Top 16 Things To Do In Chicago, Illinois

Chicago – ‘The Windy City’ and the third largest city in the United States is not only famous for its world-class architecture but it has the second largest skylines and downtown in the United States with plenty of attractions for any age. The Chi-town offers some world-renowned museums, shopping district, beautiful parks, buzzing nightlife and dining places as well as several indoor and outdoor activities to entice any visitor!

I visited Chicago last month and had an amazing time! Based on my trip, here’s my list of top 16 things to do in Chicago that will make your trip memorable!

1) Take some positive vibes at Millennium Park

A first-time visit to Chicago isn’t complete without a stop at Millennium Park. Moreover, this is a free attraction famous for its iconic structure – Cloud Gate, also known as “The Bean” which has around 110-ton bean-shaped sculpture forged from stainless steel. The Bean’s elliptical shape reflects the Chicago skyline. This is a perfect place to sit for some time and just soak in the surrounding!

Top 16 Things To Do In Chicago, Illinois

The second attraction of the Millennium Park is the Crown Fountain which features two 50-foot towers that face each other at opposite ends of a shallow reflecting pool. The towers’ LED screens project the faces of 1,000 different Chicago residents, which are perfectly aligned with spouts so that it appears they are spitting water on passersby. This is the fun place for kids where they can get some splash and adults can enjoy the refreshing view!

You can also see a concert at the Jay Pritzker Pavilion on the select nights, stroll through the Lurie Garden or the Boeing Galleries (where the contemporary sculpture is displayed outdoors).

Top 16 Things To Do In Chicago, Illinois

2) Go to Skydeck Chicago / Willis Tower

If you’re fascinated by heights and want to experience the breathtaking view from the 103rd floor of the Chi-town from the second tallest building in the United States (after One World Trade Center, NYC), you should totally visit the city’s most iconic landmark – Willis Tower’s Skydeck Chicago! The locals still call it as Sears Tower. I visited on a bright sunny noon and could see far beyond Chicago’s borders to Indiana, Michigan, Wisconsin and other parts of Illinois!

Top 16 Things To Do In Chicago, Illinois

The most famous attraction of Skydeck Chicago is The Ledge’s glass boxes which extend out 4.3 feet from the Skydeck. No trip to Skydeck would be complete without getting yourself clicked on the Ledge! This is the most crowded part of the Skydeck. Sometimes you may have to stand for hours in the queue to take your pictures but it’s totally worth it!


3) Go to 360 CHICAGO Observation Deck

If you need some more adrenaline rush and want to experience more breathtaking views, go to 360 CHICAGO Observation Deck located on the 94th floor of the John Hancock Center. Also Known locally as ‘Big John’ is the 100-story and second tallest building in Chicago. The deck has the interactive screens that will help you to identify different landmarks that appear in your panorama. The ‘Tilt’ is the unique feature of the 360 Chicago from where you’ll get a moving experience that leans 8 adult visitors at a time towards the street below. There is an additional cost to enjoy the tilt. There is an Architect’s Corner Cafe and Bar that offers coffee,  full bar with cocktails and snacks.

Top 16 Things To Do In Chicago, Illinois

However, the best view comes from the (Women’s restroom only) at THE SIGNATURE Lounge, an upscale high-end lounge located on the 96th floor of the John Hancock Center. Therefore you should totally enjoy a privilege the men’s washroom doesn’t afford!

Top 16 Things To Do In Chicago, Illinois

4) Visit Grant Park & Buckingham Fountain

The Grant Park is often referred to as “Chicago’s front yard,” which has the world’s largest fountain known as Buckingham Fountain. The water feature boasts 133 jets that shoot water as high as 150 feet into the air during 20-minute choreographed displays (which take place every hour on the hour between 9 a.m. and 10:35 p.m. from April to October). At night, the fountain’s performance is accompanied by lights and music. This is a free attraction and must visit for any first time Chicago visitor!

Top 16 Things To Do In Chicago, Illinois

5) Explore some great paintings & sculptors at the Art Institute of Chicago

You could spend years getting to know this encyclopedic institution, which owns more than 300,000 artworks and artifacts. The Art Institute of Chicago is a home to one of the country’s most impressive collections of impressionist and post-impressionist art along with works from numerous other genres. Renzo Piano’s light-filled Modern Wing is the perfect place to enjoy the architecture and design collection, modern and contemporary art and a splendid view of the Millenium Park.


