Chicago in October: Top 12 October Events, Weather, Travelling Tips and More

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With the crisp smell of pumpkins in the air, locals dressed in cosy sweaters and festive preparations, Chicago in October is a splendid destination for tourists, travellers, foodies and artisans worldwide. As the official spooky month sets in, Chicago lights up in fiery pomp while you explore the many drive-in theaters, film festivals, botanical gardens, global museums, nightlife, paths lit with Jack-o-lanterns and local programs.

Chicago in October
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Weather in Chicago in October

Chicago in October
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Chicago experiences fall season in October, the foliage taking its peak colour. As soon as the peak tourist season of summer ends, it becomes convenient to visit Chicago in October and walk through fall trees with jolly locals. Due to cool, ambient weather, you can participate in all the festivities of Chicago in October. It is a pleasant time to explore the city on foot, enjoy white-hot culinary delights and spectate events that are unique to Chicago. While some nights may drop below freezing point, the average temperatures range between 43°F and 62°F with a lot of sunshine.

Dressing Up For Chicago in October

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It definitely gets chilly during the nights in Chicago in October but it’s not time to bring out heavyweight winter clothing or boots yet. Instead, opt for woollen sweaters, shearlings and light overcoats that can be slipped on top of flannel and sweatshirts. For those planning to explore on foot, remember to carry sunscreen, comfy sandals and an umbrella or hat.

With Halloween around the corner, Chicago turns into a stylish red carpet of innovative Halloween costumes. It is ideal to grab yours for parties, haunted house tours and costume parades. H&M, Chicago Costume and Fancy Costumes stock up on the hottest Halloween trends, accessories and wigs.

12 Things to Do in Chicago in October

Chicago in October - The Neo Monolithics
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Here is a detailed list about the best things to do in Chicago in October: -

1. Watch the Chicago International Film Festival

Chicago International Film Festival
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Chicago International Film Festival is the longest running competitive film festival in North America. Showcasing international hits and the art of moviemaking for the past 57 years, the festival has become Chicago's year-round icon of culture. Being a part of this film festival offers the opportunity of audience-filmmaker interactions. The Festival hosts screenings, discussion panels, educational workshops and Q&A sessions about an expansive genre of movies, Cineyouth and theater.

This festival gains the largest number of visitors in Chicago in October on prize ceremony days, honoring actors, directors and industry members with Silver and Gold Hugo Awards. This event brings cherished movies with both in-house and drive-in options. A special screening of movies made by Illinois locals is also shown at the evening after-parties and meet-and-greet.
Location: 212 West Van Buren Street, Suite 400, Chicago, Illinois
Dates: October 12 - October 26, 2021
Timings: 2:30pm - 8pm
List of Events:
International Competition
New Directors Competition
Black Perspectives
Cines of the Americas
Reel Women

2. Taste the Flavors of Germany at St. Alphonsus Oktoberfest

St Alphonsus Oktoberfest, Chicago
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Welcome fall on the first day of October with St. Alphonsus Oktoberfest, a decades-old German tradition followed at the St. Alphonsus Lakeview church. Acclaimed at the best night out spot in Chicago, the fall fête wraps up the cultural season with all-day live Bavarian music at two stages, delivered by authentic German bands. A requisite selection of lip-smacking Bratwurst, chilled Lager beers, pretzels, freshly plucked apple and spiked ciders are sold by local vendors. Craft beer events take place on weekend nights with lively bonfires and dances. Hire an informative docent to tour the grounds and learn more about Oktoberfest’s historical significance. St. Alphonsus Oktoberfest also has a KinderFest section family-friendly activities.
Location: 1429 West Wellington Avenue, Chicago, Illinois 60657
Date: October 1, 2021
Timings: 9am - 12pm
Tickets
USD 5 before 5pm
USD 10 after 5pm
Free entry on Sunday

3. Explore History at Open House Chicago

Open House Chicago
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If you have been wondering what treasures sit within the old-world buildings, mansions and cobblestone houses of Chicago, the Architectural Open House Chicago offers the premium opportunity to explore more than 200 of the city’s heritage houses. Since these are off-limits to the public during the rest of the year, locals and visitors gather in groups to enjoy the free, docent-led access to buildings of historical and architectural importance.

You would be guided on foot along 20 neighbourhoods showcasing vintage and intricately built houses, dotted with vendors of hot and tasty American snacks, Italian deep-dish pizzas and desserts. Open House Chicago represents the diverse culture and dynamic legends of Chicago’s neighbourhoods, as well as community traditions. 
Dates: October 16 - October 17, 2021
Live Event Hosts:
Vocalo 91.1
Chicago Magazine
WBEZ 91.5 Chicago
Best Buildings to Explore:
Tribune Tower
Federal Reserve Bank of Chicago
Chicago Temple Building
Aon Center
Emil Bach House
Elks National Memorial

4. Take a Safari on Adults Night Out

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An exclusively 18+ event, Adults Night Out is your chance to leave your kids behind and take a thrilling night safari at Lincoln Park Zoo. Pristine lakes, lush canopies and natural animal habitats create a riveting backdrop for photography. You can enjoy creative animal chats, wildlife workshops and a tour of the entire park.

