Tours in Chicago

$35 for a Bike and Yoga Tour for One from Bike and Roll Chicago ($60 Value)

Bike and Roll Chicago

Millenium Park

Bike down the Lakefront Trail to various parks, where the surroundings will lend serenity to Vinyasa yoga classes

$60 $35

View Deal

$59 for Scavenger Dash for a Team of Two from Sierra Adventure Sports on Saturday, June 13 ($127.59 Value)

Sierra Adventure Sports

Citizen Bar

Teams of two traverse the streets of Chicago as they find clues, collect items, take pictures, and complete challenges

$127.59 $59

View Deal

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

View Deal

Wine and Cheese Tour of Chicago with 12 Tastings and Pairings from Great Food Tours (Up to 58% Off)

Great Food Tours

Great Food Tours

Stroll along the Magnificent Mile and through the Gold Coast as you sample 12 bites of cheese paired with sips of wine

$100 $49

View Deal

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

Waxwing Puzzle Co.

Waxwing Puzzle Company

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

$40 $20

View Deal

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

Tiki Party Boat

Island Party Boat

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

View Deal

Three-Hour Historical Bus Tour for Two or Four from Weird Chicago Tours (Up to 39% Off)

Weird Chicago Tours

Pick up location

Travel by bus to the former crime scenes, red-light districts, gangster hangouts, or ghost-sighting spots of Chicago’s storied past

$70 $45

View Deal

St. Patrick's Day Pub Crawl for Two or Four on March 13–17 from (Up to 56% Off)

Pub Crawl

Roadhouse 66

Three-day pub crawl celebrates St. Patrick’s Day with specials on domestic drafts and bottles, wells cocktails, and Irish whiskey shots

$40 $18

View Deal

Select Local Merchants

  • Chicago Sports Tour
    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]]
    Read More
    430 North Michigan Avenue
    Chicago, IL US
  • Sidewalk Food Tours of Chicago
    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.
    Read More
    222 W Merchandise Mart Plz.
    Chicago, IL US
  • Chicago Food Planet Food Tours
    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.
    Read More
    830 N Michigan Ave
    Chicago, IL US
  • Chicago Crime Tours
    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.
    Read More
    163 E Pearson St.
    Chicago, IL US
  • Chicago Pizza
    Wrap up your busy week with a signature pizza or custom pizza at Chicago Pizza. No need to miss out on Chicago Pizza just because you are avoiding fat or gluten. The pizzeria has tons of options that can accommodate your dietary needs. Have a few picky young eaters in the family? Not a problem at Chicago Pizza, where the food and ambience are perfect for family dining. null If cycling is more your speed, you'll find plenty of space to stash your bike outside the pizzeria. The grub at Chicago Pizza is also a downright bargain — most people can chow down for less than $15.
    Read More
    79 W Monroe St
    Chicago, IL US
  • Spice of Life Tours
    True to their name, Spice of Life Tours leads exciting expeditions into the diverse cultural landscape of West Rogers Park, Chicago. Their walking trips take visitors through Devon Avenue, an area rich with South Asian influence. Guests stop at numerous Pakistani or Indian eateries to sample local flavors, and explore boutiques. Along the way, company owner, guide, and teacher Mohammad Ali shares his knowledge about the neighborhood, pointing out unusual architecture and perhaps divulging the name of his favorite historian.
    Read More
    2541 W Devon Ave
    Chicago, IL US

Groupon Guide