Welcome to Chicago


Art & Architecture

It's hard to know what to gawp at first. High-flying architecture is everywhere, from the stratospheric, glass-floored Willis Tower to Frank Gehry's swooping silver Pritzker Pavilion to Frank Lloyd Wright's stained-glass Robie House. Whimsical public art studs the streets; you might be walking along and wham, there's an abstract Picasso statue that's not only cool to look at, but you're allowed to go right up and climb on it. For art museums, take your pick: impressionist masterpieces at the massive Art Institute, psychedelic paintings at the mid-sized Museum of Mexican Art or outsider drawings at the small Intuit gallery.

Chowhounds' Delight

Loosen your belt – you've got a lot of eating to do. On the menu: peanut-butter-and-banana-topped waffles for breakfast (at Stephanie Izard's Little Goat), a chicken, apple and cranberry hot dog for lunch (at Hot G Dog), and 20 courses of centrifuged, encapsulated molecular gastronomy for dinner (at Grant Achatz' Alinea). You can also chow down on a superb range of ethnic eats from Vietnamese pho to Mexican carnitas, Polish pierogi and Macanese fat rice. Still hungry? Order a late-night deep-dish pizza.

Sports Fanatics

Chicago is a maniacal sports town, with a pro team for every season (two teams, in baseball's case). Watching a game is a local rite of passage, whether you slather on the blue-and-orange body paint for a Bears football game, join the raucous baseball crowd in Wrigley Field's bleachers, or plop down on a bar stool at the neighborhood tavern for whatever match is on TV. Count on making lots of spirited new friends. Should the excitement rub off and inspire you to get active yourself, the city's 26 beaches and 580 parks offer a huge array of play options.

Rollicking Festivals

Chicago knows how to rock a festival. Between March and September it throws around 200 shindigs. The specialty is music. Blues Fest brings half a million people to Millennium Park to hear guitar notes slide and bass lines roll, all for free. During the four-day Lollapalooza mega-party, rock bands thrash while the audience dances in an arm-flailing frenzy. Smaller, barbecue-scented street fests take place in the neighborhoods each weekend – though some rival downtown for star power on their stages (oh, hey, Olivia Newton-John at Northalsted Market Days).


Top experiences in Chicago

Amazing hotels and hostels

We've pre-picked the best hotels, hostels and bed and breakfasts to make your stay as enjoyable as possible.

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Chicago activities

$41.44 Cruises, Sailing & Water Tours

Chicago Architecture 75-Minute River Cruise Guided Tour

Take an architecture cruise down the Chicago River and learn about the city’s famed architecture from your knowledgeable guide. Board your tour at Navy Pier for an exciting journey that takes you down all three branches of the historic Chicago River and past impressive architectural landmarks. Pass by more than 40 distinctive buildings on your cruise including the John Hancock Center, the Wrigley Building, the Aon Center, Willis Tower (Sears Tower), the IBM Building and more. Your guide, an expert in architecture, will recount the two major events that helped shape the architectural history of the city. Learn about how the invention of balloon-frame construction revolutionized how homes were built, and hear the dramatic story of Chicago's rise from the Great Fire of 1871. Both of these milestones led Chicago to become one of the cradles of modern American architecture.Along the scenic 75-minute route, see buildings by world-famous architects including Mies van der Rohe, Helmut Jahn and Skidmore, Owings and Merrill (SOM). This river tour provides the best advantage point to admire the distinct city skyline and marvel at world-famous architecture while learning about Chicago's fascinating history.For a full list of Chicago architectural wonders seen on this tour, see the Itinerary section below.

$30.99 Tours & Sightseeing

Chicago City Hop-On Hop-Off Bus Trolley Tour Pass

Your narrated trolley (heated in winter) or double-decker bus will tour 14 magnificent miles of Chicago's downtown areas including The Loop, The Magnificent Mile and River North, taking you by the city's premier shopping, dining and attractions. The tour is about two hours if you do not hop off. During the summer, your ticket includes the Night Tour and Wrigley Field/Lincoln Park Zoo Tour. These tours will return in Spring 2019. With a foreign language app available, you can choose to have the tour narrated in your choice of German, Chinese, Spanish, or Portuguese. Once you purchase your ticket, you can download the mobile app and select your language preference.

$22 Sightseeing Tickets & Passes

Skydeck Chicago Admission

Marvel at Chicago from an unparalleled viewpoint during this exciting Skydeck experience. Located in Willis Tower, formerly Sears Tower, the Skydeck offers spectacular sweeping vistas of Chicago and beyond from the 103rd floor. Walk out onto the Ledge, a glass box-like balcony that extends 4.3 feet (1.3 meters) from the building, and experience an unconventional view--straight-down! Admire the lofty views of top Chicago attractions, like Wrigley Field, the Navy Pier and Millennium Park, all from a breathtaking height of 1,353 feet (412.4 meters). On a clear day, you can see up to 50 miles (80.5 km) out! It’s also the perfect vantage point for great sunset and twinkling nightscape views. Bring your camera or treat yourself to a professional photo available at the gift shop.You can also explore several exhibits designed for the whole family, like interactive digital floor displays, touch-screen activities, and scavenger hunts that not only highlight Chicago's iconic landmark, but also celebrate the Windy City's sports, architecture, pop culture, history, food, music, and people. Challenge yourself with a Chicago trivia game, compare the heights of the tallest structures in the world, and see just how many of your bodies it would take to reach the height of Willis Tower.

