Five Days in Chicago: Icons, Museums & Neighborhoods

Downtown parks, the Art Institute, an architecture cruise, and Willis Tower.

1. Morning

   Millennium Park & Cloud Gate

   Start at Cloud Gate, Crown Fountain, and the Lurie Garden while the park is quiet. It's the ideal orientation point for a first full day downtown.

2. Late Morning

   Art Institute of Chicago

   Devote two hours to the Impressionists, the Modern Wing, and American Gothic in one of the world's finest museums, an easy walk from the park.

3. Lunch

   Chicago Riverwalk

   Lunch along the Riverwalk with the bridges and boat traffic beside you, a scenic pause before the afternoon cruise departs from the same stretch.

4. Afternoon

   Architecture River Cruise

   Take the Chicago Architecture Center cruise for the definitive skyline primer, gliding past landmark towers along all three branches of the river.

5. Late Afternoon

   Willis Tower Skydeck

   Ascend to the 103rd-floor Skydeck and step onto The Ledge. Late-day light and clear skies reward you with sweeping four-state views.

6. Evening

   Deep dish dinner

   Close the day with Chicago's iconic deep-dish pizza at Lou Malnati's or Pequod's, ordering early to allow for the long bake time.

The Field, Shedd, and Adler plus Buckingham Fountain along the lakefront.

1. Morning

   Field Museum

   Begin with SUE the T. rex and the Egyptian and evolution halls. Arriving at opening helps you outpace the day's school groups.

2. Late Morning

   Shedd Aquarium

   Move next door to the Shedd for belugas, sharks, and the Amazon Rising exhibit. A timed entry ticket keeps waits short.

3. Lunch

   Museum Campus lawns

   Enjoy a casual or picnic lunch on the campus greens, framed by Lake Michigan on one side and the skyline on the other.

4. Afternoon

   Adler Planetarium

   Walk to the Adler for immersive sky shows and, from its peninsula, the single best skyline vantage point in the city.

5. Late Afternoon

   Buckingham Fountain

   Stroll north through Grant Park to the grand Buckingham Fountain, whose hourly water shows run through the warm-weather season.

6. Evening

   South Loop dinner

   Dine in the South Loop, whose restaurants along Wabash and State cover everything from soul food to modern American cuisine.

Trails, murals, boutiques, and celebrated independent dining on the Northwest Side.

1. Morning

   The 606 Trail

   Walk or bike the elevated 606 through Bucktown and Wicker Park, a green ribbon of gardens and public art above the neighborhood streets.

2. Late Morning

   Wicker Park boutiques

   Explore the independent shops, record stores, and bookshops around Milwaukee, North, and Damen, plus the murals tucked down nearby side streets.

3. Lunch

   Big Star tacos

   Settle in at Big Star for tacos and a lively patio, or choose from the neighborhood's many acclaimed casual eateries.

4. Afternoon

   Damen Avenue, Bucktown

   Wander north on Damen past Bucktown's design shops and cafés, a stylish, unhurried afternoon of browsing.

5. Evening

   Logan Square dinner

   Head to Logan Square for dinner along its historic boulevard, home to some of Chicago's most lauded independent restaurants.

6. Evening

   Cocktail bar nightcap

   Finish with a drink at one of Logan Square's inventive cocktail bars, soaking up the neighborhood's easygoing creative vibe.

A landmark science museum, a Gothic campus, and Frank Lloyd Wright architecture.

1. Morning

   Museum of Science and Industry

   Spend the morning at this vast museum, exploring the U-505 submarine, the coal mine, and the Science Storms exhibits, a highlight for all ages.

2. Lunch

   Hyde Park cafés

   Grab lunch near the University of Chicago campus, where student-friendly cafés and international spots line the blocks around 53rd and 57th Streets.

3. Afternoon

   University of Chicago campus

   Wander the neo-Gothic quadrangles, then visit the Robie House, Frank Lloyd Wright's Prairie-style masterpiece just off campus.

4. Late Afternoon

   Frederick C. Robie House

   Tour the Robie House interior to see Wright's revolutionary open plan and art-glass windows up close, an architecture pilgrimage worth booking ahead.

5. Evening

   Promontory Point

   Walk out to Promontory Point on the lakefront for a peaceful skyline view across the water before heading back downtown.

6. Evening

   South Side dinner

   Have dinner in Hyde Park or grab classic South Side barbecue before returning north for the evening.

Ballpark energy, lakefront beaches, and Magnificent Mile shopping to close the trip.

1. Morning

   Wrigley Field

   Visit historic Wrigley Field, home of the Cubs since 1914. Take a ballpark tour, or catch a day game if the schedule aligns with your trip.

2. Lunch

   Wrigleyville eats

   Lunch in the lively blocks around the ballpark, from sports bars to the pizza and sandwich spots that fill Clark Street on game days.

3. Afternoon

   Lincoln Park Zoo & Conservatory

   Head south to the free Lincoln Park Zoo and adjoining Victorian conservatory, an easy, budget-friendly pairing beside the lakefront.

4. Late Afternoon

   North Avenue Beach

   Relax at North Avenue Beach and stroll the Lakefront Trail for classic skyline-over-the-sand photos.

5. Evening

   Magnificent Mile

   Finish shopping along Michigan Avenue, passing the historic Water Tower and the Wrigley Building near the river.

6. Evening

   River North farewell dinner

   End your trip with dinner in River North's dense restaurant district; reserve ahead for the city's steakhouses and standout tables.