Chicago, from the water up.
Architecture cruises down the river, deep dish in the Loop, Capone’s old haunts and the skyline from the lake. Here is what each tour is really like, what it costs, and where to book it.
Seven you’ll be glad you booked.
First trip or fifth, these carry the itinerary. The architecture cruise everyone photographs, a deep-dish lunch in the Loop, and the Capone-era corners your hotel desk will not mention.
Chicago River 90-Minute Architecture Tour
Enjoy a 90-minute Chicago River architecture cruise with indoor and outdoor seating, expert narration, and views from Michigan Avenue for $45.
From $45 per person
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Ninety minutes, a century of skyline.
Board at the river’s edge downtown and let the guide read the skyline like a book. The Wrigley Building in white terracotta, Marina City’s twin corncobs, the black steel of the old Sears Tower, bridges swinging open behind you as you drift toward the lake. This is the tour people plan the trip around.
How should you see the skyline?
The skyline is Chicago’s headline act, and there are three good ways to meet it: from the river, from the sidewalk, or from a thousand feet up. Here is what each one shows you, so you can pick the view that fits your day.
From the water
The river cruise
1 hour to 1 hour 30 minutes (approx.) · from $39 · 15,756 reviews
Ninety easy minutes on the water while a docent names every tower along the main branch and the south fork. You cover more architecture per hour here than any other way, and you stay sitting down the whole time. The best first look at the city.
Compare the river cruises →
On foot
The walking tour
4 hours 30 minutes (approx.) · from $100 · 1,153 reviews
Street level, where the skyscraper was invented. A guide walks you through the Deco lobbies, the Rookery light court, and the glass towers, close enough to read the stonework. For travelers who want the detail, not just the outline.
See the walking tours →
From the top
The observation deck
30 min · from $29 · 3,173 reviews
Ninety-four floors up 360 Chicago, or out on the Willis Skydeck ledge with nothing under your feet but glass and a quarter mile of air. Go near sunset when the lights come on. The whole grid laid out flat, all the way to Indiana.
See the sky decks →
The skyline turns on at night.
After sunset the lakefront becomes a different city. A dinner cruise gliding past the lit towers, fireworks over Navy Pier on summer weekends, a jazz set in a speakeasy behind an unmarked Loop door. The best seats are out on the water.
Deep dish is only the start.
Chicago eats big. A deep-dish slice thick as a doorstop, an Italian beef dripping down your wrist, a West Loop tasting crawl, a Pilsen taqueria run. If you book three food hours in this city, make them these.
The city Capone built.
Al Capone ran the town from a South Side hotel, and the speakeasies and bullet-marked corners are still on the map if you know the doors. These tours take in the St. Valentine’s Day site, the hidden bars, and the ghost stories the postcards leave out.
Chicago’s best rooms are indoors.
The Loop hides its finest spaces inside: the Rookery’s sunlit atrium, the Cultural Center’s Tiffany dome, the Art Institute galleries a block off the Bean. A century of Deco, Beaux-Arts, and quiet marble, still open to anyone who books the right walk.
Pick your Chicago, block by block.
The city works block by block. The Riverwalk for the architecture. The lakefront for the long view. Navy Pier for the Ferris wheel. Pilsen for the murals and the tacos, the South Side for the history the tour buses skip.
Know what you’re after?
A dozen ways into the same city. Pick the one that sounds like your kind of day, and every option behind it is already reviewed and priced.
Three days, done right.
You can’t see all of Chicago in one trip, but you can absolutely nail the right three days. This is the order we’d hand a friend flying into O’Hare tomorrow.
Day 1
Downtown and the river
Ride the architecture cruise while the light is good, walk the Riverwalk out to the lake, then a deep-dish lunch in the Loop. The whole skyline in one afternoon.
Plan day one →
Day 2
The lakefront and the museums
The Art Institute at opening, Millennium Park and the Bean, then bike the lakefront trail down to the Museum Campus with the skyline in the window the whole way.
Plan day two →
Day 3
The other Chicago
A Capone-era mob tour through the old gangland corners, tacos and murals in Pilsen, then a speakeasy nightcap behind an unmarked door. The city the postcards skip.
Plan day three →
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