Historic Chicago Bars Walking Tour

1 Day

Get some history lessons on the Historic Chicago Bars Walking Tour with your pub crawl! Our walking tour of Chicago will show you the most authentic and historic Windy City bars!

Finally, a tour of a local Chicago tavern, pub, and dive bar. We’ll take you to five of Chicago’s most popular drinking establishments. These aren’t your typical tourist traps. These are the genuine article! The West Loop is the focus of the bar walking tour.

It’s a genuine Chicago neighborhood with local bars where folks can unwind and interact. At each pub, we’ll spend roughly 30 minutes. That should be ample time for you to meet some regulars and get a feel for the place. You can rely on us. You’ll want to return to one of these classic establishments the next time you visit Chicago or the neighborhood.

Walking tour to Chicago dive bars

It takes roughly 10 to 15 minutes to walk between pubs. You’ll have the opportunity to look about the area. Who knows, maybe you’ll want to relocate there someday. We’ll visit an Irish pub, some local taverns, and a dive bar. It’ll be a lot of fun. We’ll arrive at the intersection of Halsted, Grand, and Milwaukee, allowing you to quickly return to the loop or wherever you’re headed next.

You could even wish to continue the activities! It’s entirely up to you. This isn’t like any other pub tour you’ve ever been on. These are the Chicago drinking foundations that have been there for decades!


  • Michigan Ave, aka “Magnificent Mile”
  • Tribune Tower
  • Chicago’s underground layers
  • The famous Billy Goat Tavern
  • A former historic jazz club and speakeasy
  • A 19th-century mansion

Historic Chicago Bars Walking Tour

Join us for an educational twist to a historic Chicago pub crawl! You’re going to explore the entertainment history of Chicago and learn about prohibition, jazz, theater, vices, and social clubs. In addition to the stories of the tour guide, guests interact on shared iPads with historic photos and videos to connect with the party past of Chicago.

Our evening walking tour remains predominantly indoors, making it great for any weather. At three drink stops, we will enjoy our appetizers and your choice of wine or beer and explore history and architecture between them. Our groups see magnificent lobbies, Gilded Age mansions, and multiple underground layers of Chicago as well as bar stops.

Haunted Chicago Ghost and Pub Walking Tour

Drinks are on you-see below, please.

Who’s coming on a Chicago historic pub crawl tour? Many visitors enjoy the fun and social dynamics of the tour. Travelers on their own often join us. It can be a fun thing to do with your boyfriend or girlfriend in Chicago as a great Chicago date idea. The tour is also made by groups of friends into a cool weekend event. It’s loved by family groups!

This tour is more than a historic crawl pub in Chicago–you’re going to eat, drink, and learn about architecture, history of the Prohibition Age, and party culture.

We’d like to say it’s a Speakeasy Tour or a Chicago Prohibition Tour, but in fact very few bars remaining in Chicago today have always been speakeasies. On our tour, however, we found one stop that was a real speakeasy and an early Chicago jazz club to boot!

The Historic Chicago Bar Walking Tour is like a mix of a food tour, a walking tour of architecture, and a movable documentary movie. Book your tour early as it often sells out the historic Chicago pub crawl. Doing this summer is a unique thing in Chicago!

Tour Highlights
• Michigan Ave, aka “Magnificent Mile”
• Tribune Tower
• Chicago’s underground layers
• The famous Billy Goat Tavern
• A former historic jazz club and speakeasy
• A 19th-century mansion

Stories and Ideas
• Architecture as a cultural artifact
• The “Hex of the Billy Goat”
• Chicago jazz era
• History of Chicago breweries
• Prohibition and gangsters
• 1960’s swanky nightlife
• Private clubs and debauchery

Historic Chicago Pub Crawl Prices
Reservations are $38.00 per person. Guests bring cash for beverages. Total cost is $39.00-$58.00 per tour guest inclusive of tour, food, beer, wine, gratuities, taxes.

Check availability

Chicago and United States travel guides

Here are handy travel guides for Chicago and the US, so you can learn a thing or two about these destinations. For a comprehensive list of our travel guides, please visit our travel guides page.

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Cheap flights and hotels discounts for Chicago

The peak season for flights to Chicago is June, July and August. The low season for purchasing tickets is January, March and November.

