See Chicago from the river first. Then from 1,353 feet up.
Which architecture cruise is worth the ninety minutes. What the glass boxes on the Skydeck cost. Whether the deep dish walk beats the gangster tour on a cold night. Reviews of every Chicago tour and ticket you can book.
The river cruise, the Ledge, Capone’s Loop, then deep dish.
Book these four and the rest of a first Chicago weekend sorts itself out. What each costs and what the people who went thought of it.
01The first morningChicago Architecture River CruiseAn hour or so down the main branch with a guide naming the Wrigley Building, Marina City and the rest as they slide past. The tour almost every visitor takes, and the right first one.
02The high pointWillis Tower Skydeck and The Ledge TicketThe 103rd floor of Willis Tower and a glass balcony that sticks out past the wall. Entry is timed: opening hour or after five keeps the crowd down.
03The Prohibition walkGangsters and Ghosts Walking TourCapone, bootleggers and a few hotel ghosts, about a mile and a half through the Loop with a historian doing the talking.
04The long lunchChicago Favorites Ultimate Food and Walking TourDeep dish, a Chicago dog, Italian beef and Garrett’s popcorn in one three-hour walk past Millennium Park and the river.
The Chicago River or Lake Michigan. Pick your deck.
From the river you look up at a century of towers; from the lake you see the whole skyline at once. Four kinds of Chicago boat ride, and what it costs to board each.
★★★★★★★★★★ 4.5 · Chicago River 90-Minute Architecture Tour · from $45
River architecture cruisesA guide, three branches of the river, the buildings that taught America to build up.
Lake Michigan cruisesOut past the breakwater for the full skyline, by day or at sunset.
Fireworks cruisesNavy Pier’s summer show, watched from the water.
KayaksThe river and the lakefront at paddle height.
All 74 Chicago boat tours →
Glass boxes, Capone’s city and the Prairie house: only in Chicago.
Plenty of cities have a tall tower and a river. Fewer hang glass boxes off the 103rd floor, keep a Prohibition gang map you can walk, or hold the houses where Frank Lloyd Wright worked out a new way to build.
The Ledge and TILT
Skydeck Chicago sits on the 103rd floor of Willis Tower, 1,353 feet above the Loop, and the Ledge is a set of glass boxes that reach about four feet out from the wall. You stand with nothing but glass under your shoes. Up at 360 Chicago, on the 94th floor of the old John Hancock Center, TILT tips you out over Michigan Avenue instead.
- 1Willis Tower Skydeck and The Ledge Ticket★★★★★★★★★★ 4.6 · 4,350 reviews
- 2360 CHICAGO Observation Deck Ticket★★★★★★★★★★ 4.5 · 3,173 reviews
- 3Navy Pier Centennial Wheel Ticket★★★★★★★★★★ 4.5 · 1,807 reviews
Capone’s City
Prohibition turned Chicago into the bootlegging capital of the country, and Al Capone ran his share of it from the Lexington Hotel on Michigan Avenue. The St. Valentine’s Day Massacre took place in a North Clark Street garage in 1929; the garage is long gone, the story is not. The Green Mill in Uptown, one of his old haunts, still pours drinks to live jazz.
- 1Gangsters and Ghosts Walking Tour★★★★★★★★★★ 5.0 · 7,155 reviews
- 2Chicago Crime and Mob Bus Tour★★★★★★★★★★ 4.5 · 3,186 reviews
- 3Chicago Gangster and Food Walking Tour★★★★★★★★★★ 5.0 · 471 reviews
Frank Lloyd Wright
Wright built his own Home and Studio in Oak Park in 1889 and spent twenty years there shaping the Prairie style: low roofs, long horizontal lines, rooms that run into each other like the flat land around the city. Oak Park still holds more of his buildings than anywhere else. Robie House, in Hyde Park by the University of Chicago, is the idea fully formed.
- 1Frank Lloyd Wright’s Home & Studio Tour Ticket★★★★★★★★★★ 4.5 · 133 reviews
- 2Frank Lloyd Wright Robie House Admission★★★★★★★★★★ 4.0 · 130 reviews
- 3Private Frank Lloyd Wright Architectural Tour by Luxury Vehicle★★★★★★★★★★ 3.5 · 7 reviews
Chicago’s most-booked tours and tickets.
See all Chicago reviews →The river cruises, sky decks and Loop walks more travellers book than anything else in the city, and what earns each its place.
1
Chicago Architecture River Cruise
Cruise Chicago’s river for about 60 to 90 minutes with a live guide, passing landmarks such as the Wrigley Building, Willis Tower, and Marina City. Choose a departure from Navy Pier or Michigan Avenue. The boat has restrooms and a bar, and dogs are welcome. Guides such as Sam, Jim, and Ashley have led especially engaging trips, though the guide varies.
From · $39
Read our review →
2
Chicago River 90-Minute Architecture Tour
from $45
3
Chicago River: 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
Chicago Crime and Mob Bus Tour
from $49
Deep dish, Italian beef, a donut at nine: Chicago eats on foot.
The city’s food is a set of arguments best settled in person: pan pizza or tavern-cut, dipped beef or dry, mustard but never ketchup. Book the walk that settles them, the brewery bus, or the class that ends with your own pie.
Four Chicago bookings that will not wait for you.
Most of this city can be sorted the morning of. These four run on timed entry, capped groups and a summer season that is shorter than you would like.
- 01Chicago Architecture Center River Cruise aboard First LadyArchitecture Center docents lead this one, and summer weekend departures go days ahead of the date.
- 02Willis Tower Skydeck and The Ledge TicketEntry runs on timed slots. Opening hour and after five are the calm ones; the slot before sunset is the one everybody wants.
- 03Fireworks Cruise with Lake or River Viewing OptionsNavy Pier’s fireworks are a summer-only show on set nights, and the boats that watch from the lake fill up first.
- 04Frank Lloyd Wright Robie House AdmissionInside visits run at set start times with a cap on each group. Without one you only see the brickwork.
When the boats leave the river and the wind comes off the lake.
The river cruises run spring to late autumn, and a January walking tour in the Loop is a test of character. The winter answer is to go up or go in: the sky decks, the Art Institute and the Field Museum, an indoor skydiving tunnel, a food tour that ducks inside every few blocks.
From a river ticket to a helicopter: what Chicago days cost.
Every tour on the site, sorted by price. A good share of the best Chicago days cost less than a deep dish for two.
The 45-minute river cruises, both sky decks, the big museums and most of the Loop walking tours.
Food walks, the 90-minute docent cruises, dinner out on the lake and the attraction passes.
Helicopter flights over the lakefront, private guides and the long days out of the city.
By landmark, from the Mag Mile to Oak Park
By kind of day: boat, tower, walk or table
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