Chicago Travel Guide

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3-day Itinerary in Chicago

Explore the best things to do in Chicago in 3 days based on recommendations from local experts.

Day 1

  • 1
    #7
    Art Institute of Chicago
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    #7 in Chicago
    Museums
    TYPE
    2 hours to Half Day
    TIME TO SPEND
    Museums
    TYPE
    2 hours to Half Day
    TIME TO SPEND

    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.

    The Art Institute of Chicago earns high praise from recent visitors, thanks in part to its impressive collection. Art enthusiasts particularly commend the museum's impressionist collection, which features pieces from famous artists like van Gogh, Monet and Renoir.

    10 minute walk
  • 2
    #2
    Millennium Park
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    #2 in Chicago
    Parks and Gardens, Sightseeing, Free
    TYPE
    1 to 2 hours
    TIME TO SPEND
    Parks and Gardens, Sightseeing, Free
    TYPE
    1 to 2 hours
    TIME TO SPEND

    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.

    There are plenty of other reasons to visit Millennium Park: You can see a concert at the Frank Gehry-designed Jay Pritzker Pavilion, stroll through the Lurie Garden or the Boeing Galleries (where contemporary sculpture is displayed outdoors), or sign up for a Segway tour at the McDonald's Cycle Center.

    15-25 minute walk
  • 3
    #11
    Chicago Architecture River Cruise
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    #11 in Chicago
    Sightseeing, Tours
    TYPE
    1 to 2 hours
    TIME TO SPEND
    Sightseeing, Tours
    TYPE
    1 to 2 hours
    TIME TO SPEND

    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.

    Though several companies, including Wendella Sightseeing Co. and Chicago Line Cruises, offer architecture river cruises, most travelers recommend climbing aboard a Chicago's First Lady Cruises boat with a Chicago Architecture Foundation docent. You'll learn tons of information about the area's architecture, plus catch superb skyline photo ops.

    15-25 minute walk
  • 4
    #4
    The Magnificent Mile
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    #4 in Chicago
    Cafes, Shopping, Free, Neighborhood/Area
    TYPE
    2 hours to Half Day
    TIME TO SPEND
    Cafes, Shopping, Free, Neighborhood/Area
    TYPE
    2 hours to Half Day
    TIME TO SPEND

    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.

    Architecture buffs will also appreciate a stroll down this street thanks to its eclectic collection of buildings. While you're walking around, turn your eyes upward for views of the Historic Water Tower, which survived the Great Chicago Fire of 1871 and is the longest standing structure on Michigan Avenue. Other structural highlights include the Wrigley Building (once the headquarters of chewing gum magnate William Wrigley Jr.) and Tribune Tower (home to the Chicago Tribune daily newspaper).

    5-15 minute walk
  • 5
    #9
    360 CHICAGO Observation Deck
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    #9 in Chicago
    Sightseeing
    TYPE
    1 to 2 hours
    TIME TO SPEND
    Sightseeing
    TYPE
    1 to 2 hours
    TIME TO SPEND

    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.

    For a different point of view (and an adrenaline rush), test out 360 CHICAGO's TILT. In this mechanized room, visitors hold on to handlebars as the top of the room's windows extend outward, tilting you toward bustling North Michigan Avenue down below. Should you prefer to experience the view without feeling your heart skip a beat, grab a cup of coffee, a glass of wine or a snack at the cafe and bar or look for souvenirs in the gift shop.

Day 2

  • 1
    #1
    Grant Park and Buckingham Fountain
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    #1 in Chicago
    Parks and Gardens, Recreation, Free
    TYPE
    Half Day to Full Day
    TIME TO SPEND
    Parks and Gardens, Recreation, Free
    TYPE
    Half Day to Full Day
    TIME TO SPEND

    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.

    At the heart of Grant Park is Buckingham Fountain. One of the largest fountains in the world, this tiered water feature boasts 133 jets that shoot water as high as 150 feet into the air during 20-minute choreographed displays (which take place every hour on the hour between 9 a.m. and 10:35 p.m. from April to October). At night, the fountain's performance is accompanied by lights and music.

    15-20 minute walk; 5 minutes by car
  • 2
    #8
    The Field Museum
    View all Photos
    #8 in Chicago
    Museums
    TYPE
    2 hours to Half Day
    TIME TO SPEND
    Museums
    TYPE
    2 hours to Half Day
    TIME TO SPEND

    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.

    Travelers say there's plenty to see in this museum, so allot at least a few hours here. Also, consider purchasing a Chicago CityPASS or a Go Chicago Card, which include admissions to the museum. The Chicago CityPASS also covers access to a 3-D film.

