The best tour in Chicago leaves from the river. Then the city opens up.
Which architecture cruise really gets you the Loop from the water. What the Ledge costs and which slot to take. Whether the mob walk beats the ghost tour after dark. Reviews of every tour you can book in Chicago.
The river cruise, the Ledge, a mob walk and a plate of deep dish.
The four bookings a first Chicago trip gets built around. What each one costs, and what the people who took it say.
01The first afternoonChicago Architecture River CruiseNinety minutes on the river with the Loop going up on both banks. Take a late sailing and the glass turns gold.
02The high oneWillis Tower Skydeck and The Ledge TicketThe Ledge at Willis Tower, 103 floors up with the lake filling the horizon. Entry is timed, so the slot is the decision.
03After darkGangsters and Ghosts Walking TourProhibition corners and haunted blocks on foot, through doorways you would walk straight past on your own.
04The one that fills youChicago Favorites Ultimate Food and Walking TourDeep dish, an Italian beef and a Chicago dog across one afternoon and several neighborhoods.
Six Chicago days: the river, the lake, the high floors, the mob map, the table.
The city reads differently from a boat deck, from 1,353 feet up, and from a bar stool in a basement that used to be a speakeasy. Six starting points, and the best day out in each.
In Chicago the best seat in the house is a boat deck.
The river runs straight through the Loop and the lake hands you the whole skyline at once. Three other kinds of sailing, what it costs to board each one, and what you actually see from the rail.
Chicago invented the skyscraper and has been explaining it ever since.
The Loop is a working museum of steel, terracotta and glass, and the good tours start by pointing at the water it was all built beside. These three carry more travellers than anything else in the city.
The Chicago days out more travellers take than any other.
Every Chicago review →Summer here is short and everybody wants the same afternoon, so these fill from the top down.
1
Chicago Architecture River Cruise
See Chicago’s skyline from the river on a guided architecture cruise with expert stories, famous buildings, onboard restrooms, and flexible departure times.
From · $39
Read our review →
2
Chicago River 90-Minute Architecture Tour
from $45
3
1.5-Hour Guided Architecture Cruise
from $44
4
Gangsters and Ghosts Walking Tour
from $52
5
Chicago Architecture Center River Cruise aboard First Lady
from $57
6
Willis Tower Skydeck and The Ledge Ticket
from $42
7
Architecture River Cruise Skip-the-Ticket Line
from $39
8
360 CHICAGO Observation Deck Ticket
from $29
What a day out in Chicago actually costs.
Every tour on the site, grouped by price. Plenty of the best Chicago afternoons come in under the price of a ticket to the game.
River cruises, museum entry, the observation decks and the self-guided walks.
Full-day food walks, mob bus tours, dinner sailings and the small-boat upgrades.
Private guides, helicopter runs over the lakefront and the passes that cover a whole week.
Three things that only happen in Chicago.
Skylines and food walks exist everywhere. A river turned round to run backwards through a canyon of towers, a Prohibition map you can still walk, and a pizza served like a pie do not.
The river that runs through the Loop
Engineers reversed the Chicago River in 1900 so it drained away from the lake, and the banks turned into the best gallery of tall buildings anywhere. A boat sits low enough to show how a tower meets the ground, which is the part every photograph misses. Sailings run from spring to late autumn and stop when the ice comes.
- 1Chicago Architecture River Cruise★★★★★★★★★★ 5.0 · 15,756 reviews
- 2Chicago River 90-Minute Architecture Tour★★★★★★★★★★ 4.5 · 9,629 reviews
- 31.5-Hour Guided Architecture Cruise★★★★★★★★★★ 4.8 · 8,046 reviews
The mob map is still legible
Capone ran the operation out of Cicero and the Loop, and enough addresses survive that a guide points at doorways instead of plaques. The Biograph is still a cinema. The garage on North Clark is a parking lot now, which somehow makes the story land harder. Most of these go out in the evening and cover ground on foot.
- 1Gangsters and Ghosts Walking Tour★★★★★★★★★★ 5.0 · 7,155 reviews
- 2Gangsters and Ghosts Guided Walking Tour★★★★★★★★★★ 4.7 · 1,697 reviews
- 3Chicago Gangster and Food Walking Tour★★★★★★★★★★ 5.0 · 471 reviews
Deep dish, beef, and a dog with no ketchup
Eating here comes with rules: the pizza is a pie you take apart with a knife, the Italian beef is dipped and eaten standing up, and the hot dog carries celery salt and never ketchup. The good walks cross two or three neighborhoods, so you get the argument from both sides in one afternoon.
- 1Chicago Loop District Food Tour with Deep Dish & Beef Sandwich★★★★★★★★★★ 5.0 · 870 reviews
- 2Chicago Pizza Tour★★★★★★★★★★ 5.0 · 454 reviews
- 3Downtown Chicago Walking Pizza Tour★★★★★★★★★★ 5.0 · 106 reviews
Four Chicago bookings that will not wait.
Most of this city can be settled over breakfast. These four run on timed slots, a short season and a schedule drawn up months before you land.
- 01Willis Tower Skydeck and The Ledge TicketEntry runs on timed slots, and the late-afternoon ones, the good light, go first.
- 02360 CHICAGO Observation Deck TicketThe deck is small and the sunset hour sells out well before the rest of the day does.
- 03Fireworks Cruise with Lake or River Viewing OptionsThe Navy Pier fireworks only run on set summer nights, and the boats sell against that calendar.
- 04Chicago Cubs Baseball Game Ticket at Wrigley FieldWrigley only has home dates, and the good ones are gone long before you arrive.
Chicago keeps one season for boats and one for basements.
From November the wind off Lake Michigan turns into a physical object and the cruise boats come out of the water. The city answers indoors: the Field Museum, the Art Institute, a taproom on the West Side, a deep-dish table, and the skyline from behind glass a thousand feet up.
Deep dish, Italian beef, and a bar that used to be a speakeasy.
Eat across the Loop, Chinatown and the West Side in one afternoon, or give an evening to a brewery bus. Book the food walks early: they go out in small groups and they fill.
By landmark and neighborhood
By kind of day — deck, tower, table or tour bus
Friday to Sunday: the river, the Ledge, the mob map, a museum and a table.
Prohibition
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