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Best Things To Do in Chicago

Chicago has all the offerings you'd expect from a major city: world-class museums, vibrant shopping districts and ample nightlife venues, just to name a few. If you're here to learn, plan to spend a fair amount of time in Grant Park: This area is home to such notable institutions as the Art Institute of Chicago and The Field Museum. For a more Windy City-centric education, start your vacation with an architecture river cruise – which can provide background on Chicago's famous skyscrapers like the Willis Tower and Tribune Tower – before exploring the city's innovative roots at the Museum of Science and Industry. Just save time for some of the city's quintessential experiences like catching a game at Wrigley Field and window-shopping along The Magnificent Mile.

How we rank Things to Do.

#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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#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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#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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#4

#4 in Chicago

Local Pick: Must-see ?
Shedd Aquarium is one of the world's largest indoor aquariums, housing around 32,000 creatures. While you're here, you can feel stingrays float beneath your fingers, listen to sea lions bark and learn all about a variety of turtles. A visit to Shedd Aquarium will lead you through a cornucopia of habitats, where you'll find additional animals like penguins, piranhas, sharks and beluga whales. Or, for an additional fee, you can participate in specialty experiences like animal encounters, feeding experiences and behind-the-scenes tours.
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Zoos and Aquariums Type
2 hours to Half Day Time to Spend
Shedd Aquarium
Shedd Aquarium is one of the world's largest indoor aquariums, housing around 32,000 creatures. While you're here, you can feel stingrays float beneath your fingers, listen to sea lions bark and learn all about a variety of turtles. A visit to Shedd Aquarium will lead you through a cornucopia of habitats, where you'll find additional animals like penguins, piranhas, sharks and beluga whales. Or, for an additional fee, you can participate in specialty experiences like animal encounters, feeding experiences and behind-the-scenes tours.
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#5

#5 in Chicago

Local Pick: Must-see ?
Any fan of "Saturday Night Live" knows that Chicagoans take their love of sports very seriously. So for a real taste of Chicago culture, head north of the Loop to Wrigley Field to see "da Cubs" play ball. History buffs will also appreciate this sports treasure, which was built in 1914 and holds the honor of being the second-oldest MLB ballpark in the country (after Fenway Park in Boston).
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Sports Type
2 hours to Half Day Time to Spend
Wrigley Field
Any fan of "Saturday Night Live" knows that Chicagoans take their love of sports very seriously. So for a real taste of Chicago culture, head north of the Loop to Wrigley Field to see "da Cubs" play ball. History buffs will also appreciate this sports treasure, which was built in 1914 and holds the honor of being the second-oldest MLB ballpark in the country (after Fenway Park in Boston).
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#6

#6 in Chicago

Local Pick: Recommended ? Free
Often referred to as "Chicago's front yard," Grant Park is a 319-acre swath of green space that starts at the eastern edge of the Loop and stretches down to the northern fringes of the Near South Side. First-time visitors should plan on spending a fair amount of time in Grant Park: This is where you'll find several of Chicago's most popular things to do, including The Field Museum, the Art Institute of Chicago and Shedd Aquarium. (Millennium Park also rubs elbows with the northwest corner of Grant Park.) Baseball diamonds, flower gardens, walking paths and wide-open grassy terrain are available as well.
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Parks and Gardens Type
Half Day to Full Day Time to Spend
Grant Park and Buckingham Fountain
Often referred to as "Chicago's front yard," Grant Park is a 319-acre swath of green space that starts at the eastern edge of the Loop and stretches down to the northern fringes of the Near South Side. First-time visitors should plan on spending a fair amount of time in Grant Park: This is where you'll find several of Chicago's most popular things to do, including The Field Museum, the Art Institute of Chicago and Shedd Aquarium. (Millennium Park also rubs elbows with the northwest corner of Grant Park.) Baseball diamonds, flower gardens, walking paths and wide-open grassy terrain are available as well.
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#7

