Explore exciting events across Chicagoland this winter… from music and community celebrations to wellness and more! With so many opportunities to enjoy the season, here are a few of our top picks to check out this weekend.
Listen to Smooth Sounds at Jazz Thaw
Downtown Oak Park turns up the heat with an afternoon of free live jazz across local bars, restaurants, and shops. Stroll the district while taking in smooth saxophone solos and energetic ensembles. Whether you’re a jazz aficionado or just looking to liven up your weekend, this event offers the perfect excuse to explore Oak Park’s bustling dining and shopping scene.
Date: March 8
Time: Sat 1PM-12AM; Sun 11AM-2PM
Cost: Free
Location: Various Locations, Oak Park
More Info: downtownoakpark.net
Throw Bags & Sip Beers
Pitch your perfect game for a chance to be crowned the 2025 Lisle Bags Champion! Your entry ticket includes entry to the bags tournament, two beers, snacks, kid’s activities, and a raffle entry. Enjoy a fun time for a good cause—proceeds go towards providing scholarships Lisle High School students.
Date: March 9
Time: 1–4:30PM
Cost: $45
Location: Alter Brewing, 2300 Wisconsin Ave #213, Downers Grove
More Info: eventbrite.com
Shop Local at JHL Craft & Vintage Market
This event brings together a curated mix of local makers selling everything from handmade ceramics and retro finds to quirky soaps and one-of-a-kind jewelry. With 12 vendors offering a range of goods, it’s an ideal stop for gift shopping—or just treating yourself to something unique.
Date: March 9
Time: 11AM-4PM
Cost: Free
Location: Friendly Music Community, 6731 Roosevelt, Berwyn
More Info: allevents.in
Taste the Best of North Side Restaurant Week
Chicago’s far north neighborhoods serve up a global culinary tour during this annual dining event. Spanning Lincoln Square, Albany Park, Rogers Park, Uptown, and beyond, the week features special prix fixe menus highlighting everything from Serbian and Argentinian fare to French bistro classics and modern American favorites. It’s the perfect excuse to explore new restaurants or revisit old favorites before the event wraps up March 9.
Date: March 7-9
Time: Restaurant Availability
Cost: Various Offers
Location: Various Locations
More Info: northsiderestaurantweek.org
Experience Chicago Psych Fest
Now in its 15th year, this mind-bending festival assembles a who’s who of Chicago’s underground music scene. The two-night lineup spans everything from spacey psych-pop to avant-garde jazz and electronic noise rock, with performances from artists like The Flying Luttenbachers, Bobby Conn, and Spiral Galaxy. Expect a mix of legacy acts and experimental newcomers, all bringing their own brand of musical weirdness to the Hideout.
Date: March 7-8
Time: 8:30PM
Cost: $30
Location: Hideout Chicago, 1354 W Wabansia Ave
More Info: hideoutchicago.com
Discover New Favorites at Uncorked: Chicago Wine Festival
Wine lovers take over the Field Museum for an evening of tastings, music, and late-night exploring. More than 100 wines and bubblies from around the world will be available to sample, with a new Zero Proof lounge offering N/A wines and craft mocktails. VIP ticket holders can enjoy an expanded downstairs experience with premium pours, while DJs keep the party atmosphere going all night.
Date: March 8
Time: 7PM-11PM
Cost: $70+
Location: Field Museum, 1400 S Lake Shore Dr
More Info: uncorkedwinefestivals.com
Savor Every Bite at Sausagefest
Beer and bratwurst take center stage as Haymarket Pub & Brewery celebrates 14 years of its beloved Sausagefest. The West Loop staple pairs award-winning craft brews with housemade sausages, all served up in a lively festival setting. Whether you’re a fan of classic bratwurst or something a little more adventurous, expect plenty of options—and, of course, plenty of beer to wash it all down.
Date: March 8
Time: 12PM-4PM
Cost: $65
Location: Haymarket Pub & Brewery, 737 W Randolph St
More Info: haymarketbeer.com
Have a Good Time at St. Patrick’s Day Musical Story Time
Get into the St. Patrick’s Day spirit with a lively mix of storytelling, music, and crafts. Local author Laura Bityou Beriau joins musician Ray Hogan (aka Mr. Ray) for an interactive story time featuring Irish-themed tales, singalongs, and hands-on activities. After the event, personalized book signings will be available, making for a fun and festive keepsake.
Date: March 8
Time: 11AM-12PM
Cost: Free
Location: Time Out Market Chicago, 916 W Fulton Market
More Info: eventbrite.com
