Chicago: Where to Go, Eat & Drink

“The Windy City” hails some of the country’s best restaurants (Chicago was named the 2017 Restaurant City of the Year) and stunning skyline views. Throughout my time living there, it’s easy to say that boredom is not a challenge and weekends consistently tested my indecisiveness. With that said, I’ve compiled a list of spots to check out. Whether you’re new in town or visiting for only a few days, browse through this list to get inspired during your time in Chicago, enjoy!


  • Millennium Park & Cloud Gate (“The Bean”): Stop by for the iconic Bean sculpture and check out movie screenings & outdoor festivals during the summer -- ice skating during the winter

  • Chicago Riverwalk: Stroll through the riverwalk for beautiful skyline views or kayak through the river for waterfront views

  • Chicago Architecture Tour: A must-go if you're curious about Chicago's history; it's a great activity to do during your first day in town; it was named one of the most popular tours in America.

  • Skydeck Chicago on Willis Tower: Take photos of the skyline on a glass balcony extending four feet outside the 103rd floor

  • The Art Institute of Chicago (a must): Stop by one America's oldest and biggest museums; it's one of my favorite museums as it includes iconic pieces like Georges Seurat's A Sunday on La Grande Jatte, Pablo Picasso's The Old Guitarist, Edward Hopper's Nighthawks, and Grant Wood's American Gothic.

  • Broadway In Chicago: Watch a show on Broadway! Tickets here are more affordable than LA's and New York's.

  • North Avenue Beach: Stroll through the beach for stunning skyline views in front of the water; in the summertime, watch fireworks on Wednesday at 9:30 PM and Saturday at 10:15 PM.

  • The 606: Take a breather from the city and ride your bike along this elevated pedestrian path. It runs 2.7 miles through Logan Square, Humboldt Park, Bucktown and Wicker Park and makes a perfect place to walk out your food-coma.


  • Pequot’s Pizza ($-$$): Deep dish pizzas are a must when visiting Chicago; Pequot's is my favorite because of it's unique caramelized crust.

  • Au Cheval ($$): “the best burger in town” infamous for 2-5 hour waits; no reservations

  • Small Cheval ($) is a similar chain that offers the casual version of Au Cheval.

  • Girl & The Goat ($$$): small plates with adventurous ingredients, family style, 2-3 months prior reservations recommended.

  • Duck Duck Goat ($$-$$$): Chinese fusion small plates; same chef as above; truly 10/10 creative and delicious.

  • Roister (brunch $$; dinner $$$$): amazing brunch alert; the BEST chicken and waffles I’ve ever had.

  • Serai ($-$$): AMAZING Malaysian/Singaporean restaurant.

  • 90 Miles Cuban Cafe ($$): Great Cuban food with nice outdoor seatings.

  • Chicken Farm and Shop ($$): just WOW, the chicken biscuit and potatoes are a must try.

  • Qing Xiang Yuan Dumplings ($$): housemade dumplings with various choices for fillings.

  • Ming Hin Chinatown location ($$): affordable and authentic dim sum experience.


Coffee shops:

  • Gaslight Coffee

  • Roasters

  • Ipsento 606

  • Sawada Coffee

  • Sip Coffee House

  • Limitless Coffee Fulton Market


  • The Violet Hour

  • Scofflaw

  • Bangers & Lace

  • Three Dots and Dash (tiki bar)

  • The Heavy Feather (on top of Slippery Slope)

  • The Barrelhouse Flat

  • Moneygun.

Rooftop bars:

  • Cindy’s

  • LondonHouse Chicago

  • Raised

  • Cerise

  • Apogee

  • The Up Room.


  • The Violet Hour

  • The Library

  • Blind Barber

  • Booze Box

  • The Office

  • Room 13

Drink & Play:

  • Point & Feather (dart bar)

  • Flight Club (dart bar)

  • Emporium (Barcade in Wicker Park and Logan Square)

  • The Royal Palms Shuffleboard Club (shuffleboards)

  • The Green Lady (trivia nights)

  • Brando’s Speakeasy (karaoke).


  • Hip Hop: Underground, Studio Paris, Celeste, PRYSM

  • Techno & EDM: PRYSM, Spybar, smartbar, Sound-Bar, Berlin

  • Bar/casual dancing: Lottie’s Pub, Slippery Slope, Joy District, Beauty Bar

  • LGBTQ: Boystown (Chicago’s gay district), Side Track, Elixir, Kit Kat Lounge

I hope the recommendations above can get the ball rolling on your start to Chicago. Enjoy the city and stay warm if you’re visiting this winter