Chicago’s drinking tours offer memorable ways to taste the city’s best brews and spirits while learning its colorful history. The Craft Brewery Barrel Bus Tour stands out with its comfortable, all-weather transportation and excellent selection of local craft beers. History buffs will appreciate the Sin and Suds Beer Tour, which combines fascinating Prohibition-era stories with stops at century-old taverns.
For a uniquely Chicago experience, we love the Lake Michigan Sunday Funday cruise – nothing beats sipping mimosas while viewing the magnificent skyline. The Lake and River Beer and BBQ Cruise earns our top recommendation by pairing local brews with classic Chicago barbecue.
Let’s explore these outstanding Chicago drinking tours in detail.
Good To Know
Chicago offers a variety of brewery and beer tours, including the Chicago Craft Brewery Barrel Bus Tour featuring 45-55 ounces of craft beer sampling.
The Sin and Suds Chicago Beer Tour explores historic pubs in the Loop and South Loop neighborhoods, offering beer tastings paired with pizza.
The Chicago Skyline Tiki Bar Cruise and Sunday Funday Mimosa/Bloody Tiki Bar Cruise provide scenic sightseeing experiences with affordable alcoholic beverages.
The Chicago Lake and River Beer and BBQ Cruise offers an immersive experience with local craft beer and BBQ, departing from the Chicago Riverwalk.
Tour accessibility and fitness levels are accommodated, with bike tours suitable for moderate fitness and cruises providing comfortable seating for all passengers.
Chicago Food Tour: Deep Dish Pizza, Beer, Brownies, and More
Operated by Bobbys Bike Hike, the Chicago Favorites Ultimate Food and Walking Tour immerses participants in the city’s iconic culinary landscape.
This 3-hour, 1.5-mile excursion features 4-5 food stops with generous tastings, including deep-dish pizza, hot dogs, Italian beef sandwiches, and the original brownie.
Guides provide insights into Chicago’s history and culture, while an optional craft beer tasting enhances the experience.
With consistent 5-star reviews, the tour accommodates various dietary needs and fitness levels, making it an excellent choice for those interested in both food and local exploration.
The inclusion of a complimentary 2-hour bike or kayak rental (weather permitting) adds to the well-rounded nature of this highly recommended tour.
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
For those seeking an immersive exploration of Chicago’s iconic cuisine, the Bikes, Bites, and Brews tour is a must-try experience.
This 4.5-hour, 13-mile bike tour takes participants through the city’s vibrant neighborhoods, stopping at top-rated spots for deep-dish pizza, hot dogs, and craft beer.
Led by knowledgeable local guides, the tour provides cultural insights into Chicago’s food traditions while allowing travelers to sample the city’s signature dishes.
With a maximum group size of 16 and a 99% traveler recommendation, this tour is an efficient and enjoyable way to experience the best of Chicago’s culinary landscape.
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Chicago Craft Brewery Barrel Bus Tour
Transporting guests aboard a climate-controlled barrel bus with Prohibition-era styling, the Chicago Craft Brewery Barrel Bus Tour offers an immersive exploration of the city’s thriving craft beer scene.
With consistently high ratings and 97% of travelers recommending the tour, it provides an opportunity to visit various breweries, including production facility tours, and sample 45-55 ounces of craft beer.
Led by a professional guide, the experience highlights the brewing process and history, as well as encourages group interaction and makes new friends.
Priced from $99.60 per person, the tour departs 15 minutes prior to the scheduled time outside McDonald’s, across from Rainforest Cafe, and returns to the same meeting point.
Read our full review: Chicago Craft Brewery Barrel Bus Tour Review
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Sin and Suds Chicago Beer Tour
The Sin and Suds Chicago Beer Tour whisks guests through the city’s Loop and South Loop neighborhoods, where they’ll explore the area’s criminal past and sample local brews.
The 3-hour tour includes stops at iconic establishments like Exchequer Pub, Berghoff, and Buddy Guy’s Legends, and features beer tastings paired with pizza.
With a 100% traveler recommendation and a Badge of Excellence, the tour promises an engaging experience led by enthusiastic and knowledgeable guides.
Covering 1.5 miles, the tour is wheelchair-accessible and welcomes guests aged 21 and above.
Whether you’re a tourist or a local, the Sin and Suds Chicago Beer Tour offers a unique blend of history, craft beer, and entertainment.
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Haunted Chicago Ghost and Pub Walking Tour
Venturing beyond the city’s boozy past, the Haunted Chicago Booze and Boos Ghost Walking Tour invites guests to explore the supernatural side of the Windy City.
With a 95% recommendation rate from 131 reviewers, the 5-star tour guides participants through Chicago’s haunted hotspots, from Glascott’s Saloon to Lilly’s Bar.
Led by knowledgeable local experts, the experience includes spooky tales, historical insights, and the chance to purchase alcoholic drinks.
While some guests noted difficulty hearing stories in noisy bars, the tour’s unique blend of spirits and spirits has made it a popular option for events like bachelorette parties.
With a maximum of 12 travelers, the Haunted Chicago tour offers an intimate, memorable exploration of the city’s ghostly side.
