Things to Do in Chicago This Weekend: Top Events and Activities

Chicago is a city that never runs out of interesting events; on weekends, this energetic city constantly offers something fresh to explore. Whether you are a local looking for weekend activities or a visitor wishing to take in the finest that the Windy City has to offer, there is a great range of cultural events, celebrations, concerts, and activities fit for families to engage in.

Chicago hosts a lot of highly vital events on the weekend of February 15–16, 2025. Including the Chicago Auto Show, live events, and Black History Month celebrations, this list will show the best activities in Chicago this weekend. You should seize these chances if you wish to maximize your visit to the city.

Chicago Auto Show: A Paradise for Car Enthusiasts

Held at McCormick Place, the Chicago Auto Show is among the most significant events scheduled for Chicago this weekend. Showcasing the most modern cars, trucks, and concept vehicles from the most recognized manufacturers, the United States Auto Show is the biggest and longest-running auto exhibition in the nation.

Visitors can:

• Explore cutting-edge automobile technology, including electric vehicles and self-driving cars.
• Test-drive select vehicles from major brands.
• Experience virtual reality simulations and interactive exhibits.
• Check out exclusive concept cars and futuristic designs.

Running from February 8 to 17, 2025, this event is a must-visit for car lovers and families who want to experience the future of automotive innovation.

Chicago Theatre Week: A Celebration of Performing Arts

During Chicago Theatre Week, which runs from February 6 to February 16, 2025, theatre buffs will have the chance to witness world-class events at subsidized rates at subsidized rates. Staged over several sites, over one hundred pieces highlight a broad spectrum of theatrical genres, including classic plays, modern performances, and experimental theatre.

Highlights include:

• Broadway-caliber performances at iconic theaters such as the Goodman Theatre and Steppenwolf Theatre.
• New and emerging talent featured in off-Broadway and indie productions.
• Special discounted tickets, making high-quality theater accessible to all audiences.

If you love live performances, this event is one of the best things to do in Chicago this weekend.

Valentine’s Day Weekend Activities: Romantic and Fun Experiences

Valentine’s Day is on February 1. Hence, the celebrations will go all through the long weekend. Chicago offers plenty of romantic and exciting events suitable for couples as well as solitary people.

Some popular options include:

• Fine dining experiences at top restaurants offering exclusive Valentine’s Day menus.
• 1920s Mder Mystery at the Speakeasy**, an interactive night of entertainment filled with suspense.
• Cupids Ball On The Yacht is a romantic cruise along Lake Michigan, providing stunning views of the Chicago skyline.

Whether couples are looking for a conventional candlelit dinner or an event of a different kind, Chicago provides a large range of Valentine’s weekend activities that could be appreciated by them.

Winter Tequila Tasting Festival: A Flavorful Experience

For those who enjoy tequila, the Winter Tequila Tasting Festival—which will take place on February 15—offers a great chance to sample a variety of tequila brands while also savoring live music and great food combinations.

What to expect:

• Dozens of premium tequila samples, including rare and aged varieties.
• Live music performances to set the mood.
• Food pairings that complement different tequila flavors.

This event is perfect for those looking to warm up with a good drink and a lively atmosphere.

Second Annual Cupid’s Vintage & Artisan Fest: Unique Shopping Experience

If you enjoy shopping for antique things and gathering vintage items and handcrafted goods, then you absolutely should visit the Second Annual Cupid AntiqueQue e& Artisan Fest. This market, which will take place on February 15 and 16 at Artefact Events, will unite very gifted locally based artists and vendors.

Visitors can:

• Shop for one-of-a-kind vintage clothing, jewelry, and antiques.
• Enjoy live music while browsing the market.
• Participate in hands-on workshops led by skilled artisans.

It’s an ideal place to find unique gifts and support small businesses.

Black History Month Celebrations: Honoring African American Culture

February is Black History Month, and Chicago hosts several events to celebrate African American history, art, and contributions.

