City Guides

Chicago City Guide

From world famous landmarks to well sought cuisine, discover why Chicago is more than just the “Second City.”

PACKING LIST From classic downtown chic to vintage bohemian, Chicagoans’ eclectic fashion sense is inspired by the city’s ethnic diversity and dictated by the fickle weather of the Windy City. Dressing light and bringing lots of layering pieces is the way to go to ensure a comfortably chic visit:

- Leather tote to hold all your essentials - Colorful printed scarf-- When it’s not decorating your neck, it’s the perfect accessory for your bag. - Mirrored sunglasses – Sunglasses are a travel must so try slipping on a trend-right mirrored style - Knotted floral head wrap-- It’ll keep your mane tamed when the Chicago wind is at its worse. - Leather motorcycle or bomber jacket - Studded or embellished ballet flats for seeing the sights - High-Low cotton T-shirt - Textured printed pants - Long silk chiffon maxi skirt or dress. - Sleek heeled booties or pumps - A playful romper -- This essential piece paired with your heels will easily take you from daytime fun to nighttime rooftop cocktail sipping.

TIPS The El train is the most efficient way to get from place to place. Discounted 3-day passes serve as the most cost effective at $12 for unlimited rides day and night.

Want to see the famous Chicago skyline? Skip the lines and expensive passes at the Willis Tower. Opt for the ROOF on theWit or Vertigo Sky Lounge where you’ll take in exquisite views while mingling with some of the city’s hippest natives.

STAY Public Hotel The Gold Coast neighborhood, home to the Public Hotel, is Chicago’s most famous neighborhood with its historical grey- and brownstone homes. Easy access to the El stop and some of Chicago’s famous landmarks make this is a prime location to settle while visiting. Steps away from Oak Street Beach on Lake Michigan and The Museum of Contemporary art, here you’ll feel like real local.

The Wit Hotel This hip and trendy hotel located in the Chicago Loop (or simply, The Loop) puts you in the center of the city. Hotel rooms offer views of the famous Canal and sits near the River North district, a hotbed of Chicago’s most sought restaurants and bars. The Wit Hotel is a city destination itself with a rooftop bar and lounge made famous by its sweeping views and cool Chicago crowd.

DINE Gilt Bar A super glossy, super sexy gastro-pub, Gilt Bar’s cuisine is crafted with creativity and finesse. The roasted cauliflower side and grilled pork belly main are an absolute must try and there’s something on the menu to tickle anyone’s fancy. After dinner head downstairs to the lounge to sip Gilt Bar’s finely crafted cocktails and take in the cool music. Because this place is such a city wide favorite, reservations are a must.

Elly’s Pancake House In Chicago, brunch is not just a type of cuisine; it’s a way of life. Located in the very quaint Old Town neighborhood, Elly’s Pancake House offers contemporary brunch dining around the clock. The menu also has plenty of lunch and dinner options but the brunch here is definitely the headliner.

Pizano’s If you know anything about Chicago, than you know Deep Dish Pizza is a famed specialty. With loads of self-proclaimed “famous” pizza joints, it can be difficult to figure out which is really the best. Go where the locals (and Chicago-native Oprah) get their pies and head to Pizano’s. Since 1943, this family owned restaurant has been making sought-after deep dish and thin crust delights. There’s no fussy décor or fancy drinks, just good pizza.

DRINK American Junkie Situated in the happening River North neighborhood, American Junkie’s sprawling space boasts retractable walls and roof making it one of the most unique places to be in the city. During the week the mild crowd makes it a great place to grab a glass of Junkie’s private label wines. American Junkie also caters to the late night weekend set with craft cocktails.

The Underground If you want to rub shoulders with celebrities, The Underground is the place to be. From famed DJ appearances to run-ins with some of the city’s most well-known faces, a night of drinks and dancing at this exclusive hot spot never disappoints. With a newly renovated space, The Underground is twice as cool as it used to be-- and that’s saying a lot.

Drumbar In Chicago, the craft cocktail is what it’s all about and you’ll find one of the best cocktail menus in the city at Drumbar. If you’re looking for a tamer crowd and a more lounge like atmosphere, this cozy rooftop bar certainly fits the bill. With décor like that of a rich hunting lodge and a beautiful outdoor terrace with views of Lake Michigan, it makes any patron—locals and visitors alike-- feel right at home.

DO Wicker Park Home to some of the coolest record, vintage, and antique shops, Wicker Park is currently the hippest neighborhood in Chicago. Enjoy eats and specialty beers at Piece and specialty cocktails at the Prohibition-era inspired lounge The Violet Hour.

Seadog Architectural Boat Tour Docked at the famous Navy Pier, a former navel landing strip, Sea Dog Cruises are the best way to take in the beautiful architecture of the city. Sail through the Chicago Canal and feast your eyes on some of the city’s historical buildings and iconic landmarks. With views you can only get from the water, even Chicago natives can be seen frequently on these tours.

Museum Campus Home to the world-famous Field Museum, Shedd Aquarium, and Adler Planetarium, the 57-acre park Museum Campus is one of the most frequented and celebrated places in the city.


Kaira Townsend is the Midwest Southwest Merchandiser for Oliver Peoples, Inc. When she’s not traveling across the country in the name of eyewear, she’s also the Contributing Fashion Editor for Design Bureau Magazine.