure to grab a quick bite at one of the many authentic German restaurants in the neighborhood and experience the ways in which the German-American community has influenced Chicago with its culture and customs. The DANK Haus is open Monday and Wednesday thru Friday from 9 AM to 5 PM.

13. Walk or bike along Lake Michigan on the Lakefront Trail

The Chicago Lakefront Trail is an 18-mile long path that runs north and south along Lake Michigan. Whether you’re looking to go for a relaxing walk or trying to fit your daily run into your vacation schedule, the Lakefront Trail is where you want to be. There are also a  few options for bike rentals near the Lakefront Trail so you can rent a bicycle and ride along the lake if that’s more your style.

25 Free Things to Do in Chicago

14. Admire the landscape and artwork on the 606

The 606 is one of the newest additions to Chicago and one of my favorite places to be in the city when the weather’s nice. It is an elevated path built on an old railroad that has since been abandoned. Today, the 606 path is lined on both sides with greenery and parks, and you will find areas of artwork throughout the path as well. Take in the city from above all the traffic and congestion on the 606.

15. Explore the ancient world at the Oriental Institute in Hyde Park

Go back in history to the ancient Near-East world at the Oriental Institute in Hyde Park. The museum inside showcases the history, art, and archaeology of the ancient Near-East. This site is jam packed with history and culture, and it’s truly a wonder that admission is free!

16. Have a photo shoot at the Chicago Cultural Center

The Chicago Cultural Center is one of the most beautiful buildings in Chicago. As soon as you walk in, you will see an open lobby with an intricately designed ceiling held up by beautiful pillars. This is one place where you will not want to forget to bring your camera, and even better, the cultural center is free to enter and offers public tours at certain times throughout the week as well.

17. Take a dance break at SummerDance

Between June and September, the Spirit of Music Garden in Grant Park transforms into an outdoor open dance floor. There are regular performances by all sorts of dance groups, and of course you are always welcome to dance along!

25 Free Things to Do in Chicago

18. Take in all the free smells at the Taste of Chicago

Another fun summer event is the Taste of Chicago, an outdoor food festival showcasing the diverse range of foods that make up Chicago. Although the food is not free, it is free to walk around and take in all the smells.

19. Take in more free smells at the Maxwell Street Market every Sunday

The Maxwell Street Market is located on Desplaines between Polk and Taylor and is an iconic Chicago market steeped in history and tradition. It is also one of the only places in the city where you can bargain for what you buy. The merchandise sold at the market include an eclectic mix of products ranging from clothing to collectibles to fresh produce to tires. You can also find some of the best Mexican street food in Chicago at the Maxwell Street Market. If you want to see and taste something interesting and unique, the Maxwell Street Market is for you.

20. Peruse Whole Foods for free samples

There are a number of Whole Foods markets scattered throughout the city, and you can often find free samples inside. After a long walk, duck into a Whole Foods and try your luck at scoring some delicious free samples.

READ MORE:  15 Reasons to Visit St. Augustine, Florida: The Oldest City in the U.S.

25 Free Things to Do in Chicago

21. Tour a brewery

Chicago’s brewery scene has been growing quickly in the last few years, and many breweries offer free brewery tours. My favorite is Lagunitas, a California based brewery that opened only a few years ago in our Pilsen neighborhood. Tours are offered every day of the week, but free samples are only given on weekday tours. Other Chicago area breweries that offer free tours include Revolution, Two Brothers, and 3 Floyds.

22. Eat free wings at Burwood Tap every Monday – Thursday at 8:30 PM

Every Monday thru Thursday starting at 8:30 PM, Burwood Tap offers free wings. Head on over for some free wings over a tasty beer and game of pool.

23. Admire the Chicago waterways from the Chicago Riverwalk

The Chicago riverwalk is a brand new, beautiful pathway running along the Chicago river and connecting to the Lakefront Trail and Lake Michigan. There are bars and restaurants along the riverwalk that are bustling with people and energy in the warmer months, and the riverwalk is illuminated by lights at night. Plus, you can also capture great views of the bridge system in Chicago from the riverwalk. This is another spot where you do not want to forget to bring your camera.

