Chicago itinerary: 1 to 7 days
Plans for one to seven days in Chicago, day by day: Willis Tower, the Chicago Theatre and Navy Pier first, then Cloud Gate in Millennium Park, the Art Institute, the Field Museum, the Magnificent Mile, the ballparks and the Museum of Science and Industry as you add days. Every stop has a typical visit length.
How long do you have?
Map: 3 days
Chicago in 1 day
Day 1
Willis Tower Must see
The former Sears Tower, with the Skydeck and its glass-floored Ledge on the 103rd floor.
Cloud Gate Must see
Anish Kapoor's mirrored stainless-steel sculpture, known as 'the Bean', in Millennium Park, reflecting the skyline.
Art Institute of Chicago
One of the oldest and largest art museums in the US, with Seurat, Hopper's Nighthawks, American Gothic and many Impressionists.
Chicago Theatre Must see
The 1921 movie palace on State Street, known for its vertical 'C-H-I-C-A-G-O' sign over the marquee.
Navy Pier Must see
A long pier on Lake Michigan with a Ferris wheel, restaurants, boat tours and views back to the skyline.
Chicago in 2 days
Day 1
Harold Washington Library Must see
Chicago's central public library, a large 1991 building with owl-topped roof ornaments and a ninth-floor winter garden.
Willis Tower Must see
The former Sears Tower, with the Skydeck and its glass-floored Ledge on the 103rd floor.
Wrigley Field Must see
The 1914 ballpark of the Chicago Cubs on the North Side, famous for its ivy-covered outfield walls.
Day 2
John Hancock Center Must see
The 100-storey tapering black tower on the Magnificent Mile, now 875 North Michigan Avenue, with the 360 Chicago observation deck.
Chicago Water Tower Must see
A castle-like 1869 water tower on Michigan Avenue, one of the few buildings to survive the Great Chicago Fire of 1871.
Navy Pier Must see
A long pier on Lake Michigan with a Ferris wheel, restaurants, boat tours and views back to the skyline.
Chicago in 3 days
Day 1
Willis Tower Must see
The former Sears Tower, with the Skydeck and its glass-floored Ledge on the 103rd floor.
Harold Washington Library Must see
Chicago's central public library, a large 1991 building with owl-topped roof ornaments and a ninth-floor winter garden.
Soldier Field Must see
The lakefront stadium of the Chicago Bears, opened in 1924, with classical colonnades along its sides.
Cloud Gate Must see
Anish Kapoor's mirrored stainless-steel sculpture, known as 'the Bean', in Millennium Park, reflecting the skyline.
Navy Pier Must see
A long pier on Lake Michigan with a Ferris wheel, restaurants, boat tours and views back to the skyline.
Day 2
John Hancock Center Must see
The 100-storey tapering black tower on the Magnificent Mile, now 875 North Michigan Avenue, with the 360 Chicago observation deck.
Wrigley Field Must see
The 1914 ballpark of the Chicago Cubs on the North Side, famous for its ivy-covered outfield walls.
Day 3
Buckingham Fountain Must see
A huge 1927 fountain in the centre of Grant Park, with water displays in the warmer months.
Field Museum of Natural History Must see
A large natural history museum on the lakefront, home of Sue, one of the most complete T. rex skeletons found.
Art Institute of Chicago
One of the oldest and largest art museums in the US, with Seurat, Hopper's Nighthawks, American Gothic and many Impressionists.
Chicago in 4 days
Day 1
Willis Tower Must see
The former Sears Tower, with the Skydeck and its glass-floored Ledge on the 103rd floor.
Harold Washington Library Must see
Chicago's central public library, a large 1991 building with owl-topped roof ornaments and a ninth-floor winter garden.
Soldier Field Must see
The lakefront stadium of the Chicago Bears, opened in 1924, with classical colonnades along its sides.
Cloud Gate Must see
Anish Kapoor's mirrored stainless-steel sculpture, known as 'the Bean', in Millennium Park, reflecting the skyline.
Navy Pier Must see
A long pier on Lake Michigan with a Ferris wheel, restaurants, boat tours and views back to the skyline.
