Travel Magazine

8 Things To Do in Chicago This October

By Urbanmatter Chicago @UMatterChicago

If you thought September was awesome, just wait until you see what October has in store.

From marathons to comedy shows and everything in-between, next month is absolutely jam-packed with some of the city’s most anticipated events. Not sure what to do first? Don’t worry, we’ve got you covered.

Here are eight of the best things to check out in Chicago this October.

Chicago Ideas Week

To Do Chicago - Ideas Week

Photo Credit: Chicago Ideas Facebook

October 16-22 @ various locations

Get your life together this October at Chicago Ideas Week. The seven-day festival brings together thought leaders and innovators from around the world to discuss everything from the hottest new tech to leadership principals. This year, the event features former NFL linebacker Otis Wilson, Fashion Designer Zac Posen, Founder & CEO of Whole Foods John Mackey and more. Most individual events costs an economical $15, buy your tickets here.

Vintage Garage Flea Market

To Do Chicago - Vintage Garage

Photo Credit: Vintage Garage Facebook

 October 15 @ Vintage Garage

The Vintage Garage closes out their 2017 season with a bang on October 15th. An antique fair held in an actual parking garage in downtown Chicago, this event showcases vinyl records, extra-creepy Halloween decorations and more.

Open House Chicago

To Do Chicago - Open House

Photo Credit: Chicago Architecture Foundation Instagram

October 14-15 @ various locations

The Chicago Architecture Foundation’s Open House in back again. Showcasing over 200 of Chicago’s coolest buildings, the Open House allows visitors to explore some of the city’s best hidden gems. Better yet, its completely, 100 percent free.

Hot Chocolate 15K 

To Do Chicago - Hot Chocolate 15k

Photo Credit: Hot Chocolate 15k

 October 29 @ Grant Park

Feelin a little sporty this month? Stop by the Hot Chocolate 15K for one of the best races of the year. After a thrilling (re: exhausting) run through the city you will be rewarded with a piping hot cup (re: bowl) of Chicago’s finest hot chocolate. For those a bit less ambitious, the event also offers a 5k route. Buy tickets here.

Trevor Noah @ The Chicago Theater

To Do Chicago October

Photo Credit: Trevor Noah Instagram

 October 20, 21 & 28

Buy your tickets now, comedian Trevor Noah pops into the city for just a few nights this October. As the host of Comedy Central’s The Daily Show you can expect his material to be both topical and hilarious. Be sure to swing by for a much needed a laugh.

Adler Afraid of the Dark?

To Do Chicago October

Photo Credit: Adler Planetarium Facebook

October 19 @ Adler Planetarium 

Adler Planetarium’s monthly event, “Adler After Dark,” takes a turn for the spooky this month. The 21+ only event is themed after the beloved 90’s TV show Are You Afraid of the Dark? and features the creepier sides of the universe. If you attend, be prepared for an intense Thriller dance off and some ~ghostly~ science experiments. Tickets go on sale September 22.

Bank of America Chicago Marathon

To Do Chicago October

Photo Credit: Chicago Marathon Instagram

 October 8 @ Grant Park

Cheer on the city’s fastest runners at the Bank of America Chicago Marathon. The route follows 26.2 miles of the city’s most beautiful scenery and welcomes athletes and leisure runners alike!

Bloody Mary Fest

To Do Chicago October

Photo Credit: Bloody Mary Chi Instagram

October 1 @ Theater on the Lake

Is there anything better than sipping a Bloody Mary on Sunday morning? Drop by Theater on the Lake on October 1st to try out Chicago’s tastiest Bloody Marys, craft beers, brunch bites and more. The event also features a Bloody Mary competition, so place your bets now! Buy tickets here.


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