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Top 10 things to do in Chicago in Fall!

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Check out our Chicago Visitors Guide, with budget advice, travel guides, and information about local Chicago attractions

Chicago MarketsHere are our Top 10 things to do in Chicago this Fall. Do it while the sun is still out!

1) Go to one of the downtown Chicago Farmer’s Markets and enjoy a crisp local apple or basket of strawberries. Go early, it is open from 7am-3pm. The Daley Plaza and Willis Tower Plaza markets take place on Tuesdays and the Federal Plaza and Museum of Contemporary Art markets take place on Thursdays all the way through October.

 

Chicago Ice Cream2) Eat ice cream.  Outdoors.  Some Chicago favorites include: Margie’s a third-generation home-made candy and ice-cream parlor, located 20 minutes northeast of the Loop on 1960 N Western, near the Western O’Hare stop of the blue line. They are open daily from 9am-12am. They are famous for their white clamshell dishes filled with 3 scoops of ice cream of your choice, hot fudge, cream and nuts. Delicious! There is also Original Rainbow Cone. This history-rich ice-cream parlor’s special thing is to serve your ice cream in layers, so that it looks like a rainbow. Even though it is located 20 minutes southeast from the Loop by car on 9233 S. Western Ave, in the South Side, it is very “Chicago” and ice cream fans should not miss it. They are open from March to November 2nd, 12pm-8pm (closed on Mondays).

 

Chicago Beach3) Take off your shoes and wiggle your toes in the sand at the Ohio Street Beach adjacent to Navy Pier. The beach is a short 25 minute walk away from the Millennium Park and since it’s close to the Navy Pier you have food, shops, and bathrooms close by at the Pier. The beach is nice and clean, and great for people watching or to get a nice view of the Lake and the Chicago skyline.

 

Chicago cloud millennium park4) Walk around Millennium Park and feast your eyes on the gardens and flowers of the City in the Garden. There is tons of public art in Millennium Park, don’t miss the Cloud Gate and the brick wall fountains of course. Bring your lunch, relax and do some people watching.

 

Chicago Buckingham Fountain park

 

5) Go to Grant Park and watch the 15,000 gallons of water per minute spray 150 into the air from Buckingham Fountain.  Take a picture in front of it just like the Bundy’s did in the TV show Married With Children. It’s a short 10 minute walk away from the Millennium Park and on the hour there will be a 10 minute water show.
Chicago howells6) Enjoy a meal at a restaurant with outdoor seating!  Follow your nose and happen upon some delicious delights.  Or check out The Purple Pig located on 500 North Michigan Avenue near the Magnificent Mile. They have Mediterranean antipasti and a nice wine list.  For the beer fans among you, right opposite at 435 N. Michigan Avenue is Howls and Hood, they serve a wide choice of craft beer on tap and creative food with a twist. Sit on their patio and enjoy the view.

 

7) Attend a festival!  Eat, drink, and be merry at said festival.  Here is a calendar.

 

Chicago Water tower

 

8) Visit the Watertower, one of the few structures that survived the Chicago fire on 806 N. Michigan Ave. (near red line stop Chicago). There is FREE admission and it’s open daily from 10am-6:30pm (till 4pm on holidays). Bring a book and read on the park benches outside while snacking on the Garrett’s Popcorn you bought a few blocks away on 625 N Michigan Ave. Choose between different tastes such as caramel crisp, pumpkin spice, or cheese corn. Bring several wet naps in that case.

 

9) Get a cocktail or a dessert on a rooftop bar.  Take a lot of pictures.  Check out the Trump Tower, or The Wit. They have rooftops, so enjoy them while you can.

Chicago Free Tours Mel

 

 

10) Join Free Tours By Foot for a fabulous tour of Chicago!  (Obviously!) Check out our calendar for tours and dates.

 

Happy October!

About The Author

Stephen Pickhardt

Stephen is the CEO of Free Tours by Foot and has overseen the transformation of a local walking tour company into a global tour community and traveler’s advice platform. He has personally led thousands of group tours in the US and Europe, and is an expert in trip planning and sightseeing, with a focus on budget travelers. Stephen has been published and featured in dozens of publications including The Wall Street Journal, BBC, Yahoo, Washington.org, and more.
Updated: September 26th, 2021
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