A weekday in Chicago usually means hustle, commute, work, repeat. If you’re anything like me, Monday through Friday can feel like a blur, with all your energy focused on just making it to the weekend.
But what if you didn’t have to wait for weekend events? What if your Tuesday night in Chicago felt just as exciting as your Saturday?
Once upon a time, I did go up on a Tuesday, and honestly, I miss those spontaneous weeknights. That’s exactly what this guide is for: the best weekday events and things to do in Chicago, from after-work happy hours and free summer movies to pop-up markets and happenings Monday through Thursday.
Whether you’re looking for something chill, something free, or just something different, this curated list will help you break out of the weekday routine, one fun plan at a time.
Things to Do on a Weekday in Chicago
Use the quick links navigation below to explore fun weekday events and happenings in Chicago.
Haute Tip: Arrive early to avoid lines or snag a good seat, especially for popular free events.
Monday Events in Chicago
Weiner Wars at Perilla Fare Patio: Chicago’s hottest chefs go head-to-head in the ultimate hot dog showdown all summer long. Tickets at $15 at the door, which gets you a dog from each contender and chips. First come, first to chow.
Family Monday Meal at Spilt Milk Tavern: Start your week with a chef-made plate and a drink on the Spilt Milk patio. $25 gets you a rotating menu by top local chefs, supporting Culinary Care: every Monday, rain or shine, 5 p.m. until sellout.
AfroBeats on the Beach: Spend some time after work at the beach at this black-owned bar on Chicago’s Southside. Every Monday, enjoy Afrobeats at Pier 31 with a live DJ starting at 4 p.m.
Monday Night Foodball at Frank and Mary’s Tavern: The Reader’s chef pop-up series brings a different culinary star to Avondale every Monday. Think Korean comfort food one week, Polish pierogi the next. Come hungry.
Take a Tour of Soldier Field: Did you know that the stadium where the Bears play offers tours during the weekday? Go behind the scenes of one of Chicago’s iconic stadiums. This walking tour includes locker rooms and suites; a VIP version is also available that includes a 15-minute on-field experience. Checkout Tours run every Monday and Friday. VIP version includes on-field access.
Music Mondays at Beverly Arts Center: Now through mid-August, visit the Beverly Arts Center for their neighborhood music series. Each Monday, this free event welcomes local performers to the center’s courtyard. Music Mondays are free and open to everyone, with a suggested $10 donation to support the BAC. Space is limited and available on a first-come, first-served basis.
Tuesday Events in Chicago
Tuesdays on the Terrace at MCA: Free outdoor music with Chicago’s top jazz, R&B, and soul artists in the MCA sculpture garden. Bring a picnic (no booze!) or grab drinks and food on site. Gates at 4:30 p.m., music 5:30–8 p.m.
Rush Hour Concerts at St. James Cathedral: Catch world-class classical music for free after work in a short and lovely format. Ruch Hour Concerts take place every Tuesday from 5:45–6:30 p.m., June 3–Aug 19.
Tuesday Night Bingo at ERIS Brewery: Enjoy BINGO every second Tuesday of the month at this woman-owned brewery in Chicago. $5 ticket goes right back to your tab and holds your spot for BINGO.
Millennium Park Summer Film Series: Bring a blanket and snacks for free movies in downtown Chicago at the Jay Pritzker Pavilion. This event takes place every Tuesday in July through September.
Wednesday Events in Chicago
South Shore Social Club: Ol’ School Wednesdays: Chicago DJs spin classic hip hop and R&B every Wednesday from 6–9 p.m. at this lakefront patio hangout. Full bar, beach views, and major 90s vibes.
Rhythm Room Wednesdays at The Pearl Club: Live jazz, soul, Latin, and more at one of the sexiest listening lounges in town. Every Wednesday, 8:30 p.m. to midnight.
Summer Nights on the Oasis at Shore Club: $35 gets you a sangria, cheeseboard, and a front-row sunbed for the lakefront sunset. Group-friendly, date-perfect, every Wednesday.
Chicago SummerDance (Various Parks): Free dance lessons and live music citywide. Learn salsa, swing, and more from pro instructors. Wednesdays, Thursdays, and Fridays all summer long.
Bottomless Margaritas & Fireworks on the Riverwalk: For $35 every Wednesday at Island Party Hut enjoy two hours of bottomless margs, chips and salsa, and a front-row seat to the fireworks.
