Top Chicago Food, Wine & Nightlife

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Chicago Helicopter Tour Nighttime Experience

• 3 Reviews
• Soar above the city lights of Chicago on a 15-minute nighttime helicopter ride with live narration by experienced pilots. Enjoy birds-eye views of downtown landmarks, then bank past Navy Pier to Lincoln Park and Uptown. Hear about the history of the city as you take in unforgettable views of downtown’s bristling skyscrapers, and see Willis Tower, Millennium Park and Soldier Field. This unique experience offers a once in a lifetime view of the Second City at its most stunning.
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2.5-Hour Cupcake Tour Of Chicago

• Visit the best dessert boutiques along the Magnificent Mile in Chicago on a 2.5-hour cupcake tour led by a guide. Skip-the-line access and all cupcakes are included as you visit up to five bakeries. You'll also see landmarks like the Wrigley Building, Water Tower Place, John Hancock Center, and the Chicago River, and hear commentary about Chicago from your guide.
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WINTER CHOCOLATE, CUPCAKES & SWEETS TOUR

• Go on a sugar filled excursion on the famed Magnificent Mile. This is where all the great sweets spots in Chicago are.We have tastings at some of Chicago's most well known spots like Ghirardelli and Candyality as well as trendy boutique shops you may have never heard of like Sacred Grounds Bakery. There are 5-7 stops for chocolate, gourmet cupcakes, candy and more. We modify this tour in the winter to keep everyone inside and warm almost the whole tour. Just as many sweet treats with none of the cold! This is a chocolate and sweet lovers dream and makes a great start to a romantic day for two. This tour is great for anyone including families and is popular as a unique birthday party for kids
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Underground Donut Tour - Chicago's First Donut Tour

• 5 Reviews
• Sample some of the Windy City’s tastiest donuts on this 2-hour Underground Donut Tour, celebrating the magic of Chicago’s tastiest sugar-filled concoctions. Donut-lovers are sure to enjoy this visit four of Chicago’s tastiest donut purveyors, offering a chance to savor all of your favorite varieties, on the city's only donut-themed excursion. All tastings are included, and gluten- and nut-free options are also available.
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Chicago Favorites Food and Walking Tour

• 53 Reviews
• Stroll through downtown Chicago on this 2.5-hour food tour. Visit Millennium Park, the Palmer House Hotel and other city landmarks. Taste quintessential Chicago foods such as deep-dish pizza, hot dogs, brownies, and local beer. All tastings and beverages are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels.
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Chicago Craft Brewery Barrel Bus Tour

• 3 Reviews
• Learn about Chicago’s brewpub scene and taste different types of craft beer on this guided, 4-hour brewery tour. Visit three unique breweries for craft beer samples plus an additional brewing production facility for an in-depth tour. Discover the science behind the brewing process, complete with step-by-step procedures, and enjoy approximately 50 ounces of beer total throughout the tour. Round-trip transportation in a Prohibition-era-styled barrel bus is included.
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Chicago Prohibition Tour

• 108 Reviews
• Visit four historic bars in operation since Prohibition in Chicago, and learn from a knowledgeable guide about the surreptitious world of the speakeasy. This adults-only tour takes you by coach to once-illicit establishments in Old Town, Wicker Park and the Chicago Loop where liquor, jazz and mobsters ruled. You’ll hear about Chicago gangsters like Al Capone and learn the historical context for the decade-long ban of alcohol. If you’d like, you can purchase recommended craft cocktails and signature drinks of the 1920s.
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Famous Tastes of Chicago Food Tour

• 70 Reviews
• Discover Chicago’s food, history, architecture and culture on this 3-hour, small-group walking tour. Try six of the Windy City’s quintessential staples from local restaurants and specialty food shops like Pizano’s Pizza and the Berghoff, the oldest family run-establishment in Chicago. Taste local favorites including deep-dish pizza,  Chicago Italian Beef Sandwich and chocolates from Fannie May, just to name a few. Along the way, see and learn about the historical, cultural and architectural components that make up this legendary town.
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Chicago Prohibition Cocktail Workshop

• Enjoy a hands on cocktail making instructional, teaching everything from balancing and ratios to specific tools and techniques in our private speakeasy.  Learn mixology 101 and bring the bar experience home. Begin your mastery of techniques to become a better home bartender. This workshop is in partnership with FIG Catering & Drinks. Must be 21, drinks and snacks included.
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Tour Chinatown With Miss China!

