5-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.

Chicago Cultural Center

Step inside the free Chicago Cultural Center to see the world's largest Tiffany glass dome, then grab coffee nearby.

Art Institute of Chicago

Arrive at opening and head straight for American Gothic, Nighthawks and the Impressionist galleries before crowds arrive.

Maggie Daley Park and Buckingham Fountain

Walk across the Nichols Bridgeway to Maggie Daley Park, then south through Grant Park to Buckingham Fountain (water shows run in warmer months).

Theater night in the Loop

See a Broadway in Chicago show or a play in the Loop theater district, then grab an Italian beef or a late slice afterward.

Field Museum

Meet SUE, one of the most complete T. rex skeletons ever found, and explore ancient Egypt and natural history exhibits.

Shedd Aquarium

See beluga whales, sea otters and the Caribbean Reef exhibit; book timed tickets ahead in summer.

Adler Planetarium and Northerly Island

Walk out to the Adler Planetarium for its sky shows and one of the city's best skyline views, then stroll Northerly Island's lakeside trails.

Dinner in Chinatown

Ride the Red Line or a seasonal water taxi to Chinatown for dim sum, hot pot or noodles along Wentworth Avenue and Chinatown Square.