3-Day Chicago Itinerary

Arrive and ride the L downtown

From O'Hare take the Blue Line, or from Midway the Orange Line, straight into the Loop for a few dollars, then check in and drop your bags.

Millennium Park and Cloud Gate

Walk to Millennium Park for photos at Cloud Gate, the Crown Fountain and the Lurie Garden, all free and steps from Michigan Avenue.

Stroll the Chicago Riverwalk

Head north to the river and wander the Riverwalk west from Michigan Avenue, watching tour boats and water taxis glide beneath the bridges.

Deep-dish pizza dinner

Order a deep-dish at a long-running Chicago pizzeria such as Lou Malnati's or Giordano's; pies take about 40-45 minutes, so order as soon as you sit down.

Breakfast and a Loop architecture walk

Have breakfast at a classic diner, then walk past the Rookery, the Chicago Board of Trade and the Monadnock Building.

Chicago Architecture River Cruise

Board a 75- to 90-minute narrated cruise along all three branches of the river; sit up top for the best photos.

Willis Tower Skydeck and The Ledge

Ride to the 103rd floor and step onto the glass Ledge, then look for the river you just cruised far below.

Riverwalk drinks and live blues

Return to the Riverwalk for a drink as the river lights up, then catch a set at Buddy Guy's Legends, a long-running South Loop blues club.

Ride the L like a local

Tap your card or buy a day pass, then ride the Brown Line around the elevated Loop tracks for rooftop views; avoid rush hour if you have luggage.

Wicker Park and Bucktown

Take the Blue Line to Damen for vintage shops, record stores and murals, and grab a Chicago-style hot dog with everything but ketchup.

Bike the Lakefront Trail

Rent a Divvy bike and ride part of the 18-mile Lakefront Trail past Oak Street Beach and North Avenue Beach, with the lake on one side and towers on the other.

Lakefront sunset

End at North Avenue Beach or the Museum Campus peninsula near the Adler Planetarium as the skyline glows gold and the city lights flicker on.