Things to Do

What to do in Chicago this October

The end of summer marks the arrival of autumn, and with it arrives Halloween, fruit festivals, and the new NBA season.

If you are in Chicago at the start of this fall, make yourself a part of the kindling series of autumn fruit festivals, Halloween parties, parades, and NBA games. From smashing pumpkins with an axe to running from one top brewery to another for a pint of beer, Chicago’s October event line-up complements the freshness of a turning new season.

Boxed Experience

(Throughout October)

Boxed Experience

An interactive theatrical experience that brings out your inner detective! Think escape room, but better. Become one of the jury members and decide the fate of the man who is guilty of committing a horrible crime. The 90-minute immersive theatrical experience takes place in multiple rooms jam-packed with activities such as projections, interaction with live actors, and clues scattered across as you prepare to challenge the day-to-day internal social biases of the judicial system.

Each room will have a crime scene with clues and evidence to work with, so you can decide whether the accused is innocent or guilty! Located inside the Roosevelt Collection Shops, Boxed Experience is one event Sherlock Holmes fans will surely geek out on.

Ticket prices - $35 to $55 per person.

Location - 1023 S Delano Ct, Chicago, IL 60607.

Timings - Closed (Monday to Tuesday)
                5 pm to 9 pm (Wednesday to Friday)
                3 pm to 9.30 pm (Saturday)
                2 pm to 6.30 pm (Sunday)

Book your tickets here.

Jack’s Pumpkin Pop-Up

(Throughout October)

Jack's Pumpkin Pop Up

Jack’s Pumpkin Pop-Up, Source: Website

Jack’s Pumpkin Pop-Up comes to life in a two-acre corn maze in Goose Island. Find yourself surrounded by thousands of pumpkins and activities like axe throwing, carnival games, and more. The full bar will keep the drinks flowing while you take in the Halloween vibes. Turning up in the heart of Chicago every autumn, the event paints the town orange with a lot of fun affairs. Whether you are planning to host a party or just wanting to spend time with your friend group, Jack’s Pumpkin Pop-Up will not disappoint. The regular ticket provides access to the pop-up but you can buy add ons for other activities like axe throwing, availing signature pumpkin shots from the full bar, and even take a pumpkin home with you after a memorable experience. 

Ticket prices - $33 to $62 per person.

Location - 1467 N Elston Ave, Chicago, IL 60642.

Timings - provided with the type of ticket you choose. 

Book your tickets here.

Marvel: Universe of Super-Heroes

(Until October 24)

Marvel: Universe of Superheroes at Museum of Science and Industry

Marvel: Universe of Superheroes at Museum of Science and Industry, Chicago, Source: Facebook

Celebrating Marvel’s 80-year-old history, Marvel: Universe of Super-Heroes will present more than 300 artifacts from the Marvel universe such as sculptures, interactive displays, comic book pages, costumes, and more. Step in Iron Man’s lab and witness various Mark suits in the making or head to Doctor Strange’s mirror room for multi-dimensional visuals. You will find the origin stories of iconic characters like the Hulk, Spider-Man, Black Panther, and Captain Marvel, highlighting how their characters developed over time in the Marvel universe.

Ticket prices - Daytime ($18) and Nighttime ($35).

Location - 5700 S Lake Shore Dr, Chicago, IL 60637.

Timings - Closed (Monday)
                9.30 am to 4 pm (Tuesday to Sunday)

Book your tickets here.

Illinois Brewery Running Series

(Until October 24)

Run for Beer - Cruz Blanca

Herding inspiration to be active, have fun and give back to the community, Illinois Brewery Running Series is a family-friendly 5k running event that starts and ends at some of Illinois’ best breweries. Participate and receive a craft brew along with a collector’s pint glass or a seasonal swag item. Also, you will be granted access to the after-event feature with food, drinks, live music, and goodies with the ticket. The event is spanned across five different breweries on five different dates in the month. Now the question is, how far will you run for beer?

Ticket prices - $30 to $45 per person (children below 10 are allowed to run for free).