Key events include:

• “Love Chicago” at the DuSable Black History Museum and Education Center (February 15), featuring performances, art exhibits, and educational discussions.
• “Voices of the Past, Power of Today: A Black History Celebration” (February 21) showcasing influential speakers, music, and storytelling.

These events provide an insightful and engaging way to learn about African American history and culture.

Live Music and Concerts: Exciting Performances in Chicago

Chicago’s music scene is thriving, and this weekend is packed with exciting concerts. Some highlights include:

• Alan Walker at Byline Bank Aragon Ballroom (February 15) – For electronic music lovers.
• 10,000 Maniacs at City Winery (February 15) – A great event for alternative rock fans.
• The Plot In You, Holding Absence & Boundaries at The Vic Theatre – Perfect for those who enjoy post-hardcore and alternative rock music.

Live music is one of the best ways to enjoy a Chicago weekend and discover new artists.

Cultural Exhibits and Art Shows

Art lovers can explore Chicago’s vibrant art scene through various exhibits:

• The Art Institute of Chicago is hosting a special exhibition on modern art.
• Museum of Contemporary Art – Showcasing works from emerging artists.

Both locations provide an immersive cultural experience for visitors.

Outdoor Activities: Ice Skating and Architecture Tours

Despite the winter weather, Chicago offers fantastic outdoor activities for those who love adventure.

• Ice Skating at Maggie Daley Park – The park’s ice ribbon provides a stunning backdrop of the Chicago skyline while skating.
• Guided Architecture Walking Tours – A chance to explore Chicago’s iconic buildings and learn about their history.

These activities provide a unique way to experience the city in winter.

Dining Experiences: Discover Chicago’s Culinary Scene

Food lovers can explore new restaurants opening this weekend, offering diverse cuisines from all over the world. Some top recommendations include:

• Contemporary American cuisine at newly opened fine dining spots.
• Authentic international dishes, including Mexican, Italian, and Asian-inspired restaurants.

Reservations are recommended, as these dining spots fill up quickly.

Family-Friendly Attractions

Families can enjoy kid-friendly activities at:

• Shedd Aquarium – Featuring interactive exhibits and marine life displays.
• Field Museum – A great place for science and history lovers.
• Chicago Children’s Museum – Offering hands-on activities for kids of all ages.

These venues ensure a fun and educational weekend for the whole family.

Comedy Shows: Laugh the Night Away

Chicago’s comedy clubs feature top comedians and improv shows this weekend. The Second City presents:

• “The Best of The Second City” – A collection of their most famous sketches.

It’s the perfect way to enjoy a night of humor and entertainment.

Sports Events: Chicago Bulls Game

Sports fans can watch the Chicago Bulls in action at the United Center on February 15. The exciting atmosphere and high-energy gameplay make for an unforgettable evening.

Workshops and Classes: Learn Something New

For those interested in learning new skills, Chicago offers various workshops this weekend:

• Cooking classes focusing on Chicago-style dishes.
• Painting and pottery workshops for art enthusiasts.

These hands-on experiences are great for beginners and experts alike.

Film Screenings: Special Movie Events

Film lovers can attend special screenings at theaters across the city. A great option is:

• 2025 Oscar-nominated Live Action Shorts at Music Box Theatre.

This exclusive screening is a fantastic opportunity to watch award-worthy short films.

Guided Tours: Experience Chicago the Right Way

For visitors who want a deeper understanding of Chicago’s history and architecture, guided tours are an excellent choice. Whether you’re exploring the city’s iconic skyscrapers, historic neighborhoods, or famous food spots, a knowledgeable guide can make all the difference in your experience.

However, selecting the right tour guide is crucial to ensuring a great trip. Booking an unqualified or misleading guide can lead to disappointment and missed opportunities to truly appreciate the city. To avoid such mistakes, check out this insightful article on what happens when the traveler hires the wrong tour guide before planning your tour.

If you appreciate shopping for old items, gathering antiques, and buying handcrafted things, you really should visit the Second Annual Cupid’s Antique & Artisan Fest. This market, which will take place at Artefact Events on February 15 and 16, will unite a collection of specially gifted local artists and vendors.