Top 16 Things To Do In Chicago, Illinois

6) Delight your taste buds with Giordano’s Pizza

No trip to Chicago would be complete without having Giordano’s authentic Chicago style stuffed, deep dish and thin crust pizza! Try to have any stuffed deep dish pizza which is baked in a pan that gives the pizza its characteristically high edge and a deep surface for large amounts of cheese and a chunky tomato sauce. Oh boy! it looks so delicious and mouth-watering that you couldn’t ask for anything more and I bet, you won’t be able to finish it alone!


7) Take Chicago Architecture River Cruise

If you want to know the history of the world-class Chicago architecture, you must go for Architecture River Cruise! During a river cruise, you’ll gain great views and historical insight about well-known structures of the Chi-town. There’re several companies that offer architecture river cruises including Wendella Sightseeing Co. and Chicago Line Cruises. However, I climbed aboard a Chicago’s First Lady Cruise boat with a Chicago Architecture Foundation docent. Our tour guide was knowledgeable and he shared tons of information as well as told us some great spots to click the pictures!

Top 16 Things To Do In Chicago, Illinois

8) Visit Navy Pier for some fun time

Navy Pier — the former U.S. Navy training center is one of the popular family-friendly attractions in Chicago. The first thing you’ll spot once you set foot on the pier is the towering Ferris wheel (which stands 196 feet tall) that offers unparalleled views of the Chicago skylines. You’ll also find a swing-seat ride and a carousel for kids entertainments. You can also explore the Chicago Children’s Museum, with hands-on exhibits ranging from treehouses to firetrucks. Grown-ups can catch a show at the Chicago Shakespeare Theater, flex some credit card muscle at a variety of shops, restaurants, fine-dining places or go for boat dining cruises!

Top 16 Things To Do In Chicago, Illinois9) Burn your money at Magnificent Mile

If you’re a millionaire and looking for some place to burn your money, this is a place! The Magnificient Mile or The Mag Mile is an upscale section of Chicago’s Michigan Avenue which stretches between Lake Shore Drive and the Chicago River. It is a shopper’s paradise with department stores, luxury boutiques, multi-story megamalls, brand name retail chains – all in a row. Among the Mag Mile stores, upscale outlets such as Bloomingdale’s, Nordstrom, Macy’s, Neiman Marcus and Saks Fifth Avenue anchor the area with elaborate window displays and proffer some of the biggest style names. The Mag Mile is also the home to several top-notch eateries and luxury hotels. Even if you don’t want your credit card burning a hole in your wallet, go for a window shopping or just stroll on the street and admire the architecture of the beautiful skyscrapers around!

Top 16 Things To Do In Chicago, Illinois

10) Explore some History at The Field Museum of Natural History

See dinos, marvel at ancient artifacts from a royal Egyptian tomb or take a stroll through the Halls of Gems and Gade, this massive natural history museum has more than 30 permanent exhibitions covering around 300,000 square feet. But no visit to The Field Museum would be complete without some quality time with SUE, the facility’s Tyrannosaurus rex who just happens to be the largest, most complete T. rex ever discovered. Sue is 42 feet long from nose to tail and boasts 58 terrifying teeth. The museum is a must visit for kids as it has a lot of educational value. However, as an adult, I too had an amazing time exploring the museum!

Top 16 Things To Do In Chicago, Illinois

11) Explore the marine world at Shedd Aquarium

Shedd Aquarium is home to around 32,000 creatures, anchoring the aquatic offerings are enduring favorites such as dolphins, belugas whales, and sharks. You’ll also encounter an 80-plus-year-old Australian lungfish believed to be the longest-living fish in any aquarium in the world.  For an additional fee, you can even participate in specialty experiences like animal encounters, feeding experiences and behind-the-scenes tours.

Top 16 Things To Do In Chicago, Illinois

12) Explore the universe at Adler Planetarium and Astronomy Museum

Adler Planetarium is classified as a history, planetarium, and science and technology museum. This museum is fun for adults and kids who love to learn. You can browse through various exhibits such as antique astronomical instrument, historic scientific instruments, rare and modern books, works on paper, photography, paintings, models, and archives. Adler museum’s real draw is the virtual-reality trips in the Sky Theater, which uses 20 projectors to create an image and an entire experience is exhilarating!

Top 16 Things To Do In Chicago, Illinois

13) Visit home of the Chicago Cubs at Wrigley Field

If you want a real taste of Chicago culture and wants to experience how Chicagoans take their love of sports,  head to Wrigley Field to see “da Cubs” play!  If you can’t score game tickets, consider signing up for a guided tour of the ballpark. You’ll get a close-up view of the friendly confines, press box, and batting cages. Tour itineraries vary depending on whether or not there’s a game scheduled for that day. On non-game days, tours also include stops at the clubhouse and dugout.

