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Top Nightlife Experiences in Chicago

Top Nightlife Experiences in Chicago

Home to everything from bars and craft breweries to comedy clubs and critically-acclaimed restaurants, the Windy City has a lot to offer after the sun sets. Here are a few of the best ways to spend an evening in Chicago. 

Prohibition-Themed Excursions

Chicago’s insalubrious past has since become part of the Windy City’s allure; 1920s and ’30s-themed tours typically introduce you to former residents such as Al Capone and visit some historic speakeasies. Book an evening excursion to discover local history and enjoy classic cocktails in flapper fashion.

Craft Beer Crawls

The existence of dozens of breweries show that Chicago takes its beer seriously. Explore some of the city’s pioneering breweries and destination-worthy bars on a bar crawl or freewheeling beer tour, and leave the logistics (and driving) to your guide.

See a Show

The Windy City is packed with theaters and performance venues, all of which offer after-dark entertainment. If you’re visiting with kids, take in a blockbuster musical at the Loop’s historical theaters. Or, if you’re into late-night laughs, Chicago has a surfeit of comedy clubs, including the renowned Second City.

Dinner Cruises

Combine sightseeing with dinner on an evening cruise of the Windy City’s waterways. Whether you sail on the Chicago River or head to the waters of Lake Michigan for glittering skyline views, you’ll enjoy gourmet eats, delectable wine pairings, and incomparable scenery. 

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Free Cancellation:Get a full refund up to 24 hours in advance on most experiences.See Details

4 Tours and Activities

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Chicago Sunset Dinner Cruise on Lake Michigan
Likely to Sell OutLikely to Sell Out

Chicago Sunset Dinner Cruise on Lake Michigan

star-4
137
Make your evening in Chicago one to remember with this luxury sunset cruise featuring dinner, sightseeing and dancing along the shores of Lake Michigan. Feast your eyes on incredible views of iconic Windy City sights like Navy Pier, the Willis (Sears) Tower, Buckingham Fountain and Soldier Field, then fill your belly with a bountiful all-you-can-eat buffet. Continue the celebration with a live DJ who will mix up a selection of dance favorites.
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  • 3 hours
From
$115.46
From
$115.46

Premier Chicago River Dinner Cruise
Likely to Sell OutLikely to Sell Out

Premier Chicago River Dinner Cruise

star-3.5
14
Cruise down the Chicago River in style during this 3-hour dinner cruise aboard the Odyssey. Watch the beautiful city and its architecture pass by through the ship’s panoramic windows. Then sit down to delicious 3-course meal accompanied by DJ entertainment to set the mood for your journey. A full-service bar complete with microbrews, creative cocktails, and a wine list is also available for purchase.
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  • 3 hours
From
$172.58
From
$172.58

Chicago Craft Brewery Barrel Bus Tour

Chicago Craft Brewery Barrel Bus Tour

star-4.5
45
Learn about Chicago’s brewpub scene and taste different types of craft beer on this guided brewery tour. Visit unique breweries for craft beer samples plus an additional brewing production facility for an in-depth tour. Discover the science behind the brewing process, complete with step-by-step procedures, and enjoy plenty of beer samples throughout the tour. Round-trip transportation in a Prohibition-era-styled barrel bus is included.
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  • 3 hours 30 minutes
  • Free Cancellation
From
$89.60
From
$89.60

Private Speakeasy Pub Crawl in Chicago with Local Historian
Likely to Sell OutLikely to Sell Out

Private Speakeasy Pub Crawl in Chicago with Local Historian

star-4.5
3
Travel back in time to the 1920s, when Chicago was a prohibition era hub for lively speakeasies. Your guide, a local historian in period dress, will lead you through secret entrances to speakeasies once frequented by bank robbers and Chicago gangsters like Al Capone. Order prohibition era cocktails (additional cost) and listen to stories about bootlegging and racketeering in 1920s Chicago. Guests are welcome to come in period dress.
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  • 3 hours
  • Free Cancellation
From
$330.00
Price varies by group size
From
$330.00
Price varies by group size