Chicago from the water up.
The architecture boats, the ledge on the ninety-fourth floor, the Prohibition walks and the tables that serve pizza by the pound: what each one is like, what it costs, and where to book it.
Seven that carry a Chicago weekend.
The boat under the bridges, the glass box hanging off the ninety-fourth floor, a walk through the addresses Capone kept, and a table where the pizza arrives forty minutes after you order it.
Chicago River 90-Minute Architecture Tour
Wendella’s 90-minute Chicago River architecture cruise with indoor warmth, big skyline views, and stories from 130+ years.
From $45 per person
Read the review →
★ 4.8Safe betChicago River: 1.5-Hour Guided Architecture CruiseFrom $448,046 reviews
★ 5.0Sells out earlyChicago Architecture Center River Cruise aboard First LadyFrom $575,536 reviews
★ 4.8Crowd favouriteArchitecture River Cruise Skip-the-Ticket LineFrom $394,325 reviews
★ 4.5Worth the ticketChicago Crime and Mob Bus TourFrom $493,186 reviews
★ 4.5Easy win360 CHICAGO Observation Deck TicketFrom $293,173 reviews
★ 4.5First-timer classicChicago River 45-Minute Architecture Tour from Magnificent MileFrom $282,924 reviews
The buildings explain themselves from the river.
Ninety minutes between the bridges with a docent naming every tower as it passes: white terracotta on the Wrigley Building, the corncob balconies at Marina City, black steel everywhere the Loop turns a corner. Nothing else teaches you this city as fast.
River boat or lake boat?
Everybody gets on the water here, and the boat you choose sets the shape of the afternoon. Three ways to do it, with sailing times and prices on each.
Docent on board
The architecture hour
1 hour 30 minutes (approx.) · from $45 · 9,629 reviews
Up the main branch, down the south, back under Michigan Avenue, with a guide naming architects the whole way. Enclosed lower deck for the days the wind comes off the lake. Book this one if you only get on the water once.
Compare the river cruises →
Out past the locks
The lake run
1 hour 30 minutes (approx.) · from $45 · 2,308 reviews
Through the lock beside Navy Pier and onto open water, where the whole downtown finally stands up in one piece. Bring a layer: it runs ten degrees cooler a mile out, even in July.
See the lakefront cruises →
Dinner on deck
The long evening
from $89 · 348 reviews
Three hours, a table, and the towers switching their lights on course by course. Boarding is at Navy Pier, and the window seats go to whoever booked earliest.
See the dinner cruises →
The city keeps its receipts.
Speakeasy doors that still open, the alley beside the Biograph, a bus that runs the old mob addresses once the offices empty out. Chicago tells these stories better than any city has a right to.
The museums are the other skyline.
Sue the tyrannosaur on Museum Campus, Hopper’s all-night diner at the Art Institute, a whale shark circling the tank at the Shedd. Timed tickets and guided entry, priced below.
Deep dish is the start, not the point.
Italian beef dipped at the counter, a Chinatown walk that finishes in dumplings, doughnuts eaten between stops downtown. These are the tours that get through the most of it.
The Loop rewards a slow walk.
Art Deco lobbies you are allowed to walk into, the pedway running warm under the whole downtown, a Calder in a plaza most people cross without looking up. A guide gets you through the doors that look private.
Pick your part of the city.
The river for the buildings. The lakefront for the long view back. Museum Campus for a cold Saturday. The Loop for everything that happens in between.
Chicago by the kind of day you want.
Twelve ways into the same city. Pick the one that sounds like your kind of day, and everything behind it is already priced and rated.
Three days that get Chicago right.
You will not see all of it in one trip; you can absolutely get the shape of the place in three days. This is the order to take them in.
Day 1
Get on the river
Board at Michigan Avenue while the light is still low, then walk the Riverwalk back east and eat where the boats tie up. Easy on the legs after a flight.
Plan day one →
Day 2
Lakefront and museums
The Field Museum as the doors open, the Shedd after lunch, then the path north past the planetarium for the postcard view back at the towers.
Plan day two →
Day 3
Under the surface
A Prohibition walk through the South Loop, the pedway at street level minus the street, and one last Italian beef before the airport train.
Plan day three →
Latest Chicago tour reviews.
★ 3.5Private Transfer from Chicago Airport (ORD)From $763 reviews
★ 5.0Self-Guided Chicago Loop Tour Explore the City at Your Own PaceFrom $93 reviews
★ 3.5Private Vacation Photoshoot with Photographer in ChicagoFrom $1543 reviews
★ 5.0Welcome to Chicago: Private Half-Day Tour with 360 Observation DeckFrom $2403 reviews
Chicago’s Luxury Minibus City Sightseeing TourFrom $1013 reviews
Architecture and Engineering Marvels Walking TourFrom $303 reviews
★ 5.0Private Holiday City TourFrom $4993 reviews
★ 4.5Private Downtown Chicago TV and Movie Sites Guided Walking TourFrom $1323 reviews