Chicago

CHICAGO · BAR CRAWLS

5 Best Chicago Bar Crawls

The nights worth heading out for.

The 5 chicago bar crawls worth heading out for. The nights groups still talk about the next morning, with prices, run times and who runs the crawl.

5 Best Chicago Bar Crawls

Chicago River: Guided Sunset Cocktail & Architecture Tour - Cocktails, coffee, and the onboard bar reality

Chicago, Tour Reviews

Chicago River: Guided Sunset Cocktail & Architecture Tour

/ June 20, 2026

1.Chicago River: Guided Sunset Cocktail & Architecture Tour

Sunset Chicago River architecture cruise with included cocktail, award-winning docents, 50+ buildings, and 100-year-old bascule bridges.

Most Popular★ 4.6

“I attended this tour yesterday. Sunset and cocktails. It was def worth it. The tour guide as a female (7th grade school teacher) and phenomenal at her job. The tour offers two drinks tickets. Def worth it. The boat was clean. Crew was super sweet and kind. I would say the meet up point can…”

203 reviews1.5 hoursFrom $68by Empire Tours & Productions (Chicago River Boat Architecture Tours)

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Chicago River Cocktail Cruise - Stop 4: Magnificent Mile pass-by for river-to-street planning

Chicago, Tour Reviews

Chicago River Cocktail Cruise

/ June 20, 2026

2.Chicago River Cocktail Cruise

Ride a Chicago River cocktail cruise for 90 minutes of skyline architecture, included drinks, and live narration near Wrigley and Michigan Ave.

“Beautiful Experience!! My family and I will definitely be coming back to do this again. The tour guy gave a historical and architectural background for all the buildings in Chicago. The drinks were really good and the boat crew provided a great customer service. Chicago is beautiful, clean and has a lot of wonderful sightseeing…”

86 reviewsFrom $49by Chicago River Boat Architecture Tours

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Vito's Vault Chicago finest dinner theatre speakeasy - Food That Holds Up: Steak, Salmon, Chicken, and Meatball Comfort

Chicago, Tour Reviews

Vito’s Vault Chicago finest dinner theatre speakeasy

/ July 1, 2026

3.Vito’s Vault Chicago finest dinner theatre speakeasy

Step into a 1929 speakeasy for dinner, homemade-style hooch, and a 90-minute twenties musical comedy show in Chicago.

“Absolutely brilliant evening! Vito and the team put on a fantastic night.”

14 reviews3 hours (approx.)From $88.00by Vito's Vault

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Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour - What the secret entrance really changes

Chicago, Tour Reviews

Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

/ July 28, 2026

4.Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

Private 3-hour Chicago speakeasy VIP tour with secret entrances, Prohibition stories, and luxury chauffeur transport to 3–4 working bars.

7 reviews3 hoursFrom $950by Empire Tours & Productions (Chicago Gangsters and Ghosts Tours)

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Private Speakeasy Pub Crawl in Chicago with Local Historian - Your historian guide: what the stories add to the night

Chicago, Tour Reviews

Private Speakeasy Pub Crawl in Chicago with Local Historian

/ July 31, 2026

5.Private Speakeasy Pub Crawl in Chicago with Local Historian

A private 1920s Prohibition-style pub crawl in Chicago with a local historian, secret entrances, and period cocktails you’ll budget for separately.

“We had an amazing time and learned so much. Definitely a night to remember! The Untitled was my favorite place that we went to.”

5 reviewsFrom $101by Chicago Tours

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