• Tour Chicago’s Chinatown with local celebrity Jennifer Zhang. Crowned Miss Chicago Chinese 2015, and Miss China International 2017, Jennifer is also a model, actress, singer, social media influencer, and award-winning travel writer. She has written extensively about Chicago’s Chinatown and shares her inside knowledge with you on this tour. Stop to taste local specialities, and to explore significant landmarks on a one and a half hour-tour.
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Private Chicago Craft Beer and Pizza Tour

• Visit three of Chicago’s top craft breweries on a customizable 4-hour tour. Bring your own group of 4 to 11 people on this all-inclusive tour led by a private guide, who shares details about Chicago’s craft brewing scene. Choose the breweries you wish to visit, and pair those suds with an included pizza dinner as well. You’ll learn how these hand-crafted beers are produced, and tour one of the brewery facilities (if available). No need to worry about getting from place to place: Transportation and hotel pickup and drop-off has included, so all you'll have to worry about is which beer to try first.
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Underground Donut Tour - Wicker Park Edition

• Wicker Park is one of Chicago’s coolest and most food-oriented neighborhoods—and on this one-of-a-kind walking tour, you’ll see the sights while seeking out the best donuts that the area has to offer. Meet your guide in the morning in Wicker Park, and set out on foot. You'll visit four popular cafes and bakeries, will sample numerous creative donut flavors, and will learn more about the neighborhood. Additional drinks and treats are also available for purchase, if you wish.
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Duneland Wine Country with Gourmet Lunch

• 1 Review
• Discover the wines and farm-to-table cuisine of the Indiana dunes on a full-day gourmet tour from Chicago with an experienced vintner. Visit a series of three wineries for guided tastings of wines made from cold hardy, locally-grown grapes. Explore a unique landscape of quaint villages while learning the terroir of Illinois wines, then enjoy a luxurious lunch of contemporary farm-fresh fare in Chesterton, whose old-fashioned Main Street is a slice of small town Americana in the heart of Duneland.
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Bacon and Brewing Beer Tour in Lakeview and Lincoln Park

• 7 Reviews
• Sip your way through Lakeview and Lincoln Park’s best beers on a 3-hour walking tour of these iconic Chicago neighborhoods. Follow your guide to a series of bars and breweries for flights of regional craft brews, and raise a glass as you learn how Chicago’s immigrant cultures created a proud brewing tradition. Experience the bar scene like a local, try a classic Midwestern pairing at a beer-and-bacon bar, and see what’s on draft in the Windy City.
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Pasta Making Night in Chicago

• Educated as a fashion designer yet rooted in her kitchen, Tamar expresses that her heritage and love for aesthetics (as well as special bond with everything dessert-related) are what guide her in the kitchen. Born in Mexico and of Syrian, Polish, Lebanese, and Russian descent, Tamar mixes and matches everything with a little twist (or splash of Tahini). She and her husband Aslan also have a crazy love for meeting people and feeding them. They invite you to dine with them in their loft!
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Hard Rock Cafe Chicago

• 1 Review
• When it's time to refuel in the Windy City, stop into Hard Rock Cafe Chicago for a tasty, filling, and enjoyable meal of classic American fare. Choose from a 2- or 3-course menu that's themed on musical styles all served with dessert and a drink. When ordering from this popular prix-fixe menu, entrees include salmon, steak, chicken, or a half-rack of hickory smoked ribs, and once you've enjoyed each succulent bite, stick around to explore the collection of music-themed memorabilia.
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Pizza City USA Pizza Tour

