Chicago is a city you read from the water.
Which architecture cruise runs the full river and which one turns back at the bridge. What the Skydeck costs before the queue. Where the deep dish is worth ninety minutes. Reviews of every tour you can book in Chicago.
From the riverChicago Architecture River CruiseNinety minutes under the bridges, the whole skyline explained.
From the 103rd floorWillis Tower Skydeck and The Ledge TicketA glass box hung off the Willis Tower, 1,353 feet up.
Inside the lobbiesOriginal Chicago Architecture Interiors Tour: Dazzling InteriorsMarble, brass and gold vaults the office workers walk past.
Four bookings a first Chicago weekend is built around.
The river, the mob, the tallest ledge in the Midwest and a meal you have to lie down after. What each one costs and how long it takes.
01Saturday morningGangsters and Ghosts Walking TourTwo hours through the Loop on the stories the city used to deny. Ends near the river, which is where you want to be next.
02When it rainsOriginal Chicago Architecture Interiors Tour: Dazzling InteriorsA tour of interiors: banking halls, theatre lobbies and light courts, all of it indoors and warm.
03Golden hourLake Michigan Sunset Cruise in ChicagoOut past the locks as the towers switch their lights on. Take the last sailing before sunset, not after it.
04Come hungryChicago Favorites Ultimate Food and Walking TourDeep dish, an Italian beef and a Chicago dog in one afternoon. Skip lunch. Genuinely.
Chicago invented the skyscraper. Pick how you want to look at one.
Every visitor books an architecture tour and most book the wrong kind. From the water you get the skyline as a whole; on foot you get the ground floors; from the observation decks you get the grid. Three different days, three different prices.
The Loop, the lakefront, Chinatown and the long way round.
Chicago is flat, gridded and walkable for about three hours, after which you want a boat, a bike or somebody else driving. Six ways to spend a day here, and the best of each.
Two waterfronts, and the good hour is on the lake.
The river runs backwards through the middle of the Loop and out to a lake that behaves like a sea. Architecture boats work the river; skyline, sunset and fireworks sailings work the lake; the speedboats do both and get you wet.
Chicago’s most-booked days out.
Every Chicago tour we have reviewed →More travellers take these than anything else in the city, and there is a reason behind each one.
1
Chicago Architecture River Cruise
Cruise from Navy Pier or Michigan Avenue through the Chicago River while an architecture guide explains landmarks, design, and Chicago’s Great Fire. You’ll see the Wrigley Building, Tribune Tower, Hancock Center, Willis Tower, Marina City, and Aqua. Boats have restrooms and a full bar, and dogs are welcome.
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
Chicago is a walking city for exactly as long as the wind allows.
The Loop is a grid you can learn in a morning: eight blocks to the mile, the river on two sides, the lake on the third. Guides here lean on history rather than scenery, which is the right call in a city where the good stories are all about money and fire.
- 1Gangsters and Ghosts Walking Tourfrom $52
- 2Chicago Favorites Ultimate Food and Walking Tourfrom $84
- 3Gangsters and Ghosts Guided Walking Tourfrom $36
What a day out in Chicago actually costs.
Every tour on the site, grouped by price. The city is cheaper than its skyline suggests: plenty of the best days here cost less than dinner.
River cruises, museum entry, the observation decks and most of the walking tours.
Food walks, lake sailings, the bus and boat combinations and the small-group days.
Private guides, helicopter time, attraction passes and the once-a-trip splurges.
Three things that only happen in Chicago.
Skylines and food tours exist everywhere. A river engineered to flow the wrong way, a Prohibition map you can still walk, and lobbies built to prove a point do not.
The Architecture River Cruise
In 1900 the city turned the Chicago River around so its sewage flowed away from the drinking water rather than into it, and the engineering held. What it left behind is a working canyon of towers standing shoulder to shoulder on both banks, best read from a flat deck moving at walking pace. The docent-led boats run roughly April to November; in February there is nothing to board.
- 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
Capone’s Chicago
For sixty years the city refused to sell the mob as a tourist attraction, on the grounds that it was embarrassing rather than historic. That stopped. The garage on North Clark is a car park now and the Lexington Hotel is gone, but the corners, the churches and half a dozen surviving speakeasies are all still standing, and the guides are specific about which stories are documented and which are folklore.
- 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
The Lobbies
The skyscraper was worked out here in the 1880s, and the ground floors were where the owners showed off: a glass-roofed light court in the Rookery that Frank Lloyd Wright remodelled, gold vaults, mosaic ceilings and banking halls the size of churches. Almost all of it is behind an ordinary office door that anyone can push open on a weekday, if you know which door.
- 1Original Chicago Architecture Interiors Tour: Dazzling Interiors★★★★★★★★★★ 5.0 · 1,489 reviews
- 2Chicago’s Secret Interiors Architectural Walking Tour★★★★★★★★★★ 5.0 · 635 reviews
- 3Secret Interiors Architecture Walking Tour★★★★★★★★★★ 4.9 · 498 reviews
Four Chicago bookings that will not wait.
Most of this city can be arranged over breakfast. These four run on a season, a fixture list or a timed entry slot, none of which cares what day your flight lands.
- 01Chicago Architecture River CruiseThe river boats run a season, roughly spring to late autumn. In deep winter the docks are closed and there is nothing to book.
- 02Willis Tower Skydeck and The Ledge TicketEntry is by timed slot and the late-afternoon ones, the only slots that give you daylight and lights, go first.
- 03Chicago Cubs Baseball Game Ticket at Wrigley FieldA fixture list decides this one. There are 81 home dates a season and you cannot move any of them.
- 04Fireworks Cruise with Lake or River Viewing OptionsThe Navy Pier fireworks run on set summer nights, not nightly. The sailings sell out on the ones that count.
The wind comes off the lake and the plan changes.
From November the lakefront is genuinely hostile and the boats stop running; in July a storm can cancel a sailing in an hour. Both have the same answer, and it is a good one: this city built its best rooms indoors. Museums, banking halls, theatre lobbies, an aquarium and a bar with a door you have to knock on.
The skyline switches on at dusk and the city gets better.
Chicago lights its towers deliberately, so the hour after sunset is the one worth paying for. Take it from the water, from a dinner deck, or on foot with somebody telling you what happened on each corner.
Every evening out →
By landmark - the ones people fly in for
Friday night to Sunday lunch: the order that works.
The Loop
Deep dish
The lakefrontThe newest Chicago tour reviews.
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Field Museum of Natural History Early Access Ticket
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Chicago White Sox Baseball Game Ticket at Guaranteed Rate Field
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Chicago Cubs Baseball Game Ticket at Wrigley Field
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2-Hour Chicago’s Chinatown History and Culture Tour
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Chicago Cubs Baseball Game Ticket at Wrigley Field
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Skydeck Chicago: Pie in the Sky VIP Dinner at Willis Tower
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