25 Free Things to Do in Chicago

24. Give your eyes an aesthetic recharge at the Chicago Design Museum

The Chicago Design Museum is located on the third floor of Block Thirty Seven, a collection of shops and restaurants in the heart of downtown Chicago. It is open Tuesday thru Saturday from 12:00 PM to 7:00 PM. Stop by here when you’re taking a break from shopping, and if you feel your sweet tooth acting up, check out Magnolia Bakery on the first floor of Block Thirty Seven for the best red velvet cupcakes and banana pudding.

25. Explore Chicago’s underground pedway system

There are over 40 blocks of underground pedestrian way (pedway) in downtown Chicago, linking many of the subway stops, restaurants, and shops, to make getting around in the winter a bit more bearable. If you’re traveling in the winter months, make sure to take advantage of this system to avoid the cold. Regardless of the weather, take a walk through the underground system and see if you don’t get lost in the maze-like tunnels!

26. Catch the sunrise or sunset at Humboldt Park

Humboldt Park is a 219 acre park on the west side of Chicago. Situated in the middle of that is an iconic field houses a fitness center, meeting rooms, an inland beach, and historic lagoons and a boat house. While a sunrise or sunset over Lake Michigan is beautiful, the view from Humboldt Park is much more unique and full of character.

27. Get smart at the Smart Museum of Art

The Smart Museum of Art is the fine arts museum of the University of Chicago. It houses over 15,000 unique art objects ranging from modern masterpieces to centuries old Chinese artifacts. It is free and open to the public Tuesday thru Sunday from 10:00 AM to 5:00 PM (8:00 PM on Thursdays).

28. Read a book at the Chicago Botanic Gardens

Situated on 385 acres in the northern suburb of Glencoe, the Chicago Botanic Gardens are the perfect place to spend an afternoon relaxing with a book or taking a stroll through the beautiful gardens with a loved one.

29. Experience free theatre at the Free Street Theatre

The Free Street Theatre is exactly what it sounds like – a place for artists to freely express their ideas, for the public to freely view the shows, and for aspiring performers to take free classes. Click here for a calendar of upcoming events – any performance you choose will be interesting for sure.

25 Free Things to Do in Chicago

30. Show off your dance moves at Beauty Bar

As your day’s winding down, head over to Beauty Bar for cocktails, dancing, and even a manicure. The 60s vibe is in full force here, and you will see people dressed to the times. Arrive between 7-9 PM for free admission.

31. Attend a free comedy show every 1st and 3rd Monday at 8:30 PM at Gman Tavern

Who can say no to free comedy? Gman Tavern is an old-school, local bar with a very low-key vibe. In addition to free comedy, you will also find pinball and pool at the tavern, as well as some of the area’s best craft beer.

32. Admire the architecture at the Harold Washington Library

Located in the heart of downtown, Harold Washington Library is the main library in the Chicago Public Libraries group. The library is named after Harold Washington, Chicago’s first African American mayor. The interior is beautiful – make sure you make your way up to the top floor to take in all the views. The library is open on weekdays from 9:00 AM to 9:00 PM and operates more limited hours on weekends.

33. Let your kids run wild at Maggie Daley Park

Maggie Daley Park is one of the newest additions to Chicago and an energetic 20 acre park that includes an ice skating ribbon and outdoor climbing wall. This is a fun park for adults and kids alike, and with its prime location on the north end of Grant Park, you have no excuse not to stop by.

25 Free Things to Do in Chicago

34. Enjoy local art at one of the city’s most treasured landmarks

The historic Water Tower on Michigan Avenue is much more than just a shopping mall. It is also home to the City Gallery, a rotating art exhibit showcasing the works of local artists. Make sure you stop by here on your shopping break and admire the wealth of artistic talent springing from the local Chicago community.

35. Watch a water show every hour at Buckingham Fountain

The Buckingham Fountain, located on the south end of Grant Park, is one of the largest fountains in the world. You can catch a water show here every hour, and the after dark shows are choreographed with music and lights. The fountain runs from April until October from 8:00 AM to 11:00 PM daily.

