Where to Go Out: the 4 Best Chicago Bar Crawls

1.Chicago River: Guided Sunset Cocktail & Architecture Tour

★★★★★★★★★★4.6 · 203 reviews · 1h 30m · from $68Our pick

Spend 90 minutes cruising the Chicago River at dusk while an English-speaking guide explains more than 50 buildings, from Art Deco towers to modern skyscrapers. Your ticket includes one or two drinks, depending on the option selected, plus coffee, soda, and bottled water. Bring layers, and find the boat at the final dock.

“Fun trip, excellent, knowledgeable guide. Good drinks. Friendly staff. Accommodating to my unexpected schedule change. Crowded and fairly small boat, but still I would highly recommend.”

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2.Chicago River Cocktail Cruise

★★★★★★★★★★4.5 · 86 reviews · from $49

You’ll spend 90 minutes cruising Chicago’s river past more than 50 notable buildings, including the Wrigley Building, Michigan Avenue Bridge, and Magnificent Mile. Choose a package with one or two alcoholic drinks, then listen to guides such as Justine, Brian, Jim, or Ed explain the city’s architecture. The boat has a restroom, snacks, coffee, tea, soda, and water.

“A Fun way to see Chicago and learn a little history and architecture, with booze as an extra incentive.”

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3.Tiki Bar Cruise on Chicago River or Lake Michigan

★★★★★★★★★★3.8 · 16 reviews · 1h 15m · from $41Best value

Board Island Party Boat at Dock 12 for a 75-minute tiki-themed cruise along Chicago’s main, North, and South river branches, or out on Lake Michigan. Expect palm trees, thatch roofing, music, climate control, restrooms, and a full bar where drinks cost extra. It suits relaxed afternoons, celebrations, and post-sightseeing downtime.

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4.Vito’s Vault Chicago finest dinner theatre speakeasy

★★★★★★★★★★5.0 · 14 reviews · 3 hours (approx.) · from $88Top rated

At Vito’s Vault, you enter a 1929 speakeasy at 5901 W Lawrence Ave, give the password, enjoy dinner and homemade hooch, then watch a 90-minute musical revue. Vito and his gang stay in character as servers and performers, mixing songs, dancing, comedy, and audience participation into a three-hour evening.

“Wonderful experience! Friendly, welcoming, and a lot of fun. Food was good and show was fantastic. Service was very good and wait staff were very personable.”

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