#7 in Chicago

Local Pick: Recommended ?
This extensive natural history museum occupies half an acre of Grant Park's Museum Campus and houses extensive exhibits that showcase artifacts from multiple eras and destinations, making it a must-see for kids (as well as any fans of the "Indiana Jones" movies). Some of the most popular parts of the museum include the Inside Ancient Egypt exhibit, which features a reconstruction of a three-story Egyptian tomb and interactive representations of life on the Nile, and the Restoring Earth area in the Abbott Hall of Conservation, where visitors can learn more about sustainability through hands-on activities. But no visit to The Field Museum would be complete without some quality time with SUE, the facility's T. rex who just happens to be the largest, most complete T. rex ever discovered. Sue is 42 feet long from nose to tail and boasts 58 terrifying teeth.
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Museums Type
2 hours to Half Day Time to Spend
The Field Museum
This extensive natural history museum occupies half an acre of Grant Park's Museum Campus and houses extensive exhibits that showcase artifacts from multiple eras and destinations, making it a must-see for kids (as well as any fans of the "Indiana Jones" movies). Some of the most popular parts of the museum include the Inside Ancient Egypt exhibit, which features a reconstruction of a three-story Egyptian tomb and interactive representations of life on the Nile, and the Restoring Earth area in the Abbott Hall of Conservation, where visitors can learn more about sustainability through hands-on activities. But no visit to The Field Museum would be complete without some quality time with SUE, the facility's T. rex who just happens to be the largest, most complete T. rex ever discovered. Sue is 42 feet long from nose to tail and boasts 58 terrifying teeth.
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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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#9

#9 in Chicago

Local Pick: Recommended ? Free
Extending out onto Lake Michigan, Navy Pier offers plenty in the way of family-friendly entertainment. The first thing you'll spot once you set foot on the pier is the towering Ferris wheel (which stands 196 feet tall); you'll also find a swing-seat ride and a carousel. Once the kids have had their fill of thrill rides, you can spend some time practicing your putt at the 18-hole miniature golf course or spend a few hours exploring the Chicago Children's Museum, with hands-on exhibits ranging from treehouses to firetrucks.
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Amusement Parks Type
2 hours to Half Day Time to Spend
Navy Pier
Extending out onto Lake Michigan, Navy Pier offers plenty in the way of family-friendly entertainment. The first thing you'll spot once you set foot on the pier is the towering Ferris wheel (which stands 196 feet tall); you'll also find a swing-seat ride and a carousel. Once the kids have had their fill of thrill rides, you can spend some time practicing your putt at the 18-hole miniature golf course or spend a few hours exploring the Chicago Children's Museum, with hands-on exhibits ranging from treehouses to firetrucks.
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#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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#11

#11 in Chicago

Local Pick: Recommended ?
Chicago's extensive Museum of Science and Industry pays tribute to the city's innovative roots, showcasing more than 35,000 artifacts and a variety of hands-on exhibits meant to inspire creativity. The museum resides in the 14-acre former Palace of Fine Arts, which hosted the famous World's Columbian Exposition in 1893. The fair brought together some of the world's greatest scientific minds, including Thomas Edison and Nikola Tesla, who at the time were competing to prove which type of electricity – direct current or alternating current – was more effective.  
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Museums Type
2 hours to Half Day Time to Spend
Museum of Science and Industry
Chicago's extensive Museum of Science and Industry pays tribute to the city's innovative roots, showcasing more than 35,000 artifacts and a variety of hands-on exhibits meant to inspire creativity. The museum resides in the 14-acre former Palace of Fine Arts, which hosted the famous World's Columbian Exposition in 1893. The fair brought together some of the world's greatest scientific minds, including Thomas Edison and Nikola Tesla, who at the time were competing to prove which type of electricity – direct current or alternating current – was more effective.  
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#12

#12 in Chicago

Local Pick: Recommended ?
Nearly 2 million people make their way to Willis Tower's Skydeck Chicago each year, and it's easy to see why. Occupying the 103rd floor – that's nine floors higher than 360 CHICAGO – of the 110-story Willis Tower (the second-tallest building in North America after One World Trade Center), Skydeck Chicago boasts breathtaking views of the city. Visit on a sunny day and you may be able to see far beyond Chicago's borders to Indiana, Michigan, Wisconsin and other parts of Illinois.
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Sightseeing Type
1 to 2 hours Time to Spend
Skydeck Chicago
Nearly 2 million people make their way to Willis Tower's Skydeck Chicago each year, and it's easy to see why. Occupying the 103rd floor – that's nine floors higher than 360 CHICAGO – of the 110-story Willis Tower (the second-tallest building in North America after One World Trade Center), Skydeck Chicago boasts breathtaking views of the city. Visit on a sunny day and you may be able to see far beyond Chicago's borders to Indiana, Michigan, Wisconsin and other parts of Illinois.
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#13