    5 minute walk
  • 3
    #14
    Shedd Aquarium
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    #14 in Chicago
    Zoos and Aquariums
    TYPE
    2 hours to Half Day
    TIME TO SPEND
    Zoos and Aquariums
    TYPE
    2 hours to Half Day
    TIME TO SPEND

    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.

    Though many travelers said they enjoyed their time at the aquarium, a few bemoaned the additional fees incurred here for parking, special exhibits and hands-on experiences. Lines to get into the aquarium are also known to get long, so it's best to purchase upgraded tickets online (general admission tickets are not available online) or arrive early.

    15 minutes by boat; 10-20 minutes by car
  • 4
    #6
    Navy Pier
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    #6 in Chicago
    Amusement Parks, Sightseeing, Free
    TYPE
    2 hours to Half Day
    TIME TO SPEND
    Amusement Parks, Sightseeing, Free
    TYPE
    2 hours to Half Day
    TIME TO SPEND

    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.

    But you don't have to be a kid to enjoy a visit to Navy Pier. Grown-ups can catch a show at the Chicago Shakespeare Theater, flex some credit card muscle at a variety of shops or grab a drink at the Miller Lite Beer Garden. And be sure to check Navy Pier's website for a list of events: Concerts are often held here, and during the summer (and New Year's Eve), impressive fireworks displays are the norm. In fact, many of the city's top Segway tours offer special summer evening tours to the pier to catch the semiweekly fireworks show.

    15-20 minutes by car
  • 5
    #15
    Skydeck Chicago
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    #15 in Chicago
    Sightseeing
    TYPE
    1 to 2 hours
    TIME TO SPEND
    Sightseeing
    TYPE
    1 to 2 hours
    TIME TO SPEND

    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.

    The highlight for most visitors is the Ledge. Extending beyond the building's exterior, this platform is made entirely of glass – even the floor. Travelers also liked the video screens that show what it would be like to stand 103 floors above other Chicago attractions, including Wrigley Field and Millennium Park. However, long lines quickly form for Skydeck Chicago, so plan on arriving early or purchasing a Chicago CityPASS, which covers Fast Pass admission into the attraction. Or, visit on a Saturday or Sunday and buy an Early Bird ticket to get into the Skydeck before it opens to the public.

Day 3

  • 1
    #12
    The Chicago Theatre
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    #12 in Chicago
    Entertainment and Nightlife, Sightseeing, Tours
    TYPE
    1 to 2 hours
    TIME TO SPEND
    Entertainment and Nightlife, Sightseeing, Tours
    TYPE
    1 to 2 hours
    TIME TO SPEND

    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.

    According to past patrons, the theater's historic appearance enhances the overall experience of catching an event here. If you're unable to score tickets to an event, travelers recommend participating in a one-hour theater tour, which are offered daily at noon (excluding Thanksgiving, Christmas and select event days) and take you through the lobby, into the theater and backstage. And remember, cameras and video cameras, including those on cell phones, cannot be used during tours or performances.

    10-15 minutes by car
  • 2
    #3
    Lincoln Park Zoo
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    #3 in Chicago
    Zoos and Aquariums, Free
    TYPE
    2 hours to Half Day
    TIME TO SPEND
    Zoos and Aquariums, Free
    TYPE
    2 hours to Half Day
    TIME TO SPEND

    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.

    Travelers appreciated all of the large mammal species found here, as well as the zoo's lack of an entrance fee. If you have kids in tow, head to the Farm-in-the-Zoo exhibit, where little ones can meet barnyard favorites like cows, pigs and goats. Also, plan on using public transportation or a taxi to get to the zoo since there's limited availability in the zoo's parking lot and parking fees start at $20 per vehicle (or $25 per vehicle on weekends) for 31 minutes to 2 hours of parking.

    10-15 minutes by car; 15-20 minutes by bus
  • 3
    #16
    Wrigley Field
    View all Photos
    #16 in Chicago
    Sports, Tours
    TYPE
    2 hours to Half Day
    TIME TO SPEND
    Sports, Tours
    TYPE
    2 hours to Half Day
    TIME TO SPEND

    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).

    Those who have been to a game at Wrigley Field say that the experience is unforgettable – mostly because of the fans' enthusiasm (though the hot dogs also receive a thumbs-up). If you can't score game tickets, consider signing up for a guided tour of the ballpark. Basic tours cost $25 per person and last 75 to 90 minutes. Past travelers who have taken the tour described the experience as nostalgic, noting that they especially loved the stories the guides told about the teams and fans. 

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