CHICAGO · ILLINOIS
Big shoulders. Big lake. Big buildings.
Architecture cruises through the skyscraper canyon. Lake Michigan boats out past Navy Pier. Speakeasies, Skydecks, and deep-dish in every neighbourhood.
The architecture boat
If you only do one tour, this is it.
The boat ride Chicago invented in 1939, and the one every first-time visitor books before anything else. Skyline from the river, narrated floor by floor.
The classics
Chicago’s Most Popular Tours
Skydeck and 360, the river cruise and the lake boat, Capone history and the food walk. The Chicago canon — what most first-time travellers come for.
The three views
Three angles you can only get in Chicago.
The skyline from the river. The Loop through a glass floor 1,353 feet up. The Magnificent Mile tilted under your feet. Plan the trip around at least one.
Made here
Three Chicago things that started in Chicago.
The architecture boat tour, the Capone era, the deep-dish slice. Three threads that only run here — and that the rest of the country still borrows from.
Invented 1939
The Boat Tour That Defined a City
The Chicago Architecture Foundation invented the architecture cruise in 1939 to show travellers what makes the skyline work. Every architecture boat tour in every other city is a copy of this one. The original still runs every twenty minutes from the docks below Michigan Avenue, and the docents still know which buildings hide their bracing.
- 1 Chicago River 90-Minute Architecture Tour
- 2 Chicago River: 1.5-Hour Guided Architecture Cruise
- 3 Chicago Architecture Center River Cruise aboard First Lady
Prohibition Chicago
Capone, the Untouchables, the Speakeasies
Capone ran Chicago from 1925 to 1931 — speakeasies in basements, machine-gun warfare on Clark Street, federal agents called the Untouchables. The buildings, the bullet holes, the basement bars are still here. Walking tours cover the survival map and the bodies.
- 1 Chicago: Gangsters and Ghosts Walking Tour
- 2 Chicago: Gangsters and Ghosts Guided Walking Tour
- 3 Chicago Gangster and Food Walking Tour
Deep-dish, the dog, the beef
Foods That Belong Only to Chicago
Deep-dish pizza was invented at Pizzeria Uno in 1943. The Chicago dog (mustard, neon-green relish, tomato, sport peppers, no ketchup) emerged from Maxwell Street vendors in the Depression. Italian beef arrived next, the jibarito after. Food tours walk you through the whole canon.
- 1 Delicious Donuts & City Sights: Chicago’s Original Donut Tour
- 2 Chicago Loop District Food Tour with Deep Dish & Beef Sandwich
- 3 Chicago’s Chinatown Food and Walking Tour
Pick your Chicago
Six ways to see the city.
The river for the architecture. The lake for the breeze. The streets for the neighbourhoods. The plate for the food. The night for the mob history. The bike for everything in between.
By activity
Or pick how you want to spend the day.
Boat if you want the river or the lake. Walk if you want the Loop. Bike if you want the lakefront trail. Skydeck if you want the height, food tour if you want the plate, gangsters tour if you want the basement.
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