Things To Do In Chicago This Weekend: Your Ultimate Guide to the Windy City’s Best Activities

If you’re looking for the best things to do in Chicago this weekend, you’ve come to the right place. Chicago bursts with energy when the weekend rolls in. Whether you’re into museums, cultural festivals, tasty street food, or outdoor sports, you’ll find a range of activities to suit your style. The city is warm, welcoming, and full of surprises for every traveler. Even if you’ve visited before, Chicago never runs out of fresh weekend adventures. So, let’s dive right in and explore what awaits you in the heart of the Midwest.

Family-Friendly Activities

Chicago’s family-friendly scene ensures everyone has fun. You’ll find endless things to do in Chicago this weekend with your kids. There are interactive museums, vibrant parks, and unique indoor attractions perfect for little explorers. The city’s welcoming atmosphere makes it easy to create family memories. Plus, with so many venues near each other, you can pack multiple adventures into a single day.

Explore the Field Museum

This world-class museum captivates children and adults alike. Here, you’ll discover ancient fossils, dazzling gems, and exotic animal exhibits.

• Highlights:
  • Sue the T. rex, a must-see dinosaur.
  • Educational workshops and interactive displays.
  • Seasonal exhibits that change every few months.

Testimonial (TripAdvisor):
“I took my 8-year-old twins to the Field Museum. They couldn’t stop talking about Sue the T. rex! It was one of the most fascinating things to do in Chicago this weekend family style!” – Carly D.

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Visit the Shedd Aquarium

If your kids love marine life, the Shedd Aquarium is an ideal stop. It’s home to sharks, dolphins, penguins, and coral reefs.

• Highlights:
  • Dolphin shows scheduled several times a day.
  • Petting pools where kids can touch stingrays.
  • Family-friendly restaurants and café areas.

Testimonial (Yelp):
“Our family adored the Shedd Aquarium. The dolphin show made our kids’ faces light up. Without a doubt, one of our favorite things to do in Chicago this weekend!” – Mark G.

Wander Around Millennium Park

This iconic park offers green lawns, open-air concerts, and art installations like the famous Cloud Gate (a.k.a. “The Bean”).

• Highlights:
  • Outdoor movie nights in summer.
  • Interactive water fountains kids can splash around in.
  • Free yoga sessions on the lawn.

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Free Events and Activities

Weekends in Chicago don’t have to break the bank. There are plenty of free events that let you soak in the city’s culture without spending a dime. With strategic planning, you’ll find ample things to do in Chicago this weekend for free that still feel special and memorable.

Chicago Public Library Events

Libraries host readings, art sessions, and children’s storytimes. It’s a great way to discover local culture and keep everyone entertained.

• Highlights:
  • Free language classes.
  • Book clubs and author meet-and-greets.
  • Quiet reading corners for a peaceful afternoon.

Testimonial (Google Reviews):
“I attended a poetry reading at the Chicago Public Library. It was enlightening and completely free. It’s nice to have enriching things to do in Chicago this weekend on a budget.” – Lucia P.

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Free Museum Days

Several museums offer free admission on certain days. Plan ahead to catch these opportunities.

• Sample Free Entry Schedule:MuseumFree Entry DayNotesThe Art Institute of ChicagoThursdays after 5 pmExpect longer lines.Museum of Contemporary ArtTuesdays for IL residentsBring ID for proof.Adler PlanetariumSelected WednesdaysCheck official website.

Outdoor Festivals

Chicago’s calendar is filled with street fairs and outdoor festivals. You’ll enjoy live music, pop-up art galleries, and community parades.

• Highlights:
  • Cultural festivals featuring global cuisine.
  • Street performances by local musicians.
  • Craft fairs offering unique souvenirs.

Testimonial (Instagram Traveler):
“Stumbled upon a jazz festival downtown. It was free and had amazing vibes. Perfect if you’re looking for relaxed, free things to do in Chicago this weekend.” – @CityWanderer

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Romantic Getaways for Couples

Looking to impress someone special? Chicago is full of things for couples to do in Chicago this weekend that spark romance. From candlelit dinners overlooking the skyline to intimate riverside walks, the Windy City sets the stage for magical moments.

Chicago River Cruises

A sunset cruise on the Chicago River provides the perfect backdrop for love. Admire the skyline and learn city history, all while sipping a glass of wine.

Testimonial (Booking.com):
“My partner and I took a sunset cruise. The skyline was breathtaking, and the narration was top-notch. It’s one of the most romantic things to do in Chicago this weekend.” – Daniela V.

