Chicago Christmas Walk: Magnificent Mile Lights to the Christkindlmarket
Follow Michigan Avenue’s holiday lights past landmarks that span Chicago’s history, then turn toward State Street’s festive windows.
Illinois
Things to do in Chicago: walks and drives
3 tours in Chicago
Route 66 in Illinois: Chicago to the Chain of Rocks Bridge
Follow the Mother Road south from Chicago past diners, service stations and a towering astronaut.
Chicago Loop Architecture Walking Tour
Walk the Loop’s canyons and see how Chicago’s architects made height a symbol of commercial ambition.
Chicago on foot
After the Great Fire of 1871 burned the center of Chicago, the city rebuilt fast and then built up. In the decades that followed, architects in the Loop worked out how to stand tall office buildings on soft lakeshore clay, fill them with light and make them handsome, and the skyscraper as we know it came out of a few downtown blocks. Our walk tells that story in eight stops. It starts at the Chicago Board of Trade, the Art Deco tower at the foot of LaSalle Street with the grain goddess Ceres on top, and the palace that stood there first until the mud next door brought it down. At the Rookery, named for the crows and politicians that roosted on the site before it, you hear about Burnham and Root's light court. The Monadnock was kept plain on its owner's orders and turned out beautiful anyway. The Marquette Building got its lost cornice back. The Reliance Building, nearly all glass, looks newer than its 1895 date. At the Carson, Pirie, Scott Building you look up at Louis Sullivan's ironwork over the corner door. The Chicago Cultural Center began as the city's first central library, and the walk ends at the Michigan Avenue Bridge, the 1920 bridge that pulled downtown north across the river. The walk is 2.2 miles on flat sidewalks and takes about 1 hour 19 minutes with the stories. Look up often: the best details are high. Chicago is also where Route 66 begins. Our drive starts at Lou Mitchell's, the diner on Jackson Boulevard that was serving breakfast before the highway existed, and follows the old road 299 miles southwest across Illinois: past the old Joliet prison, the Gemini Giant astronaut in Wilmington, Ambler's Texaco in Dwight, the little Standard Oil station in Odell, the old timber of Funks Grove, the Cozy Dog Drive In in Springfield and the Ariston Cafe in Litchfield, to the Chain of Rocks Bridge, the old Mississippi crossing with a bend in the middle. It's about 7 hours 42 minutes of driving and listening, so plan a full day or split it over two. U.S. Route 66 was created in November 1926, so the road turns 100 this year.
Chicago: questions people ask
How long is the Chicago architecture walking tour?
It's 2.2 miles from the Chicago Board of Trade to the Michigan Avenue Bridge and takes about 1 hour 19 minutes with all eight stories.
Where does the walk start?
At the Chicago Board of Trade Building, where LaSalle Street meets Jackson Boulevard. It ends at the Michigan Avenue Bridge over the Chicago River.
Is this the same as an architecture river cruise?
No. This is a self-guided walk through the Loop at street level, and it ends at the river by the Michigan Avenue Bridge.
Can I drive Route 66 from Chicago with a guide in the car?
Yes. The Route 66 in Illinois drive starts at Lou Mitchell's in Chicago and ends 299 miles later at the Chain of Rocks Bridge on the Mississippi, with nine stops and a story at each. It takes about 7 hours 42 minutes with the stories.
Is there a self-guided tour of Chicago?
Yes. 3 tours, including "Chicago Christmas Walk: Magnificent Mile Lights to the Christkindlmarket", are on Stories. Unlock it once for your group for $4.99 and play it in your browser; the app plays each story as you arrive.
Every Stories tour plays in your browser, no app needed. How it works
Know someone headed to Chicago? Give a walk as a gift, emailed on the day you pick.