7 days in Chicago

Day by day

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

   Millennium Park and Cloud Gate and Art Institute of Chicago, then Chicago Riverwalk in the evening.

   1. Morning

      Millennium Park and Cloud Gate

      The Loop · 1–2 hours · free.

   2. Late morning

      Art Institute of Chicago

      The Loop · 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. 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: Willis Tower Skydeck and Chicago Cultural Center

   Willis Tower Skydeck and Chicago Cultural Center, then The Second City in the evening.

   1. Morning

      Willis Tower Skydeck

      The Loop · 1.5–2 hours · mid-priced. Queues for The Ledge can be long in summer; timed tickets bought online shorten the wait.

   2. Late morning

      Chicago Cultural Center

      The Loop · 45 minutes · free.

   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. 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: Maggie Daley Park and Chicago Architecture Center river cruise

   Maggie Daley Park and Chicago Architecture Center river cruise, then 360 Chicago observation deck in the evening.

   1. Morning

      Maggie Daley Park

      The Loop · 1–2 hours · free.

   2. Late morning

      Chicago Architecture Center river cruise

      Chicago River · About 75–90 minutes · mid-priced. Summer weekend and sunset sailings sell out; book a day or more ahead.

   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. 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

      Ernest Hemingway was born here too, and his birthplace home can be visited.

   3. Evening

      Back in Chicago

      Dinner: try Italian beef.

5. Day 5: Field Museum and Shedd Aquarium

   Field Museum and Shedd Aquarium, then Navy Pier in the evening.

   1. Morning

      Field Museum

      Museum Campus · 3–4 hours · mid-priced.

   2. Late morning

      Shedd Aquarium

      Museum Campus · 2–3 hours · mid-priced. Buy timed tickets online; on summer weekends and school holidays the entry queue can stretch around the building.

   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. Evening

      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.

6. Day 6: Day trip to Indiana Dunes National Park

   About 1 hour 15 minutes to 1 hour 30 minutes by train each way. Getting there: South Shore Line from Millennium Station.

   1. Morning

      Travel to Indiana Dunes National Park

      About 1 hour 15 minutes to 1 hour 30 minutes by train (South Shore Line from Millennium Station); about 80 km.

   2. Day

      Indiana Dunes National Park

      Hike the dune trails at West Beach, or try the steep 3 Dune Challenge in the neighbouring Indiana Dunes State Park.

   3. Evening

      Back in Chicago

      Dinner: try Maxwell Street Polish.

7. Day 7: Adler Planetarium and Wrigley Field

   Adler Planetarium and Wrigley Field, then Lincoln Park blues bars in the evening.

   1. Morning

      Adler Planetarium

      Museum Campus · 2 hours · mid-priced.

   2. Late morning

      Wrigley Field

      Wrigleyville · 3–4 hours for a game · mid-priced. Weekend and rivalry games sell out; buy through the Cubs' official ticketing rather than street resellers.

   3. Lunch

      Lunch: Maxwell Street Polish

      Jim's Original near the University of Illinois Chicago campus, and grill stands across the South and West sides.

   4. 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 and The Second City before you travel; the rest of this plan needs no advance booking.

Where to stay for this itinerary

With 7 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 25–33 hours of visiting over 7 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
• 5 days in Chicago

Questions travellers ask