CHICAGO · ILLINOIS
The best of Chicago.
The 15 most popular things to do in Chicago. Architecture river cruises, the Willis Tower Skydeck, gangster and speakeasy walks, lakefront cruises and the city’s best food tours, all in one place.
Chicago Architecture River Cruise with live expert commentary, skyline views, mobile tickets, pet-friendly boats, and about 1 hour on the water.
Most Popular“This was absolutely amazing. I went with my 17-year-old son. We both just loved it. The tour guide on the boat was funny and nice and so educational and Chicago is just a sunny city which I have a deeper appreciation for now.”
A 90-minute Chicago River cruise with architecture narration, indoor climate control, and major-sight views of Wrigley Building, Marina City, and more.
“Very nice everything is amazing beautiful place people very kind whit my family probably be back next year”
Chicago River 1.5-hour architecture cruise covers main stem plus north and south branches. Expert guides, indoor comfort, deck views.
“It was the most interesting architecture tour I have ever been!! The tour guide was very charismatic and made us laugh at lot, we explained everything in a very passionate way and we had a blast!”
A historian-led Chicago Loop walk mixing Prohibition-era mob stories and reported ghost sites, with optional minibus upgrade for $52.
“Such a fun way to see the city and learn some more about its history. Our tour guide was great and answered all of our questions.”
Chicago Architecture Center cruise aboard First Lady. 90 minutes of docent-led river views of Willis, Marina City, Navy Pier, and more.
“Had an amazing time on this in depth tour! Guide was upbeat and so knowledgeable, and kept the tour lively the whole time. Nice variety of architecture and local history. Loved the context part showing how each building is in conversation with those around it. Highly recommend!”
Willis Tower Skydeck with The Ledge glass balcony in Chicago. Timed entry, museum exhibits, and a thrilling skyline view for about 45 minutes.
“A must-do Chicago experience. There's a small but interesting museum about Chicago and the Tower to go through en route to the Skydeck which was an added bonus (though you can skip it). The views from the Skydeck and the Ledge are fabulous. We went at 7.30 p.m so got the sunset and the night…”
Skip the ticket line for Chicago’s architecture river cruise with a live docent, 40 landmarks, and a cash bar on 3 river branches.
“Really interesting, great tour guide Chicago Bob and beautiful view”
A $49 coach tour through Chicago’s mob history with photo stops, mini museum, and story-first guides. 90–120 minutes of crime scenes.
“Great tour guide! Windows of bus were fogged, couldn’t see anything but stories were great! Good length but they need to fix the windows in winter with fogging!”
Take a 45-minute Chicago River architecture cruise from the Magnificent Mile with live narration, top-deck views, and major landmarks.
“Great information and well presented, we did a January tour and is was freezing but fun! Boat staff was friendly.”
Skip the ticket desk for fast access to 360 Chicago’s 94th-floor views, Lake Michigan panoramas, and optional TILT upgrade.
“Great experience, beautiful view. Sometimes the windows could be a bit cleaner and more explanations (yes, they want you to download the app but I wasn't keen on this and would have loved more explanations onsite.). But overall a nice experience.”
One-and-a-half-hour Chicago architecture boat tour with live narration, River and Lake Michigan views, skyline photos, and climate-controlled seating.
“Very informative. Bring a small blanket- it was chilly. But if you’re hot, you could sit on the blanket. The chairs were pretty uncomfortable.”
A 45-minute Chicago River family architecture cruise with live English guide, indoor and outdoor decks, and skip-the-line entry for $28.
“I booked the evening tour for my anniversary. The views were beautiful in the evening. Check the weather before in case it gets cold. There is a lower deck in the event it's too cold.”
Hop-on, hop-off Big Bus Chicago gives you open-top views, audio commentary, and easy stops at top sights with 24/48/72-hour flexibility.
“I take these tours in every city. This was the worst by far. Workers were rude. They didn’t have enough headphones.”
Chicago’s River and Lake Michigan architecture cruise. 90 minutes, expert narration, Chicago Lock, skyline photos, and indoor or deck seating.
“It was awesome, I loved the information the guide was able to bless us with.”
Taste Chicago classics on a 3-hour walking tour with deep-dish, Italian beef, hot dogs, brownie and popcorn plus a free 2-hour bike or kayak.
“Excellent tour of a number of iconic food spots whilst enjoying the walking tour of the city and the history. Our tour guide Gabe was awesome.”
From the river and the skyline to the gangster trails, the lakefront and the deep-dish counters, every way to spend a day in the city.