Here are some of our favorite tours and resources if you have a few extra dollars to spare:

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Hi, I'm Diana, the big sister in the sister duo. I left my job as an attorney in March 2017 to pursue the work-from-anywhere/travel-everywhere life aka The Dream. I blog about off the beaten trail travel destinations, adventure travel, immersing in local cultures, and publish plenty of travel guides for all you who are too lazy to plan your own trips. I've traveled to 61 countries to date, and some of my recent adventures include hiking Mt. Kilimanjaro, visiting a child I've sponsored for over 10 years in Rwanda, and exploring the Middle East.

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78 Responses
  1. A lot of people think the beer in the US is a joke but it’s actually very good! I need to confirm this, you can get a free brewery tour and on weekdays you get free samples of the beer on the free brewery tour? There are also free wings at Burwood Tap after 8-30, I wish I had read this before I visited Chicago. The views of the city look pretty amazing from the Maggie Daley Park too.

    1. Yep, you’re 100% correct. Might I add too that the free samples on weekdays are quite generous and will get you quite buzzed before you’ve spent a penny. Let me know when you’re headed back to Chicago! 🙂

      1. This is a fantastic list but I HAVE A FEW ADDITIONS:
        *96th floor in the Hancock building. The ride up is absolutely free. Go on a week day, during the day and it will not be crowded with lines. You may buy a drink or not. Sit to look out at the PHENOMENAL views. I’ve been up there, walked around, went to the ladies room (BEST VIEWS ARE FROM THERE ACTUALLY… HE HE HE). No one bothered us and we simply went back down the elevator and ALL ABSOLUTELY FREE.
        *The Chicago Athletic Association Hotel. OMG. This place is gorgeous, with antique, intricately carved woodwork GALORE. I wandered around and went from floor to floor and no one bothered me. On the 13th floor there is a ROOFTOP BAR CALLED CINDY’S. It’s a bit pricey. But I wandered out to the veranda, which overlooks Millennium Park and the Lake… took some pics and then left with no one bothering me. This was during the day, during off peak hours again. The views from up there are FANTASTIC! FREE.
        *The historic MARSHALL FIELDS building, now occupied by Macys. The ceiling inside and architecture is worth a visit. During spring they have the whole place decorated with flowers and greens like a botanical garden. Instagram pic heaven. FREE. During the holidays they have the windows to see. FREE.
        *Restoration Hardware. This place is unREAL! it’s in a completely renovated, historic, brick building. Gorgeous atrium roof over a lovely restaurant with a fountain. They have a bar there and also FREE valet parking. But the best part is that it’s a multi-level store… like 10 stories or so. You can wander at will , FOR FREE, through the whole place. The upper level is open to pretty cool views. You can sit up there and chat. Or take pics.. You can take drinks up there too if you like. The top floor is all decorated like an outdoor space with furniture by Restoration Hardware. There is also an open to air — deck area. There’s also an ART floor. You will be lost in this place for hours. FOR FREE!
        *Trump Tower. Okay, I went during the election time. I was surprised that I was able to just walk in the doors and take the elevator up to their restaurant. There’s an outdoor veranda area for warm weather fun. It’s not free. But the views of the river and city are gorgeous. I was able to take pics up there for FREE. Again, no one bothered me. Maybe I’m invisible and just don’t realize it. If so, I’m not minding it one bit! LOL
        Chicago is a wonderful place to visit. And the newly renovated river walk has opened up another glorious avenue to revel in! Have fun!

  2. Awesome listing. This is most definitely important for every budget traveler! When I visited in London, my first online search was for the free things to do. Only after that I went on to do the paid things!! Lolz!!!

  3. I have never been to the windy city and would so love to visit. We always travel with the kids and enjoy seeing things through their eyes. We would never miss something as iconic as the bean!! Love stuff like that and so do the kids.

  4. What a great post of things you can do in Chicago! The Windy City is one of our favorite places to go for a quick weekend getaway (I mean, why not, it’s a cheap flight and only an hour or so from Minneapolis!), and I’m elated to see that while we’ve done several of these (love seeing the Bean, and walking along the waterfront is so fun), there’s plenty else to do on our next trip. Sounds like there’s a lot of bars and art left to explore. 😀

    Also, I had to chuckle at the Whole Foods bit. We used to live right down the street from Whole Foods and often went to sample their wares, mainly cheese and crackers. Good times! I miss it.

