Chicago’s drinking tours offer practical ways to experience the city’s best bars and brews. I’m especially fond of two standout options: the Barrel Bus Tour and Sin and Suds crawl, which generously serve up to 55 ounces of local craft beer while keeping groups intimate and manageable. History buffs will appreciate the atmospheric Private Speakeasy Crawl, featuring authentic Prohibition-era lounges, while the Lake Michigan Sunday Funday Cruise combines spectacular skyline views with classic brunch cocktails. All tours accommodate dietary restrictions and accessibility needs. Let’s explore my favorite Chicago drinking tours in detail…
Good To Know
- The Craft Beer Tours, including the Brewery Barrel Bus Tour and Sin and Suds Tour, offer craft beer sampling experiences with insights into beer-making.
- The Lake Michigan Sunday Funday Cruise provides scenic views of the Chicago skyline and lakefront with $3 mimosas and $5 Bloody Marys.
- The Haunted Booze Tour combines a 1-mile walking tour with visits to three bars, sharing stories of haunted sites in Chicago.
- The Private Speakeasy Crawl offers a unique social experience exploring Prohibition-era speakeasies with historical insights.
- The Chicago Lake and River Beer and BBQ Cruise features local craft beer samples and BBQ fare, including Sweet Baby Ray’s sliders and sides.
Chicago Food Tour: Deep Dish Pizza, Beer, Brownies, and More
One of the key highlights of the Chicago Favorites Ultimate Food and Walking Tour is the opportunity to sample the city’s iconic deep-dish pizza, among other local delicacies.
Over the course of approximately 3 hours, the tour covers 1.5 miles in downtown Chicago, showcasing major landmarks like Millennium Park and the Chicago River.
Along the way, travelers can indulge in 4-5 food stops featuring generous tastings of dishes like hot dogs, Italian beef sandwiches, original brownies, and more.
The tour also includes optional local craft beer samples.
With a maximum group size of 16, the guided experience provides historical context and insider tips from knowledgeable local guides.
Read our full review: Chicago Food Tour: Deep Dish Pizza, Beer, Brownies, and More Review
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Chicago Food Tour by Bike With Pizza, Beer, Hot Dogs, Cupcakes
The Bikes, Bites, and Brews: Chicago’s Signature Dishes Bike Tour provides a unique and engaging way to discover the city’s iconic foods.
Covering 13 miles over a half-day, the tour offers samples of Chicago-style hot dogs, deep-dish pizza, brownies, and craft beer.
Led by expert local guides, the tour explores neighborhoods like Wrigleyville, Lincoln Park, and the Gold Coast, providing cultural insights along the way.
With a 99% recommendation rate and 4.9/5 rating, the tour is suitable for most travelers, requiring only a moderate fitness level.
Travelers praise the informative guides and memorable experiences, making this an excellent choice for families, friends, and business groups looking to explore Chicago’s culinary scene.
Read our full review: Chicago Food Tour by Bike With Pizza, Beer, Hot Dogs, Cupcakes Review
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Chicago Craft Brewery Barrel Bus Tour
For travelers seeking a unique way to explore Chicago’s vibrant craft beer scene, the Chicago Craft Brewery Barrel Bus Tour offers an immersive and engaging experience.
Rated 4.9 out of 269 reviews, this guided tour takes guests on a journey through the city’s brewpub scene, where they can sample up to 55 ounces of craft beer from large and small breweries.
The tour includes a visit to a brewing production facility, where guests can learn the science behind beer-making.
With a Prohibition-era-styled barrel bus, round-trip transportation, and a knowledgeable guide, this tour provides a well-rounded introduction to Chicago’s thriving craft beer culture.
Read our full review: Chicago Craft Brewery Barrel Bus Tour Review
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Sin and Suds Chicago Beer Tour
Travelers seeking to uncover Chicago’s storied past while sampling the city’s vibrant craft beer scene will find the Sin and Suds Chicago Beer Tour an engaging and informative experience.