Top 16 Things To Do In Chicago, Illinois

14) Visit the home of the Chicago Bears of the National Football League at The Soldier Field

An American football stadium dedicated to the men and women of the armed services and home of the Chicago Bears. Soldier Field is also host to world-class concerts, college football, international soccer & rugby along with many other timeless events. The Soldier Field also offers behind the scenes tours that include the South Courtyard, Doughboy Statue, Field, Visitor’s Locker Room, Skyline Suite, and Colonnades. This is a must visit for any Chicago Bears fan or someone who loves American Football!

Top 16 Things To Do In Chicago, Illinois

15) Explore some wildlife at Lincoln Park Zoo

One of the few free zoos left in the country, this city mainstay is small – only 35 acres but attractions such as the Kovler Lion House, the Regenstein Center for African Apes and Kovler Seal Pool to get up close and personal with harbor seals is quite amazing! You’ll also see dozens of species of animals including zebras, sloths, and hippos. Try to use the public transport or taxi as there’s limited availability in the zoo’s parking lot!

Top 16 Things To Do In Chicago, Illinois

16) Go for a walk or cycling at Chicago Lakefront Trail

Chicago Lakefront trail is the best place for riding a bike, jogging or simply walking on the foreshore way along the coast of Lake Michigan, breathing some fresh air and soaking the view of the breathtaking skyline around! I walked the trail from the Shedd Aquarium to the Navy Pier for around 75 minutes and couldn’t stop myself admiring the scenic views around! If you want some exercise while in the city, you’ll love this trail!



Tips for visiting Chicago

  • The best months to visit Chicago are April through May and between September and October when the temperatures are warm.
  • The seasonal range in Chicago runs from bone-chilling winters to sweltering summers. Other than maybe the mildest of transitional spring and fall days, packing for Chicago is not a no-brainer. In winter, hat and boots are a must. Ditto sun hat and sun block in summer. You can’t predict a 60-degree August afternoon, but the best way to plan for it is to pack layers.     
  • For the first time Chicago visitor, most of the attractions are located in the downtown. So try to look for hotels in the downtown area so that your time won’t get wasted in commuting from the suburbs.
  • Buy Go Chicago® Card for sightseeing various attractions in discounted price. It’s a nice way to save few bucks if you want to explore all the major attractions where the admission fee is allowed for entrance.
  • The public transport in Chicago is amazing! The Chicago Transit Authority (CTA) buses and trains are available to see downtown, North Michigan Avenue and a few places beyond. The CTA runs buses and subway trains that serve Chicago and 35 nearby suburbs. For more information, you can check here. Plus there are taxis and Uber drivers everywhere.
  • There’re several hop-on-hop-off sightseeing as well as private rentals tours are available for exploring the city as per your areas of interest. For more information, you can check here.

Final Verdict

There’s so much to see and do in Chicago that it will be a struggle for visitors to decide between the world-class museums, the miles of shopping, the Broadway theater shows and the creative guided tours led on foot, bikes, boats and segways. Even if you just chill along the surreal Lake Michigan shore, or stroll through Millenium Park, you’ll be awed by Chicago’s beauty and charm!

Do share your experience if you’ve visited Chicago, Illinois in the comments below? If not, what do you think about this city?

Happy Traveling!

**Please Note that this post has been transformed into an app by GPSMyCity and you can download it from here for your ios devices on iTunes App Store or the Android app on Google Play. The app works offline so no data plan is needed when traveling abroad.

Top 16 Things To Do In Chicago, Illinois


    1. Hi Ana, you made my day, i would like to see all of these places, Chicago is in my wishlist and Illinois is just amazing, ill try giordano’s piizza, it looks delicious 🙂

      Great stuff

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    1. A glass of wine at the top of the John Hancock Center to watch a sunset is one of my favorite things to do on Earth! And I prefer that deck to the Sears Tower (yeah yeah, I still call it that too!) because form the Hancock you can look AT the Sears Tower rather than just being in it 🙂

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    1. These are some quite good and useful tips for people visiting Chicago. The Millenium park does have quite positive vibes which is evident even from the pictures. I would spend quite some time at the Museum of Natural History though.

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    1. So many articles around Chicago and all of them have 3 things in common – Waterfront, the zoo and Deep Dish. Very detailed post 🙂

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    1. Great list, but as a former native of Chicago I have to disagree with one thing…in my opinion in the words of Kanye West “Summertime Chi” is the best time to visit 🙂

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    1. the Millenium Park looks awesome, not sure I would go into that high building, I am a little scared of heights, lol. Still, I loved your pictures, maybe I should add Chicago to my bucket travel list after all. Blessings!

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