We’re off to the Windy City…my kind of town. I was fortunate enough to call it my own sweet home for a few years in the ‘90s––and I try to get back as often as possible. Divided into neighborhoods, it’s easy to get to know and make your way around. In town for a quick visit? Here’s a guide of what to see and do. If all else fails, take a cue from Ferris and do what he did on his day off. He knew how to do the city right.



I have stayed in a lot of motels and hotels in the city. From a Motel 6 to well-known chains, boutique hotels to the iconic Palmer House…all have a variety of offerings, but here are two of my favorites:

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The Drake Hotel: 140 E. Walton Pl. Situated at the top of Michigan Avenue, in the prestigious Gold Coast neighborhood, The Drake is a Chicago icon of historic elegance. Overlooking Lake Michigan and Oak Street Beach, the luxurious rooms feature elegant décor and the opulent lobby is a location worthy of any movie set.

Have a drink in the (no longer smoky) dark, wooded Coq D’Or, one of the first establishments in Chicago to serve alcohol after the repeal of Prohibition. If it’s more of a regal setting you’re looking for, The Palm Court, just off the lobby, offers English afternoon tea and once hosted Queen Elizabeth herself, as well as the late Princess Diana.

The Park Hyatt: 800 N. Michigan Ave. The location is excellent…and just steps away from Michigan Avenue with many rooms overlooking the historic Water Tower. Rooms are spacious, service is top notch, the hotel is pet-friendly and it’s got a cool, modern look and feel you won’t find at too many historic hotels. The NoMI lounge offers refreshing cocktails with a phenomenal cityscape view.



Once you’ve unpacked, hit the streets. Chicago is definitely walkable, but a short cab, train or bus ride will get you where you need to go in a hurry. Grab a CityPASS® for discounts all around town.



The Field Museum: Explore natural history and ancient artifacts from around the globe.

Shedd Aquarium: Dive deep inside the aquatic world and watch sharks, penguins, frogs and fish (to name just a few…).

Museum of Science + Industry: It’s the largest science museum in the country, housing a WW II German submarine, human-sized hamster wheel, a 40-foot tornado and more.

Adler Planetarium: America’s first planetarium, discover planets and galaxies far, far away.



Is there a game in town? With such legendary stadiums, get to one if you can.


Wrigley Field: Home of The beloved Cubs, located just a bit north of the city in the Wrigleyville neighborhood, it’s the second oldest ballpark and a no-frills operation. Get a cold Budweiser, admire the ivy-covered outfield brick wall and sing “Take Me Out to the Ballgame” just like Harry Caray used to.

U.S. Cellular Filed (the old Comiskey Park): Operated by the Chicago White Sox, it sits just south of the city and is a newly-renovated facility with high-tech features, upper deck seating and many food and beverage options.

Soldier Field: It’s where the Chicago Bears play their home games, but it’s also hosted University of Notre Dame football, the Chicago Fire of Major League Soccer, as well as games from the 1994 FIFA World Cup and 1999 FIFA Women’s World Cup



Art Institute of Chicago: One of the oldest and largest U.S. art museums, it houses such famed work as Georges Seurat’s A Sunday on La Grande Jatte, Grant Wood’s American Gothic, as well as various traveling collections.

Architecture Boat Tour: Climb aboard and take a leisurely ride down the Chicago River while viewing noted city architecture.

The Skydeck: Step out onto the enclosed glass ledge of the Willis Tower (formerly Sears), 1,353 feet in the air, and take in the city from a new, very high perspective. Not for the faint of heart.

Kingston Mines: For some after-hours entertainment, head to Lincoln Park and take in a set at this world-famous Blues nightclub.

Buddy Guy’s Legends: Head down near The Loop and sit in on a jam session, plus dine on some down-home Cajun classics (after all, Buddy was born and raised in Louisiana).

Travelling with kids? Make sure you head to Navy Pier for The Children’s Museum, then cab it over to the (free) Lincoln Park Zoo. Need some green space to walk around? Take in the sights at Millennium Park, the world’s largest rooftop garden––it actually sits atop a parking garage and commuter rail station.



Before I moved here, someone gave me a Zagat Guide and thus, my love affair with cuisine across the city took off. I seriously could eat my way through town…and have personally made a pretty good attempt. Here are some of my favorites that go from street fare to five-star dining.

Superdawg: 6363 N. Milwaukee Ave. Order a Chicago-style dawg: pickle, tomato, celery salt…don’t even think about adding ketchup.


Giordano’s Pizza: 730 N. Rush St. A stuffed, deep-dish delight, right here. Try the sausage…and yes, the sauce is supposed to be on top.

The Billy Goat Tavern: 430 N. Michigan Ave. (Lower Level) Lots of legends here, from the to curse of the billy goat to what really put this place on the map, the Saturday Night Live skit featuring John Belushi, Dan Aykroyd, Bill Murray and Loraine Newman. It’s nearly impossible to order without quoting “Cheezborger, Cheezborger, Cheezborger!”

Café Ba-Ba Reeba: 2024 N. Halsted St. A short cab ride up to Lincoln Park is worth it for the Spanish tapas and sangria.

Mike Ditkas: 100 E. Chestnut St. Pay homage to Da Bears Coach and indulge in a juicy steak.

Le Colonial: 937 N. Rush St. For ambiance alone, this Vietnamese restaurant captures the look and feel of French Southeast Asia, situated in the Gold Coast neighborhood. With authentic flavors and fresh ingredients, it’s sure to become one of your favorites, too.

Carmine’s: 1043 N. Rush St. Family-style Italian doesn’t get much better than this.

Spiaggia: 980 N. Michigan Ave. Fine dining, with a modern Italian flair, with sweeping views of Lake Michigan. One of President Obama’s favorites.

Don’t forget to stop by our flagship DXL store just steps off the Magnificent Mile (it’s actually across from The Park Hyatt)…on Chicago Avenue.


This road trip’s far from over, so head downstate along I-57 and take in some of America’s most majestic farmland. You’ll hit rolling hills along Southern Illinois, and if you have the time, veer off the interstate and head south of Carbondale. Stretch your legs a bit and hike around Giant City State Park. Be sure to stop into the lodge for a good old-fashioned, family-style chicken-and-dumplins dinner.
Keep heading south…we’re on our way to Nashville, Memphis and New Orleans, next.

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