The 3-hour walking tour explores the city’s Loop and South Loop neighborhoods, visiting popular downtown establishments and sampling local brews. Guests will learn about Chicago’s criminal history, including Al Capone and the local mob scene, while experiencing beer tastings and a pizza pairing.
With a maximum group size of 18, the tour offers an intimate and personalized experience, receiving overwhelmingly positive reviews from both locals and travelers alike.
The tour is wheelchair accessible and allows service animals, making it an inclusive experience for all.
Read our full review: Sin and Suds Chicago Beer Tour Review
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Haunted Chicago Ghost and Pub Walking Tour
Exploring Chicago’s haunted past and vibrant bar scene, the Haunted Chicago Booze and Boos Ghost Walking Tour immerses guests in the city’s eerie history.
Led by costumed guides, this 1-mile journey takes visitors to three bars, while sharing engaging stories about Chicago’s haunted sites.
With a 95% recommendation rate and a Badge of Excellence, the tour offers an entertaining and informative experience, perfect for social outings or special events.
Though some guests have noted noise levels in bars affecting the storytelling, the tour generally receives positive reviews for its knowledgeable guides and unique blend of booze and boos.
For those seeking a spooky yet social experience, this walking tour is a must-try.
Read our full review: Haunted Chicago Ghost and Pub Walking Tour Review
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Chicago Skyline Tiki Bar Cruise From Chicago Riverwalk
The Chicago Skyline Tiki Bar Cruise on Lake Michigan offers a unique opportunity to experience the city’s iconic skyline from the water.
For $35 per person, visitors can enjoy this 90-minute cruise, which features an air-conditioned, climate-controlled space and restrooms on board.
While alcoholic beverages and snacks are available for purchase, the cruise has a maximum capacity of 40 travelers.
Reviews are mixed, with some praising the friendly staff and breathtaking views, while others report issues with boat cancellations and limited parking.
Located at the Chicago Riverwalk, the cruise is easily accessible by public transportation, though it’s not wheelchair-friendly.
Read our full review: Chicago Skyline Tiki Bar Cruise From Chicago Riverwalk Review
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Private Speakeasy Pub Crawl in Chicago With Local Historian
Chicago’s private speakeasy pub crawl transports guests back to the Prohibition era, led by a local historian decked out in period attire.
Visitors explore secret entrances to speakeasies frequented by notorious gangsters like Al Capone, hearing tales of bootlegging and racketeering.
The luxury private tour includes transportation, bottled water, and guaranteed skip-the-line access.
While alcoholic drinks are available for purchase, the minimum drinking age is 21.
Though the £703.49 per person price tag may be high, guests appreciate the memorable experiences and historical insights provided by the knowledgeable guides.
The tour is wheelchair accessible and near public transportation, making it an engaging way to experience Chicago’s prohibition past.
Read our full review: Private Speakeasy Pub Crawl in Chicago With Local Historian Review
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Chicago River Sunday Funday Mimosa/Bloody Tiki Bar Cruise
Cruisers can embark on a lively Sunday Funday experience by joining the Chicago River Mimosa or Bloody Mary Party Cruise.
The cruise offers a unique combination of a river cruise and brunch drinks, allowing passengers to enjoy mimosas ($3) and Bloody Marys ($5) while taking in the iconic Chicago skyline.
The experience includes mingling with other travelers, listening to island tunes, and a well-stocked cash bar. Food is available for purchase, though options are limited.
The cruise departs from the Island Party Hut on the Chicago Riverwalk and lasts approximately 60-75 minutes, with a maximum of 90 travelers allowed.
Pricing starts at $35 per person, and reviews highlight the scenic views and enjoyable atmosphere.
Read our full review: Chicago River Sunday Funday Mimosa/Bloody Tiki Bar Cruise Review
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Walking Tour to Chicago Dive Bars
For those seeking a more authentic side of Chicago’s bar scene, the Walking Tour to Chicago Dive Bars offers an immersive experience.
Capped at 12 participants, the small-group format provides a personal encounter as you discover five notable dive bars and classic taverns.
Led by an experienced guide, the tour delves into the city’s bar culture and history, with the included “Dive Right In” book enhancing your understanding of tavern etiquette.
