Top Chicago Wine, Beer & Spirits

21 results

Immerse yourself in Chicago's thriving craft beer scene—and visit locals-loved breweries you'd be unlikely to stumble across otherwise—on this half-day brewery tour. Travel in style, and get in the spirit, aboard a traditional Prohibition–style barrel bus. Visit several unique breweries, and go on behind-the-scenes production facility tours. Discover the science behind the brewing process, and enjoy plenty of beer samples throughout the tour.

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Chicago Craft Brewery Barrel Bus Tour

3 hours 45 minutesFree Cancellation

4.9

(353)

from $100

Likely to Sell Out

City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

Kick back and enjoy a great meal while taking in the sights of Chicago's most famed landmarks on this scenic lunch cruise along Lake Michigan. 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.

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City Cruises Chicago: Signature Lunch Cruise on Lake Michigan

2 hoursFree Cancellation

3.9

(359)

from $63

Likely to Sell Out

Join us in the daytime or evening for City lights and breathtaking views

Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.

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Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

4.7

(3,274)

from $28

Taste deep-dish pizza, a Chicago-style hot dog, Italian beef, Garrett’s popcorn & the original 1893 brownie on our top-rated Chicago Food Tours—the ultimate Chicago Culinary Tour experience!

Eat your way through downtown Chicago on a walking food tour. Visit Millennium Park, the Palmer House Hotel, and other city landmarks and taste quintessential Chicago foods such as deep-dish pizza, hot dogs, and chocolate brownies. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. A bike or kayak rental is also included in the tour cost.

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Chicago Favorites Ultimate Food and Walking Tour

3 hoursFree Cancellation

4.8

(2,120)

from $85

Likely to Sell Out

Explore Chicago's legendary architecture and history.

Discover the architectural gems of the Windy City from an ideal vantage point—and learn insider facts and stories about the city's top attractions—on this Chicago River cruise. Travel in comfort aboard a boat equipped with both indoor and outdoor seating areas. Covering more than 130 years of architectural history, this tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

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Chicago River 90-Minute Architecture Tour

1 hour 30 minutesFree Cancellation

4.7

(10,174)

from $45

A picture of Chicago Chinatown’s landscape shows vibrant streets, iconic arches, and rich culture—everything guests explore on our Chinatown Food Tours. Food Tours in Chinatown bring it all to life.

Immerse yourself in one of Chicago's most vibrant neighborhoods—and head off the tourist trail to discover sights and bites many visitors miss—on this small-group Chinatown food and walking tour. With your guide in the lead, learn about the cuisine of different regions of China, and discover the history of Chicago's Chinatown. Along the way, enjoy a generous array of tastings, from dim sum to Sichuan cuisine and beyond.

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Chicago's Chinatown Food and Walking Tour

3 hoursFree Cancellation

4.9

(701)

from $80

Special Offer

Haunted Chicago Booze and Boos Ghost Walking Tour

2 hours 30 minutesFree Cancellation

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.

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Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

4 hours 30 minutesFree Cancellation

4.9

(750)

from $89

Visit the Skydeck, located on the 103rd floor of the Willis Tower (formerly the Sears Tower), with ease thanks to this prebooked ticket option. Avoid long lines at the ticket office and enter directly to access the highest point in Chicago. Peruse interactive displays and exhibits showcasing Chicago's history. Then walk out on to the Ledge, a glass balcony that offers unimpeded views of Navy Pier and Wrigley Field.

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Skydeck - Willis Tower Admission

30 minutes to 1 hour 30 minutesFree Cancellation

4.3

(1,847)

from $44

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

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Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

4.8

(16,256)

from $39

Taste robust flavors on our Chicago Food & Bike Tour. Ride a Bicycle through the Westside and savor bold bites—one of the top Culinary Things to do in Chicago.

Taste food from around the world—and immerse yourself in some of the Windy City's most characterful, locally beloved neighborhoods—on this half-day biking and tasting tour of Chicago. With just a small group for company, you'll follow your guide through the city streets, stopping for views of Chicago’s famous architecture and seeing more than you could if traveling on foot. In between, stop for bites like Polish pierogis, locally made chocolates, and Mexican tacos.

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Chicago's West Side Foodie Ride Bike Tour

4 hoursFree Cancellation

4.9

(113)

from $99

Likely to Sell Out

Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich

Explore Chicago's buzzing food scene—and see some of its best-known landmarks on the way—on this two-in-one walking tour. The small group size offers are more intimate experience as you stroll around the vibrant Loop area, spotting highlights from the Willis Tower to the Rookery building. Indulge in a variety of famous Chicago foods, from deep-dish pizza to the world-famous dipped Italian beef sandwiches.

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Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich

3 hoursFree Cancellation

4.9

(932)

from $85

Price varies by group size

Likely to Sell Out

This tour cruises the Chicago River and Lake Michigan.

