From modern wonders to landmark buildings, see Chicago's architecture by adding these tours & observation decks to your itinerary.

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The birthplace of the modern skyscraper, Chicago is home to unique and innovative designs that have shaped American architecture. Travel + Leisure readers voted Chicago as the nation's “Best Skyline” and it is quite stunning if we do say so ourselves. And since we're bragging, we might add that we look pretty good from every angle as well — up in the sky from one of our skyscrapers or down below street level along the Chicago River.

Where should you start? Everywhere you look there’s a treasure trove of architectural wonders both old and new from the gleaming-white Wrigley Building and Gothic-style Tribune Tower manning the Mag Mile, to the Gehry-designed Pritzker Pavilion in Millennium Park and award-winning Aqua Tower. 

Here is a primer on how to soak in that skyline and appreciate the history, beauty and brilliance behind it.

Great Heights

For a bird’s eye view of the city at 1,300 feet, step out onto The Ledge, a clear glass box suspended from the Willis Tower, at Skydeck Chicago. For those who fear heights, yes it can be terrifying, but seeing Chicago at your feet is a memorable way to experience this world-renowned building (the tallest in the Western Hemisphere in fact).

Or zoom up 1,000 feet for a 360-degree view of four states from 360CHICAGO (formerly known as the John Hancock Observatory) — voted Chicago’s best view by the Chicago Tribune and TripAdvisor. Its newest addition TILT! is a moving enclosure that slowly leans you over the edge of the tower. Five minutes never felt so long!

You can also take in the sites while sipping on a cocktail. Views from The Signature Room on the 95th floor of the John Hancock Center are exceptional, and from the Trump International Hotel & Tower, the restaurant Sixteen and the 16th floor Terrace boast panoramas worth every cent of the cost of that martini. Other alfresco options with a view include Terzo Piano (a modern stunner perched atop the Art Institute of Chicago) and The J. Parker (which shows off both the skyline and our lakefront parks).

Tour Allure

There are many ways to see Chicago's architectural gems so find a tour that meets your style — you can explore either by foot, on wheels or even by boat.

Walk the city with top Chicago tour companies Chicago Detours, Inside Chicago Walking Tours, Wild Onion Walks, or Tours-R-Us. These local pros have hiked countless steps perfecting routes that show off our famed architecture. From quirky to classic (think everything from ghost stories, red light districts and underground tunnels to decorative columns, dazzling stained glass and gold-covered interiors), their tours uncover the fascinating facets of the city and tell them with truly local color.

The granddaddy of them all is the Chicago Architecture Foundation. Known for its incredibly insightful river boat tours, this highly-respected organization does it all: walking, bus, bike, trolley, even 'L' train tours. Let their docents wow you with their architectural prowess — they can rattle off facts about buildings, architects, engineers, city planners and more for hours (though many tours are limited to 60-90 minutes so each one packs a punch).

If bridges are your thing, Chicago Loop Bridges will take you over, under and inside as you wander the 2 miles along the riverfront that contain 18 magnificent bridges. Another specialty tour, Chicago Photo Safaris leads you on a point-and-click journey while teaching you how to best capture architectural beauty shots on camera.

For the design-o-phile that is also budget-minded, the free program Chicago Greeter pairs you with a local who can highlight architecture both downtown and in the neighborhoods. A pay-what-you-want model, offered by Free Tours By Foot, is another way to go.

Zip and zoom on wheels with a Segway sightseeing tour by Absolutely Segway, City Segway ToursSegway Experience of Chicago and Steve's Segway Tours.

Biking tours will also cover a lot of ground, and in Chicago, there's a lot to see! Consider Bike and Roll and Bobby’s Bike Hike to check out the skyline architecture from such scenic lookout spots as Museum Campus and North Avenue Beach. 

For those who like to explore on their own, consider a Metrowalkz Self-Guided Walking Tour or the Chicago Trolley & Double Decker Co. Hop On Hop Off Tour that covers miles of city attractions and sights.

The Wright Stuff

No other place in the world has better examples of Frank Lloyd Wright’s Prairie style designs than Chicagoland. Visit the Frank Lloyd Wright Home and Studio in nearby Oak Park. Daily tours allow you to explore Wright's home and studio, as well as Unity Temple and the Historic District where they are located. 

Then when you are in the city, head to the University of Chicago’s campus in the beautiful Hyde Park neighborhood to see Frank Lloyd Wright’s Robie House, considered one of the most important buildings in American architecture.

Check out the Glessner House, a national historic landmark in Chicago’s South Loop Prairie Avenue District, where a young Wright got his inspiration. The Glessner House was designed by American architect Henry Hobson Richardson and was a radical departure from the traditional Victorian architecture of its era. 

And on the other side of town in the North Shore neighborhood of Rogers Park, you can tour the Bach House, a late Prairie style residence that looks toward the architect's future stylistic directions. 

City Segway Tours - Chicago
910 S. Michigan Ave.
Chicago, IL 60605
(312) 819-0186
#1 Chicago Tours
155 N. Harbor Dr
Chicago, IL 60601
(312) 946-9467
Segway Experience of Chicago
224 S. Michigan Ave., Ste. 113
Chicago, IL 60604
(312) 663-0600
Absolutely Chicago Segway Tours
238 E. Monroe
Chicago, IL 60603
(312) 552-5100
360 CHICAGO (formerly John Hancock Observatory)
875 N. Michigan Ave. 94th Floor
Chicago, IL 60611
(888) 875-8439
Skydeck Chicago
233 S. Wacker Dr.
Chicago, IL 60606
(312) 875-9696
Terzo Piano
159 E. Monroe St.
Chicago, IL 60603
(312) 443-8650
Frank Lloyd Wright Home and Studio
951 Chicago Ave.
Oak Park, IL 60302
(312) 994-4000
Frank Lloyd Wright's Robie House
5757 S. Woodlawn Ave.
Chicago, IL 60637
(312) 994-4000
Chicago Photo Safaris
55 N. Michigan Ave.
Chicago, IL 60611
(312) 470-6704
Chicago Photo Safaris
55 N. Michigan Ave.
Chicago, IL 60611
(312) 470-6704
MetroWalkz Self-Guided Walking Tours
500 N. Michigan Ave.
Chicago, IL 60611
(312) 504-7058
Chicago Detours
Various Locations
Chicago, IL 60603
(312) 350-1131
Bobby's Bike Hike - Quality Tours, Rentals, & Urban Adventures
540 N. Lake Shore Dr.
Chicago, IL 60611
(312) 915-0995
Chicago Trolley and Double Decker Co.
Water Tower Pumping Station
Chicago, IL 60611
(773) 648-5000
401 N. Wabash Ave.
Chicago, IL 60611
(312) 588-8030
Chicago Greeter
72 E. Randolph St.
Chicago, IL 60603
(312) 945-4231
Chicago Architecture Foundation
224 S. Michigan Ave.
Chicago, IL 60604
(312) 922-3432
Chicago Loop Bridges
155 N. Harbor Dr.
Chicago, IL 60601
(312) 540-0696
Wild Onion Walks Chicago
1423 W. Hollywood Ave.
Chicago, IL 60660
(773) 960-5470
Tours R Us Chicago LLC
2600 N. Lakeview Ave.
Chicago, IL 60614
(773) 575-3176
Free Tours by Foot
2231 N. Kimball Ave.
Chicago, IL 60647
(312) 612-0826
Inside Chicago Walking Tours
Chicago, IL 60625
(312) 799-0164
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