7 Cozy Things to Do in Chicago This Fall

During the fall season in Chicago, the leaves change to vibrant colors, the breeze is perfectly crisp, and it’s still warm enough to enjoy your time outdoors. Whether you’re traveling with friends or family, there are several exciting, fall-related activities to do during this season in the city. Here are some of the coziest things to do during the fall season this year in Chicago.

Sample the best pies in Chicago

Nothing says fall like pie! Pie is a staple fall food item, especially since Thanksgiving is near. Chicago is filled with delicious pie shops, you just need to know where to look. Some of Chicago’s famous pie shops include First Slice, which has a famous apple pie—Food & Wine hailed First Slice’s apple pie as one of the best in the country. Or, you could visit Sweet Mandy B’s, a Lincoln Park shop that has whole nine-inch pies, with flavors such as banana cream, apple cherry, and lemon meringue. Check out some of Chicago’s best pie shops on Eater Chicago.

View Monet’s masterpieces

Cozy up at the Art Institute of Chicago while viewing Monet’s artwork. The exhibit opened September 5 and is the largest Monet collection in the world outside of Paris. Make sure to buy your ticket in advance.

See fall foliage at a park

Red, orange, and yellow hues—experience all of the classic fall colors at one of Chicago’s parks. At Millennium Park, you’ll be able to see the famous Cloudgate sculpture, otherwise known as the Bean, with a perfect frame of fall colors around it. Or, visit one of Chicago’s other famous parks, like Lincoln Park or Grant Park. 

Celebrate Oktoberfest

Even though many large Oktoberfest activities have been canceled or postponed this year, you can still celebrate on your own. Visit one of Chicago’s beer gardens, located throughout the city. The Northman Beer and Cider Garden is located right on the Chicago Riverwalk, if you want to experience beautiful views while sipping a drink. Or, head over to Piece Brewery and Pizzeria, the most award-winning brewpub in Chicago. Piece brews have won an impressive total of 28 medals at the World Beer Cup and the Great American Beer Festival. 

Visit the world’s largest Starbucks

Impress your friends with a photo at the world’s largest Starbucks that just opened last year on Michigan Avenue. Order your favorite coffee, and then sit back and relax in the glassy 43,000-square-foot space. You’ll definitely stay warm while sipping on a steaming drink. This Starbucks also has interactive tours and special drinks inspired by Chicago. Oh, and don’t forget, you can order Italian food like pizza if you’re hungry. Take a break from shopping on Michigan Avenue to warm up and grab a cup of steaming joe.

Go apple picking at an orchard

There’s nothing better than biting into a crispy, juicy apple, especially one that you’ve picked yourself. There are many apple orchards located near Chicago, which makes for a perfect day trip. Head out to Woodstock, where you’ll find various apple orchards, like Homestead Orchard, All Seasons Orchard, and Lang’s Orchard. Check their websites before heading out to see what time and days they are open for picking.

Experience Jack’s Pumpkin Pop-Up

Every year, Jack’s Pumpkin Pop-Up brings fun and games to Chicago. Experience Chicago’s largest corn maze, carnival games, ax throwing, food and drinks, and three full-service bars. Visit their website to see the hours and days that they are open.

Planning your visit

Whether you choose to visit Chicago this fall or in the future, you’ll have a unique and exciting experience. After you’ve selected your travel dates, you’ll need to decide where you’ll stay on your trip. Consider booking a hotel located in the heart of the city, close to many of these activities. Next up, pack your bags with essentials like comfortable walking shoes and a face covering to keep you safe and healthy. Now you’re ready for your upcoming trip to Chicago filled with breathtaking adventures and spectacular sights. 

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