Curator’s statement
Chicago has a special place in my heart, and I truly love it in every season. It is especially beautiful in the fall — the foliage is incredibly beautiful. Whether you stroll through a local park to enjoy the scenery, attend a fall festival or make s'mores at a trendy restaurant, there is something for everyone to enjoy the Windy City in favorable conditions!
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Things to do in Chicago
Sightseeing:
Lincoln Park: Take a stroll down the Nature Boardwalk, visit the Conservatory or the North Pond area to see beautiful fall foliage.
Humboldt Park: Perfect place for a picnic, as the tree colors reflect in the water
Jackson Park: Japanese strolling garden that is vibrant in the fall
Chicago Botanic Garden: Breathtaking views of fall foliage as you stroll through the garden
Millenium Park: Cloudgate, “The Bean,” has been under construction but is now available to visit! A Chicago must!
Fall fun
Jack’s Pumpkin Pop-Up: Chicago’s largest fall festival with more pumpkins than you can imagine
Rooftop movie night: Watch a movie at the Rooftop Cinema Club in Fulton Market with a panoramic view of the city! They also have free wine on Wednesdays!
Fall boat cruise: Cruise the river in style as you learn about Chicago’s history and architecture with stunning views.
Chicago ghost tours: Walk through the Windy City while hearing some of the most gruesome and creepy Chicago stories
Lincoln Square Apple Fest: Join the fun October 5-6, 2024, and participate in a long-standing tradition in Lincoln Square. Apple Fest brings the community together while celebrating the beginning of autumn, so you will feel just like a local!
Places to eat & drink in Chicago
Off-the-beaten-path restaurants (eat like a local!):
Replay Lincoln Park: Super fun arcade bar in Lincoln Park. Check out their Stranger Things pop-up this October for all the fall vibes!
The Publican: This restaurant features a hip setting and communal tables, serving up a seafood and pork-focused menu. Also check out their global brews to change it up from your norm and to get out of your comfort zone.
Himmel’s: Italian and German-focused fare with amazing wood-fired pizzas (deep dish is great, but Chicago has amazing pizza besides that!) located in Lincoln Square.
Park + Field: Multiple fire pits make this the ultimate fall cozy spot. Relax on the Adirondack chairs and make yourself a s’more!
The Dawson: Feel like you are on the set of Yellowstone with the fall-rustic vibes and beautiful outdoor space. Enjoy an eclectic menu and handcrafted cocktails.
Must-try restaurants for travelers:
Giordano's: One of the best deep-dish pizzas in the city! Make sure you go to the one on E Randolph St--it is the original location and is within walking distance of Millenium Park! The bruschetta is also a must-try.
Girl and the Goat: Beautiful open kitchen serving innovative small plates. Open for dinner only and is great for sharing because you will want to try many globally inspired menu items!
La Scarola: You will definitely need to make reservations for this special Italian restaurant. The staff is friendly, fun and charismatic. Be part of the history displayed on the walls of special celebrity guests served there!
Chicago Curry House: If you are a fan of Indian cuisine, this is one of my absolute favorite places to go in Chicago! And if you haven't tried Indian cuisine and would like to, they offer buffet-style so you can try a little of everything. Also, if you order online, you get 10% off automatically!
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Haley Harrington
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This guide is part of our ongoing series on travel to Chicago. Looking for more travel inspiration? Check out Meghan Irle's guide, Chicago: Lollapalooza Weekend.