The Top 7 Must-See Spots in Chicago During the Fall

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September 20, 2017

Fall is a beautiful time in our fair city of Chicago and there are plenty of fun things to do before the snow begins to fall.

From great restaurants with a view to costume contests and trick or treating for the kids to breweries for the adults, there is so much to do and see during a Chicagoan autumn. Here are the top 7 must-see spots in Chicago during the fall.

1. Cindy’s

This rooftop restaurant and bar at the Chicago Athletic Association offers some of the best views of the city and a great view of Millennium Park’s fall colors.

Enjoy these iconic views of changing leaves, cityscapes, and Lake Michigan as you enjoy Cindy’s fresh cuisine and cocktails.

2. Morton Arboretum

Just a short drive outside of the city, the Morton Arboretum sits on 175 acres of trails, gardens, wetlands, and other natural areas.

Go for a beautiful autumn hike through the Arboretum or check out some upcoming events for you and your family to enjoy.

3. Halloween at Navy Pier

The Navy Pier also has plenty to offer for Halloween, including free outdoor movies and fireworks for the whole family, concerts, costume contests, cruises, and even a ball! With fun for both the kids and adults, you can’t go wrong at Navy Pier this fall.

4. Boo at the Zoo

From October 21 – 22 and 28 – 29, take the kids and head to Brookfield Zoo for Boo at the Zoo and enjoy games and activities, a hayride, and a costume parade.

There are also plenty of family and educational activities at the Hamill Family Play Zoo.

5. Hot Chocolate 15k/5k

Who said chocolate and running don’t mix?!

On October 29th at Grant Park, the MB Financial Hot Chocolate run is back and turning 10! Get more information and sign up here.

6. Bacon and Beer Classic

Sample 50+ craft beers from regional breweries and try 25+original bacon dishes and unlimited bacon strips at the Daley Center Plaza on September 30, 2017.

Tickets are on sale now, so don’t wait to get yours!

7. Visit a Pumpkin Patch

What is autumn without the iconic pumpkin? Rent a trolley or coach bus and head over to Bengston’s Pumpkin Farm for a full day of fun!

Hours and pricing from September 15 – October 30 vary at the farm, so check the calendar to plan your day.


Enjoy all Chicago has to offer during your next trip this autumn. And don’t forget to book your tour of the city on a spectacular hop on hop off tour!