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How to Spend 3 Days in Chicago

How to Spend 3 Days in Chicago

From skyscrapers to museums to vibrant neighborhoods to public parks, Chicago has something for everyone, and three days is more than enough time to explore its highlights. Travel by bus, bike, or on foot; linger in the bustling Loop; or head out of town on a day trip. Here’s how to plan your 3-day Windy City itinerary.

 

Day 1: Chicago’s Top Attractions

Explore Chicago’s most popular landmarks, many of which are concentrated in the Loop neighborhood, including Millenium Park and the Willis Tower Skydeck. Bus and bicycle tours of the area make it possible to see more in less time, while a hop-on hop-off bus itinerary offers a seamless overview of the city (plus the chance to disembark where and when you wish). Alternatively, combine your Loop adventures with a trip to another part of town. Catch an afternoon Cubs game at Wrigley Field on the North Side, or head to the South Side to explore Chinatown.

 

Day 2: Museums, Architecture, and Other Historical Highlights

Learn about Chicago’s past on an architecture tour—hop aboard a riverboat and cruise all three branches of the Chicago River, spotting highlights such as the Tribute Tower and the Merchandise Mart as you go, or head off on an intimate walking tour to view landmarks firsthand. Then, delve into Chicago’s esteemed museums, including the Field Museum of Natural History, Museum of Science and Industry, and the Art Institute of Chicago.

 

Day 3: Chicago Area Day Trip

Frank Lloyd Wright, a longtime Chicago resident and one of the 20th century’s most celebrated architects, designed a number of buildings in the Chicago area. Discover some of his best-known works on a day trip to the Frank Lloyd Wright Home and Studio in Oak Park, a village located just beyond Chicago’s western edge. Here you'll discover where the architect lived and worked for the first two decades of his career, and where he developed his signature Prairie School style. Oak Park’s other architectural gems include the Frank Lloyd Wright Historic District, Unity Temple, and the Arthur B. Heurtley House.

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10 Tours and Activities | All Chicago Tours

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Chicago Architecture River Cruise

Chicago Architecture River Cruise

star-5
Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).
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  • 1 hour
  • Free Cancellation
  • Taking safety measures
From
$38.85
From
$38.85
Taking safety measures

Go Chicago Explorer Pass with SkyDeck and 360 Chicago

Go Chicago Explorer Pass with SkyDeck and 360 Chicago

star-4.5
The easiest and most affordable way to explore some of Chicago's top attractions at your own pace, the Go Chicago Explorer Pass saves you up to 45 percent on regular ticket prices. Create your own sightseeing itinerary by choosing 2, 3, 4, or 5 attractions, tours, and activities from among more than 30 top sites, including SkyDeck, 360 Chicago, the Field Museum, a shoreline sightseeing cruise, a hop-on hop-off Big Bus tour, Lincoln Park Zoo, Navy Pier, and LEGOLAND® Discovery Center. Please note: Enjoy the extra flexibility in case your travel plans need to change: All passes (purchased by December 31) are valid for two year from purchase date and only become activated with your first attraction visit. After activation your pass will be valid for 60 days and/or the remaining number of attraction choices purchased.
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  • 60 days
From
$66.00
From
$66.00

Chicago Grand Half-Day Bus Tour

Chicago Grand Half-Day Bus Tour

star-3.5
Get the perfect introduction to the wealth of sights in the Windy City during this 4-hour Chicago day tour. Discover the many landmarks spanning both the city's North Side and South Side, enjoying a scenic ride along Lake Michigan on Chicago's Outer Drive along the way. You'll also have the chance to admire the city's Washington and Grant Parks, explore inside the Lincoln Park Conservatory, see Adler Planetarium and visit the iconic Wrigley Building. This Chicago in a half day tour also includes transport between all sites and tour narration.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$52.95
From
$52.95
Taking safety measures

