Autumn in the Windy City: Unleash the Fall Fun with Chicago's Must-Do Activities!
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  • Chicago Hotel Collection

Autumn in the Windy City: Unleash the Fall Fun with Chicago's Must-Do Activities!


Unleash the fall fun with Chicago's must-do activities!

Fall is one of the most vibrant seasons in Chicago, when the city is bathed in warm colors and the air is crisp with anticipation. Whether you're a local or a visitor, you'll find a plethora of must-do activities to make your fall unforgettable. Stay at The Chicago Hotel Collection to enjoy the best of the season, and don't forget to take advantage of our exclusive guest amenities package, which can help you save on many of these wonderful Chicago activities!

Biking Along Lakefront Trail
Biking Along Lakefront Trail

Outdoor Fun

  • Apple Picking at Nearby Orchards: Embrace the harvest season by handpicking apples at one of the scenic orchards around Chicago.

  • Fall Foliage Cruise on Lake Michigan: Enjoy a relaxing cruise on Lake Michigan and witness the stunning autumn colors on display along the shoreline.

  • Biking Along Lakefront Trail: Rent a bike and explore the city's 18-mile lakefront trail, with beautiful views of Lake Michigan and colorful fall foliage.

  • Tailgating at a Chicago Bears Game: Grab some friends and your favorite grilling essentials to cheer on the Bears this football season.

Chicago Gourmet Festival
Chicago Gourmet Festival

Food & Drink Delights

  • Savor Chicago's Comfort Food: Fall is the perfect time to indulge in deep-dish pizza, hot dogs, and other Windy City favorites.

  • Explore Local Breweries: Warm up with some craft beer from one of Chicago's innovative breweries.

  • Oktoberfest Celebrations: Join the locals for German-inspired fun, food, and brews at various Oktoberfest events around the city.

  • Chicago Gourmet Festival: A food lover's paradise, with tastings from top chefs, wine, and seasonal treats in Millennium Park.

Chicago Architecture Biennial
Chicago Architecture Biennial

Cultural & Artistic Exploration

  • Chicago Architecture Biennial: Dive into the world of design and explore architectural marvels from across the globe.

  • Chicago International Film Festival: Be the first to see international and local films in various genres at this premier event.

  • Visit the Art Institute of Chicago: Admire world-class art collections, including iconic paintings and sculptures, with discounted entry using your Chicago Hotel Collection guest amenities package.

Lincoln Park Zoo Fall Fest
Lincoln Park Zoo Fall Fest

Family Activities

  • Lincoln Park Zoo Fall Fest: A family-friendly festival offering hayrides, corn mazes, pumpkin patches, and more, all inside the city's free zoo.

  • Night of 1,000 Jack-o'-Lanterns at Chicago Botanic Garden: A magical evening event where hand-carved pumpkins light up the night.

  • Haunted House Visits: Embrace the spooky season with a thrilling visit to one of Chicago's top haunted houses.

Green Mill Cocktail Lounge for Jazz
Green Mill Cocktail Lounge for Jazz

Music & Entertainment

  • Catch an Improv Show at Second City: Laugh your way through an evening with some of Chicago's up-and-coming comedy stars.

  • See a Show at Chicago Symphony Orchestra: Experience world-class orchestral performances in a stunning setting.

  • Green Mill Cocktail Lounge for Jazz: Step back in time and enjoy live jazz in this Prohibition-era club.

Stay at The Chicago Hotel Collection
Stay at The Chicago Hotel Collection

Exclusive Experiences

  • Open House Chicago: Gain rare access to some of the city's most iconic and hidden architectural gems.

  • Stay at The Chicago Hotel Collection: With multiple locations across the city, we offer convenient access to all these fall activities. Our exclusive guest amenities package offers savings and special offers to help you experience more of Chicago!

Shop Along the Magnificent Mile
Shop Along the Magnificent Mile

Shopping & Fashion

  • Thrifting in Wicker Park: Discover unique finds in vintage shops and thrift stores in the trendy Wicker Park neighborhood.

  • Shop Along the Magnificent Mile: Explore world-renowned shops and boutiques, all while enjoying the fall decorations.


There's no shortage of things to do this fall in Chicago. From outdoor fun to cultural explorations, food festivals to family events, the city offers endless opportunities to embrace the season. Remember, staying at The Chicago Hotel Collection not only puts you at the center of all these activities but also offers you our exclusive guest amenities package to help you save on some of the best experiences in the city.


So pack your bags, grab a scarf, and come fall in love with Chicago. Whether it's biting into a juicy apple you just picked or laughing at a Second City comedy show, the Windy City is ready to welcome you with open arms and the unparalleled comfort of The Chicago Hotel Collection. See you soon!

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