Chicago, from the water up.
Which river cruise gets the good guide. Where the deep dish is worth the wait. Whether the Ledge is worth 103 floors of queue. Every tour in Chicago, reviewed and ranked.
The river cruise is how Chicago introduces itself.
All 74 architecture tours →
Ninety minutes, thirty-odd buildings, one docent who can tell you which one Mies did and why the Tribune Tower has a chunk of the Parthenon stuck in it. Three boats carry most of the traffic; the rest split by length, dock and how cold you are willing to get.
The classic river run, Michigan Avenue to the locks
East to the lock gates, back up the south branch, and the whole century of the skyline explained in the order it was built.
Out through the locks onto open water
The one that leaves the river. You get the canyon first, then the lock, then the entire city standing up out of the lake behind you.
Dinner while the skyline switches on
Board before sunset, eat somewhere off Navy Pier, and come back in under a city that has turned every window on.
Deep dish, the Ledge and the boats: what Chicago is booked for.
Six things this city does that nowhere else does the same way, and the best way to book each of them.
From an L fare to a chartered boat: what Chicago costs.
Every tour on the site, sorted by what it actually costs. A very good Chicago afternoon starts under fifty dollars.
Walking tours, museum entry, the shorter river boats and the observation decks.
The full-length cruises, food tours with the pizza included, Segway and bike days.
Private guides, helicopter seats over the lake and chartered evenings on the water.
Chicago’s most-taken tours, river cruises first.
Every review →More travellers take these than anything else in the city — and what each one is actually like once you are aboard.
1
Chicago Architecture River Cruise
See Chicago’s best buildings in about an hour with live guide commentary, pet-friendly boats, and strong value at $39.
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
Chicago Crime and Mob Bus Tour
from $49
Capone’s Chicago is a walking tour now.
The Biograph is still a theatre. The Green Mill still has the booth. The garage on Clark Street is a parking lot with a plaque nobody put up. Guides who know which is which are worth the two hours.
In Chicago the pizza is a knife-and-fork situation.
Deep dish takes forty-five minutes in the oven, so the good tours order ahead and walk you somewhere else while it bakes. Then the Italian beef, dipped, and a hot dog that will never see ketchup.
Chicago invented the skyscraper, then hung a glass box off one.
The Ledge sticks out four feet from the 103rd floor of Willis Tower with nothing under your shoes but Wacker Drive. 360 Chicago, up on the old Hancock, tilts you out over Michigan Avenue instead. Both sell timed entry; both have a queue at sunset.
- 1Willis Tower Skydeck and The Ledge Ticketfrom $42
- 2Skydeck – Willis Tower Admissionfrom $44
- 3Chicago Explorer Pass: 2 to 7 Attractions including SkyDeckfrom $79
The boats, the Bean and the deep dish.
Every big city has museums and bus tours. The docent-led architecture cruise, the mirrored bean in Millennium Park and a pizza you eat with cutlery are Chicago inventions.
The Architecture Cruise
The Chicago Architecture Center has been putting volunteer docents on boats since the 1980s, and the format spread from here to every river city that has one. The docents are trained and tested, they are not tour guides reading a script, and it shows about four buildings in. Book the first sailing of the day if you want the light on the east faces.
- 1Chicago Architecture River Cruise★★★★★★★★★★ 5.0 · 15,756 reviews
- 21.5-Hour Guided Architecture Cruise★★★★★★★★★★ 4.8 · 8,046 reviews
- 3Chicago Architecture Center River Cruise aboard First Lady★★★★★★★★★★ 5.0 · 5,536 reviews
The Bean & the Park
Millennium Park sits on top of a working rail yard and a car park, which is why it was late and over budget and why nobody minds now. Cloud Gate — nobody local calls it that — is polished steel with no visible seams, and the underside is the part people actually queue for. The park is free, always open, and the tours are about what is around it.
- 1Art, Skyscrapers, Millennium Park & “The Bean”★★★★★★★★★★ 5.0 · 6 reviews
- 2Chicago Millennium Park Self-Guided Walking Tour★★★★★★★★★★ 4.5 · 5 reviews
- 3Downtown Loop & Millennium Park 2 Hour Walking Tour★★★★★★★★★★ 5.0 · 5 reviews
Deep Dish
It goes in a steel pan, crust up the sides, cheese under the sauce so the top does not burn in the time it takes. That time is the whole reason deep-dish tours are structured the way they are: order first, walk the block, come back and eat. Anyone who serves it to you in ten minutes reheated it.
- 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
Chicago lights the bridges and the evening starts.
All evening tours →
Chicago Night Driving Tour with Skydeck and River Cruise
Read our review →
Chicago Signature Dinner Cruise on Lake Michigan
Read our review →In Chicago these run on a calendar, not on your schedule.
Most of this city can be booked from the hotel lobby the night before. These cannot — they run on seasons, home fixtures and aircraft that seat four.
- 01Chicago Architecture River CruiseA warm-season fixture. The boats tie up for winter and the good summer slots go weeks ahead.
- 02Chicago Cubs Baseball Game Ticket at Wrigley FieldHome fixtures only, on a schedule published months out. No home game that week, no ticket.
- 03Private 45-Minute Chicago Skyline Helicopter TourThree or four seats an aircraft, weather-dependent, and the sunset slots are spoken for first.
- 04Chicago Signature Dinner Cruise on Lake MichiganFixed departures with a set table count — Saturday evenings on the lake go long before you land.
By landmark — what you came to see
The Loop & the river74 tours
The lakefront36 tours
Willis Tower7 tours
360 Chicago8 tours
Millennium Park7 tours
The Art Institute7 tours
The Field Museum4 tours- Every Chicago review →
A first weekend in Chicago, in the order it works.
Sat am · the Loop
Sat · deep dish
Sun · Museum Campus
The lake decides Chicago’s weather, and it is not always on your side.
The wind comes off the water from October, the boats stop running, and the city goes indoors without complaining about it. That is when the museums, the decks and the long lunch tours earn their keep — and when you can get a same-week ticket to any of them.
The most recent reviews, Chicago-wide.
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