October 24th – 27th: Fun Things to Do in Chicago this Weekend

The last weekend in October is full of fun, free, and family focused events. Check out the full list of fun things to do in Chicago this weekend.


Maker’s Market

Saturday | October 26th | 11:00 a.m. – 6:00 p.m.

Hyde Park| 1506 E 53rd St. | Free

Image | Slvvrrm

Connect with local brands this Saturday in Hyde Park. Every 4th Saturday, the Slvrrm hosts a makers market featuring local Chicagoland vendors who showcase and sell their goods at the well known retailer. Stop by and peruse handcrafted, artisan goods this weekend in Chicago.

Randolph Street Market

Saturday and Sunday | October 25th – 26th| 10:00 a.m. – 5:00 p.m.

Plumbers Hall | 1341 W Washington Blvd. | $10 – $200

Image | Randolph Street Market

Find fashion picks and treats at Randolph Street Market this weekend in Chicago. The local antique and vintage market features 125 vendors selling art, decor, ephemera, vintage fashion for men/women, fancy foods, global goods and more. Enjoy a fun day of shopping and entertainment this weekend in the West Loop.

Food + Drink: 

Oxtail And Grits

Saturday | October 26th | 11:00 a.m. – 3:00 p.m.

Mr. Brown’s Lounge | 2301 West Chicago Ave. | Free

Image | Mr. Brown’s Lounge

Brunch on a Caribbean inspired feast this weekend in Chicago. Oxtail and Grits features bottomless mimosas, caribbean inspired dishes, live music, and more at Mr. Brown’s Lounge in West Town. For more details and tickets to the event, visit the website here.

James Beard Foundation’s Taste America Gala Dinner

Friday | October 25th | 6:00 p.m.

Zhou B Art Center | 1029 W 35th St. | $400 – $3500

Image | James Beard Foundation

Experience a glittering gala style dinner this Friday at Zhou B Art Center. James Beard Foundation’s Taste America® presented by Capital One® hosts an evening of lively conversation and tasty bites by Chicago’s most well known chefs. Enjoy thoughtful programming, a silent auction, and more at this unique food and wine event. For tickets and more details, visit the website here.


3rd Annual Cocktails For the Cure

Friday | October 25th | 5:30 p.m. – 7:30 p.m.

Loft on Lake | 1366 W Lake St. | $25 – $75

Cocktails for a Cure_TGIN_The Haute Seeker_ Chicago Events
Image | TGIN

Wrap of Breast Cancer Awareness Month with the 3rd Annual Cocktails for Cure. Join the CEO of Thank God It’s Natural, Chris-Tia Donaldson, this Friday as she hosts a fundraiser in connection with The tgin Foundation to raise money for uninsured women undergoing cancer treatment and for our Waiting Room Renovation Project. Sip complimentary cocktails, dance, as you support uninsured women currently battling breast cancer. For tickets to this fundraiser, visit the event page here.

Arts + Culture:

Drumming For Resistance

Saturday | October 26th | 5:00 p.m. – 8:00 p.m.

Chase Park | 4701 N Ashland Ave. | $10

Image | Inherit Chicago

Join the American Indian Center, HANA Center and the Japanese Service Committee for a cultural dinner and drum performance this Saturday in Chicago. Hosted by Inherit Chicago, the evening kicks off with food from the American Indian, Korean and Japanese communities and a short presentation about the importance of drums within the respective cultural communities. After dinner, all three groups will showcase their own cultural drum performance, ending with a collaborative drum piece that combines all three drum styles with audience participation. For tickets to the event, visit the website here.

Pier Pumpkin Lights

Friday – Saturday | October 25th – November 1st | Time Varies

Navy Pier | 600 E Grand St. | Free

Image | Navy Pier

Enjoy a spooky and festive weekend in Chicago. Navy Pier is home to a free pumpkin-pop up experience. Explore a variety of pumpkin pop-up installations throughout the Pier and enjoy fabulous fall deals at the first-ever Pier Pumpkin Lights, a month-long seasonal celebration. From jack o’lantern towers to light displays, Chicago’s iconic lakefront destination will be decked out for fall.

Find the best things to do this October by checking out this month’s events guide. Need more ideas on this go do? Check out 32 of the best fall events happening in Chicago.

One Comment

Share your thoughts! We would love to hear from you.

This site uses Akismet to reduce spam. Learn how your comment data is processed.