Chicago South Side Tour with Optional River Cruise

Chicago South Side Tour with Optional River Cruise

star-4.5
See the landmarks of Chicago’s South Side on a 2-hour coach tour through this historic, diverse and culturally-rich neighborhood. Take in views of Jackson Park and the University of Chicago, pause at the foot of the stunning Lake Point Towers then watch the bustling crowd at Navy Pier. Get a glimpse of American history as you explore President Obama’s former neighborhood and see the President and First Lady’s home; with an optional upgrade, you can finish your trip with a scenic cruise along the Chicago River.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$34.95
From
$34.95
Taking safety measures

Chicago Grand Tour and Admission to 360 Chicago (formerly John Hancock Observatory)

Chicago Grand Tour and Admission to 360 Chicago (formerly John Hancock Observatory)

star-3.5
This Chicago grand tour covers four hours of sightseeing with admission to 360 Chicago (John Hancock Observatory). Get oriented to the Windy City on a coach tour that takes you along a scenic route on Lake Shore Drive, and past North Side and South Side highlights including Museum Campus, Lincoln Park, Washington Park, Grant Park and Wrigley Field. Finish on the 94th floor of the Hancock Center, one of Chicago's tallest landmarks, for panoramic views of the Magnificent Mile from the open-air observation deck.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$73.95
From
$73.95
Taking safety measures

Chicago North Side Tour

Chicago North Side Tour

star-4.5
Explore the North Side of Chicago on this guided sightseeing tour by coach. During this 2-hour tour, experience the bustle of the Loop, the central business district and one of the financial centers of the country. Visit State Street, an important thoroughfare in Chicago's history and the Magnificent Mile along Michigan Avenue. Learn about the history and culture of the city from your local guide; upgrade your tour to include a Chicago River cruise.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$34.95
From
$34.95
Taking safety measures

Chicago Lakefront and Museum Campus Small-Group Segway Tour

Chicago Lakefront and Museum Campus Small-Group Segway Tour

star-5
Experience Chicago like never before on this small-group Segway tour. Visit Chicago’s ‘front yard,’ the beautiful lakefront and 57-acre Museum Campus. Glide along the fragrant floral paths to famous Buckingham Fountain. Then travel along the banks of Lake Michigan, past Monroe Harbor to the Museum Campus for a breathtaking view of the city’s iconic skyline. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.
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  • 2 hours 30 minutes
  • Free Cancellation
From
$79.06
From
$79.06

Small-Group Chicago Food Tour of Chinatown

Small-Group Chicago Food Tour of Chinatown

star-5
Sample different styles and varieties of Chinese food during this gourmet walking tour of Chicago's Chinatown. Follow your local food-loving guide through one of the oldest Chinese neighborhoods in the country to taste several Chinese regional delicacies. The price of this small-group tour, limited to 12 people, includes tastings at restaurants; enough food to add up to a full lunch.
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  • 3 hours
  • Free Cancellation
From
$80.00
From
$80.00

Chicago Bike Rental

Chicago Bike Rental

star-5
Discover Chicago's many delights from the comfort of two wheels. Simply pick up your full-day bike rental with lock, map and helmet and start exploring, either solo or with friends. Make your way through Millennium Park and to historic Wrigley Field, stop for a visit at Navy Pier or spend a couple hours watching sea turtles, penguins and even a piranha at Shedd Aquarium. You get to tour Chicago independently at your own pace and leisure without having to deal with parking or public transit.
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  • 1 day
  • Free Cancellation
  • Taking safety measures
From
$25.99
From
$25.99
Taking safety measures

2-Hour History of Chicago Architecture and Art Segway Tour

2-Hour History of Chicago Architecture and Art Segway Tour

star-5
Explore the art and architectural highlights of Chicago on a Segway during this guided tour. This family-friendly tour takes visitors by the outdoor sculptures, landmark buildings, and iconic skyline of the city. Accompanied by educational and informative commentary, this city tour saves you from hours of walking and lets you see all of Chicago's top art and architectural attractions in one tour.
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  • 2 hours
  • Free Cancellation
From
$75.10
From
$75.10


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