10-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.

Lakeview neighborhood stroll

Take the Red Line to Addison and wander Lakeview's tree-lined streets, coffee shops and the Southport Corridor's boutiques.

Wrigley Field tour

Tour the ivy-covered ballpark, open since 1914, to see the dugouts, press box and historic hand-turned scoreboard (tours vary by season).

Cubs game or Gallagher Way

Catch a Cubs day game from April to September, or relax in the plaza at Gallagher Way next to the stadium.

Wrigleyville and Lakeview nights

Join the crowds at rooftop bars and neighborhood pubs, or find a comedy or improv show in Lakeview.

Magnificent Mile

Walk North Michigan Avenue from the river past the Tribune Tower and the historic Water Tower, popping into flagship stores.

360 Chicago observation deck

Ride up the former John Hancock Center for close-up views of the lakefront and beaches, and try the tilting TILT experience if you're brave.

Navy Pier and the Centennial Wheel

Head to Navy Pier for the Centennial Wheel, lakefront walks and boat tours; summer brings outdoor events.

Navy Pier fireworks or a lake cruise

In summer, catch Navy Pier fireworks on scheduled nights or take a sunset lake cruise to see the skyline from offshore.

Lincoln Park Zoo

Arrive early to see the gorillas, lions and polar bears while animals are active; it's completely free to enter.

Lincoln Park Conservatory and Nature Boardwalk

Warm up among palms and ferns in the free conservatory, then walk the boardwalk at South Pond for a skyline photo.

North Avenue Beach

Spend the afternoon on Chicago's most popular beach, with volleyball courts, a beach house and skyline views (swimming is seasonal).

Second City in Old Town

See a show at The Second City, the legendary improv theater, then grab dinner nearby in Old Town.

Green Line to Oak Park

Ride the Green Line about 25 minutes west to Oak Park, home to the world's largest collection of Frank Lloyd Wright buildings.

Frank Lloyd Wright Home and Studio

Take a guided tour of the house where Wright developed the Prairie style; book ahead, as tours sell out.

Unity Temple and the historic district

Visit Wright's Unity Temple and walk the streets lined with his Prairie-style houses, plus Ernest Hemingway's birthplace.

Dinner on Randolph Street

Return to the West Loop for dinner on Restaurant Row along Randolph and Fulton Market, one of the city's top food scenes.

Farewell brunch

Have a hearty brunch in River North or the West Loop, and pick up a tin of caramel-and-cheese popcorn for the flight.

Last-minute souvenirs

Shop for Chicago gifts on State Street or Michigan Avenue, from sports gear to local design goods.

One last Riverwalk stroll

Take a final walk along the Riverwalk to say goodbye to the skyline.

Ride the L to the airport

Take the Blue Line to O'Hare or the Orange Line to Midway; allow about 45-60 minutes for the train ride plus security.