River North Speakeasy Crawl

River North$$$4 hoursEvening
~$174 for two
Get directions to all stops
Chicago Riverwalk
1
Walk

Chicago Riverwalk

Start at the Riverwalk — stroll along the river past bars, kayak rentals, and architectural highlights. The best urban walk in America.

$0 pp30 minChicago Riverwalk, Chicago, IL 60601
RPM Italian
2
Meal

RPM Italian

5 min walk. Stylish Italian from the Lettuce Entertain You group. The thin crust pizza and pappardelle bolognese are outstanding. Celebrity spotting is common.

$45 pp1 hr 15 min52 W Illinois St, Chicago, IL 60654
The Drifter
3
Drinks

The Drifter

5 min walk. Hidden speakeasy inside the Green Door Tavern — find the unmarked door, descend the stairs, and enter a burlesque-era cocktail den. Magic shows and live performances.

$20 pp1 hr676 N Orleans St, Chicago, IL 60654
Three Dots and a Dash
4
Drinks

Three Dots and a Dash

5 min walk. Another hidden bar — find the alley entrance off Clark St. Elaborate tiki drinks, treasure chest cocktails for two, and a tropical underground vibe.

$22 pp1 hr435 N Clark St, Chicago, IL 60654
110 couples completed this

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Comments

TwoTonight TeamStaffMar 2026

Order the treasure chest at Three Dots — it's a shareable cocktail served in an actual treasure chest with sparklers. Instagram gold.

Total (for two)~$174
Duration4 hours
Best For

Couples

Best Time

Weekend

Tags

Best Seasons

All Year

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