4 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 Chicago Riverwalk in the evening.

   1. Morning

      Millennium Park and Cloud Gate

      Allow 1–2 hours (free). See the Bean early in the morning before the crowds, then cross Gehry's winding BP Bridge to Maggie Daley Park.

   2. Late morning

      Art Institute of Chicago

      Highlights include Seurat's A Sunday on La Grande Jatte, Hopper's Nighthawks, Grant Wood's American Gothic, a deep Impressionist collection with several of Monet's Stacks of Wheat, Chagall's America Windows and the Thorne Miniature Rooms. Renzo Piano's Modern Wing holds 20th-century art.

   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

      Allow 1.5–2 hours (mid-priced). Check the visibility before buying; low cloud can hide the view completely, and a late-afternoon visit gives you daylight and sunset in one ticket.

   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.

2. Day 2: Chicago Cultural Center and Maggie Daley Park

   Chicago Cultural Center, Maggie Daley Park and Chicago Architecture Center river cruise, then The Second City in the evening.

   1. Morning

      Chicago Cultural Center

      It sits directly across Michigan Avenue from Millennium Park.

   2. Late morning

      Maggie Daley Park

      Allow 1–2 hours (free). Skate-rental queues are long on winter weekends; a weekday afternoon is much calmer.

   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

      Chicago Architecture Center river cruise

      The Chicago Architecture Center's docent-led cruise, departing from the Riverwalk at Michigan Avenue, passes dozens of buildings including the Wrigley Building, Tribune Tower, Marina City's corncob towers and the Merchandise Mart.

   5. Evening

      The Second City

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

3. Day 3: Field Museum and Shedd Aquarium

   Field Museum, Shedd Aquarium and Adler Planetarium, then 360 Chicago observation deck in the evening.

   1. Morning

      Field Museum

      Allow 3–4 hours (mid-priced). Arrive at opening and do the Field in the morning; the Shedd is a five-minute walk away for the afternoon.

   2. Late morning

      Shedd Aquarium

      Opened in 1930 in a Beaux-Arts building on the lake, the Shedd's highlights are the Caribbean Reef, a circular tank in the central rotunda, the Wild Reef shark exhibit, Amazon Rising and the Abbott Oceanarium, where beluga whales and Pacific white-sided dolphins swim in front of windows that look out onto Lake Michigan.

   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

      Allow 2 hours (mid-priced). Even if you skip the museum, walk out to the Adler around sunset for the view back across the harbour to downtown.

   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.

4. Day 4: Day trip to Oak Park

   About 25 minutes by L or Metra each way. Getting there: CTA Green Line to Oak Park or Harlem/Lake, or Metra from Ogilvie.

   1. Morning

      Travel to Oak Park

      About 25 minutes by L or Metra (CTA Green Line to Oak Park or Harlem/Lake, or Metra from Ogilvie); about 15 km.

   2. Day

      Oak Park

      Frank Lloyd Wright lived and worked in Oak Park for 20 years, and the suburb holds his Home and Studio, Unity Temple and the largest concentration of his buildings anywhere, best seen on a guided or self-guided walking tour. Ernest Hemingway was born here too, and his birthplace home can be visited.

   3. Evening

      Back in Chicago

      Dinner: try Italian beef.

Before you go

Reserve timed tickets for Chicago Architecture Center river cruise, Willis Tower Skydeck, Shedd Aquarium and The Second City before you travel; the rest of this plan needs no advance booking.

Where to stay for this itinerary

With 4 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 20–26 hours of visiting over 4 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
• 3 days in Chicago
• 5 days in Chicago
• 7 days in Chicago

Questions travellers ask