Welcome to Chicago


Art & Architecture

It's hard to know what to gawk 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), pork-shoulder posole and garlicky yucca enchiladas for lunch (at Dove's Luncheonette) and fine dining on foraged foods for dinner (at Iliana Regan's Elizabeth). You can also chow down on a superb range of global eats from Vietnamese pho to Mexican carnitas, Polish pierogi and Macanese fat rice. Still hungry? Order a late-night deep-dish pizza or seek out a hot and spicy Italian beef sandwich at a local fast-food joint.

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.

Recent articles

Travel guides

Starting at $13.99

Image for Image for

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 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.Please note: all tours through March 31, 2019 are 60 minutes in length.  All tours beginning April 1, 2019 are 75 minutes in length.

$19 Kid Friendly

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

ItineraryHop On Hop Off TourRoute Duration: 2 hoursStops on the Hop On Hop Off Tour:ChicagoAttractions on the Hop On Hop Off Tour:Skydeck Chicago - Willis Tower / The Loop / The Magnificent Mile / 360 Chicago Observation Deck / Navy Pier / The Chicago Theatre / Adler Planetarium / The Art Institute of Chicago / Shedd Aquarium / The Field MuseumOperates: Hop On Hop Off Schedule May 1-19: Every 30 minutes May 20-September 29: Every 15 minutes September 30-November 2: Every 30 minutes

$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.

$108 Sightseeing Tickets & Passes

Chicago CityPASS, with Shedd Aquarium, Skydeck Chicago

Visit: Shedd Aquarium, Chicago, IllinoisGet ready for unforgettable encounters with belugas and bluegills, stingrays and sturgeons, sea stars and sea otters—and so many more animals from aquatic environments around the world! See penguins fly through chilly waters, alligators bask on a riverbank and monkeys scamper through rainforest trees. At Shedd, you can look nature in the eye, reach out and touch it, investigate and discover. And get ready for beauty that surprises, mesmerizes, inspires and moves you!Duration: 4 hoursVisit: Skydeck Chicago - Willis Tower, Chicago, IllinoisTreat yourself to unparalleled 360-degree views of up to four states from the top of the world-renowned Willis Tower (formerly Sears Tower), the Western Hemisphere’s second-tallest building. Take a deep breath and step out onto The Ledge – glass floor balconies 103 floors over Chicago! Complete your visit with interactive exhibits, photo ops and a movie about Willis Tower’s rise to prominence.Duration: 3 hoursVisit: The Field Museum, Chicago, IllinoisSee the world’s wonders at the Field Museum. Experience SUE, the largest, most complete, and best-preserved Tyrannosaurus rex ever discovered, descend into an ancient Egyptian tomb, and explore over 10,000 years of Chinese history and culture. With 4.6 billion years in one place, you’ll be taken around the world and back in time.Duration: 4 hoursVisit: Adler Planetarium, Chicago, IllinoisExplore space at America’s first planetarium! Experience hands-on, minds-on activities and discover mind-blowing facts about the Universe. With two domed theaters, 60,000 square feet of exhibitions and the Doane Observatory’s research quality telescope, spend a day seeing why “Space is Freaking Awesome.”Duration: 4 hoursVisit: The Art Institute of Chicago, Chicago, IllinoisView the greatest Impressionist collection outside Paris. Stand before classics like Van Gogh’s Self-Portrait, and travel the globe through galleries featuring the art of ancient Greece, Japan, Africa, and the Americas.Duration: 3 hoursVisit: Museum of Science and Industry, Chicago, IllinoisExplore mind-blowing exhibits at MSI, the largest science museum in the country — it’s unlike any museum you have ever seen.Duration: 3 hoursVisit: 360 Chicago Observation Deck, Chicago, IllinoisExperience breathtaking 360-degree views of Chicago’s skyline and lakefront and four neighboring states from 1,030 feet above The Magnificent Mile. Enhance your visit with interactive multimedia exhibits and learn about the city’s history, architecture, natural scenery and culture.Duration: 3 hours

$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.