$106 Sightseeing Tickets & Passes

Chicago CityPASS, with Shedd Aquarium, Skydeck Chicago

Chicago CityPASS® tickets include prepaid admission to five of Chicago’s must-see attractions and saves the traveler 51% off the price of the same tickets purchased separately. Extra perk: CityPASS travelers skip most main-entrance ticket lines. Spend less, experience more.   Buy now and save 51%  CityPASS tickets are valid for nine consecutive days, beginning with the first day of use.  Admission includes:   Shedd Aquarium – VIP entry, all permanent exhibits, animal presentations, special exhibit, and Stingray Touch (May-Oct), plus a 4-D Experience. Special exhibit subject to change. 4 D Experience and animal presentation are subject to availability Skydeck Chicago – Fast Pass Admission and The Ledge Field Museum – All-Access Pass (admission to all permanent and regularly-priced ticketed exhibitions, and your choice of one digital 3D film). Film selection subject to availability. Additional charges may apply for specially ticketed exhibitions outside of the All Access Pass. Option Ticket 1: Adler Planetarium – Unlimited VIP access to all available shows, including the latest sky show, Planet Nine, exhibitions and experiences, like the historic Atwood Sphere. OR Art Institute of Chicago – Fast Pass Admission to permanent collection and non-ticketed special exhibitions; includes audio tour. Option Ticket 2: Museum of Science and Industry, Chicago – Museum Entry (Science Storms, U-505 Submarine exhibit, YOU! The Experience, and more), PLUS ONE timed-entry experience (Giant Dome Theater film, Fab Lab, or Coal Mine tour) AND a Motion Simulator Ride. (Excludes the U 505 On board tour and other special exhibitions or experiences) OR 360 CHICAGO Observation Deck – Express Entry Admission

$70.85 Tours & Sightseeing

Chicago Segway Tour

The tour begins with a 30 minute training session. You'll glide from the peninsula through Museum Campus to the Shedd Aquarium and the Field Museum. Then you'll cruise along Lakeshore Drive at the edge of Lake Michigan all the way to Millennium Park at the foot of famous Michigan Avenue. You'll see Navy Pier, the Lincoln statue, Buckingham Fountain and of course, ride the coolest machine in the world the entire time! As you cruise along Lake Michigan, through Grant Park and the Museum Campus, you will receive a great orientation, informative historical and current-day information, heaps of unique and fascinating stories, fantastic photo ops and superb personal service from your guide. The Segway is the first of its kind - a self-balancing, personal transportation device that's designed to operate in any pedestrian environment. It's new, it's cool and a ton of fun! Tours are limited to 8 clients with 1 guide so you can count on a great, intimate experience. Discover what it's like to be a Windy City celebrity as everyone turns to watch you glide by! City Segway Tours are proud to be the first guided tour using Segways in the world! No one can match their experience. Be sure you glide with the original! All riders must be at least 12 years of age to participate.

$39.95 Cultural & Theme Tours

Chicago Criminals, Mobsters and Gangsters Bus History Tour

Meet your guide across from the Water Tower Place shopping mall in Chicago’s Near North Side at your selected time. Hop aboard a luxury climate-controlled coach and begin your 1.5-2 hour tour of the history of Chicago crime, from 19th century to today. Your guide will share the lawless history of Chicago’s criminals, gangsters and mobsters as you explore the city’s most famous crime scenes. Your tour takes you through River North, the Gold Coast, Lincoln Park, Old Town, the Loop and Magnificent Mile. Hear fascinating stories about Al Capone, The Untouchables, the Chicago Mob, John Dillinger, ‘Terrible’ Tommy O'Conner, Leopold and Loeb and ‘Cap’ George Streeter, all who made their notorious criminal mark on Chicago. Grab your camera for a ‘drive-by shooting’ of the historic criminal courthouse, an architectural landmark where some of Chicago's most famous cases were tried. Stake out crime scenes including the Biograph Theatre, Holy Name Cathedral, and see the site of the 1929 St Valentine's Day Massacre, one of Chicago's most notorious murder scenes. This Prohibition-era conflict between two powerful Chicago gangs -- the South Side gang led by Al Capone and the North Side gang led by Bugs Moran -- ended in the brutal murder of seven Mob members. In addition to your comfortable, narrated drive through the city, you’ll also hop off the coach to visit some areas by foot for a more immersive experience. Your guide will offer in-depth narration as you follow the path that Chicago gangsters John Dillinger and Hymie Weiss walked right before their deaths. Hop back on the coach and return to the Near North Side to conclude your Chicago crime and gangsters tour.