Location(s) - 4055 W Peterson Ave, Suite Rear, Chicago, IL 60646 (Alarmist Brewing).
6833 Stanley Ave, Berwyn, IL 60402 (Flapjack Brewery).
1801 W Foster Ave, Chicago, IL 60640 (Empirical Brewery).
2000 Dempster St, Evanston, IL 60202 (Temperance Beer Company).
2024 W Balmoral Ave, Chicago, IL 60625 (Spiteful Brewing).

Timings - 11 am to 2 pm (Alarmist Brewing)
                10 am to 1 am (Flapjack Brewery)
                11 am to 2 pm (Empirical Brewery)
                11 am to 2 pm (Temperance Beer Company)
                11 am to 2 pm (Spiteful Brewing)

Book your tickets for the event on October 2 (Alarmist Brewing).
Book your tickets for the event on October 3 (Flapjack Brewery).
Book your tickets for the event on October 16 (Empirical Brewery).
Book your tickets for the event on October 17 (Temperance Beer Company).
Book your tickets for the event on October 24 (Spiteful Brewing).

Lincoln Square Ravenswood Apple Fest

(Saturday, October 2 to Sunday, October 3)

Lincoln Square's annual Apple Fest

Usher in the fall with the 34th annual Lincoln Square Ravenswood Apple Fest. You will find plenty of apple commodities from ciders, apple doughnuts, apple beers, apple munchies, apple stuffed cheese, and others made from local vendors and restaurants. The fest will exhibit a farmer’s market, so make sure you bring your companions along for this free for all fest, with food and drinks available for purchase (pets are allowed).

Location - 2611 W Lawrence Ave, Chicago, IL 60625.

Timings - 9 am to 6 pm (Saturday and Sunday)

Chicago Pride Parade

(Sunday, October 3)

Chicago Pride Parade

Chicago Pride Parade in full swing, Source: Website, image by Steven Koch

After taking a hit in the pandemic, Chicago Pride Parade returns with a year’s absence from the calendar. Winding its way through the north side of the city, ending near the intersection of Diversey Parkway and Sheridan Road in Lincoln Park, the 51st annual Chicago Pride Parade is estimated to attract 1 million spectators like it usually does. Be sure you arrive early and warm up your spot. The Boystown neighborhood is where you will find the parade to be in its liveliest form.

Location - 4400 N Broadway, Chicago, IL 60640.

Timings - steps off at 12 pm

Haunted Halloween Ball

(Saturday, October 30)

Haunted Halloween Ball

The list would have been incomplete without a Halloween bash. The Haunted Halloween Ball at the Congress Plaza Hotel is one where you find people dressed up in spooky avatars. Renowned DJs from the city will throw in the beats while zombies run the show at the abandoned hotel. The 20,000 square foot ballrooms of the 122-year hotel combine elements of a VIP nightclub and a lavish lounge. There is a costume contest and a sum total of $2000 up for grabs in prizes. 

Ticket prices - start at $20 per person.

Location - 520 S Michigan Ave, Chicago, IL 60605.

Timings - 9 pm to 3 am

Book your tickets here.

Chicago Bulls v/s New York Knicks

(Sunday, October 31)

Zack Lavine (Chicago Bulls) and R J Barett (New York Knicks)

Zack Lavine (Chicago Bulls) and R J Barett (New York Knicks) battling it out, Source: Facebook

Two past eastern conference heavyweights, Chicago Bulls, and New York Knicks will clash in the opening month of the new NBA season. The Bulls are heading into a new direction in search of a playoff place after signing Lonzo Ball and Alex Caruso during free agency. During the opening month, the Bulls will play four games at United Center headlined by their clash against New York Knicks. Will the Bulls claim a playoff spot this season?

Ticket prices - $48 to $447 per person.

Location - 1901 W Madison St, Chicago, IL 60612.

Timings - starting at 7 pm

Book your tickets here.

Header image - Chicago Pride Parade, source: Website

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