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 beauties 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 with Chicago's top tour companies and observatory decks. For more of a self-guided tour, mix-and-match from the highlights on our Chicago Architecture Itinerary.


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 875 N Michigan (formerly 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 DetoursInside Chicago Walking ToursWild 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 Center. 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 tours are limited to 60-90 minutes so each one packs a punch). Some of the all time popular options include:

  • Chicago Architecture Foundation Center River Cruise Aboard Chicago’s First Lady
  • Architectural Highlights by Bus
  • Historic Downtown (South Loop: Rise of the Skyscraper)
  • Modern Skyscrapers (1950s-Present)
  • Skyscraper Walk Through Time 

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 SegwayCity 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 Prairie-style designs than Chicagoland. Don't miss the Frank Lloyd Wright Home and Studio in nearby Oak Park. Daily interior tours with the Frank Lloyd Wright Trust 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.

In the heart of the downtown Loop's financial district is another landmark gem, The Rookery, with guided tours that soak in one of Frank Lloyd Wright's most dramatic interior compositions — a luminous and brilliantly articulated central light court.

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. 


Related Listings

360 CHICAGO (formerly John Hancock Observatory)
875 N. Michigan Ave.
Chicago, IL 60611
(888) 875-8439

Shoreline Sightseeing Company
Navy Pier
Chicago, IL 60611
(312) 222-9328

Frank Lloyd Wright Home and Studio
951 Chicago Ave.
Oak Park, IL 60302
(312) 994-4000

MetroWalkz Self-Guided Walking Tours
500 N. Michigan Ave.
Chicago, IL 60611
(312) 504-7058

Chicago's First Lady Cruises
112 E. Wacker Dr. on Chicago's Riverwalk
Chicago, IL 60601
(847) 358-1330

The Signature Room at the 95th
875 N. Michigan Ave.
Chicago, IL 60611
(312) 787-9596

Skydeck Chicago
233 S. Wacker Dr.
Chicago, IL 60606
(312) 875-9696

Wendella Sightseeing Boats
400 N. Michigan Ave.
Chicago, IL 60611
(312) 337-1446

Frank Lloyd Wright's Robie House
5757 S. Woodlawn Ave.
Chicago, IL 60637
(312) 994-4000

Chicago Detours
Various Locations
Chicago, IL 60603
(312) 350-1131

Chicago Line Cruises
Ogden Slip
Chicago, IL 60611
(312) 527-2002

Inside Chicago Walking Tours
Chicago, IL 60625
(312) 799-0164

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