Wheelchair accessible and suitable for most travelers, this tour allows you to explore Chicago’s local side, with drinks and snacks at your own expense.
With a perfect 5.0 rating from previous participants, this dive bar walking tour is a unique way to experience the Windy City.
Read our full review: Walking Tour to Chicago Dive Bars Review
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Chicago Local Brewery Expedition With Homemade Guacamole
Nestled within the bustling city, the Chicago Local Brewery Expedition takes travelers on an immersive journey through the local craft beer scene.
Exploring up to 3-5 different handcrafted beers, the tour offers a 15-ounce sampling of the region’s finest brews. Complementing the beer tasting is homemade guacamole and corn tortillas prepared by Chef Carla.
With a maximum of 20 participants, the expedition provides an intimate experience for beer enthusiasts. Conveniently located near public transportation, the tour starts and ends at easily accessible points in the city.
Priced from €51.95 per person, the Chicago Local Brewery Expedition is a must-try for anyone seeking a taste of Chicago’s vibrant craft beer culture.
Read our full review: Chicago Local Brewery Expedition With Homemade Guacamole Review
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Fun Chicago Bike Tour With Pizza, Hot Dogs, Cupcakes and Beer
Explore Chicago’s vibrant neighborhoods and savor its iconic culinary delights on this Fun Chicago Bike Tour.
Featuring morning and evening start times, this 2-hour guided tour takes you to sample local favorites like pizza, hot dogs, cupcakes, and beer.
With a friendly local guide, you’ll explore the city by bicycle, stopping at two breweries, a bakery, a hot-dog stand, and a pizza shop for tasty samples.
Suitable for all fitness levels, the tour provides a bicycle, helmet, and water bottle.
Dietary accommodations are available, and gratuities are included.
Confirmation is provided at booking, and free cancellation is allowed up to 24 hours in advance.
Read our full review: Fun Chicago Bike Tour With Pizza, Hot Dogs, Cupcakes and Beer Review
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Lake Michigan Sunday Funday Mimosa/Bloody Mary Tiki Bar Cruise
Departing from the Chicago Riverwalk, the Chicago Skyline Sunday Funday Mimosa/Bloody Mary Party Cruise takes guests on a lively journey to enjoy the city’s iconic lakefront views.
The cruise includes an air-conditioned vessel, restrooms, and the option to purchase alcoholic beverages like $3 mimosas and $5 Bloody Marys.
With a maximum of 50 travelers, the cruise offers an intimate experience to relax and take in the Chicago skyline.
Based on the two reviews, the cruise seems to provide a fun and enjoyable time, with friendly staff and good drinks enhancing the experience, especially on a pleasant day.
Guests can easily access the meeting point via the Chicago Riverwalk and nearby street parking.
Read our full review: Lake Michigan Sunday Funday Mimosa/Bloody Mary Tiki Bar Cruise Review
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Chicago Lake and River Beer and BBQ Cruise
The Chicago Lake and River Beer and BBQ Cruise offers a unique opportunity to experience the city’s iconic waterways while savoring local craft beer and delectable BBQ fare.
Departing from Wendella’s Dock 4 along the riverwalk, the cruise provides an array of inclusions, including samples of local craft beer, Sweet Baby Rays sliders and two sides, and soda. A full-service cash bar is also available for additional drinks.
The cruise is accessible to strollers, and service animals are allowed. While not wheelchair accessible, the cruise can accommodate up to 150 travelers, making it a suitable option for most visitors.
Confirmation is received at booking, though special requests can’t be guaranteed.
Read our full review: Chicago Lake and River Beer and BBQ Cruise Review
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The Sum Up
Whether you’re a beer enthusiast, a foodie, or a thrill-seeker, Chicago’s diverse range of drinking tours offers something for all. From deep-dish pizza and craft brewery excursions to haunted pub crawls and lakeside cruises, the city’s vibrant food and beverage scene is sure to tantalize your taste buds and quench your thirst. With so many options, you’re bound to find the perfect tour to suit your interests and create unforgettable memories in the Windy City.