Lincoln Park Zoo hosts the event with focus on raising awareness of wildlife preservation, so it is common to come across educationalists for conversations. The after-hours event includes a music and craft beer festival and lots of refreshing booze at the neon-lit cash bars scattered throughout the park. The two most popular joints every year are Snowy’s Spirits and S’more Pop-Up Bar and Enchanted Forest.
Location: Lincoln Park, 2001 North Clark, Chicago, Illinois 60614
Date: October 12, 2021
Timings: 6:30pm - 10pm
Tickets: (only for adults above 18)$15 ($12 for Lincoln Park Zoo members)$20 at the door if tickets remain

5.  Join Arts In The Dark Halloween Parade

Arts in The Dark, Chicago
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Chicago takes its Halloween parades seriously, bringing a large number of people together to celebrate the day with pomp and ceremony. Arts in the Dark is a family-friendly Halloween parade in Chicago in October, held to honor diverse cultural communities. This free evening event gathers over 100,000 visitors, participants and celebrates Halloween as an “artist’s holiday”.

Major parts of the city from Washington Park to State Street are decorated with lit-up floats, blood-soaked spectacle puppets and dances by talented contingents and professionals of Arts in the Dark. Gather your fearless friends to showcase your cultural diversity, costumes and artistic skills -  be it music, or dance or painting. Though the event is free, online reservations are required.
Check-in Location: General Richard Jones Armory Parking Lot, South Cottage Grove Avenue, Chicago, Illinois 60615
Date: October 31, 2021
Reservation slots: 12pm, 1pm, 2pm
Bookings: artsinthedark.com

6. Cook with Chefs at Harvest Fest

Fulton Market, Chicago
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Foodies rejoice - Harvest Fest in Chicago in October is a massive 4-day event led by Stephanie Izard at Fulton Market. The all-outdoor event includes beverage making classes, wine tastings by the day, live cooking demonstrations and chef-led meals to relish. Harvest Fest Kick-off Dinner officially starts the festival and then culinary shows take over.

Embracing the soothing season, fall-themed eateries and tented craft beer corners are put up throughout Fulton Market. You can opt for romantic brunch, free dinner appetizers and interact with chefs at every restaurant. Notable chefs listed to go live in 2021 are Paul Kahan, Sarah Grueneberg, Rick Bayless, Brian Jupiter and more.
Location: 2872 Cedar Lane, Chicago, Illinois 
Dates: October 15 - October 18, 2021
Timings: 12pm - 6pm
List of Events:
Pumpkins and Pancakes
Moet and Chandon Bubbles Tasting Class
Solemn Oath Beer Tasting Class
Pumpkin BBQ
Duck Duck Goat and Bubbles Brunch

7. Relish National Pizza Month

Chicago Deep-dish Pizza
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Deep-dish pizza is synonymous to the word Chicago in October, symbolizing the city’s love for authentic gourmet food. National Pizza Month is celebrated every weekend in October since 1984. Thin crust Neapolitan pizzas with oil based toppings inspired by global cuisines are their signature menu and got the extra mile to accommodate special gluten free food.

Iconic heritage restaurants and eminent food chains like The Dearborn and Windy City Pizza come together to Order your favorite pizza at these food joints and post a snap on social media with #NationalPizzaMonth. To keep a memoir of your weekend spree, be it breakfast, lunch or dinner, grab a pizza-themed magazine at The Dearborn.
Dates: October 2 - October 30, 2021
Timings: 10am - 6pm
Best Deep-Dish Chicago Places:
Uno Pizzeria and Grill - Ohio Street
Lou Malnati’s Pizzeria - Lincolnwood
Giordano’s - South Side
Lincoln Park Pizzeria - North Lincoln Avenue
Chicago Pizza and Oven Grinder Co. - North Clark Street

8. Run for Bank of America Chicago Marathon

Chicago Bank of America Marathon
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Chicago always kickstarts October with this feat of athleticism where over 45,000 runners gather to compete for a marathon through downtown Chicago. The Chicago Marathon is sponsored by Bank of America in Chicago, begins at Grant Park and ends there. This spans 30 neighbourhoods boasting of mesmerizing cityscapes, historical mansions, upscale shopping districts and riversides. It is also known as the official IAAF Gold Label Races. Even if you do not participate, gather around the track corners, cheer on your favorite participants and watch thousands of talented athletes in action.
Start Location: 337 East Randolph Street, Chicago, Illinois 60601
Date: October 10, 2021
Start Time: 7:30am
Participation Fee: USD 205 (US Residents), USD 230 (non-US residents)

