Chicago happens to be my place of birth and I’ve always felt a special connection to the city. It has been a while since I’ve visited, so when my mom asked if I wanted to come up and stay in her condo, I gladly accepted. We stayed in Streeterville and had a fun day exploring the city. Here’s a quick rundown of what to eat, drink and do on your next day trip to the Windy City!
Gino’s East: Serving up the city’s famous deep dish pizza since 1966, Gino’s East is a must on any day trip to Chicago. It’s a great place for lunch, dinner or catching a game. On warmer days, take advantage of the 3rd floor rooftop terrace during happy hour, weekdays from 3pm-6pm. Bring a sharpie with you or better yet, a bottle of white nail polish and leave your mark on the graffiti walls!
Beatrix: If you’re up early enough, consider having breakfast at Beatrix. This elegant eatery serves breakfast weekdays from 7am-11am and all day on weekends.
Travel Tip: The fluffy lemon pancakes with lemon syrup are life changing!
Stan’s Donuts: Want to start your day with a sweet treat? If so, Stan’s Donuts is the place for you. And for even more decadence, head around the corner to Do-Rite Donuts & Chicken, which serves up fresh donuts and fried chicken, a play on the oh-so-popular chicken and waffles.
Sayat Nova: This Armenian gem nestled in the heart of Streeterville. Sayat Nova has been serving authentic Middle Eastern cuisine since 1970 and is a great spot for a relaxed lunch or dinner.
Drumbar: This speakeasy style cocktail bar is located on the 18th floor of the Rafaello Hotel. Its dim lighting and leather couches create a sultry atmosphere perfect for enjoying an after-hours spirit. During warmer months, Drumbar guests can mingle on the outdoor terrace offering lake and city views.
Signature Lounge: If you’re planning on spending any time in Chicago, the Signature Lounge on the 96th floor of the historic John Hancock building is not to be missed. The lounge overlooks the Signature Room restaurant and offers up stunning views of the city. Head up in the late afternoon and enjoy a cocktail and some appetizers while watching the sun set over the Windy City.
360 Chicago: For a thrill with a view check out TILT, a recently added attraction to the 360 Chicago observation deck located at the top of the John Hancock building. TILT allows you to see the city from a whole new perspective. Visitors stand against a glass wall that gradually tilts out over the Chicago skyline.
Those not ready to try TILT can still enjoy the observation deck, which is open daily. Guests can even participate in different themed days such as tripod day for photographers and yoga classes held on Saturdays. Click here for more info on visiting 360 Chicago.
Shopping on the Magnificent Mile: Those in need of a little retail therapy should head to the Magnificent Mile. You’ll find endless options of high end stores, malls and specialty shops that stretch along Michigan Avenue from the Chicago River to the Near North Side at Oak Street.
Chicago Christkindlmarkt: This festive market has been a source of holiday cheer in Chicago since 1996. The Christkindlmarkt is modeled after a traditional German market and features a variety of vendors selling various gifts and souvenirs as well as yummy eats and sweet treats. The market is open daily from November 17th through Christmas Eve.
Beach: No matter what time of year you visit Chicago, you’ll want to set aside some time to spend at its main attraction, the beach! The city sits along the shores of beautiful Lake Michigan and offers up serene lakeside views year round.
How would you spend a day in the Windy City? Share your comments below!