Top Illinois Wine Tours

Sample some of the Windy City’s tastiest donuts on this Underground Donut Tour, celebrating the magic of Chicago’s tastiest sugar-filled concoctions. Donut-lovers are sure to enjoy this visit to some 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 vegan, gluten-, and nut-free options are also available.

An excellent choice for first-time visitors, this tour provides a comprehensive overview of the city and hits on both classic attractions and little-known sites. Beginning at the Chicago Theatre, work your way to the Chicago Pedway, an elaborate network of underground tunnels used by locals and commuters. Stroll the Chicago Riverwalk and see Millennium Park; then, embark on a food tour to taste some of the city’s famous foods.

Experience a colorful side of Chicago history with this gangsters and ghosts tour. With a historian as your guide, you’ll step back to the Roaring Twenties, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.

Chicago dogs, deep-dish pizza, brownies, and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following your guide at a moderate pace through Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and the Lakefront Trail. As you go, stop for generous food and beer tasters.

Take a gourmet dinner cruise on a high-end luxury yacht with the stunning skyline of Chicago serving 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 Navy Pier, plus musical entertainment provided by the onboard DJ.

Explore Chicago's buzzing food scene in a small group (or upgrade for a private experience) on this walking tour. Stroll around Downtown, learning how how important the immigrants that built this city are to its food scene. Taste classic Chicago foods, from deep-dish pizza to the world-famous dipped Italian beef sandwiches. At the end, you'll enjoy a delicious secret dish that will be revealed only on the day of the tour.

Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like the Wrigley Building and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).

Perfect for families, groups, and corporate outings, the Spirit of Chicago lunch cruise lets you kick back and enjoy a great meal while taking in the sights of Chicago's most famed landmarks. See and photograph the dramatic city skyline, Navy Pier, Soldier Field, and Shedd Aquarium. The cruise includes a delicious buffet lunch with salads, entrees, desserts, and unlimited nonalcoholic beverages. There's also a DJ, games, and a dance floor to keep your group entertained.

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.

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.

Discover some of the Windy City’s spookiest ghost stories—and step back in time to the era of gangsters, bootleggers, jazz performers, and more—on this small-group walking tour. Meet your guide in Chicago’s Lincoln Park neighborhood, and set off after dark. You’ll visit supposedly haunted former burial grounds, pubs, theaters, and more—and will hear about macabre legends and unexplained happenings as you go.

We invite you to join us on a holiday themed, festive and fun foodie adventure! This tour is just like our normal food tour, but with a holiday twist! Dig out those ugly Christmas sweaters and get ready to see the Hallmark of the Midwest in a new and foodie way. PLUS, rock out that ugly sweater and you will be in our contest to win a free tour! You will join your festive foodie guide down the famous Main Street of Galena enjoying some of the best food and drinks the town has to offer. Definitely bring an empty stomach and your holiday cheer!

This tour has something for everyone with stops at a winery, distillery and brewery. Ticket includes a tasting experience of 6 wines, samples of 3 whiskeys, and a flight of 5 beers! Take the train out or drive over to the Geneva Metra Station where we start our leisurely ride through the countryside west of the 'burbs in the comforts of our Brews Mobile bus. The tour includes stops at Acquaviva Winery, Whiskey Acres Distillery and Obscurity Brewery. Ticket includes a tasting experience of 6 wines, samples of three whiskeys, and a flight of 5 beers!