Tours in Chicago

$12 for a Two-Hour Guided Walking Tour from the Chicago Architecture Foundation ($20 Value)

Chicago Architecture Foundation

CAF Shop & Tour Center

Stroll past Chicago icons designed by renowned architects such as Frank Lloyd Wright, Daniel Burnham, Louis Sullivan, and Frank Gehry

$20 $12

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Two or Four Tickets to a Tour of the Frank Lloyd Wright Home and Studio or Frederick C. Robie House (50% Off)

Frank Lloyd Wright Trust

Multiple Locations

Guided tour of one of two local architectural marvels that stand as seminal works in Frank Lloyd Wright’s legendary career

$34 $17

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$50 for a Taste of the Pedway Tour or Pedway Brunch Tour for Two from Chicago's Finest Tours ($100 Value)

Chicago's Finest Tours

The Loop

Guests enjoy food samples or a full buffet while exploring the Pedway’s network of heated tunnels and sky bridges between landmarks

$100 $50

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Italian Food Tour of Chicago with Five Tastings for One, Two, or Four from Great Food Tours (Up to 60% Off)

Great Food Tours

Chicago

Sample Chicago-style pizza, italian beef, and artisan products during a two-hour Italian-food tour along the Magnificent Mile

$50 $26

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"Speakeasy" Social Game Experience for One, Two, Four, or Eight at Waxwing Puzzle Co. (Up to 57% Off)

Waxwing Puzzle Co.

Lincoln Square

Players take part in a role-playing event that is set in the prohibition era and pulls from mob folklore

$40 $20

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$39 for a Two-Hour Wednesday-Night Fireworks Cruise from Island Party Boat ($75 Value)

Island Party Boat

Chicago

Take in fireworks lighting up the Chicago skyline on an island-themed 50-foot boat equipped with a sundeck, lounge, and premium sound system

$75 $39

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$69 for a Segways at Sunset Tour for Two from Bike and Roll Chicago (Up to $138 value)

Bike and Roll Chicago

Millennium Park

Easily maneuverable segway vehicles traverse the lakefront for views of the Chicago skyline, parks, and lakeside museums

$138 $69

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Select Local Merchants

The bronze likeness of Michael Jordan—the Bulls' #23 and basketball's undisputed king—leaps into the air in front of the United Center, ascending into the annals of sports history. Across town, the sound of Babe Ruth's most famous homer rebounds off of the iconic walls of Wrigley Field. The Roman-meets-modern architecture of Soldier Field—where Walter Payton, Mike Ditka, and "The Fridge" grew to larger-than-life—straddles Chicago's lakefront. The resounding Black Sox scandal clashes with the victorious 2005 World Series Champs banners at U.S. Cellular Field, where the White Sox's famous exploding scoreboard towers above the Bridgeport neighborhood.

During an air-conditioned bus ride, local comedians wax historic as tourists are brought within earshot and camera-shot of Chicago's proudest pro-sports franchises. The Chicago Sports Tour parades from the North to the South side, brushing shoulders with famous ballparks and weaving through more than a century of athletic anecdotes and civic pride. Augmented by laughs and entertainment, it reveals more than the brick-and-mortar façades of the famous stadiums. The guides bring each building to life with fascinating anecdotes, and rides from one stadium to the next cover neighborhoods such as Wrigleyville, Bridgeport, and Little Italy—where fans and players alike eat, drink, and argue about their favorite peanut vendors.:m]]

430 North Michigan Avenue
Chicago,
IL
US

Sidewalk Food Tours of Chicago introduces tourists and locals to the Windy City's thriving food scene via deep-dish pizzas, hot dogs, and ethnic cuisine. Two neighborhoods in particular brim with famous restaurants and hidden eateries: Wicker Park and River North.

On their streets, Sidewalk Food Tours of Chicago's local guides lead groups on walking explorations, pausing frequently to taste everything from cupcakes to Top Chef Masters winner Rick Bayless's Mexican cuisine. Food stands at the crossroads of each neighborhood's culture, and the guides use it as a jumping off point to discuss local history and architecture. They might spin tales of how Wicker Park was once a hotbed of European immigration or how River North accumulated a wealth that would make John D. Rockefeller's piggy bank tremble with envy.

222 W Merchandise Mart Plz.
Chicago,
IL
US

A truly innovative concept, Chicago Food Planet Tours offer a taste of Chicago like none other. If you are on a timeline and can’t decide which incredible restaurant to try, then try a bit of each with Chicago Food Planet. Pay a flat fee and they will escort you on a tasting menu like none other. Enjoy a small plate at every restaurant on the tour alongside demonstrations and explanations from knowledgeable chefs and staff. Tours are themed by Chicago districts from Chinatown to Gold Coast and Old Town. Don’t feel like being social? Book a private tour of your selection! An absolutely fantastic deal (you’re really getting a lot of bang for your buck here, guys) try out a tour with Chicago Food Planet.

830 N Michigan Ave
Chicago,
IL
US

Millennium Trolley Tours offers the only way to explore Chicago like a Californian. The tour company takes customers throughout historical and popular city areas aboard San Francisco-style trolley cars that mirror the aesthetic of the city's iconic rail transports. While traveling to various Chicago hot spots, such as the Theatre District or the Hancock Building, tour guides share historical facts about the city and its landmarks. Though you can stay aboard the trolley for the entire one-hour, 45-minute tour, passengers can also hop off to explore areas of interest, and hop back on to avoid walking on the city’s numerous hot-coal sidewalks.

440 N Wabash suite 2307
Chicago,
IL
US

Specially designed to slip effortlessly under the Potomac's low bridges, the Odyssey III has been constructed with transparent walls and open decks for hosting elegant cruises that drift by some of Washington's most scenic vistas. Cruises take advantage of the yacht?s glass windows, passing by the neoclassical splendor of the Lincoln Memorial or drifting under an illuminated night sky on full-moon cruises. Lunch, dinner, and brunch outings serve guests with delectable multicourse meals. Live music accompanies evening cruises, meaning guest can hit the boat's dance floor and show off their Nobel Prize?winning dance moves before night?s end.

600 E Grand Ave.
Chicago,
IL
US

Chicago?s beautiful architecture and pristine parks stretch like a thin, deceptively pretty layer of varnish over the city?s storied criminal history. The guides at Chicago Crime Tours peel back the fa?ade to reveal the city?s darkest days, replete with visits to crime scenes and tales of some of Chicago?s most dastardly villains. Groups explore the hideouts of Al Capone left in the wake of mob shootouts. The guides? catalog of criminal knowledge reaches all the way back to city?s infancy in the 19th century and includes such tales as the Saint Valentine?s Day Massacre and the great baby-rattle heist of 1870.

163 E Pearson St.
Chicago,
IL
US

Groupon Guide