Day 2
Hyde Park Art Center
Chicago's oldest alternative exhibition space, showing contemporary art in the Hyde Park neighbourhood.
John Hancock Center Must see
The 100-storey tapering black tower on the Magnificent Mile, now 875 North Michigan Avenue, with the 360 Chicago observation deck.
Wrigley Field Must see
The 1914 ballpark of the Chicago Cubs on the North Side, famous for its ivy-covered outfield walls.
Day 3
Buckingham Fountain Must see
A huge 1927 fountain in the centre of Grant Park, with water displays in the warmer months.
Field Museum of Natural History Must see
A large natural history museum on the lakefront, home of Sue, one of the most complete T. rex skeletons found.
Art Institute of Chicago
One of the oldest and largest art museums in the US, with Seurat, Hopper's Nighthawks, American Gothic and many Impressionists.
Day 4
Museum of Science and Industry
A huge science museum in Jackson Park, with a captured German U-boat and a replica coal mine.
Guaranteed Rate Field Must see
The South Side ballpark of the Chicago White Sox baseball team, opened in 1991.
Chicago in 5 days
Day 1
Willis Tower Must see
The former Sears Tower, with the Skydeck and its glass-floored Ledge on the 103rd floor.
Harold Washington Library Must see
Chicago's central public library, a large 1991 building with owl-topped roof ornaments and a ninth-floor winter garden.
Wrigley Field Must see
The 1914 ballpark of the Chicago Cubs on the North Side, famous for its ivy-covered outfield walls.
Day 2
Cloud Gate Must see
Anish Kapoor's mirrored stainless-steel sculpture, known as 'the Bean', in Millennium Park, reflecting the skyline.
Magnificent Mile
Michigan Avenue's mile of department stores, flagship shops and skyscrapers from the Chicago River to Oak Street, the city's main shopping promenade.
Museum of Contemporary Art, Chicago Must see
One of the largest contemporary art museums in the US, just off Michigan Avenue near the Water Tower.
Chicago Shakespeare Theater Must see
A professional theatre company with stages on Navy Pier, performing Shakespeare and other plays.
Navy Pier Must see
A long pier on Lake Michigan with a Ferris wheel, restaurants, boat tours and views back to the skyline.
Day 3
Soldier Field Must see
The lakefront stadium of the Chicago Bears, opened in 1924, with classical colonnades along its sides.
Field Museum of Natural History Must see
A large natural history museum on the lakefront, home of Sue, one of the most complete T. rex skeletons found.
Shedd Aquarium
A lakeside aquarium with beluga whales, dolphins, sharks and Amazon and coral-reef galleries, set in a neoclassical building near the Museum Campus.
Buckingham Fountain Must see
A huge 1927 fountain in the centre of Grant Park, with water displays in the warmer months.
Day 4
Chicago Riverwalk
A walkway along the main branch of the Chicago River, with cafés, boat tours and views of the architecture.
Chicago Water Tower Must see
A castle-like 1869 water tower on Michigan Avenue, one of the few buildings to survive the Great Chicago Fire of 1871.
Water Tower Place Must see
A vertical shopping mall on the Magnificent Mile, with shops on eight levels around an atrium.
John Hancock Center Must see
The 100-storey tapering black tower on the Magnificent Mile, now 875 North Michigan Avenue, with the 360 Chicago observation deck.
Day 5
Bank of America Theatre Must see
A 1906 theatre in the Loop, now named the CIBC Theatre, staging Broadway musicals and touring shows.
Oriental Theatre Must see
A 1926 movie palace on Randolph Street, now named the Nederlander Theatre, staging Broadway shows.
Chicago Theatre Must see
The 1921 movie palace on State Street, known for its vertical 'C-H-I-C-A-G-O' sign over the marquee.
Poetry Foundation Must see
The publisher of Poetry magazine, with a poetry library and exhibitions open to the public in its River North building.
Chicago in 6 days
Day 1
Willis Tower Must see
The former Sears Tower, with the Skydeck and its glass-floored Ledge on the 103rd floor.
Harold Washington Library Must see
Chicago's central public library, a large 1991 building with owl-topped roof ornaments and a ninth-floor winter garden.