#13 in Chicago

Local Pick: Recommended ? Free
Located 2 miles north of the Loop in the North Side neighborhood of Lincoln Park, the Lincoln Park Zoo is home to dozens of species, such as zebras, sloths and hippos. Visitors can view the zoo's furry (or scaly) friends in their natural habitats: Check out the gorillas in the sprawling Regenstein Center for African Apes, or head to the Kovler Seal Pool to get up close and personal with harbor seals.
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Zoos and Aquariums Type
2 hours to Half Day Time to Spend
Lincoln Park Zoo
Located 2 miles north of the Loop in the North Side neighborhood of Lincoln Park, the Lincoln Park Zoo is home to dozens of species, such as zebras, sloths and hippos. Visitors can view the zoo's furry (or scaly) friends in their natural habitats: Check out the gorillas in the sprawling Regenstein Center for African Apes, or head to the Kovler Seal Pool to get up close and personal with harbor seals.
... more
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#14

#14 in Chicago

Local Pick: If Time Allows ?
Aside from Cloud Gate and Buckingham Fountain, The Chicago Theatre's red and yellow marquee is perhaps one of the city's most recognizable landmarks. Illuminating North State Street at the northern edge of the Loop, The Chicago Theatre first opened its doors in 1921 as an extravagant movie theater and performance venue. Throughout its history, the theater has hosted such big names as Duke Ellington, Diana Ross and Lewis Black in addition to screening blockbuster flicks. Though the theater fell into disarray in the '70s, new management and a full renovation in the '80s helped return the venue to its former glory. Today, the theater is still used for a variety of comedic, theatrical and musical performances.
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Entertainment and Nightlife Type
1 to 2 hours Time to Spend
The Chicago Theatre
Aside from Cloud Gate and Buckingham Fountain, The Chicago Theatre's red and yellow marquee is perhaps one of the city's most recognizable landmarks. Illuminating North State Street at the northern edge of the Loop, The Chicago Theatre first opened its doors in 1921 as an extravagant movie theater and performance venue. Throughout its history, the theater has hosted such big names as Duke Ellington, Diana Ross and Lewis Black in addition to screening blockbuster flicks. Though the theater fell into disarray in the '70s, new management and a full renovation in the '80s helped return the venue to its former glory. Today, the theater is still used for a variety of comedic, theatrical and musical performances.
... more

Until relatively recently, notorious mobsters like Al Capone and John Dillinger were the characters who may have come to mind when someone mentioned the Windy City. Chicago Crime Tours takes visitors on a bus tour highlighting these gangsters' lives. The route weaves across the city, highlighting memorable crime scenes and educating travelers on Chicago history from the 19th century to modern times. There is also a walking tour option that includes samples of the city's famous pizza.
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Churches/Religious Sites Type
1 to 2 hours Time to Spend
Chicago Crime Tours
Until relatively recently, notorious mobsters like Al Capone and John Dillinger were the characters who may have come to mind when someone mentioned the Windy City. Chicago Crime Tours takes visitors on a bus tour highlighting these gangsters' lives. The route weaves across the city, highlighting memorable crime scenes and educating travelers on Chicago history from the 19th century to modern times. There is also a walking tour option that includes samples of the city's famous pizza.
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Free
Parks and Gardens Type
1 to 2 hours Time to Spend

The 606 Free

Free
Dividing Chicago's Logan Square and Humboldt Park neighborhoods, The 606 is a former industrial rail line that's been transformed into a nature trail and a public space. In addition to being an excellent place to enjoy the outdoors, the 2.7-mile-long park hosts an assortment of events and shows for visitors to experience.
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Parks and Gardens Type
1 to 2 hours Time to Spend
The 606
Dividing Chicago's Logan Square and Humboldt Park neighborhoods, The 606 is a former industrial rail line that's been transformed into a nature trail and a public space. In addition to being an excellent place to enjoy the outdoors, the 2.7-mile-long park hosts an assortment of events and shows for visitors to experience.
... more
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