Embrace the crisp fall days with exciting activities that’ll make your autumn glow. From checking out charming boutiques to savoring pumpkin spice treats at seasonal festivals, there is so much to see and enjoy. Venture into fall foliage trails and local landmarks to infuse a dash of adventure into your autumn plans. Don’t miss out on these activities scheduled for this weekend to fully savor the changing leaves!
Unlock Doors at Open House Chicago
Open House Chicago, the annual architectural event presented by the Chicago Architecture Center, invites you to explore the Windy City like never before. This weekend showcases over 350 architectural treasures, offering behind-the-scenes access to iconic skyscrapers, historic mansions, and cutting-edge designs. Whether you’re a design enthusiast or simply curious about the city’s architectural wonders, Open House Chicago is a unique opportunity to unlock the doors to Chicago’s architectural past, present, and future
Date: October 14-15
Time: 10AM-5PM
Cost: Free
Location: Various Locations throughout Chicago
More info: openhousechicago.org
Cheers to Wine Rival
Wine Rival brings together wine connoisseurs and enthusiasts for an evening of friendly competition and tasteful indulgence. Held against the backdrop of Chicago’s stunning skyline, this unique gathering invites participants to blind taste a selection of exceptional wines from around the world, challenging their palates and knowledge. Wine Rival promises an entertaining and educational experience that will leave you with a deeper appreciation for the art of winemaking.
Date: October 15
Time: 5-9:30PM
Cost: $75
Location: Venue West, 221 N Paulina St, West Loop
More info: winerival.com
Lights, Camera, Chicago Film Fest!
Another annual favorite is back this weekend: the 59th Chicago International Film Festival. With movies running all day and into the night, you’re guaranteed to catch a flick that will educate, inspire, or entertain you. Check out the Oscar-contender Nyad or Mads Mikkelsen’s new movie The Promised Land
Date: runs through October 22
Time: varies, based on movie
Cost: $20+
Location: varies, across the Chicagoland area
More info: chicagofilmfestival.com
Fall’s Finest at Jack’s Pumpkin
Located in the heart of the city, this sprawling pumpkin patch and fall festival offers a cornucopia of activities, from picking the perfect pumpkin to navigating corn mazes and enjoying delicious seasonal treats. With hayrides, petting zoos, and more, Jack’s Pumpkin promises an unforgettable autumn experience for all ages.
Date: Open Daily until November 5
Time: Varies by Appointment
Cost: $31+
Location: 1265 W Le Moyne, Goose Island
More info: jackspumpkinpopup.com
Be the Skipper of a Scary Seadog Tour
Sail the “seas” of Chicago with this special haunted river cruise! You’ll learn some scary stories of old Chicago while cruising past some of the city’s most beautiful architecture. From ghosts to secret scandals, the tales on this tour will get you in the right spirit for the Halloween season.
Date: Runs on weekends until October 31
Time: 5:00PM
Cost: $50+
Location: Navy Pier, 600 E Grand, The Loop
More info: cityexperiences.com
