The 15 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 Tour by Open-top Bus with Live Guide

★★★★★★★★★★4.3 · 69 reviews · from $50

Ride 90 minutes on an open-top double-decker from River North to Museum Campus and back. A live English-speaking guide points out Willis Tower, Michigan Avenue, the Bean, Art on the Mart, and Chicago’s evening lights.

“Not very excited, definetely overpriced, the tour guide was not respectful. Also forgot an expensive scarf on the bus, the stuff even did not try to locate me although the guide asked me where I was from, what hotel I was staying in and what conference I have attended.”

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10.Historic Gangsters & Twilight Tales Night Cruise

★★★★★★★★★★4.1 · 63 reviews · from $45

Spend 90 minutes on the Chicago River with an English-speaking guide, hearing tales of the Eastland disaster, Chicago Fire, H. H. Holmes, and mobsters while landmarks such as the Wrigley Building and Willis Tower glow above the water.

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11.Chicago Night Driving Tour with Skydeck and River Cruise

★★★★★★★★★★4.4 · 44 reviews · 3h 30m · from $204

This 210-minute English-language tour pairs Willis Tower’s Skydeck and glass Ledge with a Chicago skyline cruise and narrated driving tour. Your guide collects you from a downtown hotel, visits more than 40 landmarks, and returns you downtown. Small groups are limited to six or seven people.

“Organisation désastreuse. Visite prévue de la rivière chicago annulée car le guide s est trompé. Remplace par 1 visite sur le lac non programmé fait en dernier minute et sur 1 créneau horaire en dehors du créneau horaire prévu. Des allés retours pour pallier cette incompétence et cette désorganisation qui nous ont fait perdre notre soirée.”

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12.Serene Private Sunset Sail on Lake Michigan – Navy Pier, Chicago

★★★★★★★★★★5.0 · 27 reviews · 2 hours (approx.)

Set out from Navy Pier Marina on a private two-hour sunset sail with a US Coast Guard-licensed captain such as Mike or Rich. You can request landmarks, bring food and drinks, play music through Bluetooth speakers, and watch Chicago glow from the water.

“We had a beautiful sunset said with Captain Mike. Wonderful city views, pleasant conversation about sailing, the City of Chicago, and our lives, with milk and chocolate chip cookies to celebrate our Dad's 80th birthday with a memorable experience for us all. Highly Recommended!”

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13.Chicago Night Driving Tour with Skydeck and River Cruise

★★★★★★★★★★4.5 · 26 reviews · 3 hours 30 minutes (approx.) · from $189

Spend about 3.5 hours seeing Chicago after dark with downtown pickup, a guided driving tour, Willis Tower’s Skydeck, a 40-minute river cruise, Cloud Gate, and the Adler Planetarium viewpoint. Guides such as Danny, Ruben, Andrew, and Tony are known for adding history and local context.

“LONG REVIEW!! I was skeptical for the cost because typically I would build and execute the plan myself but the convenience of someone who knows the city driving you around, then picking you up is worth the cost alone! The price point already paid for itslef by saving you time and money from walking and/or ride sharing. Now, the bonus you ask! 💯 Danny, he knows the city, the routes, the history, the Van he drives is NICE! Total style. I was flying solo on this adventure and I can't boast how nice it was to have Danny sharing my excitement of what I saw, taking my pics for me,…”

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14.Chicago Sunset Segway Tour

★★★★★★★★★★5.0 · 26 reviews · 1 hour 30 minutes (approx.) · from $75

Start at 34 S Michigan Ave at 5:30 pm for a 90-minute Segway ride through Grant Park and along the lakefront. Your guide trains you before leading you past the Field Museum, Adler Planetarium, Soldier Field, Buckingham Fountain, Millennium Park, and Chicago’s famous architecture.

“We had a great experience and a great guide! There was a lot of people to get through but overall had the best time!!”

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15.2 Hour Chicago Pier Fireworks & Evening Segway Tour

★★★★★★★★★★5.0 · 7 reviews · 2 hours · from $77

Ride a Segway through Chicago’s evening parks with a small group of up to seven. After a 15-minute lesson, your English-speaking guide leads you past Buckingham Fountain, Millennium Park, rose gardens, and Crown Fountain to a fireworks view near Navy Pier. Guides Ian and Sean have earned especially strong praise.

“Excellent - went all over the city park areas!”

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