    1. Haha glad you can relate. I don’t think all my habits from being a poor student have worn off yet. Yes – there are always new bars to explore, and that’s one of my favorite things about living here. Come visit soon!

  5. Thanks for this, I am off to Chicago next month and I didn’t know about half of these. You’ve given a list that has a little something for everyone, I can go shopping and the other half can go to the breweries 🙂

  6. the walking tour, local art and free theater does sound most interesting. This is a very comprehensive list of things to do for free, will really help everyone plan economical trips in Chicago.

  7. Your photos are gorgeous, as usual. I particularly like the one of the Bean! I visited Chicago a few years ago, but unfortunately lost a piece of jewellery that was particularly dear to me, which ruined the trip. A shame, as there are clearly plenty of fun things to do there.

  8. Thanks for the this list. I’m pinning it for when I go to Chicago. The Chicago Greeter sounds like a great concept. I also love the free walking tours. And I’ve never heard of a free zoo before!

  9. I always thought Chicago would be so expensive, but you’ve definitely made me think again. I’ve never visited but I do have friends that live out there and I’ve been putting off visiting because of budget. Armed with your free tips I think I might have to make visiting a priority now. It looks so fun!

    1. Thanks, Stephanie! There definitely are more things to do in Chicago in the summer than in the winter. Hope you’re able to make it back here in the summer so you can enjoy it more. 🙂

  10. Jackie Taylor

    Chicago looks like an amazing place to visit!! I’ve only been to their airport on a short layover, but I really want to visit one day. I love free walking tours, so I’ll definitely save this post for when I do eventually go!

  11. First of all, I admire your patience ;). Even simply writing down 35 entries is commendable. There are some great opportunities there. #25 – I still have to do it. #9, Navy Pier – I like to go to the end of it and admire Chicago skyline from there. #13, Lakefront Trail – one of my favorites too. However, there are some cruel choices too. #6, window shopping on the Magnificent Mile – nope, never worked for me. I mean “window” part. Somehow, I always quickly switched to actual shopping (terrible idea considering store names there). ##18,19 – are you kidding me? Just smells? No way! I have to taste the Taste of Chicago. Cheers!

    1. Haha you’re right, those were some cruel options. Window shopping usually works better for me when I leave my wallet at home, so there is no temptation there (or at least I can’t do anything about the temptation). The Taste of Chicago is July 5-9 this year, so if you’re free that weekend, you could consider coming to Chicago. 🙂

  12. The Windy City! We haven’t been to Chicago yet but it’s in our itinerary for 2018 when we embark on a month-long vacation to the US after my daughter finishes her college. It’s something we have been meaning to do but always end up traveling to either the East coast or West coast and never passing in any state along the way. 🙂 Thanks for sharing these free things to do while in Chicago. It’s good to know 🙂

  13. This is a great list! Chicago is one of our favorite cities in America, and we have yet to do everything you mentioned. Our favorite restaurant is Mindy’s hot chocolate, we highly recommend trying it next time you are in the city.

    1. Funny you mention that because Mindy’s was one of the first restaurants I tried when I moved here in 2011. I have never had hot chocolates as rich as the ones at Mindy’s. Glad you had the chance to experience Mindy’s, and hope you make it back soon!

  14. Awesome list and with 3 kids we always love FREE things to do – my kids and probably my hubby to would love to laugh at their reflections in the ball and me I would love the markets and the Water tower looks like a cool stop!

    1. Hahah old habits die hard, Sarah. Being a poor college/grad student for 6 years definitely instilled some “bad” habits in me that I still haven’t gotten rid of. A favorite being the free samples at Whole Foods. Glad I’m not alone. 🙂

  15. Chicago has been on my list for so long by now… Happy to see that it is not only about n.3 which is probably the most IG-posted :)) Great job putting it together and lovely pictures, girls!

  16. Chicago is such an amazing place. We just love the views of the skyline from the Shedd aquarium. We did not know there are so many free things to do while at Chicago. Loved the fountain near the Millenium park, though. Very informative post.

