Evening Experiences


CHICAGO · ILLINOIS

15 Best Evening Experiences In Chicago

The best of Chicago.

The 15 best evening experiences in Chicago, with honest prices, run times and who you book through. Which ones are worth your time downtown, and what each one actually gets you.

15 Best Evening Experiences In Chicago

Lake Michigan Sunset Cruise in Chicago - Getting to 400 N Michigan Ave (and Securing a Good Spot)
Chicago, Cruises & Boat Tours, Evening Experiences, Lake Michigan Cruises, Tour Reviews

Lake Michigan Sunset Cruise in Chicago

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1.Lake Michigan Sunset Cruise in Chicago

A 90-minute sunset cruise from the Chicago River to Lake Michigan. See skyline lights turn on, with a warm lounge and onboard bar.

Most Popular★ 4.5

“We missed the sunset cruise because we could not find parking. When we finally did find parking, it was too late. We went to the ticket office and they gave us the architecture tour instead. It was great. A beautiful clear night and a wonderful tour guide. The buildings were lit up and we learned…”

1,520 reviews1 hour 30 minutes (approx.)From $45.00by Wendella Tours & Cruises

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Chicago: 1.5-Hour Scenic Sunset Lake Cruise - From Michigan Avenue to the Chicago Locks: How the Route Changes the View
Chicago, Cruises & Boat Tours, Evening Experiences, Lake Michigan Cruises, Tour Reviews

Chicago: 1.5-Hour Scenic Sunset Lake Cruise

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Chicago: Narrated River and Lake Cruise by Night - The Landmarks the Guide Calls Out While You Float
Chicago, Cruises & Boat Tours, Evening Experiences, Lake Michigan Cruises, Tour Reviews

Chicago: Narrated River and Lake Cruise by Night

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Chicago Night Crimes Tour by Bus - Stop 1 Outside 163 E Pearson: The Mob Story Starts Here
Chicago, Evening Experiences, Gangster & Crime Tours, Tour Reviews, Tours

Chicago Night Crimes Tour by Bus

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4.Chicago Night Crimes Tour by Bus

Ride Chicago by night on a bus gangster tour with live narration, photo stops, and stops at Biograph Theatre, Nitti’s Vault, and the Water Tower.

★ 5.0

“John was great and very knowledgeable! Bus was comfortable. And enjoyed all the stops especially the last one!”

478 reviews2 hours to 2 hours 30 minutes (approx.)From $55.00by Chicago Crime Tours and Experiences LLC

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Chicago By Night River & Lake Cruise - Lock-to-lake transition: the part that feels unexpectedly “real”
Chicago, Cruises & Boat Tours, Evening Experiences, Lake Michigan Cruises, Tour Reviews

Chicago By Night River & Lake Cruise

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Chicago River: Guided Sunset Cocktail & Architecture Tour - The timing: what 90 minutes actually feels like at dusk
Chicago, Chicago River Architecture Cruises, Dinner & Cocktail Cruises, Evening Experiences, Guided, Tour Reviews, Tours

Chicago River: Guided Sunset Cocktail & Architecture Tour

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Big Bus Chicago: Sunset Tour by Open-Top Bus with Live Guide - Where You Start on Clark and Ontario (and Why Arrival Time Matters)
Chicago, Evening Experiences, Guided, Hop-On Hop-Off & Bus Tours, Tour Reviews, Tours

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

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Chicago Crimes Night Tour - The luxury coach ride: comfort matters on a 2-hour schedule
Chicago, Evening Experiences, Gangster & Crime Tours, Tour Reviews, Tours

Chicago Crimes Night Tour

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8.Chicago Crimes Night Tour

Chicago Crimes Night Tour is a 2-hour guided coach ride to the St. Valentine’s Day Massacre, Dillinger’s last steps, and mob-era stops.

★ 4.5

“John was our guide and he was so much fun to have leading us through the whole thing! He’s very knowledgeable and made the whole experience fun & interesting! Highly recommend trying this out!”

