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1-Day Itinerary in Chicago

Explore the best things to do in Chicago in 1 day based on recommendations from local experts.

Day 1

#1

#1 in Chicago

Local Pick: Must-see ?
Home to one of the country's most impressive collections of impressionist and post-impressionist art (plus works from numerous other genres), the expansive Art Institute of Chicago features more than 300,000 works from all over the world in its permanent collection. You'll find pieces created in the Byzantine era, as well as paintings done just a few decades ago. The Art Institute's exhibits also include all sorts of intriguing artifacts, from European armor to the Thorne Miniature Rooms, which showcase interior design and furnishings in Europe and America from the late 13th to early 20th centuries. In addition to the permanent collection, the Art Institute hosts traveling exhibitions covering a variety of subjects and showcasing a diverse array of artists and genres.
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Museums Type
2 hours to Half Day Time to Spend
Art Institute of Chicago
Home to one of the country's most impressive collections of impressionist and post-impressionist art (plus works from numerous other genres), the expansive Art Institute of Chicago features more than 300,000 works from all over the world in its permanent collection. You'll find pieces created in the Byzantine era, as well as paintings done just a few decades ago. The Art Institute's exhibits also include all sorts of intriguing artifacts, from European armor to the Thorne Miniature Rooms, which showcase interior design and furnishings in Europe and America from the late 13th to early 20th centuries. In addition to the permanent collection, the Art Institute hosts traveling exhibitions covering a variety of subjects and showcasing a diverse array of artists and genres.
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10 minute walk

#3

#3 in Chicago

Local Pick: Must-see ? Free
A first-time visit to Chicago isn't complete without a stop at Millennium Park. Situated in the Loop just north of the Art Institute of Chicago, this 24.5-acre space is used to showcase cutting-edge art, architecture and landscaping; it also acts as a backdrop for concerts and festivals. Most visitors come to Millennium Park to see the Crown Fountain and Cloud Gate, better known as "The Bean." Designed by Spanish artist Jaume Plensa, the Crown Fountain features two 50-foot towers that face each other at opposite ends of a shallow reflecting pool. The towers' LED screens project the faces of 1,000 different Chicago residents, which are perfectly aligned with spouts so that it appears they are spitting water on passersby. Cloud Gate – created by British artist Anish Kapoor – is a 110-ton bean-shaped sculpture forged from stainless steel. The Bean's elliptical shape reflects the Chicago skyline.
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Parks and Gardens Type
1 to 2 hours Time to Spend
Millennium Park
A first-time visit to Chicago isn't complete without a stop at Millennium Park. Situated in the Loop just north of the Art Institute of Chicago, this 24.5-acre space is used to showcase cutting-edge art, architecture and landscaping; it also acts as a backdrop for concerts and festivals. Most visitors come to Millennium Park to see the Crown Fountain and Cloud Gate, better known as "The Bean." Designed by Spanish artist Jaume Plensa, the Crown Fountain features two 50-foot towers that face each other at opposite ends of a shallow reflecting pool. The towers' LED screens project the faces of 1,000 different Chicago residents, which are perfectly aligned with spouts so that it appears they are spitting water on passersby. Cloud Gate – created by British artist Anish Kapoor – is a 110-ton bean-shaped sculpture forged from stainless steel. The Bean's elliptical shape reflects the Chicago skyline.
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15-25 minute walk

#2

#2 in Chicago

Local Pick: Must-see ?
A visit to 360 CHICAGO or Skydeck Chicago will give you a good overview of the city's layout. But if you want to learn more about Chicago's sky-high buildings, tag along on an architecture river cruise. During a river cruise, you'll gain great views and historical insight about well-known structures like The Wrigley Building, the Leo Burnett Building and the Fulton House.
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Sightseeing Type
1 to 2 hours Time to Spend
Chicago Architecture River Cruise
A visit to 360 CHICAGO or Skydeck Chicago will give you a good overview of the city's layout. But if you want to learn more about Chicago's sky-high buildings, tag along on an architecture river cruise. During a river cruise, you'll gain great views and historical insight about well-known structures like The Wrigley Building, the Leo Burnett Building and the Fulton House.
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15-25 minute walk

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#8

#8 in Chicago

Local Pick: Recommended ? Free
If you can feel your credit card burning a hole through your wallet, make your way to The Magnificent Mile. This portion of Michigan Avenue – which stretches between Lake Shore Drive and the Chicago River – beckons to shopaholics with department stores and luxury retailers like Saks Fifth Avenue, Neiman Marcus, Macy's and Lord & Taylor. Additionally, The Magnificent Mile is home to several top-notch eateries and luxury hotels, including The Drake, a Hilton Hotel the Four Seasons Hotel Chicago and the InterContinental Chicago Magnificent Mile.
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Cafes Type
2 hours to Half Day Time to Spend
The Magnificent Mile
If you can feel your credit card burning a hole through your wallet, make your way to The Magnificent Mile. This portion of Michigan Avenue – which stretches between Lake Shore Drive and the Chicago River – beckons to shopaholics with department stores and luxury retailers like Saks Fifth Avenue, Neiman Marcus, Macy's and Lord & Taylor. Additionally, The Magnificent Mile is home to several top-notch eateries and luxury hotels, including The Drake, a Hilton Hotel the Four Seasons Hotel Chicago and the InterContinental Chicago Magnificent Mile.
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5-15 minute walk

#10

#10 in Chicago

Local Pick: Recommended ?
One of Chicago's most notable attractions is its skyline, and one of the best places to experience it is at the 360 CHICAGO Observation Deck. Formerly known as the John Hancock Observatory, 360 CHICAGO towers 1,000 feet over The Magnificent Mile from its location on the 94th floor of the John Hancock Center. Encased by floor-to-ceiling windows, 360 CHICAGO boasts expansive views of the city; on a clear day, you can see for 55 miles in any direction. Meanwhile, the interactive screens will help you identify different landmarks that appear in your panorama.
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Sightseeing Type
1 to 2 hours Time to Spend
360 CHICAGO Observation Deck
One of Chicago's most notable attractions is its skyline, and one of the best places to experience it is at the 360 CHICAGO Observation Deck. Formerly known as the John Hancock Observatory, 360 CHICAGO towers 1,000 feet over The Magnificent Mile from its location on the 94th floor of the John Hancock Center. Encased by floor-to-ceiling windows, 360 CHICAGO boasts expansive views of the city; on a clear day, you can see for 55 miles in any direction. Meanwhile, the interactive screens will help you identify different landmarks that appear in your panorama.
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