  17. I haven’t been to Chicago before, I will save this list for later as it looks like a great city to visit. Free brewery tour and free wings?! That’s heaven. Nowadays, I think in every city you have free things to do that are worth trying. Thank you for your patience of writing about all of the 35 points.

  18. I didn’t realise there are so many free things to do in Chicago. Most of the things on your list are places I am not aware of and u didn’t know Chicago has the Underground city like Toronto 🙂 I have pinned for future use.

    1. Yep a lot of big cities in the north have the underground tunnels! It’s a huge necessity given how cold it gets here in the winter. Chicago has a ton of hidden gems, many of which are free. 🙂

  19. Sheena

    I’ve been to a lot of the big American cities but have never made it to Chicago for some reason – now I’m thinking it’s a good thing, I’m now armed with this amazing list of free things to do! I’ll be based in the States this year so will aim for a visit in the summer, thanks!

  20. The public ice skating ring sounds like a great idea. I recently tried ice skating for the first time in Melbourne (I know I’m way behind) and absolutely loved it. It’s fairly difficult at first but fun once you pick it up. The ring I tried was indoors so I would love to have a go outdoors.

    1. It is pretty tricky at first, but most of the people around you will be beginners as well, so you’ll feel like you’re in good company at least. Hope you get to visit Chicago and skate on an outdoor rink one day. 🙂

  21. Awesome article. I hate that I have visited here many times in the past to see family, but never actually experienced the city. Will definitely move my butt next time and do more than just snooze the weekend away when visiting family. Awesome tips!

  22. Chicago is a lot of fun and so much to do. Great list of free things here, like any city it can be a little pricey so it’s nice to have this handy when visiting. For anyone thinking of visiting the food in Chitown is wonderful.

  23. Chicago is one of my favourite cities in the world and I am obsessed with the sports teams so I will definitely save this guide for later as I am likely to be in Chicago again sooner rather than later. Some amazing tips for different times of year. Can’t wait to do as many of the things on this list as possible on my next visit!

  24. So many free things to do, this is incredible! I love panoramic views so would definitely head for Promontory Point, and the walking tours would be a fabulous way of getting your bearings and seeing the city. Cycling is always such a fantastic way of seeing a city as well so we would check out the Chicago Lakefront Trail, some of our favourite day trips have been cycling! Love the breakdancing as well .. in fact, I love so much of what there is to do for free, thank you for sharing! Pinned for future reference. #feetdotravel

  25. This is such an amazing list! Who knew that there were so many awesome free things to do in Chicago?! I haven’t been since I was a kid but after reading the list I’m ready to start looking at flights 🙂

  26. Chicago is one of the cities I still have to visit! Loved your post – full of usefull tips and ideas, very handy! Didn´t realize there were soooooo many things to do and see in Chicago!

  27. Elena

    Hey guys, thanks for all the great info! My friend introduced me to Chicago nearly four years ago; she promised I would love it, and I did! In fact, we both enjoy Chicagoso much, that now we make it our annual girls’ trip! We always go in December, and I would really like to experience summertime there- it looks beautiful at that time as well!
    Your photographs are beautiful!!
    *P.S. if you have any suggestions for visiting in the cooler weather months it would be great!!?

    1. Hi Elena! So glad to hear you loved Chicago so much it is now your annual girl’s trip! You absolutely should come back in the summertime – it is a completely different city in the summer!

      As for the winter, one of my favorite things to do is go ice skating in one of the many public ice skating rinks around the city! My favorite ones are the one by the Bean, the one at Maggie Daley Park, and if you like animals – the one at the Lincoln Park Zoo! Around Christmas time, there is a Christmas market at the Daley Plaza called Christkindlmarket where you can find lots of Christmas decor and some delicious spiced wine 🙂 Otherwise, I would recommend finding a cozy bar or cafe to spend the afternoon at, either with friends or with a book. Chicago is becoming a major food scene, as you probably have seen from your many trips here, so there is no shortage of bars, cafes and restaurants!

  28. Clara

    Loved your list, Diana! I will be making my first trip to Chicago next month and I already can’t wait to be there to visit as many of these places as possible. Happy travels!

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