Wrigley Field Must see
The 1914 ballpark of the Chicago Cubs on the North Side, famous for its ivy-covered outfield walls.
Day 2
Cloud Gate Must see
Anish Kapoor's mirrored stainless-steel sculpture, known as 'the Bean', in Millennium Park, reflecting the skyline.
Magnificent Mile
Michigan Avenue's mile of department stores, flagship shops and skyscrapers from the Chicago River to Oak Street, the city's main shopping promenade.
Museum of Contemporary Art, Chicago Must see
One of the largest contemporary art museums in the US, just off Michigan Avenue near the Water Tower.
Chicago Shakespeare Theater Must see
A professional theatre company with stages on Navy Pier, performing Shakespeare and other plays.
Navy Pier Must see
A long pier on Lake Michigan with a Ferris wheel, restaurants, boat tours and views back to the skyline.
Day 3
Soldier Field Must see
The lakefront stadium of the Chicago Bears, opened in 1924, with classical colonnades along its sides.
Field Museum of Natural History Must see
A large natural history museum on the lakefront, home of Sue, one of the most complete T. rex skeletons found.
Shedd Aquarium
A lakeside aquarium with beluga whales, dolphins, sharks and Amazon and coral-reef galleries, set in a neoclassical building near the Museum Campus.
Buckingham Fountain Must see
A huge 1927 fountain in the centre of Grant Park, with water displays in the warmer months.
Day 4
Chicago Riverwalk
A walkway along the main branch of the Chicago River, with cafés, boat tours and views of the architecture.
Chicago Water Tower Must see
A castle-like 1869 water tower on Michigan Avenue, one of the few buildings to survive the Great Chicago Fire of 1871.
Water Tower Place Must see
A vertical shopping mall on the Magnificent Mile, with shops on eight levels around an atrium.
John Hancock Center Must see
The 100-storey tapering black tower on the Magnificent Mile, now 875 North Michigan Avenue, with the 360 Chicago observation deck.
Day 5
Bank of America Theatre Must see
A 1906 theatre in the Loop, now named the CIBC Theatre, staging Broadway musicals and touring shows.
Oriental Theatre Must see
A 1926 movie palace on Randolph Street, now named the Nederlander Theatre, staging Broadway shows.
John J. Glessner House
H. H. Richardson's granite 1887 house on Prairie Avenue, a landmark of American architecture shown on guided tours.
Poetry Foundation Must see
The publisher of Poetry magazine, with a poetry library and exhibitions open to the public in its River North building.
Day 6
Guaranteed Rate Field Must see
The South Side ballpark of the Chicago White Sox baseball team, opened in 1991.
McCormick Place
The largest convention center in North America, on the lakefront south of downtown.
Arie Crown Theater
A large theatre inside the McCormick Place convention center, used for concerts and touring shows.
Chicago Theatre Must see
The 1921 movie palace on State Street, known for its vertical 'C-H-I-C-A-G-O' sign over the marquee.
Chicago in 7 days
Day 1
Willis Tower Must see
The former Sears Tower, with the Skydeck and its glass-floored Ledge on the 103rd floor.
Rookery Building
Burnham and Root's 1888 office block, with a light-filled interior court whose lobby Frank Lloyd Wright remodelled in white and gold in 1905.
Wrigley Field Must see
The 1914 ballpark of the Chicago Cubs on the North Side, famous for its ivy-covered outfield walls.
Lincoln Park Zoo
A free city zoo beside the lakefront, with gorillas, big cats and a small farm, easy to combine with a stroll through the park.
North Avenue Beach
A broad lakefront beach with beach volleyball, a boat-shaped beach house and the classic view of the downtown skyline.
Day 2
Cloud Gate Must see
Anish Kapoor's mirrored stainless-steel sculpture, known as 'the Bean', in Millennium Park, reflecting the skyline.
Magnificent Mile
Michigan Avenue's mile of department stores, flagship shops and skyscrapers from the Chicago River to Oak Street, the city's main shopping promenade.
Museum of Contemporary Art, Chicago Must see
One of the largest contemporary art museums in the US, just off Michigan Avenue near the Water Tower.
