30+ Fun Things to Do in Downtown Chicago in 2018

One of our daughters, Katie, recently asked us — What are the Top fun things to do in downtown Chicago in 2018?  So we have compiled our list of top 30+ fun things to do in downtown Chicago in 2018, one of the great cities of the world.

free things to do in chicago

And  if you need help deciding what to do on your vacation, check-out some of our favorite attractions and activities. Start your amazing walkabout in Chicago’s loop, gazing at the Chicago architecture, then do the following:

1. Find a great Chicago hotel in downtown Chicago to set up as your headquarters.

2.  Pull out your wallet and shop morning to night along Chicago’s Magnificent Mile, a roughly eight-block stretch of North Michigan Avenue offering every kind of store imaginable.

3. Take a Free Walking Tour in Downtown Chicago this summer — Beginning May 7th, there will be a free downtown Chicago tour.  No reservations required as these tours are a perfect introduction to Chicago. This 2.5 hour easy walking excursion is a great way to learn about the history, culture and lifestyle that is Chicago.

4. Check out what One Million Dollars looks like on this fun Chicago tour or take a Chicago Gangster tour.  Experience the original Gangster Tour on our new custom-built Untouchable Tours Gangster Bus: climate controlled, great air conditioning, comfortable seats!  Experience Chicago as it was during the 1920s and 1930s.  See the old gangster hot spots and hit spots and hear historically accurate accounts of the exploits of Capone, Moran, Dillinger and the rest of the boys.  Feel the excitement of jazz-age Chicago during the Prohibition Era and enjoy a journey into the past as we cruise the city in search of the old hoodlum haunts, brothels, gambling dens and sites of gangland shootouts

5. Slowly make your way through Millennium Park, an extraordinary testament and home to world-class art, music, architecture and landscape design.  Go south a block to Grant Park and marvel at the incredible water shows at the world-famous Buckingham Fountain.

6. Take your kids to the Chicago Children’s Museum, with three floors of engaging and educational exhibits.

7. Enjoy one of the world’s greatest art collections at the Art Institute of Chicago, especially when free on Thursday evenings each month


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8. You must check out Cloud Gate, or what we Chicago locals call “the Bean”. One of Chicago’s leading free attractions, “The Bean” or “Cloud Gate” is British artist Anish Kapoor’s first public outdoor work installed in the United States. The 110-ton elliptical sculpture is forged of a seamless series of perfectly polished stainless steel plates, which reflect the city’s famous skyline and the clouds above. Visitors and citizens alike are marvelling at the beauty reflected off the Bean and the near perfection of the work and it remains one of the leading things to do in Chicago. A 12-foot-high arch provides a “gate” to the concave chamber beneath the sculpture, inviting visitors to touch its mirror-like surface and see their image reflected back from a variety of perspectives. Inspired by liquid mercury, the sculpture is among the largest of its kind in the world, measuring 66-feet long by 33-feet high.

9. Make sure to check out the famed Chicago Museum Campus and come see all the fishes and more at the world-class Shedd Aquarium.

10. While not in season, go cheer for one of Chicago’s two Major League Baseball teams. Watch the Chicago Cubs (now under new ownership – yea!) at one of America’s oldest, smallest and best-loved stadiums, Wrigley Field. Or catch the Chicago White Sox at the modern Guaranteed Rate Field.

11. Visit the trendy boutiques of Oak Street or venture to revitalized State Street to browse through historic anchor Macys (the old beloved Marshall Field) and other fun shops.

12. With jogging paths and plenty of water sports, everyone will want to spend time on Lake Michigan.

13. Sail off into the sunset on one of Chicago’s dinner cruises like the Odyssey or the Spirit of Chicago.

14. For an awe-inspiring view of the city from above, go out on the ledge at the  Sears Tower er….Willis Tower Skydeck or the Hancock Observatory.

15. For family entertainment from the famous Ferris wheel to free public shows, Navy Pier is a fun place to visit.

16. Take your kids to the wild side at the free Lincoln Park Zoo.

17. Willis Tower – Formerly known as the Sears Tower, the Willis Tower enjoys the legacy of once holding the title as the tallest building in the world. Today, while no longer the tallest in the world, Willis Tower remains a favorite Chicago attraction for locals and tourists. The Skydeck is the main attraction at the Willis Tower. Make your way to the 103rd floor for staggering views of the Chicago skyline and three neighboring states. Step onto the glass balcony Ledge for added thrills. Interactive displays and historical timelines tell the story of the Willis Tower. The Skydeck is open daily. Visit www.theskydeck.com.

18. When you’re feeling blue, stop by one of the longstanding favorite haunts for blues music: Blue Chicago, Buddy Guy’s Legends, House of Blues or Kingston Mines.

19. Get jazzed! Chicago is home to some fabulous Chicago jazz venues like Andy’s Jazz Club, The Back Room and Joe’s Be Bop Café & Jazz Emporium.

20. In the summer, soak up the sun while you lie on the beach, inline skate or play sand volleyball at the Oak Street Beach, a popular spot to see and be seen.

21. Where can you find a WWII German submarine, a baby chick hatchery and the Apollo 8 Spacecraft? At the Museum of Science and Industry, the oldest museum of its kind with more than 800 exhibits and 2,000 interactive units.

22. Stroll through Grant Park, Chicago’s most prominent and beloved park, where you can enjoy an outdoor concert or throw a penny into Buckingham Fountain.

23. Imagine what the world was like when dinosaurs roamed the earth when you visit the Field Museum of Natural History, home to the largest, most complete Tyrannosaurus Rex.

24. Check out a concert happening — a visually stunning and musically powerful performance by the Blue Man Group at the Briar Street Theatre.

25. Chicago is home to a vital, vast and varied Theatre District where you can enjoy everything from traveling Broadway hits to experimental theatre to world premieres from up and coming theater companies.

26. Test your luck at one of the local casinos — Rivers Casino offers the newest and best casino gaming in Illinois, featuring over 1000 slot machines and 50 table games just minutes from downtown Chicago in Des Plaines — and other  gaming establishments like the Horseshoe Casino.

27. Walk around and admire one of Frank Lloyd Wright’s architectural masterpieces, the Robie House, a premier example of his Prairie School style.

28. Chicago pizza is a complete dining experience. That’s why a visit to the legendary Pizzeria Uno is a must for Chicagodeep-dish lovers.  Our favorite for deep-dish Chicago pizza is fresh ingredient king Edwardo’s Pizza.

29. History buffs and architecture enthusiasts will love the Tribune Tower. The facade is constructed of a collection of stones from other famous edifices, like the Parthenon, St. Peter’s Basilica, Notre Dame, the White House and the Berlin Wall.

30. Girls of all ages will love American Girl Place, a special boutique shop with the complete line of American Girl dolls.

31. Embark on a culinary adventure to Chicago’s finest restaurants on a Chicago Dine-Around. Guests are chauffeured around the city in a stylish coach bus to enjoy Hors D’oeuvres served at the first restaurant, the Main Course at a second restaurant and Dessert at a third restaurant.

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