89 reviews2 hoursFrom $55by Chicago Crime Tours and Experiences LLC

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Chicago: Sunset Tour by Open-top Bus with Live Guide - Price and what $50 buys you in real life
Chicago, Evening Experiences, Guided, Hop-On Hop-Off & Bus Tours, Tour Reviews, Tours

Chicago: Sunset Tour by Open-top Bus with Live Guide

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9.Chicago: Sunset Tour by Open-top Bus with Live Guide

Sunset views from Chicago’s open-top bus: Museum Campus skyline, Millennium Park, Art on the Mart, and a live English guide.

★ 4.3

“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.”

69 reviewsFrom $50by Big Bus - Chicago

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Chicago: Historic Gangsters & Ghosts Night Cruise - The dark-side stories you’ll hear on board
Chicago, Cruises & Boat Tours, Evening Experiences, Gangster & Crime Tours, Ghost & Haunted Tours, Historical Tours, Tour Reviews

Chicago: Historic Gangsters & Ghosts Night Cruise

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Chicago: Small-Group Night Tour w/ Skydeck & Skyline Cruise - Skip-the-line entry and the small-group advantage
Chicago, Cruises & Boat Tours, Evening Experiences, Lake Michigan Cruises, Skydeck & Observation Decks, Tour Reviews, Tours

Chicago: Small-Group Night Tour w/ Skydeck & Skyline Cruise

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11.Chicago: Small-Group Night Tour w/ Skydeck & Skyline Cruise

See Willis Tower from the 103rd floor, feel The Ledge, cruise Chicago’s lights, and tick Cloud Gate on a small-group night tour.

★ 4.3

“We had a wonderful tour in Chicago with our guide Jake Edgar, we started with a river tour where we were informed from another guide about the architecture along the river, it was interesting to see the mix of old and new bulidings in chicago and to hear about the history behind it. The tour…”

42 reviewsFrom $204by See Sight Tours Inc

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Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago - How the Route Works: Wind Direction, Landmark Requests, and Control
Chicago, Cruises & Boat Tours, Evening Experiences, Lake Michigan Cruises, Private, Tour Reviews

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

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Chicago Night Driving Tour with Skydeck and River Cruise - Willis Tower Skydeck: 103rd-floor 360 views and The Ledge
Chicago, Cruises & Boat Tours, Evening Experiences, Private & Custom City Tours, Skydeck & Observation Decks, Tour Reviews, Tours

Chicago Night Driving Tour with Skydeck and River Cruise

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13.Chicago Night Driving Tour with Skydeck and River Cruise

Chicago night driving with Willis Tower Skydeck, Cloud Gate, and a post-dark Chicago River cruise. Small group, $189, about 3.5 hours.

★ 4.5

“Our tour guide, Tony, was great! Respectful, fun, very knowledgeable about Chicago’s history and we had fun talking with him! We took one star because the boat ride was in open-air barge. The boat ride itself was wonderful! But we did not know that there was no covered seating and it was a night ride.”

26 reviews3 hours 30 minutes (approx.)From $189.00by See Sight Tours USA

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Chicago Sunset Segway Tour - Soldier Field and the Lakefront rhythm
Chicago, Evening Experiences, Segway Tours, Tour Reviews, Tours

Chicago Sunset Segway Tour

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14.Chicago Sunset Segway Tour

Sunset Segway through Chicago’s lakefront and top landmarks with hands-on coaching, a small group of 10, and helmets included for $75.

★ 5.0

“Vincent shared stories as only a true Chicagoan could. It was a beautiful ride. He also individually taught each rider, assuring safety and a great experience.”

26 reviews1 hour 30 minutes (approx.)From $75.00by Bike and Roll Chicago

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2 Hour Chicago Pier Fireworks & Evening Segway Tour - How the 15-minute Segway orientation sets you up
2-Hour Experiences, Chicago, Dinner & Cocktail Cruises, Evening Experiences, Segway Tours, Tour Reviews, Tours

2 Hour Chicago Pier Fireworks & Evening Segway Tour

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More Evening Experiences In Chicago

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