Chicago Shakespeare Theater Must see
A professional theatre company with stages on Navy Pier, performing Shakespeare and other plays.
Navy Pier Must see
A long pier on Lake Michigan with a Ferris wheel, restaurants, boat tours and views back to the skyline.
Day 3
Soldier Field Must see
The lakefront stadium of the Chicago Bears, opened in 1924, with classical colonnades along its sides.
Field Museum of Natural History Must see
A large natural history museum on the lakefront, home of Sue, one of the most complete T. rex skeletons found.
Shedd Aquarium
A lakeside aquarium with beluga whales, dolphins, sharks and Amazon and coral-reef galleries, set in a neoclassical building near the Museum Campus.
Buckingham Fountain Must see
A huge 1927 fountain in the centre of Grant Park, with water displays in the warmer months.
Day 4
Poetry Foundation Must see
The publisher of Poetry magazine, with a poetry library and exhibitions open to the public in its River North building.
Chicago Water Tower Must see
A castle-like 1869 water tower on Michigan Avenue, one of the few buildings to survive the Great Chicago Fire of 1871.
Gold Coast Historic District
Chicago's grandest residential streets, lined with 19th and 20th-century mansions and townhouses just north of the Loop, good for an architecture-spotting stroll.
Oak Street Beach
A curve of city sand on Lake Michigan below the Gold Coast, with the Chicago skyline behind it and a lakefront path alongside.
John Hancock Center Must see
The 100-storey tapering black tower on the Magnificent Mile, now 875 North Michigan Avenue, with the 360 Chicago observation deck.
Day 5
Harold Washington Library Must see
Chicago's central public library, a large 1991 building with owl-topped roof ornaments and a ninth-floor winter garden.
Chicago Cultural Center
A free 1897 civic building with a Tiffany glass dome, mosaic-lined staircases and rotating exhibitions and concerts, set just off Millennium Park.
Chicago Riverwalk
A walkway along the main branch of the Chicago River, with cafés, boat tours and views of the architecture.
Wicker Park
A lively neighbourhood of murals, record stores, vintage shops and cafés clustered around the Milwaukee, North and Damen intersection.
Day 6
Museum of Science and Industry
A huge science museum in Jackson Park, with a captured German U-boat and a replica coal mine.
Promontory Point
A landscaped limestone headland in Hyde Park jutting into Lake Michigan, with a clear skyline view across the water and a popular spot for picnics.
Robie House
Frank Lloyd Wright's Prairie-style masterpiece of long horizontal lines and art-glass windows, on the University of Chicago campus.
Chinatown, Chicago
South Side neighbourhood entered through the Chinatown Gate on Wentworth Avenue, lined with dim sum restaurants, bakeries and shops, with Ping Tom Memorial Park and its pagoda-style pavilion on the river nearby.
Day 7
Art Institute of Chicago
One of the oldest and largest art museums in the US, with Seurat, Hopper's Nighthawks, American Gothic and many Impressionists.
Millennium Park
Lakefront park in the Loop with Anish Kapoor's mirrored Cloud Gate, Gehry's bandshell, Crown Fountain and free summer concerts.
Watch: Chicago in 3 days
A one-minute look at the plan: every stop, day by day, with the map.
When to go to Chicago
May to June and September to October are the best months, with warm weather for the lakefront and the river. July and August are hot and humid, with festivals such as Lollapalooza in early August. Winter, from December to March, is very cold and windy, with snow, but hotel prices are low and the Christkindlmarket runs from late November to late December.
Plan the rest of your trip
- Where to stay: hotels in Chicago on Booking.com or Trip.com
- Skip-the-line tickets: museums and sights in Chicago on Tiqets
- Tours and day trips: things to do in Chicago on GetYourGuide or on Viator
- From the airport: a private transfer in Chicago with Kiwitaxi
- Sightseeing pass: save on Chicago's top attractions with Go City
- Data on arrival: an eSIM for United States from Airalo
- Last day: leave your bags in Chicago with Radical Storage and keep sightseeing
Some of these are affiliate links: we may earn a small commission at no extra cost to you.
