Food, Wine & Nightlife in Chicago

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!

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.

Travel back in time to the original 1893 World's Fair in Chicago for this guided, 3.5-hour food tour. Led by Chicago's 'Gold Coast Queen,' Bertha Palmer, hear her favorite memories from the great 1893 Columbian Exposition and enjoy five different food tastings from around the Windy City.

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.

Start your morning right with 1.5-hour visit to the Willis Tower Skydeck, offering stunning views of Chicago and a delicious breakfast served from 103-stories high. Head to the Skydeck of the Willis Tower, one of the tallest buildings in the Western Hemisphere, for breakfast served 1,353 feet (412m) above the Windy City. Pick from among five morning meal options, such as eggs, pastries, and steak. Enjoy eye-opening views for 1.5 hours before the Skydeck opens to other guests. Finish your morning by checking out the on-site displays of Chicago's culture and history.

Take a 2-hour food and walking tour of Wrigleyville in Chicago with a professional guide. Visit three eateries in the Lakeview neighborhood, which stands next to Wrigley Field, the second-oldest ballpark in the major leagues. Taste favorite foods including a Chicago-style hot dog, beef sandwich, and mini-cheeseburger, and snap photos of landmarks outside the Cubs baseball stadium.

Sample craft beer at several locally owned Chicago establishments during a 3-hour guided walking tour. Explore the Bucktown and Wicker Park neighborhoods on foot, stopping to learn about the city's historical architecture along the way. Visit bars dating back to the 19th century and enjoy tastings equal to four beers - with the option to book the tour without beer tastings, if you wish. Bonus: pair your brews with a Chicago-style hot dog!

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.

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.

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.

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.

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.

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.

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.

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.

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.

Taste five classic Chicago dishes during a 2.5-hour walking tour that visits several renowned restaurants in downtown Chicago. Your guide takes you to favorite eateries around River North and Streeterville, and provides skip-the-line access at popular places. Sample foods such as deep dish pizza, Italian beef sandwiches, hot dogs, sweet and savory popcorn, and other delicious bites. You'll also hear from your guide about Windy City history, and see Magnificent Mile landmarks such as the Wrigley Building, Tribune Tower, and Chicago Water Tower.

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.

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.