Read our full review: Haunted Chicago Ghost and Pub Walking Tour Review
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Chicago Skyline Tiki Bar Cruise From Chicago Riverwalk
From the Chicago Riverwalk, guests embark on a leisurely cruise across the waters of Lake Michigan, seeing the vibrant Tiki Chic atmosphere of the Chicago Skyline Tiki Bar Cruise.
With a maximum capacity of 40 travelers, the cruise offers an intimate experience with air-conditioned, climate-controlled spaces and on-board restrooms. Alcoholic beverages and snacks are available for purchase, and the cruise is dog-friendly.
Reviews are mixed, with some highlighting the great sightseeing, friendly staff, and relaxing experience, while others note issues with cancellations, rude crew, and limited snack options.
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
Travelers seeking a unique immersion into Chicago’s prohibition-era history can embark on a Private Speakeasy Pub Crawl led by a local historian.
This tour transports guests back to the 1920s, exploring historic speakeasies via secret passages while hearing stories about bootlegging and racketeering.
With a 4.5-star rating, the tour provides a professional guide, private transportation, and guaranteed skip-the-line access.
While alcoholic drinks are available for purchase, the high cost and lack of included drinks have drawn some criticism.
Nonetheless, customers praise the knowledgeable guides, great venues, and memorable experiences, making this an intriguing option for those interested in Chicago’s underground drinking culture.
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Chicago River Sunday Funday Mimosa/Bloody Tiki Bar Cruise
Those seeking a lively and boozy experience on the Chicago River can embark on the Sunday Funday Mimosa or Bloody Mary Party Cruise.
This 60-75 minute cruise offers scenic views of Chicago’s iconic skyline while passengers enjoy a range of $3 mimosas and $5 Bloody Marys.
Though the cruise has a maximum capacity of 90 travelers, some guests have reported discrepancies between the advertised and actual cruise length.
The boat features music and staff to assist passengers, but the food options are limited.
Reviews are mixed, with some complaints about air conditioning and cruise duration, but overall, the cruise is recommended for a relaxing, drink-focused experience on the water.
Read our full review: Chicago River Sunday Funday Mimosa/Bloody Tiki Bar Cruise Review
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Walking Tour to Chicago Dive Bars
The Walking Tour to Chicago Dive Bars provides visitors with an immersive experience into the city’s legendary watering holes.
Led by host Andy, the tour takes guests on a walking exploration of Chicago’s iconic dive bars, starting at the Chipp Inn. Participants receive a copy of the “Dive Right In” book, which outlines the unwritten rules of these establishments.
The tour accommodates a maximum of 12 travelers and is wheelchair accessible, with surfaces suitable for wheelchairs.
While not recommended for those with certain medical conditions, the tour offers a unique opportunity to feel like a local and enjoy great guidance, as highlighted in the positive reviews.
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Chicago Local Brewery Expedition With Homemade Guacamole
For those seeking a more immersive experience into Chicago’s thriving craft beer scene, the Chicago Local Brewery Expedition with Homemade Guacamole offers a delightful alternative to the dive bar tour.
This 5.0-rated expedition allows a maximum of 20 travelers to sample 15 ounces of handcrafted beers and indulge in homemade guacamole and corn tortillas.
The tour isn’t wheelchair accessible but is stroller-friendly and located near public transportation.
Pricing varies by group size, with a lowest price guarantee. Confirmation is provided at booking, and travelers can enjoy free cancellation up to 24 hours prior to the start of the experience.
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
Designed to delight both foodies and fitness enthusiasts, the Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes, and Beer offers a unique way to experience the city’s culinary and cultural highlights.
Operating rain or shine, the tour provides a morning or evening start time, with two distinct itineraries catering to a maximum of 15 travelers.
Inclusions feature a bicycle, helmet, water bottle, friendly local guide, and samples of iconic Chicago foods and beverages at various stops.
While the tour isn’t wheelchair accessible, it’s suitable for those with a moderate fitness level, with gratuities included in the from $179 per person price.
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 offers a lively way to experience the city’s iconic lakefront.
With a rating of 3.5/5 from 2 reviews, the cruise includes an air-conditioned vessel, restrooms, and the opportunity to purchase alcoholic beverages like $3 mimosas and $5 Bloody Marys.
The 50-passenger cruise takes guests along Lake Michigan, providing stunning views of the Chicago skyline. Reviewers praised the friendly staff and perfect weather, making for an enjoyable relaxation experience.
Located near public transportation, the cruise departs and concludes at the Island Party Hut on the Chicago Riverwalk, with street parking available nearby.
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 and immersive experience for visitors to the city.
Departing from Wendellas Dock 4, the cruise features samples of local craft beer and BBQ sliders with two sides. Passengers can enjoy the full-service cash bar for additional drinks while taking in the sights of the Chicago River and Lake Michigan.
The cruise isn’t wheelchair accessible but is stroller-friendly and allows service animals.
With a maximum capacity of 150 travelers, this tour provides a memorable way to explore Chicago’s waterways and taste its local flavors.
Read our full review: Chicago Lake and River Beer and BBQ Cruise Review
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The Sum Up
Chicago offers a variety of drinking tours to suit different tastes. From deep dish pizza and beer to haunted pubs and craft brewery cruises, there’s something for all. Visitors can explore the city’s diverse food and beverage scene while learning about its history and culture. Whether you’re a foodie or a beer enthusiast, Chicago’s drinking tours provide a unique and memorable experience.