3 days in Chicago

Day by day

1. Day 1: Millennium Park and Cloud Gate and Art Institute of Chicago

   Millennium Park and Cloud Gate, Art Institute of Chicago and Willis Tower Skydeck, then The Second City in the evening.

   1. Morning

      Millennium Park and Cloud Gate

      Chicago's showpiece park holds Anish Kapoor's mirrored Cloud Gate sculpture (universally called the Bean), the Crown Fountain's two glass-block towers that show the faces of Chicagoans and spout water in summer, Frank Gehry's Jay Pritzker Pavilion and the Lurie Garden.

   2. Late morning

      Art Institute of Chicago

      Start with the Impressionists on the second floor before tour groups arrive, then take the Modern Wing's Nichols Bridgeway straight into Millennium Park.

   3. Lunch

      Lunch: Deep-dish pizza

      Pizzeria Uno in River North, where the style is said to have started in 1943, plus Lou Malnati's, Giordano's and Pequod's, known for its caramelised cheese crust.

   4. Afternoon

      Willis Tower Skydeck

      Completed in 1973 as the Sears Tower, the 110-storey Willis Tower was the world's tallest building for about 25 years.

   5. Evening

      The Second City

      Stay after the late show for the improv set, where the cast tests new material from audience suggestions.

2. Day 2: Chicago Architecture Center river cruise and Field Museum

   Chicago Architecture Center river cruise, Field Museum and Shedd Aquarium, then 360 Chicago observation deck in the evening.

   1. Morning

      Chicago Architecture Center river cruise

      Sit on the open upper deck and bring a layer even in summer; it is several degrees cooler on the water.

   2. Late morning

      Field Museum

      One of the world's major natural-history museums, the Field holds Sue, one of the largest and most complete Tyrannosaurus rex skeletons ever found, a cast of the giant titanosaur Máximo in the main hall, a walk-through Egyptian tomb and the Evolving Planet fossil galleries.

   3. Lunch

      Lunch: Tavern-style thin-crust pizza

      Neighbourhood taverns and pizzerias across the city; Vito & Nick's on the South Side is one of the long-established names.

   4. Afternoon

      Shedd Aquarium

      Walk the lakefront path from the Shedd to the Adler Planetarium afterwards for the classic skyline photo.

   5. Evening

      360 Chicago observation deck

      Pick this over the Skydeck if you want lake and beach views; the Skydeck looks more over the city grid and the west.

3. Day 3: Wrigley Field and Navy Pier

   Wrigley Field, Navy Pier and Adler Planetarium, then Chicago Riverwalk in the evening.

   1. Morning

      Wrigley Field

      Opened in 1914 and home of the Chicago Cubs since 1916, Wrigley Field is the second-oldest ballpark in Major League Baseball, known for its ivy-covered outfield walls, hand-operated scoreboard and rooftop bleachers on the neighbouring buildings.

   2. Late morning

      Navy Pier

      Walk to the far east end for skyline views and fewer people; summer fireworks over the lake are held on some evenings, so check the pier's calendar.

   3. Lunch

      Lunch: Chicago-style hot dog

      Portillo's branches including River North, Superdawg on the Northwest Side and hot-dog stands across the city.

   4. Afternoon

      Adler Planetarium

      America's first planetarium opened in 1930 at the end of the Museum Campus peninsula.

   5. Evening

      Chicago Riverwalk

      Look into the McCormick Bridgehouse & Chicago River Museum in the DuSable Bridge tower to see the gears that raise the bridge; it opens seasonally.

Before you go

• Chicago Architecture Center river cruise: Summer weekend and sunset sailings sell out; book a day or more ahead.
• Willis Tower Skydeck: Queues for The Ledge can be long in summer; timed tickets bought online shorten the wait.
• Shedd Aquarium: Buy timed tickets online; on summer weekends and school holidays the entry queue can stretch around the building.
• Wrigley Field: Weekend and rivalry games sell out; buy through the Cubs' official ticketing rather than street resellers.
• The Second City: Weekend shows sell out; book a few days ahead.

If it rains

• Swap in Museum of Science and Industry (Hyde Park): Allow at least half a day and pick two or three big exhibits; the Metra Electric to 55th–56th–57th Street is the easiest way there from downtown.
• Swap in Chicago Cultural Center (The Loop): Go up to Preston Bradley Hall on the third floor first; lunchtime concerts are often held under the dome.
• Swap in Garfield Park Conservatory (East Garfield Park): Take the Green Line to Conservatory–Central Park Drive, which stops right next to the entrance.

Where to stay for this itinerary

With 3 nights, The Loop keeps most of this route within easy reach. For a calmer or cheaper base, Streeterville and the Magnificent Mile ($$$$) suits families, shopping, luxury and first-timers. Compare every area.

Pace and daylight

The sights in this plan add up to roughly 23–31 hours of visiting over 3 days, before meals and getting between them. Daylight runs from about 9.1 hours in December to 15.2 hours in June, so in winter start early and keep museums for the afternoon.

More or fewer days

• One day in Chicago
• 2 days in Chicago
• 4 days in Chicago
• 5 days in Chicago
• 7 days in Chicago

Questions travellers ask