Spend the weekend in Chicago shopping at local artisan markets, celebrating Fika Fest, and enjoying a popular alt-pop psych band performance. Additionally, take in a performance of TimeLine Theatre’s “Debate: Baldwin vs. Buckley,” attend a Mediterranean orchestral show, and enjoy screenings at the Architecture and Design Film Fest, among other activities.
Here are 10+ things to do in Chicago this weekend:
Chicago Restaurant Week
Chicago restaurant is back, and the deals are amazing. From Michelin-recognized establishments to local favorites, the celebration features over 470 restaurants across the city, offering special prix-fixe menus for brunch, lunch, and dinner.
📍 Location: Various restaurants across Chicago
🗓️ Dates: January 24 – February 9, 2025
Magic City Hippies — Enemies Tour
If you’re into alt-pop psych-funk party music, then we have a concert for you this weekend in Chicago. The Magic City Hippies are performing at the Metro this Friday!
📍 Location: Metro
🗓️ Dates: January 31
Chicago’s Architecture & Design Film Festival
The Chicago Architecture Center (CAC) is set to host the third annual Architecture & Design Film Festival from January 29 to February 2, 2025. This international film festival will feature 13 feature-length films focusing on architects and designers who have shaped our built environment. The festival’s diverse lineup includes films exploring sustainability in architecture, the legacy of modernist pioneers, and the intersection of design with nature. Screenings will take place at the Chicago Cultural Center and the Gene Siskel Film Center, with opportunities to engage with filmmakers through special programming.
📍 Location: Chicago Cultural Center and Gene Siskel Film Center, Chicago
🗓️ Dates: January 29 – February 2, 2025
Debate: Baldwin vs. Buckley
TimeLine Theatre presents a site-specific Chicago premiere of “Debate: Baldwin vs. Buckley” at DePaul University’s Cortelyou Commons from January 29 to March 2, 2025. This immersive production recreates the historic 1965 debate between James Baldwin and William F. Buckley Jr. on its 60th anniversary, exploring race relations and social progress. The unique theatrical experience transforms the Gothic Collegiate-style Cortelyou Commons into a replica of Cambridge Union, where the original debate took place, offering audiences a powerful glimpse into a pivotal moment in American history.
📍 Location: Cortelyou Commons, DePaul University, Chicago
🗓️ Dates: January 29 – March 2, 2025
Critical Mass Polka Ride Party
The annual Critical Mass Polka Ride Party is happening this weekend in Chicago! The Polkaholics will start playing around 8 pm and go until midnight, playing three sets of people-pleasing polka. You don’t want to miss this special mashup of all kinds of music—this event is completely free and open to the public.
📍 Location: Fuller’s Pub, 3202 W. Irving Park Road
🗓️ Dates: January 31
Lunar New Year at Maxwell Trading
To celebrate the Lunar New Year in Chicago, Maxwell Trading is hosting a special collaborative feast featuring chefs Erling Wu-Bower and Chris Jung of Maxwells Trading alongside chefs Thai Dang (HaiSous) and Gene Kato (Momotaro & Itoko). Enjoy a family-style prix-fixe menu showcasing the chefs’ favorite family traditions and recipes. Menu highlights include:
- Five Spice Braised Short Rib with Stir Fried Water Spinach
- Càri Cá, monkfish cooked in fragrant coconut broth with tía tô
- Osechi Box, a New Year sushi box
- Gỏi mực khô – dried Saigon squid, banana blossom, and Vietnamese herbs
📍Address: Maxwells Trading, 1516 West Carroll Avenue, Chicago, Illinois 60607
🗓️ Date: January 29, with seatings at 5:30 pm and 8:00 pm
Mediterranean Travels
The University Symphony Orchestra invites you to escape the winter chill with a musical voyage around the Mediterranean on February 1, 2025. This enchanting concert features colorful compositions by Elgar, Ibert, and Rimsky-Korsakov, each piece a masterful representation of Mediterranean lands and cultures. The program’s diverse repertoire includes Elgar’s “In the South,” Ibert’s “Escales,” and Rimsky-Korsakov’s “Capriccio Espagnol,” offering a vibrant musical tapestry that brings the warmth and vibrancy of the Mediterranean to Chicago’s winter.
📍 Location: Mandel Hall, University of Chicago
🗓️ Date: February 1, 2025, 8:00 PM
Bar La Rue’s Après Ski Party
Celebrate ski season at Bar La Rue this weekend in Chicago. The Après Ski Day Party promises to transport guests to a post-slope celebration with a live DJ, specialty cocktails, and an alpine atmosphere. The festive afternoon encourages attendees to don their best ski attire for an authentic mountain resort experience in the heart of Chicago. Your ticket includes entry and a welcome cocktail, making it the perfect way to kick off a winter weekend with friends.
📍 Location: Bar La Rue, Chicago
🗓️ Date: Saturday, February 1st, 2025, 2 PM – 5 PM
PINK PONY PARTY
Dance the night away at Chicago Yacht Club’s Belmont Station; they are serving Pink Pony-themed cocktails inspired by the favorite Mackinac Island bar, The Pink Pony! It’s free for members and $10 for non-members.
📍 Location: Chicago Yacht Club
🗓️ Date: Saturday, February 1st, 2025
Chicago Artisan Market
The Chicago Artisan Market returns to Ravenswood, offering a curated selection of the Midwest’s best in food, fashion, home goods, and art. This unique event celebrates the ingenuity of independent, small businesses showcasing their one-of-a-kind products. Visitors can meet and shop with artisans, learning about their creative processes and products. The market welcomes all, including children under 12, for free and well-behaved, leashed dogs, making it a perfect weekend outing for families and art enthusiasts alike.
📍 Location: Artifact Events Building, 4325 N. Ravenswood Ave, Chicago
🗓️ Dates: February 1-2, 2025, 11 am-5 pm, both days
Fika Fest
Andersonville’s beloved Fika Fest returns on February 1 & 2, 2025, celebrating the cherished Swedish tradition of taking a coffee break. One of the best things to do this weekend in Chicago, it embodies the essence of ‘fika’ – a moment for connection, conversation, and community. Experience the Swedish customs firsthand with local cafes and bakeries. It’s an ideal opportunity to slow down and savor life’s simple pleasures in true Scandinavian style.
📍 Location: Andersonville, Chicago
🗓️ Dates: February 1 & 2, 2025
Love Local: A Cute Mini Market
Stop by Amber Agave for boba and snacks, and then shop around Love Local: A Cute Mini Mart! This Sunday will feature a group of local crafters, makers, and bakers!
📍 Location: 1310 N Milwaukee Ave, Chicago, IL 60622
🗓️ Dates: February 2
Visit Marketplace 88
88 Marketplace is one of the largest Asian markets in the country, and it’s located right in Chinatown. Explore the neighborhood, and then go to the store to look at a wide variety of traditional Chinese snacks and Japanese sweets. With items ranging from Chinese herbs to kitchenware and household goods, 88 Marketplace guarantees you’ll find exactly what you need.
📍 Location: 2105 S. Jefferson Street, Chicago, Illinois 60616