A must-do to learn the city’s history from the water.

Walk, jog, or bike with skyline and lake views.

Snap a classic photo and stroll the gardens.

Ride the Centennial Wheel and enjoy lakefront views.

Perfect for a scenic walk, with restaurants and bars along the water.

Home to Sue, the world’s most complete T. rex.

Legendary comedy shows.

Try Lou Malnati’s, Giordano’s, or Pequod’s for the real deal.

Chicago has some of the best rooftop views in the country — perfect for cocktails with the skyline as your backdrop. A few favorites:

Cindy’s – Overlooks Millennium Park and Lake Michigan with a relaxed, airy vibe.

Trump Terrace – Sophisticated setting with sweeping river and skyline views.

LondonHouse – A classic rooftop right on the Chicago River with panoramic city views.

Chicago’s food scene is unbeatable — here are some favorite spots to check out while you’re in town:

Gibsons Steakhouse – A legendary Chicago institution for big steaks and classic sides.

RPM Seafood – Upscale dining on the riverfront with incredible seafood towers and views.

Au Cheval – Home to the burger that’s often called the best in America.

Rose Mary – A West Loop favorite serving a mix of Italian comfort food and Mediterranean flavors.

Sushi-San – Fresh sushi with a modern, lively vibe (don’t miss the hand rolls).

Monteverde – Warm and inviting Italian restaurant with handmade pastas and fresh flavors.

Lyra – A stylish Greek restaurant with shareable plates and a vibrant atmosphere.