5 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

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

   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. (3–4 hours, mid-priced).

   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

      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. (1.5–2 hours, mid-priced).

   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. (About 75–90 minutes, mid-priced).

   2. Late morning

      Field Museum

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

   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. (2–3 hours, mid-priced).

   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

      Day games are a Chicago tradition; take the Red Line to Addison, as driving and parking around the ballpark are difficult. (3–4 hours for a game, mid-priced).

   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. (2–3 hours, free).

   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

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

   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.

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. Best for culture and quiet stays.

   3. Evening

      Back in Chicago

      Dinner: try Italian beef.

5. Day 5: Museum of Science and Industry and Frederick C. Robie House

   Museum of Science and Industry, Frederick C. Robie House and Lincoln Park Zoo, then Lincoln Park blues bars in the evening.

   1. Morning

      Museum of Science and Industry

      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. (Half a day, mid-priced).

   2. Late morning

      Frederick C. Robie House

      Combine it with a walk through the University of Chicago quadrangles and Rockefeller Chapel, a few minutes away. (1 hour, mid-priced).

   3. Lunch

      Lunch: Italian beef

      Al's #1 Italian Beef on Taylor Street in Little Italy, Mr. Beef on Orleans Street in River North and Portillo's.

   4. Afternoon

      Lincoln Park Zoo

      Zoo parking is limited and paid; take the 151 bus up from Michigan Avenue instead. (2–3 hours, free).

   5. Evening

      Lincoln Park blues bars

      Kingston Mines and B.L.U.E.S. face each other on North Halsted Street and play live Chicago blues until late.

Before you go

Reserve timed tickets for Chicago Architecture Center river cruise, Willis Tower Skydeck, Shedd Aquarium, Wrigley Field, The Second City, Museum of Science and Industry and Frederick C. Robie House before you travel; the rest of this plan needs no advance booking.

Where to stay for this itinerary

With 5 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 29–39 hours of visiting over 5 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
• 4 days in Chicago
• 7 days in Chicago

Questions travellers ask