The crisp autumn air, vibrant foliage, and a city buzzing with excitement—Chicago transforms into a magical wonderland in October, with vibrant colors, exciting events, and a whole lot of fun waiting around every corner. Let’s dive into the best things to do in Chicago this fall or spend your time celebrating Halloween in this wonderful city. As a local, my guidance will help you plan the perfect October getaway.

Chicago boasts stunning parks and gardens that transform into vibrant canvases during fall. Take a stroll through Millennium Park, Lincoln Park, or Garfield Park. These iconic green spaces showcase fiery hues of red, orange, and yellow, providing the perfect backdrop for capturing those quintessential autumn photos.

Pro Tip: Enhance your park exploration with a “Fall Foliage in Chicago” walking tour. These tours offer fascinating insights into the city’s history and hidden green havens not found on tourist maps.

Explore more: Read the full 15-page Chicago Travel Guide to travel to Chicago easily. 

Immerse yourself in the vibrant energy of a fall festival! The IPH’s Fall Fest on the Riverwalk is a must-do. Enjoy thrilling hayrides on the scenic Chicago River, tap your feet to live music, and pick out the perfect pumpkin for carving at the on-site pumpkin patch. From delicious fall treats like warm apple cider donuts to classic carnival games, this festival offers something for everyone. Don’t miss out on the discount code TWTR for the chance to create lasting memories with your loved ones.

Want more fall festival options? Check out a comprehensive list of all the vibrant fall festivals happening in the city.

Chicago takes Halloween very seriously. The city transforms into a thrilling playground for all ages. Get your spooky at haunted houses like the infamous “Terror Dome,” or join a costume parade and contest. For family-friendly fun, head to trick-or-treating events at zoos or museums.  

Explore more: Pick up your favorite Halloween event or tour.

Chicago’s museums offer an enriching glimpse into history, art, and science. Visit world-renowned institutions like the Art Institute of Chicago, the Field Museum, or the Museum of Science and Industry. These incredible museums house captivating exhibits that will spark your curiosity and leave you wanting more.

Pro Tip: Purchase a Chicago CityPASS for discounted entry to top attractions, including the Field Museum, making your trip more budget-friendly.

Chicago is renowned for its stunning architecture. Take a 45-minute Architectural Cruise to admire iconic buildings like the Willis Tower and the Tribune Tower from a unique perspective. Learn fascinating stories about the city’s architectural history and appreciate the diverse styles shaping Chicago’s skyline.

Hop on a fall boat cruise for a unique and relaxing experience. Choose from brunch cruises, dinner cruises, or scenic sightseeing cruises. Enjoy stunning cityscape views while indulging in delicious food on these luxurious boats.

No trip to Chicago is complete without a comfortable and stylish place to stay. To help you find the perfect hotel for your needs and budget, check out my hotel list here. This list includes everything from luxurious five-star hotels to cozy boutique options.

Explore my detailed reviews to choose your favorite accommodation.

Fall in Chicago is synonymous with delicious food! Explore the city’s vibrant culinary scene at a fall-themed festival. 

• Chicago Gourmet includes a celebratory brunch, a burger competition, and an elevated tasting experience.
• St. Al’s Oktoberfest brings a lot of German cuisine, heritage, and beer to Lakeview.
• Lincoln Square Apple Fest celebrates the fall harvest with apple pie, apple cider, and other autumnal treats.
• Chicago Beer Festival features seasonal brews from more than 65 local breweries inside the iconic Field Museum.
• Lincoln Park Wine Festival lets guests sip wines while strolling an open-air market of sommeliers, food tastings, and live music.
• Cider and Ale Festival celebrates seasonal sips at the scenic Morton Arboretum just outside Chicago.
• Festival of Wood and Barrel-Aged Beers offers tastes of the rarest wood and barrel-aged beers at this prestigious competition.

Ready to Fall in Love with Chicago? Pack your bags, book your flights, and get ready for an unforgettable fall adventure.