Lincoln Park Zoo

A leisurely stroll through Lincoln Park Zoo brings you closer to nature and each other. The variety of animals and tranquil greenery is hard to beat.

Testimonial (TripAdvisor):
“We spent a lazy afternoon at Lincoln Park Zoo. It felt like a mini getaway. Such a calm place to unwind together.” – Jared T.

Rooftop Bars

Sip cocktails with panoramic city views at one of Chicago’s stylish rooftop bars. These venues often offer live music and appetizers that set the mood.

Testimonial (Yelp):
“We tried a rooftop bar in the West Loop. Fantastic cocktails and an unforgettable skyline view. A must on your list of things for couples to do in Chicago this weekend.” – Melissa R.

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Outdoor Adventures

If you crave fresh air and active fun, Chicago’s outdoors won’t disappoint. Sports enthusiasts can find tons of things to do in Chicago this weekend on trails, in parks, and along the lakefront. The city’s landscape encourages you to break a sweat while enjoying stunning views.

Biking the Lakefront Trail

Chicago’s Lakefront Trail runs along Lake Michigan and offers panoramic views. It’s perfect for a morning bike ride.

• Highlights:
  • Bike rentals available along the route.
  • Scenic pit stops at sandy beaches.
  • Waterfront cafés for quick snacks.

Testimonial (Google Reviews):
“My morning bike ride on the Lakefront Trail was a highlight of the trip. Safe, scenic, and refreshing.” – Bryan K.

Kayaking on the Chicago River

Kayak rentals let you paddle through the city’s architectural wonders. It’s a workout plus a sightseeing tour all in one.

• Highlights:
  • Guided tours that explain each building’s story.
  • Peaceful early-morning paddles.
  • Great photo opportunities from the water.

Testimonial (TripAdvisor):
“I never thought kayaking in a big city would be so fun. A unique way to see Chicago’s architecture.” – Evelyn M.

Millennium Park Ice Skating (Seasonal)

In colder months, lace up your skates and glide around the park’s ice rink. Enjoy the city lights while practicing your spins.

• Highlights:
  • Skate rentals available on-site.
  • Seasonal music events on weekends.
  • Hot cocoa stands nearby.

Testimonial (Yelp):
“Skating at Millennium Park felt magical. We visited at dusk, and the city lights looked incredible.” – Chris L.

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Cultural Experiences

Chicago’s cultural scene is vibrant. Immerse yourself in art, theater, music, and global flavors to truly understand the city’s soul. With numerous things to do in Chicago this weekend that celebrate culture, you’ll leave enriched and inspired.

Theater and Performing Arts

Catch a Broadway show or explore smaller venues offering improv and stand-up comedy. Chicago’s theater scene is world-renowned.

Testimonial (Google Reviews):
“We saw a play at the Chicago Theatre. The performers were extraordinary, and the historical venue added charm.” – Rachel M.

Art Galleries and Exhibits

You’ll find art in unexpected places, from large museums to hidden galleries. Discover paintings, sculptures, and photographs that open your mind.

Testimonial (TripAdvisor):
“I stumbled into a small gallery near River North. Ended up chatting with the artist. Such a personal and inspiring experience.” – Luis W.

Food and Drink Festivals

For a taste of global flavors, explore Chicago’s food markets and drink festivals. Sample regional specialties like deep-dish pizza or locally brewed beers.

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Practical Tips for Your Weekend in Chicago

Planning your Chicago weekend doesn’t have to be stressful. Use these tips to get around smoothly, find comfortable accommodations, stay safe, and enjoy the city’s flavors.

• Transportation:
  • Consider a CTA pass for unlimited rides.
  • Rideshare apps are widely available.
  • Bike rentals at Divvy stations are convenient.
• Accommodation:
  • Book early to secure weekend deals.
  • Downtown hotels offer easy access to main attractions.
  • Check Booking.com for user reviews and last-minute discounts.
• Safety Tips:
  • Keep valuables close in crowded areas.
  • Stick to well-lit streets at night.
  • Ask locals or hotel staff for neighborhood guidance.
• Dining Recommendations:
  • Try deep-dish pizza at Lou Malnati’s.
  • Sample street food at Maxwell Street Market.
  • Explore vegetarian options at The Chicago Diner.

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Conclusion

Looking for more? Have a favorite Chicago spot we didn’t mention? Let us know in the comments. Are you a foodie? C. Before you go, consider subscribing to our newsletter for weekly travel tips and exclusive deals. Don’t forget to share this guide with friends and fellow travelers looking for the best things to do in Chicago this weekend.
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