Top Chicago Food, Wine & Nightlife

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.

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.

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.

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.

Enjoy lunch above the clouds at the Willis Tower, where authentic Chicago-style pizza is paired with unforgettable views of the Chicago skyline. Customize your own perfect pizza from a list of gourmet ingredients, then select a salad and a traditional Italian dessert. Capture unforgettable images from the dining room on the 99th floor, then continue to The Ledge, a glass floored balcony perched near the top of America’s tallest building.

Go beyond deep-dish on this 3-hour culinary walking tour of Chicago, which includes five tastings of classic Windy City cuisine. Navigate the endless options of downtown dining with a guide who can provide insight into the best food Chicago has to offer, and skip the lines and the wait with VIP access to popular restaurants.

Elevate your Valentine with Chicago Helicopter Experience! You and your special someone will be whisked away in a luxurious helicopter over the glistening Chicago skyline. From the most unique vantage point, you'll capture the amazing views as millions of lights dot the city - lining Lake Shore Drive, dancing on Buckingham Fountain, and scattered across the iconic skyscrapers. The glowing cityscape provides a romantic backdrop to your special evening. We'll help you toast your celebration with complimentary champagne, two chocolate roses, and a keepsake photo of your unforgettable experience.

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.

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.

Take a 2.5-3 hour gourmet dinner cruise on a high-end luxury yacht with the stunning skyline of Chicago as your backdrop. Climb aboard your recently renovated vessel, featuring a sumptuously-appointed rooftop lounge and stylish interior design, for your cruise along Lake Michigan. Then sit down for a 3-course dinner, informed by some of the world’s top celebrity chefs and composed of fresh ingredients cooked right on-board. After dinner, enjoy coffee and tea, captivating views of Chicago landmarks like the Willis (formerly Sears) Tower and John Hancock building, plus musical entertainment provided by the on-board DJ.

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.

Enjoy Chicago’s only bus guided neighborhood pizza tour.  Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the best pizza.  Your local guide will teach you the science behind ingredient selection and baking as you sample slices from historic pizzerias.  In just a few hours, you’ll leave stuffed, and with an understanding of why pizza is such an important part of Chicago’s culture.

Explore Chicago's Chinese food scene on this 3-hour walking tour in the Chinatown district. With a guide, learn about the cuisine of different regions of China and how Chinese culture has influenced Chicago and other areas. You'll enjoy included tastings from restaurants and other food venues in Chinatown — a great way to start a night out in the city.

Explore Chicago's buzzing food scene with a small group on this 3-hour walking tour. Stroll around the 'Loop', stopping at hidden gems and hearing tales of the city from your guide. Taste some classic Chicago foods!

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.

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 Downtown Dogs and the World-Famous Billy Goat Tavern. Taste local favorites including deep-dish pizza, a Chicago-style hot dog 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.

Explore Chicago’s Loop and South Loop neighborhoods — and get a taste of some local beverages — on this guided, 3-hour beer tour. Visit popular downtown establishments, sample some of the city’s finest brews and learn how beer goes with Chicago’s criminal past, discovering the basics of the Windy City’s vice history. From Al Capone and the local mob scene to the infamous Sands, the toughest criminal district in the city — this tour creates a unique experience that is both fun and memorable. Beer tastings plus a pizza pairing at one location included.

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.

Sample different styles and varieties of Chinese food during this 3-hour walking tour of Chicago's Chinatown. Follow your local food-loving guide through one of the oldest Chinese neighborhoods in the country to taste Mandarin-style, Hong Kong-style and Szechuan-style delicacies. The price of this small-group tour, limited to 12 people, includes tastings at 5 restaurants; enough food to add up to a full lunch.

Explore downtown Chicago on a pub crawl with an educational twist! Your expert guide shares entertaining facts about the history of jazz, theater, social clubs, and the Prohibition era in the Windy City as you take in historic buildings and architecture. Use iPads to view historic photos and videos that accompany your guide’s stories as you stop in both famous and hidden bars for drinks and appetizers. A short walk allows plenty of time to see Chicago’s famous architecture and pubs on this tour – great for visitors and locals alike!

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

Make your evening in Chicago one to remember with this 3-hour luxury sunset cruise featuring dinner, sightseeing and dancing along the shores of Lake Michigan. Feast your eyes on incredible views of iconic Windy City sights like Navy Pier, the Willis (Sears) Tower, Buckingham Fountain and Soldier Field, then fill your belly with a bountiful all-you-can-eat buffet. Continue the celebration with a live DJ who will mix up a selection of dance favorites.

Eat and drink your way through the famous food culture of the Windy City during this 3 hour guided Chicago beer and pizza tour. Make your way by mini-coach to three local pizzerias to taste slices of the city's distinct pies, ranging from thin crust to deep dish, each of which is complemented by an included glass of beer or wine. During your ride between pizza stops, your guide will keep the fun going with facts and sights.

Enjoy an unforgettable sky-high meal during this 2-hour Willis Tower dining experience at the Skydeck, an observation room situated high above Chicago's magnificent urban landscape. This 1,353-foot (412m) viewing area provides the magical setting for your evening, accompanied by a delicious Chicago-style, deep-dish pizza. Best of all, this special excursion offers VIP after-hours access to the Skydeck, ensuring the ultimate setting for that special occasion.