Chicago Lake and River Architecture Tour

1 hour 30 minutesFree Cancellation

4.7

(2,344)

from $45

Likely to Sell Out

Chicago Crime and Mob Bus Tour

1 hour 30 minutes to 2 hoursFree Cancellation

4.6

(3,362)

from $49

Chicago Local Brewery Expedition with Homemade Guacamole

We'll explore five (5) of our favorite, Handcrafted Local Micro Breweries in two special locations of the historic, Chicago landmark district, Fulton Market; which used to be the meatpacking district, now becoming the Chicago Brewery District. Here you'll experience the fabulous, intricate world of the art of beer creation. We will all meet at the first one, introduce ourselves and try some delicious appetizers; where Carla will make a special Homemade Guacamole and Homemade Tortilla chips, and here, the first 3 handcrafted beers (3-5oz beers) are on us. Then we'll walk to the other breweries where you'll have a chance to order other beers and serve your own. Here you can stay as long as you want after the tour. During our expedition, we can all share our opinion about the flavors, the creation, etc... All the breweries are within walking distance.

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Chicago Local Brewery Expedition with Homemade Guacamole

1 hour 30 minutesFree Cancellation

5.0

(4)

from $63

Price varies by group size

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Discover the hidden gems of Chicago’s Loop area on a walking tour that showcases the best of the neighborhood’s stunning interiors and architectural must-sees. Step behind the facades to explore beautifully designed interiors—from art deco spaces to stained glass mosaics—as you follow a carefully curated route led by a guide. Along the way, learn about the city’s architecture, art, and history, and experience a side of Chicago often missed by travelers, all from a local’s perspective.

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Original Chicago Architecture Interiors Tour: Dazzling Interiors

2 hoursFree Cancellation

5.0

(1,671)

from $35

Likely to Sell Out

This Wine & Cheese Cruise is a world class Chicago experience for locals and visitors. Board our famous tour boats at Michigan Avenue, and enjoy the Chicago River and Lake Michigan while tasting wine and cheese pairings. There is also a full service bar and climate controlled cabin on the vessel's lower deck. This activity does not have a narrated tour but features light music during the cruise.

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2-Hour Chicago Wine and Cheese Cruise

2 hoursFree Cancellation

4.2

(6)

from $70

Chicago to Milwaukee Day Trip with Brewery Tour & City Highlights

Escape Chicago for a day and experience Milwaukee’s culture, food, and legendary beer scene. This curated day trip includes highlights such as the Harley-Davidson Museum, free time at the Milwaukee Public Market, and an optional Miller Brewery tour and tasting. Enjoy scenic views along the lakefront and an outside visit to the Milwaukee Art Museum before returning to Chicago. Ideal for travelers looking for a relaxed, well-rounded introduction to Milwaukee.

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Chicago to Milwaukee Day Trip with Brewery Tour & City Highlights

8 to 10 hoursFree Cancellation

4.3

(9)

from $125

Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer

Take an adventurous half-day journey through the most interesting Chicago neighborhoods with a friendly private guide and see the city from a new perspective riding a bike. Dive into the atmosphere of the city’s movement and combine it with tasting the most delicious and iconic treats of the Chi after whetting your appetite, absorbing the unique beauty of the city. Discover more sights in a shorter time using a bike Get a true taste of the City by the Lake following the tips of a local guide Discover iconic neighborhoods and be entertained with historical insights. Learn about the peculiarities of local cuisine and its origins.

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Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer

4 hoursFree Cancellation

5.0

(1)

from $179

West Town Hot Spots Tour By Studio W.I.P.

Follow an artist through Chicago’s vibrant art scene, and you’ll see the city with new eyes. On this guided tour, you’ll walk through West Town’s B-Line, a modern art corridor with 1970s origins, home to some of the best street art in the world. You’ll hear facts, trivia, a few wild stories, and more, finishing up with optional beers—and crafts!—at a hyperlocal brewery. This tour is offered in English and Spanish.

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West Town Hot Spots Tour By Studio W.I.P.

1 hour 30 minutes to 1 hour 45 minutesFree Cancellation

3.6

(5)

from $25

Custom Chicago Walking Tours

1 to 3 hoursFree Cancellation

5.0

(2)

from $20

Per group

Top Attractions in Chicago

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Attractions

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On Chicago wine, beer, and spirits tours, you’ll explore the city while enjoying a few drinks along the way. You can join brewery crawls that take you to local craft beer spots, bike tours that combine Chicago-style pizza with beer tastings, haunted pub crawls that mix ghost stories with drinks at historic bars, and barrel bus brewery tours. Tours offer a boozy perspective on the Windy City, and are typically a fun addition to any itinerary.

Top Chicago Wine, Beer & Spirits

21 results

Top Attractions in Chicago

Chicago River

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Art Institute of Chicago

Chicago Riverwalk

Chicago River

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Art Institute of Chicago

Chicago Riverwalk

Chicago River

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

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