Boxville Marketplace: Chicago’s first container market in Bronzeville brings together food, shopping, and culture with a strong community vibe. Each Wednesday, they host special events that are perfect for a weekday.
Thursday Events in Chicago
Harper Court Summer Music Series: Experience live music during the Hyde Park outdoor concert series. This event features local legends and DJs. Grab dinner from nearby spots and make it a whole night.
Argyle Night Market: The Argyle Night Market is Chicago’s only free weekly summer street festival. Located in Uptown’s Asia on Argyle district, the market features 30+ food, retail, and cultural vendors.
DuSummer Thursdays at DuSable Museum: Dance and sway the night away every Thursday at The DuSable Black History Museum and Education Center. Music styling includes everything from smooth jazz to soulful R&B and more. There’s something for everyone at this event.
Open Mic at the Getaway: Looking for free and fun entertainment? Join the Getaway in Lincoln Square for a weekly open mic night, hosted by Scott Besaw from the Old Town School of Music, where you can either perform or simply enjoy the show starting at 7:30 p.m. after signing up at 7 p.m.
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Chicago Happy Hour
Finding the best happy hour deals in Chicago should be the easier part of your work week. After all, you deserve a discounted drink, bites, and good vibes. We all do, honestly!
Save yourself a few dollars and enjoy these happy hour deals in Chicago.
Bronzeville Winery | Bronzeville
Location: 4420 S Cottage Grove Ave
When to Go: Monday–Friday, 4–6 p.m.
What you’ll find: $10 Seasonal Sangria, curated wines by the glass, and small bites.
Why It’s Worth Your Weekday: ThisBlack-owned bar and restaurant in Bronzeville offers a chic but laid-back vibe, live DJs on select nights, and a cozy patio that’s perfect for a weekday date idea or catch-up with friends.
Amaru Restaurant | Wicker Park
Location: 41904 W North Ave
When to Go: Monday–Friday, 5–6 p.m.
What you’ll find: $10 Cocktails, $5-$10 Botanas(snacks), $8 glasses of wine, and $9 beers.
Why It’s Worth Your Weekday:
Spice up the weekday with Pan-Latin cocktails and bites at this Wicker Park neighborhood restaurant with happy hour deals that let you sample their popular dinner menu.
Sunda | River North
Location: 110 W Illinois St
When to Go: Monday–Friday, 4–6 p.m.
What you’ll find: Bites like handrolls and Seoul Wings and cocktails for $10 and under.
Why It’s Worth Your Weekday:
Sunda in River North is a classic hot spot known for its Asian-inspired cuisine and posh atmosphere, and it boasts one of the best happy hours in River North. The happy hour is offered at a reasonable time, which gives you plenty of time to leisurely sample the menu plus a few drinks.
Where to Find Events Every Day of the Week in Chicago
- Navy Pier – From live music and trivia to outdoor rides and pop-up markets, Navy Pier stays active all week long with free, family-friendly fun.
- Gallagher Way – This Wrigleyville plaza near the Cubs stadium hosts weekday events like movie nights, fitness classes, and live music, all perfect for an after-work hangout.
- Chicago Farmers Markets – Neighborhood markets pop up nearly every day, offering local produce, music, and laid-back after-work energy.
- Movies in the Parks – Watch free outdoor films in parks across the city almost every night. Just bring a blanket and snacks—the perfect solo or date night activity in Chicago.
- Chicago Music Venues – you can’t go wrong with experiencing live music during the weekdays. Popular venues include Thalia Hall, Schubas, Green Mill, and more. Find concerts near you on theevents calendar.
- Comedy Clubs – After a long, stressful day, nothing is better than a good laugh. Check out popular comedy spots like the Laugh Factory, Second City, or IO Theater, which are great for weekday date nights in Chicago.
- Free Chicago Museum Days – Take advantage of select weekdays when admission is free. Some museums are even free every day.
Weekday activities in Chicago are the perfect way to break up the week and spice up your daily routine.
Whether you’re flying solo or planning a group hang, this guide is your go-to for fun, affordable things to do, no matter the day. Forget waiting for the weekend, Chicago has something happening every night, and this list makes it easy to jump in.
Want even more to do? Check out our Monthly Events Guide for the best things happening in the city all weekend long.
