CHICAGO · ILLINOIS
The skyline that rises straight off the river.
Architecture cruises down the Chicago River, a glass ledge a quarter-mile up, Capone-era speakeasies and dinner cruises on Lake Michigan. The full guide to the city that gave the world the skyscraper.
Only in Chicago
Three things you can only do in Chicago.
Boat tours, tall buildings and ghost walks turn up in every city. Floating through the birthplace of the skyscraper, standing on a glass ledge a quarter-mile up, and walking Al Capone’s actual streets do not.
Born on the river
The Architecture Cruise
After the Great Fire of 1871 cleared downtown, the architects who rebuilt it invented the steel-framed skyscraper right here. The river cruise is the only way to read that whole story off the water, gliding under the bridges past fifty landmark buildings while a guide explains why each one looks the way it does. No other city tells its skyline from a boat like this.
- 1 Chicago Architecture River Cruise
- 2 Chicago River 90-Minute Architecture Tour
- 3 Chicago River: 1.5-Hour Guided Architecture Cruise
1,353 feet up
The Glass Ledge
Willis Tower was the tallest building on Earth for twenty-five years, and The Ledge pushes glass boxes out from the 103rd floor so you stand on thin air over the city. A mile north, 360 Chicago tilts you face-first toward the street from the old Hancock. Two of the most nerve-jangling skyline views anywhere.
- 1 Chicago: Willis Tower Skydeck and The Ledge Ticket
- 2 Chicago: 360 Chicago Observation Deck General Admission
- 3 Skydeck – Willis Tower Admission
The Prohibition years
Capone's Chicago
No city wears its Prohibition history like Chicago. Al Capone ran an empire from these blocks, the St. Valentine’s Day Massacre happened on a street you can still walk, and the speakeasies that hid the liquor are bars again today. The crime and ghost tours take you to the actual corners where it all went down.
- 1 Chicago: Gangsters and Ghosts Walking Tour
- 2 Chicago Crime and Mob Bus Tour
- 3 Chicago: Gangsters and Ghosts Guided Walking Tour
Start with the boat
Chicago’s single most-booked experience.
More travellers book this than anything else on the site, and for once the crowd is right. If you lock in only one thing before you arrive, make it the river.
The classics
Chicago’s Most Popular Tours & Cruises
Architecture cruises, the Willis Tower Skydeck, the gangster bus and the lakefront sunset boats. The experiences most visitors book first.
Where to begin
The Chicago trip, built by the day.
River cruises, the skyline decks, the gangster trail, the lakefront and the food. The themes most Chicago trips are planned around, and the best of each.
The big question
Three ways to see the skyline.
Chicago’s skyline is the whole point, and there is no wrong way to take it in. Here is how the three best stack up, and who each one is for.
Born of the fire
Chicago wrote the book on the skyscraper.
When the Great Fire levelled downtown in 1871, the architects who rebuilt it tried something no one had: a building held up by a steel skeleton instead of its walls. The Home Insurance Building went up in 1885, ten storeys tall, and every tall building on Earth since traces back to it. The river cruise is where the whole story comes together, fifty landmarks deep, told from the water that runs through the middle of it all.
Read the guide: architecture river cruises →After dark
Capone’s Chicago, after dark.
For thirteen years the city ran on bootleg liquor, and Al Capone ran the city. The St. Valentine’s Day Massacre, the speakeasies behind unmarked doors, the hotels where the bosses held court: the gangster bus and walking tours take you to the actual addresses. Stay out past dark and the ghost tours pick up where the mob left off, through the alleys and old theatres that never quite emptied.
See the gangster & ghost tours →The third coast
A skyline best seen from the lake.
Chicago meets Lake Michigan along twenty-six miles of open shoreline, and the view back at the city from the water is the one on every postcard. Sunset cruises slip out as the towers light up, dinner boats turn the evening into the event, and speedboats hammer along the lakefront for anyone who would rather feel the spray.
Browse the lake cruises →A quarter-mile up
Step out onto the glass.
The Ledge at Willis Tower is a row of all-glass boxes cantilevered off the 103rd floor, 1,353 feet over the Loop, with nothing but air beneath your shoes. Across town, 360 Chicago’s TILT leans you out face-first above the Magnificent Mile. On a clear day you can see four states. Pick your nerve and pick your tower.
- 1 Chicago: Willis Tower Skydeck and The Ledge Ticket
- 2 Chicago: 360 Chicago Observation Deck General Admission
- 3 Skydeck – Willis Tower Admission
At the table
Deep dish, and everything after.
Yes, the deep dish is real, and a pizza tour settles the great Chicago argument once and for all. But the city eats far wider than that: the char-dragged hot dog with everything but ketchup, the Italian beef dipped and dripping, and the chef-driven neighbourhood spots a food walk strings together one bite at a time.
See all 33 food tours →By experience
Pick how to spend the day.
A cruise if you want the skyline, a walk if you want the detail, a food tour if you came hungry. Plus the gangster trail, the lakefront boats, bikes along the shore and the ghost walks after dark.
Plan it
Three perfect days.
First time in Chicago? A long weekend that runs the river, the skyline, the lake and the history without ever feeling rushed.
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