Millennium Park & The Bean

Snap a selfie at “The Bean” (Cloud Gate) and wander through Millennium Park’s lush landscape. In summer, there are often free concerts and events!

Skydeck Chicago at Willis Tower

Brave enough? Stand on “The Ledge” – a glass box extending 1,353 feet above the city! You’ll get breathtaking views of Chicago and beyond.

Art Institute of Chicago

Marvel at world-renowned artwork, including iconic pieces like Grant Wood’s American Gothic and Seurat’s A Sunday on La Grande Jatte.

Wicker Park & Bucktown

Known for its hipster vibe, these neighborhoods are filled with indie boutiques, cool cafes, and bars with fantastic craft cocktails.

West Loop

Chicago’s foodie paradise! Head to Randolph Street for incredible restaurants or try the famous “Au Cheval” for what many say is the city’s best burger.

Lincoln Park

Take a stroll through Lincoln Park Zoo (it’s free!) and visit the Lincoln Park Conservatory for a peaceful afternoon.

Deep-Dish Pizza at Lou Malnati’s or Giordano’s

Chicago is famous for deep-dish pizza – so make sure to grab a slice! Both spots are local favorites.

Chicago-Style Hot Dogs at Portillo’s

Try a true Chicago-style dog (no ketchup!) topped with mustard, relish, onions, tomatoes, pickles, and peppers.

Cocktails with a View at Cindy’s Rooftop

Overlooking Millennium Park, Cindy’s is a chic rooftop bar with spectacular views of Lake Michigan and the city skyline.

Architectural River Cruise

One of the best ways to see Chicago’s architecture is from the water! Learn about the city’s iconic skyscrapers on this must-do river cruise.

Lakefront Trail

Stroll or bike along Lake Michigan with beautiful views of the city skyline. You’ll pass beaches, parks, and scenic spots along the way.

Wrigley Field Tour

Visit the legendary home of the Chicago Cubs, Wrigley Field, with a guided tour. If you’re in town during baseball season, catch a game!

United Center – Home of the Bulls and Blackhawks

Check out a Bulls or Blackhawks game or tour the United Center for a bit of sports history (and see the Michael Jordan statue!).

The Second City

Enjoy a night of laughs at the comedy club where many famous comedians got their start. Shows here are legendary!

Jazz at Green Mill Cocktail Lounge

For a taste of Chicago’s jazz scene, visit this iconic, old-school jazz club. It’s a favorite with locals and has a speakeasy vibe.

Blue Chicago

Head here for an authentic Chicago blues experience in a lively setting. The music is incredible, and the atmosphere is unforgettable!

The Magnificent Mile

Walk along Michigan Avenue and enjoy luxury shops, famous department stores, and unique boutiques for all your shopping needs.

Chicago Riverwalk

Stroll along the Riverwalk for a scenic view, and stop at small shops, restaurants, or cafés along the way. Great for souvenirs and quick bites