City Guide: Chicago

The Windy City. The Second City. Chi-town. Whatever you call it, Chicago’s got it goin’ on! Whether you’re a foodie, a superfan or a mega-shopper, you’ll discover the best of the Midwest here.


For a stylish and convenient home base, check into the Sofitel Water Tower Place. You can’t miss it–just look for the 32-floor glass prism near Michigan Avenue! Staying here puts you smack dab in the middle of it all, with the Magnificent Mile, Navy Pier and Lake Michigan just steps away.

1:00 P.M.
Get a feel for the city and its colorful history aboard an architecture boat tour (tours leave hourly). See Al Capone’s Speakeasy, the innovative Boeing building and the few remnants from the Great Chicago Fire of 1871. Be sure to pop below deck to grab a pint to sip as you cruise.


3:00 P.M.
Hop on the ‘L’ and make your way to one of baseball’s last remaining shrines and home to the league’s cursed Cubs: Wrigley Field. (There’s no tourist shame in posing for a pic outside the iconic red sign!) Scoring Cubs’ tics is akin to getting your hands on Leafs tickets in Toronto–it’s tough. But not impossible: Check Craigslist on game day and you might even find some at face value.


8:00 P.M.
After a long day of sightseeing and cheering, unwind at Gioco, a South Loop gem of a restaurant. This local fave dishes up rustic Italian cuisine in the coziest of settings–think original brick, candlelight and corners made for canoodling. Sample one of the flavorful wood-fired pizzas or house-made pastas with fresh seafood.


11:00 A.M.
If you like a little punk with your pastries, grab brekkie at the rock’n roll-inspired Bleeding Heart Bakery. (We suggest the doughnut breakfast sandwich… mmmm.) This Ukranian Village café is a fave among visiting rock stars and celebs, so keep your eyes peeled for bleary-eyed musicians!

2:00 P.M.
SHOP! They don’t call Michigan Avenue the “Magnificent Mile” for nothing! Peruse chic department stores like Nordstrom and Bloomingdale‘s or pop into stylish designer boutiques to score some Midwestern duds.

7:00 P.M.
After dropping your shopping bags back at the hotel, make your way to the vibrant River West neighborhood and score a table at Public House. This bar/resto serves up mussels, Memphis-style back ribs and mini Kobe corn dogs. But the real fun is already at your table–your own set of taps to pour whisky, vodka or cool microbrews.

9:00 P.M.
Head west and catch a show at the historic Congress Theater. Built in 1926 as a movie house, this 3,500-capacity music venue features ornate interiors and a classic revival facade. It’s hosted everyone from Chuck Berry and Jerry Lee Lewis to Wu-Tang Clan.


11:00 A.M.
After kicking back with a room service breakfast, head over to the Hancock. The John Hancock Observatory remains a defining icon of Chicago’s skyline. And with the fastest elevators in America, you’ll find yourself on the 94th-floor lookout in just 39 seconds! On a clear day, you’ll see up to 80 miles and four states: Illinois, Indiana, Michigan and Wisconsin.

2:00 P.M.
Walk due east from the Hancock and make your way to the shore of glistening Lake Michigan. Nearby Oak Street Beach is like an oasis in the heart of downtown Chicago–stretches of soft sand and blue water. Rent a beach chair and soak up the sun while you enjoy your last views of the city’s world-class skyline.


Image(s): Top to bottom: Kenneth O’Quinn; Jim Kruger; Agnieszka Szymczak; Christopher Arndt

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