9. Visit Farmers Market for Apple Fest

AppleFest Chicago
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The Ravenswood Chamber of Commerce at Lincoln Square brings the biggest fall festival every year with uplifting entertainment and a fresh produce of apples. AppleFest is a 30-year-old traditional celebration with over 70,000 visitors every year. Visitors can participate in pie baking contests, run their furry friends for the AppleFest Pooch Costume Contest and Parade to win delicious treats and enjoy live music at the common central plaza. Walk along a sprawling market flanked with local vendors and small businesses selling aromatic apple pies, hot apple cider, apple pizzas, candy, milkshakes, juices and whole bushels of apples. Bring your kids along for fun apple-themed game rounds at the Kids Zone while you relax at the yoga center.
Location: 4700 Block North Lincoln Avenue, Chicago, Illinois 60625
Dates: October 3 - October 4, 2021
Timings: 9am - 6pm
Event Cost: USD 5

10. Party at WingOut Chicago

WingOut Chicago, Chicken Festival
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Brought to you by Vizzy Hard Seltzer and Green Curtain Events, Wing Series is a set of weekly outdoor block parties that attract chicken lovers in Chicago in October and November. Hosted across few of the city’s best wing vendors, WingOut Chicago has a location for a variety of flavored wings - sweet, spicy, smoked, mild, grilled, hot, specials and something for everyone. Cozy outdoor seating areas with picturesque views are featured at every wing joint. Alongside full day live music events, Wing Series is an abode for crafted cocktails and beverages. Visitors who plan to visit every event can win amazing deals on ticket packages, including guaranteed seating, unlimited wings (any flavor), 1 Vizzy Hard Seltzer, friends night out, rating card round and drink specials.
Dates: October 14 - November 18
Timings: 6pm - 8:30pm
List of Events:
Broken Barrel Bar - October 14,
November 11OG’s Chicago - October 21
Woodie’s Flat - October 28
Whiskey Business - November 18

11. Find Budding Talent Lakeshore Drive-in

Lake Shore Drive-in
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Putting gigs and art events in the hands of top industry professionals, Lakeshore Drive-in is a major music, arts and culture pop-up event for Chicagoans to enjoy live entertainment and skyline vistas. Happening along the breathtaking 15-mile long Lake Michigan shoreline with trails and outdoor parks all the way up to Hollywood Avenue, the makeshift event is focused on offering a large platform for local artisans, musicians, dancers, actors and street performers. Comedy events, concerts and movie screenings have been introduced too. Several ehtnic markets of handmade items and artist merchandise are strewn across the shady grounds for your much-needed retail therapy. An online system allows attendees to order food and beverages directly to their cars.
Location: 1362 South Linn White Drive, Chicago, Illinois 60605
Dates: October 1 - October 31
Tickets: USD 60 - USD 200
Indoor Events Location:
Adler Planetarium
Northerly Island

12. Admire Nature at Fall Color 5k Run and Walk

Fall Color 5k Run and Walk
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Fall Color 5k Run and Walk is your ticket to explore some of the most gorgeous Chicago fall foliage while unleashing the athlete in you for a socially-distanced race. Runners and walkers are spaced out in their tracks that take them down a lusciously forested car-free street in Morton Arboretum. Satisfy your inner champion while admiring the scenic, rolling race course with gigantic oaks, cedars, chaparrals and wildflowers. Once the race is finished, prizes are given out and visitors celebrate with fall-themed snacks and chilled beer at the post-race party. Each participant is offered the privilege to explore Morton Arboretum all day, making the event excellent for a family day out. The registration fee package consists of a t-shirt with Fall Color 5k logos, race bib and boxed water.
Location: 4100 Lisle, Chicago, Illinois 60532
Dates: October 3 - October 4, 2021
Race duration: 30 minutes
Timings: 7am - 1pm
Registration Fee: USD 46.44

Tips to Travel in Chicago in October

Chicago in October
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  1. While October is very quiet in terms of tourists in Chicago, certain events witness several thousands of outsiders. Hotels are quickly booked in this season. Check availability of accommodations well before the journey date on holidify.com.
  2. Take advantage of pleasant weather and explore on foot. Public transport is also convenient and affordable for getting around in Chicago.
  3. Airfare can reach a hike in Chicago in October. It is advised to book flight tickets early.
  4. Maintain social distance and wear face coverings, masks etc. at public places in Chicago.

Explore the mellow Windy City of Chicago in October and gather memories of a lifetime with fall-themed activities. Share with us your experience and queries about Chicago in October.

This post was published by Koushiki Kundu

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