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20 Things You MUST Do This Fall in Chicago

20 Things You MUST Do This Fall in Chicago


Fall is so much more than pumpkin spice lattes, football and sweater weather (but let’s be honest, those are definitely highlights!) and Chicago is one of the best places to enjoy all that the not so warm but not yet polar vortex season has to offer, as the temps dip and leaves turn.

With art and culture events, concerts, outdoor activities and making the most of the final days of rooftop season, we’re here to make your fall anything but boring; check out 20 things that are not to be missed in the city this season! Fall officially runs from September 22 until December 20.


  1. Apple pie, apple cider, Dutch apple cakes, caramel apples,apple cupcakes…You’re going to need a lot of apples. Head to one of these apple orchards close to Chicago for a day of fall fun.
  2. If you haven’t gotten a proper tour of Chicago by water, the Architectural River Tour is a must and an autumn favorite as you see the change of scenery. Ride up and down the Chicago river while learning about the fascinating architectural history and heritage of the city, with a flask in hand and don’t forget the blank or coat. Not into the river tour? Chicago Architecture Foundation’s FREE two day open house Oct. 15-16, will allow you to see 200 of Chicago’s greatest spaces in 20 different neighborhoods.
  3. Concerts not to miss: Chicago native Kanye West’s highly anticipated Saint Pablo Tour will be at United Center Oct. 7. Sia will play Oct. 16, Carrie Underwood will be in Rockford Nov. 9.
  4. Feast your eyes on this: fall foliage in the city is truly magical, but there is nowhere better to soak up all of autumns bright hues than at the Chicago Botanic Garden.  Take a fall-color tree walk  and also check out the fall mums.   
  5. Crazy for carving pumpkins? Take part in this Guiness world record attempt feat to break the world record for most pumpkins carved and lit at the same time at the Great Highwood Pumpkin Festival, October 7th-9th. They’ve partnered with Make-A-Wish foundation to grant 100 wishes. Don’t forget, it’s BYOP (Bring Your Own pumpkin!)
  6. A movie lover’s must: the Chicago International Film Festival screens more than 150 works from more than 60 countries. You might even have a few celebrity sightings. Grab your popcorn and tickets, CIFF runs from October 13-27 at AMC River East 21.
  7. Culture. 2 of Chicago’s  culture fests this fall boasts heavyweight lineup. First up from October 17-23, Chicago Ideas Week returns with a lineup of 150 Speakers that ranges from a former TV dad (Bob Saget), award wining critically acclaimed actor and now author (Bryan Cranston), Academy Award-Winning Film and Television Producer Brian Grazer WME-IMG boss Ariel Emanuel, Founder and CEO of Define America Jose Antonio Vargas, ESPN’s Linda Cohn and so much more. GA ticket prices start at $15 and you can get more info here. Chicago Humanities Festival, celebrating the social life of ideas, is taking place Oct. 29-Nov. 12 and they kicked it off with a conversation with Lin Manuel Miranda, award winning creator of the Broadway hit Hamilton. Gloria Steinem, Maureen Dowd, Footwork and more are scheduled on the lineup. Sadly there are a lot of planning wayyy ahead Pollys that have snagged some of the good tickets so act fast here.
  8. Now that the rooftops are closed and you’ll be spending more time indoors why not you make it worth your while and meet some new people and non profit organizations that you can get involved with. Chicago Cares will host the fall edition of Find Your Cause on October 18.
  9. Chicago’s creative community will show off it’s spookiest stuff at the annual Halloween Gathering. This over-the-top Halloween parade featuring large-scale creations, costumed performers, music and dance will travel across the city on October 22nd. hg-2016-fb-e1471984200632
  10. There’s still time to catch some outdoor farmer’s market before they pack up shop for the season. Head south to Hyde Park’s Farmer’s Market on Thursday and stick around through the evening (grab a bite at A10 or Promontory) for First Thursdays at Hyde Park which runs until November. You can also pick out your perfect pumpkin at these notable pumpkin patches around Chicago.
  11. From September 30th- October 2nd, get in touch with your artistic side at the West Town Art Walk.
  12. Get GQed up or put on your favorite cocktail dress an attend a social-philanthropic event. Whether its hanging out with Field Museum’s young professional board members, Green City market’s veggie affair or a fashion show with the Woman’s board of Rush Medical center you find a curation of things to do here.
  13. Get cultured thanks to the special deals from Chicago Museum Week. From October 13th-23rd, 12 of the city’s top institutions will be offering special tours, shows and even free admission.
  14. Don’t call this corny! Get lost in the best corn mazes outside the city. krolls-farm
  15. Football is synonymous with fall in Chicago but since this might be their year, the Chicago Cubs are in the playoffs and are favorites to win the World Series. If baseball’s not your thing and can’t take the heartache from the Bears, check out some of the new faces on the Chicago Bulls squad and the ladies of Chicago Sky. Northwestern, though they are off to a rocky college football season start, is also another fine fall sporting action option.
  16. Celebrate Oktoberfest at one of these local spots.
  17. Satisfy your sweet tooth at the Anderson Dessert Crawl. Yum!
  18. Want to get spooked? These haunted houses are sure to do the trick.
  19. Nigerian-American artist Iké Udé exhibition Nollywood Portraits: A Radical Beauty will run Oct 20 – Dec 23 at the Museum of Contemporary Photography (600 S Michigan Avenue). Nollywood and  the world’s second largest movie industry and Udé who went back to Nigeria for the project took photographs of 64 Nollywood personalities. The museum is also hosting a kickstarter campaign to help support this major initiative.
  20. Finally, if you just can’t help it grab yourself a pumpkin spice latte at one of these local spots — but if in the mood to try some new drinking hot spots this fall, follow the heat.


See Also
Photo image of the downtown landscape of chicago featuring tall buildings and the famous chicago cloud gate aka the bean in Millennium Park

featured image credit: photograph by Sven Brogren; Chicago Botanic Garden

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