14 Cool (and Cheap) Things to Do on a Weekday in Chicago

Last summer I shared fun things to do on a weeknight in Chicago. I am back again with a list of things to do for every cool and cheap things to do every day. I love doing things on a weekday. It helps to break up the week and gets you that much closer to the weekend. Whether you are exploring the city solo or looking for fun things to do with a large group of people, these weekly events are perfect for just that. Check out the guide of 14 cool (and cheap) things to do during the week in Chicago.


Learn Something New

Drop-In Ceramics/Wheel

Tuesdays | 6:30 p.m. – 8:00 p.m.

Art Reach Chicago | 2651 W Lake St. | $35

Two men sitting at a ceramic wheel talking. image featured on The Haute Seeker list of cool and cheap things to do on a weekday in chicago
Image | Art Reach

Join the ArtReach program every Tuesday for a wheel throwing basics. Get centered with this meditative art form. Ticket includes instructions, 3lbs of clay, glaze, and firing of your creation. For more details, visit the event page here.

Chi Hack Night

Tuesdays | 6:00 p.m. – 9:30 p.m.

Braintree office | 222 W. Merchandise Mart Plaza | Free

Chi Hack Nigh flyer.Image featured on The Haute Seeker list of cool and cheap things to do on a weekday in chicago
Image | Chi Hack Night

The Chi Hack Night is a free, weekly event in Chicago to build, share and learn about civic tech and tools to create, support, or serve the public good. Hear from exciting speakers, learn from each other and work on civic projects. Not a techie, you are still welcome to attend. To register and learn more about Chi Hack Night, visit the event page.

Tour of Soldier Field

Mondays & Fridays | 11:30 a.m. – 12:30 p.m.

Soldier Field| 1410 S Museum Campus Dr. | Free

Outside of Soldier Field Stadium. Image featured on The Haute Seeker list of cool and cheap things to do on a weekday in chicago
Image | Soldier Field

Experience both the historical and modern-day journey of Soldier Field for free every Monday and Friday in Chicago. The tour of the stadium, dedicated to the men and women of the armed services and home of the Chicago Bears includes the South Courtyard, Doughboy Statue, Field, Visitor’s Locker Room, Skyline Suite, and Colonnades. Check out the magic of one of the second-oldest stadiums and a venue, well known for hosting world-class and exclusive events. For more details on the Soldier Field Stadium tour, visit the website here.


Salsa With Sebastian

Wednesdays | 7:00 p.m. – 8:00 p.m.

The Woodlawn | 1200 East 79th St. | $12

Black man and black woman in dancewear. Image featured on The Haute Seeker list of cool and cheap things to do on a weekday in chicago
Image | The Woodlawn

Spend a Wednesday evening learning how to salsa dance on the South Side in Chicago. Salsa dance with an international competitor and instructor Salsa Sebastian. Participants will learn the basics of how to lead and follow and be introduced to the latest salsa moves. Don’t worry about having two left feet or no partner, at the end of this session you will be dancing with the stars. To register, visit the website here.

Get Great Food + Drink Specials

Taco Tuesday

Tuesdays | 4:00 p.m. – 11:00 p.m.

High Noon Saloon | 1560 N Milwaukee Ave. | Free

Two Dollar Tacos Image featured on The Haute Seeker list of cool and cheap things to do on a weekday in chicago
Image | High Noon Saloon

What is better than a taco on a Tuesday night? How about tacos every Tuesday Night. Taco Tuesday is at High Noon Saloon offers cheap tacos for $2 tacos from 4 p.m. to 11 p.m. Along with drink specials such as $3 Tecate and $3 Sauza Tequila shots. For more information, check out the event page here.

Tropics Tuesday

Tuesdays | 7:00 p.m. – 12:00 a.m.

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

Flyer of event for Mr. Browns Lounge image featured on The Haute Seeker list of cool and cheap things to do on a weekday in chicago
Image | Mr. Browns Lounge

Live music, rum punch, and Red Stripe beer abound every Tuesday night at Mr. Brown’s Lounge in West Town. The weekly event features guest DJ’s, dinner and drink specials—and most importantly no cover. Listen to Reggae, Afro Beats, SOCA and Latin music in this after work hangout spot.

Wine Down Mondays Half Price Bottles of Wine

Mondays | 5:00 p.m. – 11:59 p.m.

The Madison Bar & Kitchen | 1027 W Madison St. | Free

Wine bottle and two classes featured featured on The Haute Seeker list of cool and cheap things to do on a weekday in chicago
Image | The Madison Bar and Kitchen

Wine down at The Madison Bar and Kitchen in the West Loop with the weekly Monday night special. Each Monday, the restaurant will offer half-price bottles of wine along with other dinner delights and specialty drinks. For more details, visit the website.

