USA · CHICAGO TOURS
Chicago invented the skyscraper and the best way to look at one is from the river. The 15 below compare the architecture cruises, the observation decks and the food walks on price, sailing length and how exposed the deck is.
Chicago’s river architecture cruise pairs skyline views with expert stories, multiple departure times, a bar, restroom, and strong value at $39.
“The tour guide was very knowledgable. Definitely plan to get one if you are in Chicago and enjoy the architectural history.”
Cruise all three branches of the Chicago River for 90 minutes of architecture, history, skyline views, and practical city sightseeing.
“Loved loved this tour ! So much history and a funny host!! Really enjoyed hearing all about Chicago’s history and the history of the river ! Great views and lots to see !”
See Chicago’s greatest buildings from the river on a lively 90-minute architecture cruise with expert guides, open decks, and onboard drinks.
“guide made the trip so interesting and quite funny engaging from start to finish also enjoyed the bar”
Explore Chicago’s Loop through Al Capone stories, haunted hotels, Death Alley, Millennium Park, and the Riverwalk on a lively 2-hour walk.
“We had been walking the same area but knowing the history definitely made our trip more interesting. Sophia was great! Congrats on getting engaged Sophia!”
Review of Chicago’s First Lady architecture cruise, with river views, expert docents, practical tips, pricing, seating, and itinerary details.
“Yes please, add to Cart. Amazing history lesson and current affairs in the city of Chicago. This was a fantastic tour with an incredibly knowledgeable docant. And they have a bar on the boat for the win.”
Step onto the glass Ledge at Chicago’s Willis Tower Skydeck for wide city views, interactive exhibits, and a thrilling 103rd-floor photo stop.
“We enjoyed our whole visit. Interesting Chicago Experience Museum including a Chicago train. Great views from the Sky deck. Going on the The Ledge was amazing. Only a short queue and although only have 90 seconds you can rejoin the queue and go in as many times as you like. We had plenty of time to take some great photos. No queues for lifts ( unlike New York) but this maybe different in high season. Recommend.”
Cruise all three branches of the Chicago River, hear lively stories about 40 landmark buildings, and see the skyline from the water.
“Tour was interesting and our guide was entertaining as well as factual. Recommended.”
Chicago Crime and Mob Bus Tour review: explore Capone-era sites, the Biograph Theatre, Nitti's vault, and the St. Valentine's Day Massacre.
“It was great, learned a lot about Chicago crime family and all that. Thank you the great hospitality”
See Chicago from 1,000 feet at 360 CHICAGO, with fast elevator access, Lake Michigan views, CloudBar, and optional TILT.
“This was so much fun to see the whole city and have a romantic drink at the beautiful bar! They have great souvenirs for sale and the Tilt experience looked fun but I didn't try it myself. Our bartender (can't remember her name) was on point with her service and added some personality and humor to the night, she even recommended our dinner spot which was excellent (Doc B's)!! I love the top of the Hancock - it's iconic Chicago and Cloud Bar 360 is worth the price! The souvenir photos (order and pay to take home) they take of you when you walk in are super cute too!! Highly…”
See Chicago’s landmark buildings from the river on a 45-minute Wendella cruise with live commentary, open-air views, and shelter for $28.
“In depth commentary and beautiful night experience. Zack had a lot of interesting information about the architecture and history of Chicago.”
Cruise Chicago’s river and lakefront for 90 minutes of architecture, skyline views, lively guides, indoor seating, and practical city history.
“Guide was knowledgeable and entertaining. We learned a lot about the city and saw some great views from the boat.”
See Chicago’s famous skyline from the river on a 45-minute family cruise with live guides, indoor seating, open decks, and a cash bar.
“One of my favorite parts of our Chicago visit. The cruise was well narrated and informational.”
See Chicago’s top sights from an open-top Big Bus, with flexible 24, 48, or 72-hour passes, audio commentary, and live bus tracking.
“It’s a great way to get around town see other sites and learn some history about Chicago. Our favorite drivers were the ones that gave extra information in addition to the recording. We especially enjoyed Donnie the driver we had a few times.”
Cruise Chicago’s river and lakefront for 90 minutes of architecture, skyline views, expert stories, and a trip through the historic lock.
“We LOVED our guide Lucas, he was hilarious and very informative. 10/10 recommend!!”
Taste deep dish, hot dogs, Italian beef, brownies, and popcorn while walking Chicago landmarks, with a free bike or kayak rental included.
“Very fun tour full of delicious food. Great portions and a nice variety. Walking was just right in between stops to digest! Had two young teens with us and they enjoyed the tour as well. Would recommend!”
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