The 9 Best Evening Tours in Chicago

1.Lake Michigan Sunset Cruise in Chicago

★★★★★★★★★★4.5 · 1,520 reviews · 1 hour 30 minutes (approx.) · from $45Our pick

Board at the Wrigley Building for a 90-minute evening cruise along the Chicago River and through the lock to Lake Michigan. Enjoy skyline views as daylight fades, with narration, music, a climate-controlled lounge, restrooms, and a bar serving drinks and snacks for purchase. Arrive early for the best seats.

“I booked this experience for my husband's first weekend after retiring after 40 plus years. This first step in " the best is yet to be" did not disappoint. Despite the large crowd of participants everything flowed smoothly in getting on the boat. The guide was engaging and very knowledgeable. We learned a lot of interesting facts about Chicago history and architecture. The Skyline view at sunset was awesome. The hour and a half flew by.”

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2.Chicago by Night River and Lake Cruise

★★★★★★★★★★4.6 · 791 reviews · from $45

Board First Lady near Michigan Avenue and Wacker Drive for a 90-minute evening cruise along the Chicago River and Lake Michigan. A live English-speaking guide points out Willis Tower, Navy Pier, Buckingham Fountain, and more, while the boat passes through Chicago Harbor Lock.

“We had 1 night in Chicago and thia trip was the the best was to get the most out of the city by night... this was an amazing experience, it's just a shame we were only there for 1 night... we will definitely be back again and this will definitely be on the list again”

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3.1.5-Hour Scenic Sunset Lake Cruise

★★★★★★★★★★4.7 · 739 reviews · 1h 30m · from $45

Cruise from Michigan Avenue through the Chicago Lock and onto Lake Michigan as the sun drops behind Chicago’s skyline. You’ll see Willis Tower, the John Hancock Building, Grant Park, Soldier Field, Adler Planetarium, and Shedd Aquarium, with brief live commentary and an onboard bar.

“Fantastic boat ride with very good staff. The sunset view was amazing. Thank you.”

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4.Chicago Night Crimes Tour by Bus

★★★★★★★★★★5.0 · 478 reviews · 2 hours to 2 hours 30 minutes (approx.) · from $55Top rated

Spend about two hours tracing Chicago’s gangster past by comfortable bus. A live guide covers Al Capone, John Dillinger, Dean O’Banion, Frank Nitti, and Hymie Weiss, with stops at crime scenes, the Biograph Theater, Nitti’s Vault, and historic downtown sites.

“The tour was educational and entertaining! We would recommend to anyone who is interested in the history of the city.”

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5.Chicago By Night River & Lake Cruise

★★★★★★★★★★4.5 · 236 reviews · from $45

Cruise from 112 E Wacker Dr along the Chicago River and Lake Michigan for 90 minutes. Guides such as Andy, Seamus, Nick, Olivia, and Savannah share Chicago history and architecture as the skyline, Museum Campus, and Buckingham Fountain glow after dark.

“It was beautiful trip around the Chicago skyline at night and Savannah the tour guide made the trip interesting and funny.”

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6.Guided Sunset Cocktail & Architecture Tour

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

Cruise the Chicago River for 90 minutes with an English-speaking guide, a cocktail or soft drink, and views of more than 50 buildings. You will pass under old bascule bridges as daylight fades and downtown lights come on. A teacher-guide may lead the tour, with drinks and snacks available on board.

“The guide was very engaging and informative. Lots of fun - bartenders were also great and very speedy for how many people they had to serve”

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7.Big Bus Chicago: Sunset Tour by Open-Top Bus with Live Guide

★★★★★★★★★★4.0 · 165 reviews · from $49

Ride an open-top double-decker bus through Chicago at sunset, passing Navy Pier, the Magnificent Mile, Millennium Park, the Wrigley Building, and the Museum Campus. A live English or Spanish guide provides the stories, with guides such as Matty and Bernie praised for humor and city knowledge.

“Bug bus broke before we left We had to cancel. Big bus should have another bus to replace it and have the excursion, not cancel it.”

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8.Chicago Crimes Night Tour

★★★★★★★★★★4.5 · 89 reviews · 2 hours · from $55

Ride a comfortable, climate-controlled bus through Chicago’s crime past with a live English-speaking guide. See the Biograph Theater, massacre site, criminal courthouse, Dillinger’s final path, gang-era tunnels, and a mini mob museum with Frank Nitti’s safe and address book.

“Javier was an amazing guide. The experience was informative, fun and a unique perspective on the City.”

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9.Sunset Kayak Tour on the Chicago River

★★★★★★★★★★4.2 · 5 reviews · 1h 30m · from $57

You will paddle a downtown stretch of the Chicago River during golden hour, passing Willis Tower, the Civic Opera Building, and Merchandise Mart. Wateriders provides the kayak, safety briefing, and English-speaking guide. The small-group format suits beginners with basic swimming skills.

“Eindrückliche Kanu-Tour inmitten von Chicago beim Einnachten… Leider etwas chaotisch organisiert mit Kanus, die viele Reparaturen nötig hätten. Von den Guides keine Hinweise/Erklärungen zur Tour 😳”

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