Chicago has something for everyone, from architecture tours to top-rated comedy clubs and fine dining. Whether it’s a weekend getaway or a full vacation, find the best deals on hotels, attractions, and must-see experiences.

Best Stays in The Windy City
The comfort you want, the location you need, the deals you love.

Popular Attractions & Exhibits
From must-sees to hidden gems!

Sightseeing & Tours
See the Second City with local flair

Tickets & Events
Get Front Row Access to fun

Foodie Favorites
Bite into the best of Chi-town

Drivable Destinations
Quick escapes just a car ride away.

Beauty & Spas
Relaxation, the local way

Discover Chicago with Groupon

Chicago, the Windy City, is a world-class destination known for its stunning skyline, rich history, and vibrant cultural scene. From deep-dish pizza to jaw-dropping architecture, the Chicago City Guide on Groupon helps you explore the best this iconic city has to offer without breaking the bank.

Why Visit Chicago?

  • Iconic Landmarks: See the towering Willis Tower, the historic Wrigley Building, and the reflective Cloud Gate (aka The Bean) in Millennium Park.

  • World-Class Museums: Discover art, science, and history at the Art Institute of Chicago, Field Museum, and Museum of Science and Industry.

  • Lakefront Views: Stroll along Lake Michigan, relax on the beaches, or take a boat tour on the Chicago River.

  • Culinary Scene: Savor deep-dish pizza, Chicago-style hot dogs, and award-winning cuisine from top chefs.

  • Vibrant Neighborhoods: Explore diverse areas like Wicker Park, Chinatown, and the historic Bronzeville district.

Save on Your Chicago Adventure

From river cruises to live comedy shows, the Chicago City Guide on Groupon offers exclusive deals to make the most of your trip. Save on dining, attractions, hotels, and more.

Frequently Asked Questions (FAQ)

1. What is the best time to visit Chicago?
The best time to visit is in spring (April to June) or fall (September to October) when the weather is mild, and the city’s festivals are in full swing.

2. Are there free things to do in Chicago?
Yes! Visit Millennium Park, walk the Chicago Riverwalk, or catch free concerts and movie screenings in the summer.

3. Is Chicago family-friendly?
Absolutely! Families can enjoy the Shedd Aquarium, Lincoln Park Zoo, and the hands-on exhibits at the Chicago Children’s Museum.

4. How long should I plan to stay in Chicago?
A 3-5 day trip is perfect for experiencing the city’s major attractions, diverse neighborhoods, and vibrant food scene.

5. Can I take day trips from Chicago?
Yes, popular day trips include visiting the Indiana Dunes, historic Galena, or the charming lakeside towns of Michigan.

Ready to explore the Windy City? Discover exclusive deals and unforgettable experiences with Groupon’s Chicago City Guide.