All You Can Eat Pig Roast Every Thursday

Thursdays | 6:00 p.m. – 9:00 p.m.

90 Miles Cuban Cafe | 2540 W Armitage Ave. | $18

Man receving meat from a buffet at 90 Miles Cuban Cafe. Image featured on The Haute Seeker list of cool and cheap things to do on a weekday in chicago
Image | 90 Miles Cuban Cafe

Come hungry and leave happy every Thursday at 90 Miles Cuban Cafe. The traditional Cuban restaurant hosts a weekly all you can eat pig roast. The Logan Square location will serve up unlimited helpings of pork, Arroz Blanco (white rice), Frijoles Negro( black beans), and other traditional Cuban sides dishes. Be sure to reserve your spot by visiting the website.

Go Solo or Bring the Crew

Trap & Soul with Vic Lloyd & Selah Say

Wednesdays | 8:00 p.m.

Emporium Fulton Market | 839 W. Fulton Market | Free

Trap Soul Exp flyer image featured on The Haute Seeker list of cool and cheap things to do on a weekday in chicago
Image| Emporium Fulton Market

Every other Wednesday, join Vic Lloyd and Selah Say for a night of Trap n Soul music. Themes are curated differently for each of the free events. Save your spot and receive free game tokens here.

Taste Maker Tuesdays

Tuesdays | 5:00 p.m. – 11:59 p.m.

The Delta | 1745 W North Ave. | Free

flyer of Taste Maker Tuesday at The Delta Chicago Restaurant  image featured on The Haute Seeker list of cool and cheap things to do on a weekday in chicago
Image | The Delta Chicago

Make your way to Wicker Park for a celebration of good music, good people, and good vibes. Every Tuesday The Delta showcases some of the best DJs in Chicago alongside some of the city’s tastemakers. Check out the weekly lineup of DJs by visiting the event page.

Game Night Social

Wednesdays | 7:00 p.m.

Corner 52 | 1438 E 52nd St. | Free

One black man and one white woman smiling and playing a game image featured on The Haute Seeker list of cool and cheap things to do on a weekday in chicago
Image | Corner 52

Need options for things to do on a Wednesday night in Chicago? How about a happy hour and a free game night all in one place! Game Night Social at Corner 52 is a fun way to spend a Wednesday night in the city. Drinks, games, and good company all in one place, plus its BYOB. Grab your crew for this free weeknight event. For more information on this “hump day” weeknight event, visit the Facebook page.

Free Admission to Peggy Notebaert Nature Museum

Thursdays | 9:00 a.m. – 5:00 p.m.

Peggy Notebaert Nature Museum | Free

Butterfly on a flower mage featured on The Haute Seeker list of cool and cheap things to do on a weekday in chicago
Image | Peggy Notebaert Nature Museum

Every Thursday, Illinois residents can enjoy free admission to the Peggy Notebaert Nature Museum. Explore the entire museum – no special exhibit admission required. Plus, enjoy daily programming, including Story Time, Critter Connections, Animal Feedings, and the First Flight Butterfly Release at no additional cost. For more details on admission to this popular Chicago Museum, visit the website here.

Karaoke Mondays

Mondays | 10:00 p.m. – 1:30 a.m.

Holiday Club | 4000 N Sheridan Rd.| Free

Karaoke Mondays at the Holiday Club featured on The Haute Seeker list of cool and cheap things to do on a weekday in chicago
Image | Holiday Club

Have a case of the Mondays? A night of karaoke might be just the cure you need. Sing your favorite tunes at the Holiday Club in Uptown. Drink specials available all night. Full details as well as many more weekday events at the Holiday Club available here.

SoFar Sounds Chicago

Monday – Saturdays | 7:30 p.m.

Location Varies | $15 – $20

Artists performing at SoFar Sounds Chicago image featured on The Haute Seeker list of cool and cheap things to do on a weekday in chicago
Image | Sofar Sounds

Break up your weekday routine with cool live music acts in secret locations around Chicago. Sofar Sounds, short for Songs For a Room, reimagines the live event experience through curated, secret performances in more than 400 cities around the world. Sofar brings guests and artists together in unique locations and transforms everyday spaces into captivating music venues. I have attended a few across the city and find each and everyone super fascinating. Acts take place almost every night of the week, be sure to check out the full schedule of upcoming shows by visiting SofarSounds.com.


What is your favorite way to spend a weekday? Be sure to share it in the comments below!


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