• Taste four different styles of pizzas in about three hours. Learn about Chicago's 10 pizza styles, and discover why there's more to The Windy City than just deep-dish. Go back in the kitchens to see how pizzas are made, talk to the owners and taste the differences. Expert doughcents will share the history of Chicago pizza as well other interesting tidbits about the neighborhood you're exploring.
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Private Speakeasy Pub Crawl in Chicago

• Travel back in time to the 1920s, when Chicago was a prohibition era hub for lively speakeasies. Your guide, a local historian in period dress, will lead you through secret entrances to speakeasies once frequented by bank robbers and Chicago gangsters like Al Capone. Order prohibition era cocktails (additional cost) and listen to stories about bootlegging and racketeering in 1920s Chicago. Guests are welcome to come in period dress.
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Small-Group Chicago Food Tour: Gold Coast and Old Town

• 95 Reviews
• Savor the flavors of the Gold Coast and Old Town neighborhoods on this 3-hour Chicago food walking tour, led by an expert guide. You’ll stop at seven popular shops and eateries, including a specialty tea merchant, confectioner, European bakery and — of course — Chicago-style pizzeria. Explore these culture-rich neighborhoods just north of the downtown and learn about their architecture and history along the way. Numbers are limited to 18 participants for a small-group experience.
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Italian Food Tour Of Chicago

• 1 Review
• Get a taste of Chicago’s best Italian food on this guided, 2.5-hour culinary walking tour. Join an expert foodie guide on a leisurely stroll through the vibrant Magnificent Mile and Gold Coast districts, home of the Chicago Italian beef sandwich, deep-dish pizza and much more. Visit restaurants like Al’s Beef, known for overstuffed Italian beef sandwiches and hot dogs; Uno Pizzeria and Grill, the original home of the deep-dish pizza and Portillo’s, for the best meatball sub in the city. All food tastings and any necessary entrance fees are included.
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Chicago Neighborhood Global Food and Culture Tour

• 7 Reviews
• Savor the flavors of Chicago — the ‘City of Neighborhoods’ — on a guided, ethnic food tour. This 3.5-hour adventure explores two of Chicago's most diverse neighborhoods: Argyle and Andersonville on the city’s North Side. Sample seven distinctly different types of food, visit landmark locations and learn about the local history and culture.
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Chocolate Tour Of Chicago

• 2 Reviews
• Take a walk on the sweeter side of Chicago with a chocolate walking tour. Visit some of the city’s favorite chocolatiers. Learn about the history of the treat and see how Chicago businesses are crafting it in lots of delicious ways. And you bet, there will be samples.
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Winter Wine Walk

• Indulge in a wine tasting adventure through one of Chicago's many trendy neighborhoods. We go to 3 or 4 places on each tour to taste  different varietals of red, white and sparkling wine. At each stop we have selected a variety of food pairings to accompany your vino such as artisanal cheeses, house cured meats, pickled vegetables and fresh baked breads. The wine and food changes often as does the location.We rotate between Chicago's best neighborhoods like River North, Lakeview, Lincoln Park, Andersonville and the Gold Coast. This tour has more drinking than walking and is a great tour in the cold weather. Ladies especially, love this tour and it is great for anyone who enjoys food, fun and drinking wine.
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Best of Chicago Tour Including a Deep-Dish Pizza

• 5 Reviews
• Tour Chicago's sights aboard a luxury coach and enjoy some Chicago-style deep-dish pizza on this 5.5-hour guided tour. Visit sites like the Hancock Tower, the Lincoln Park Conservatory and the Loop. Pass through neighborhoods such as Wrigleyville, Lincoln Park and Gold Coast. Top off your tour with a visit to one of Chicago's most popular pizza restaurants to sample the famous Chicago-style deep dish pizza.
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