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

“Very crowded boat and all sat on top of each other virtually. The guide had a high opinion of himself and made jokes that were not really that funny. Didnt really tell us much about Chicago - The boat went through the lock and onto the lake and that was it. Pictures however were good…”

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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3.Chicago: Narrated River and Lake Cruise by Night

A 1.5-hour night cruise that shows the Chicago skyline from the river and Lake Michigan, including a pass through the Harbor Lock.

★ 4.6

“It was a great activity to enjoy as a family. We really enjoyed the tour guide's knowledge and explanation of the buildings and city. They allowed us to bring snacks if we wanted to, and they had a bar to purchase drinks. Overall, I highly recommend this activity to everyone visiting Chicago because the view…”

561 reviewsFrom $45by First Lady

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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

“Had an amazing time on this tour!!!! Hearing the stories and stoping at some of the same locations these gangsters and outlaws actually visited , stood, worked and even lost their lives at was quite the experience! The bus driver and tour guide were very professional . Our transportation bus was very nice, clean and…”

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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5.Chicago By Night River & Lake Cruise

A 1.5-hour Chicago River and Lake Michigan night cruise with live narration, skyline views, and Buckingham Fountain lights.

★ 4.5

“This was an amazing cruise. The sights were absolutely stunning at night. The captain and crew did a fine job. Andy was great, giving us information about the city.”

236 reviewsFrom $45.00by First Lady

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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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6.Chicago River: Guided Sunset Cocktail & Architecture Tour

90-minute Chicago River sunset cruise with included cocktails, award-winning architecture commentary, and 100-year-old bascule bridges.

★ 4.6

“Fun trip, excellent, knowledgeable guide. Good drinks. Friendly staff. Accommodating to my unexpected schedule change. Crowded and fairly small boat, but still I would highly recommend.”

203 reviews1.5 hoursFrom $68by Empire Tours & Productions (Chicago River Boat Architecture Tours)

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

A live-guided sunset ride on a Chicago open-top bus, with night skyline views, Navy Pier to the Loop, and photo stops plus easy downtown logistics.

★ 4.0

“Scenic views and a highly informative tour guide (Matty). His breadth of knowledge was quite remarkable as was his sense of humor. A smooth driving tour all done in 90 minutes. We enjoyed it!”

165 reviewsFrom $49.30by Big Bus Tours - USA

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

Private sunset sail from Navy Pier with a US Coast Guard–licensed captain, flexible route, skyline views, and Bluetooth music for up to 6.

★ 5.0

“Mike was awesome! It was my first time on a private sail with friends. We were comfortable, the sail was smooth and we had a great time. We didn’t want it to end.”

27 reviews2 hours (approx.)From $507.96by Come Sailing, Inc.

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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

“Will never book through viator, waited until a few hours before to cancel my booking. Wanted to reschedule me but i couldn't as it was my last day on my vacation. I'm still waiting on a refund!! Sad thing is I've read this on another review, should have went with my instinct. I wouldn't recommend…”

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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