Tips for Chicago
- Take an architecture boat tour on the Chicago River to see the skyline from the water.
- A Ventra card or a contactless bank card works on the 'L' trains and CTA buses.
- Book the Willis Tower Skydeck ahead and go on a clear day; queues can be long.
- The Field Museum, Shedd Aquarium and Adler Planetarium share the lakefront Museum Campus; plan them together.
- Winters are cold and windy by the lake; Navy Pier and the lakefront are best from late spring to early autumn.
Make it your own
Open the guide in Andiamo Places to see every stop on a map with walking directions, move places between days, check opening hours for your dates, and add your own finds. After the trip, your photos become a journal and, if you like, a printed photo book.
Guides are made with the help of AI and public sources such as Wikipedia, and may contain errors. Opening hours and prices change, so check before you go. Spotted a wrong photo, a pin in the wrong place, a missing stop or a better one? Write to andiamotravelapp@gmail.com: the e-mail opens with this guide filled in.
Photo credits
- Arie Crown Theater: RaymondBoyd51, CC BY-SA 3.0
- Art Institute of Chicago: ajay_suresh, CC BY 2.0
- Bank of America Theatre: Goldnpuppy, CC BY-SA 4.0
- Buckingham Fountain: Kkmd at English Wikipedia, CC BY-SA 3.0
- Chicago Cultural Center: ajay_suresh, CC BY 2.0
- Chicago Riverwalk: Victorgrigas, CC BY-SA 3.0
- Chicago Shakespeare Theater: Jason Zhang, CC BY-SA 3.0
- Chicago Theatre: Daniel Schwen, CC BY-SA 4.0
- Chicago Water Tower: Bernt Rostad, CC BY 2.0
- Chinatown, Chicago: Han Zheng, CC BY-SA 2.0
- Cloud Gate: Kapoor.jpg : team art in berlin derivative work: Torsodog ( talk ), CC BY-SA 2.0
- Field Museum of Natural History: Joe Ravi, CC BY-SA 3.0
- Gold Coast Historic District: (vincent desjardins) from Paris, France, CC BY 2.0
- Guaranteed Rate Field: redlegsfan21 from Vandalia, OH, United States, CC BY-SA 2.0
- Harold Washington Library: Ken Lund from Reno, Nevada, USA, CC BY-SA 2.0
- Hyde Park Art Center: unknown author, Public domain
- John Hancock Center: James Willamor from Raleigh, NC, USA, CC BY-SA 2.0
- John J. Glessner House: Prairieavenue at en.wikipedia, CC BY-SA 3.0
- Lincoln Park Zoo: Kenneth C. Zirkel, CC BY-SA 4.0
- Magnificent Mile: TonyTheTiger at English Wikipedia (Original text: en:User:TonyTheTiger), CC BY-SA 3.0
- McCormick Place: Jstennel, CC BY-SA 4.0
- Millennium Park: Ken Lund from Reno, Nevada, USA, CC BY-SA 2.0
- Museum of Contemporary Art, Chicago: User:JeremyA, CC BY-SA 2.5
- Museum of Science and Industry: zooey from Chicago, Illinois USA, CC BY 2.0
- Navy Pier: unknown author, Public domain
- Oak Street Beach: Chris6d, CC BY-SA 4.0
- Oriental Theatre: Alanscottwalker, CC BY 4.0
- Poetry Foundation: Alanscottwalker, CC BY-SA 3.0
- Promontory Point: Kim Scarborough, CC BY-SA 2.0
- Robie House: Teemu08, CC BY-SA 3.0
- Rookery Building: Marlene Calderon, CC BY-SA 3.0
- Shedd Aquarium: Sea Cow, CC BY-SA 4.0
- Soldier Field: unknown author, CC BY 2.0
- Water Tower Place: TonyTheTiger, CC BY-SA 3.0
- Wicker Park: David Hilowitz from San Antonio, USA, CC BY 2.0
- Willis Tower: Chris6d, Public domain
- Wrigley Field: Ryan Dickey, CC BY 2.0
Opening hours change; check before you go. Map data © OpenStreetMap contributors.