Chicago is served by these airports: Chicago Executive Airport, DuPage Airport, O’Hare International Airport, Chicago Rockford International Airport and Chicago Midway International Airport. Direct flights to Chicago are offered by 31 airlines .

Chicago and the US attractions and landmarks

Here are some of the most popular attractions and landmarks in Chicago and in the US.

17-Mile Drive Akaka Falls State Park Akatsuka Orchid Gardens Alcatraz Island Angels Landing Ansel Adams Wilderness Area Antelope Canyon Arches National Park Arlington National Cemetery Artist’s Palette Badwater Basin Barstow Outlets Bellagio Hotel and Casino Beverly Hills Boeing Factory Boston Common Boston Harbor Bridalveil Fall Brooklyn Bridge Bryce Canyon Bunker Hill Monument Canyonlands National Park Capitol Hill Cave of the Winds Central Park Charging Bull Charles River Chihuly Garden and Glass Chinatown SF Chinese Theatre Coeur d’Alene Colorado River Corning Museum of Glass Dante’s View Death Valley National Park Devil’s Golf Course Diamond Head Disney World – Magic Kingdom Disneyland Park Eagle Point El Capitan Empire State Building Epcot Center Ethel M. Chocolate Factory and Botanical Cactus Gardens FDR Memorial Fisherman’s Wharf Freedom Trail Glacier National Park Glen Canyon Dam Golden Gate Bridge Golden Gate Park Grand Canyon Grand Canyon National Park Grand Canyon of the Yellowstone Grand Canyon Skywalk Grand Canyon West Rim Grand Teton National Park Griffith Park Observatory Half Dome Halona Blowhole Hanauma Bay Harvard Square Harvard University Hawaii State Capitol Hawaii Volcanoes National Park Hearst Castle Hershey’s Chocolate World Hole in the Rock Hollywood Sign Hollywood Walk of Fame Hoover Dam Horseshoe Bend Hualapai Nation Reservation Iao Valley Independence Hall Intrepid Sea Air & Space Museum Iolani Palace Jackson Hole Kaimu Black Sand Beach Kapalua Bay Kilauea Iki Crater King Kamehameha Statue Korean War Veterans Memorial Lahaina Lake Mead Lake Michigan Lake Powell Lake Tahoe Las Vegas Strip Lava Tree State Monument Leavenworth Liberty Bell Library of Congress Lincoln Memorial Lombard Street Madame Tussauds Washington D.C. Mammoth Hot Springs Mammoth Lakes Market Street Martin Luther King Jr. Memorial Maui Tropical Plantation Mauna Loa Macadamia Nut Visitor Center Maunalua Bay Metropolitan Museum of Art Mojave Desert Monterey Bay Monument Valley Mt. Rainier Mt. Rushmore National Memorial Nani Mau Gardens National Air and Space Museum National Mall National Museum of American History Navajo Nation Niagara Falls Norris Geyser Basin NYC Trinity Church Olympic National Park Olympic Sculpture Park One World Trade Center Oue Skyspace Palace of Fine Arts Pearl Harbor Pearl Harbor National Memorial Pike Place Market Pilgrim Monument Polynesian Cultural Center Punaluu Black Sand Beach Quincy Market Rainbow Falls Red Rock Canyon Richardson Black Sand Beach Ripley’s Believe It or Not Rockefeller Center Rodeo Drive Route 66 San Francisco Bay San Francisco City Hall Santa Monica Pier SeaWorld San Diego Shoshone Falls Sierra Nevada Silicon Valley Smithsonian National Air and Space Museum Solvang Space Needle Spokane Statue of Liberty Sunset Strip Temple Square The White House Thomas A. Jaggar Museum Thomas Jefferson Memorial Thurston Lava Tube Times Square Twin Peaks Union Square San Francisco United States Capitol Universal Studios Hollywood University of California Berkeley USS Arizona Memorial Valley of Fire Vietnam Veterans Memorial Virgin River Waikele Premium Outlets Waikiki Beach Wailua River Waimea Canyon Wall Street Washington Monument Watkins Glen Park Whalers Village Whirlpool State Park White Sands Beach Whydah Pirate Wind Cave Woodbury Outlets World War II Memorial Yellowstone Lake Yellowstone National Park Yellowstone River Yosemite Falls Yosemite National Park Zabriskie Point Zion National Park

Last Updated on June 27, 2021 by Admin @ gotravelyourself.com