A 2018 Guide to Chicago

“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 weekend festivities consistently tested my indecisive nature. 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 the following to get inspired during your time in Chicago, enjoy!

Attraction & Activities

  • Millennium Park & Cloud Gate (“The Bean”):  movie screenings & outdoor festivals during the summer and ice skating during the winter.
  • Chicago Riverwalk: stroll through for beautiful skyline views or kayak through the river for waterfront views.
  • Chicago Architecture Tour: GO ON THIS! Super interesting to do on your first day in town; it was named one of the most popular tours in America.
  • Skydeck Chicago on Willis Tower: photo opportunities of the skyline on a glass balcony extending four feet outside the 103rd floor.
  • Museums: The Art Institute of Chicago (a must), Museum Of Contemporary Art Chicago, The Field Museum, Museum of Science and Industry, Adler Planetarium.
  • Broadway in Chicago: more affordable prices than NYC & LA
  • North Avenue “Beach”: stunning skyline views in front of the beach; in the summertime, watch fireworks on Wednesday at 9:30pm and Saturday at 10:15pm.
  • Navy Pier: a pier front walk way with stores and restaurants (I’d recommend a quick stroll but it’s super touristy and the attractions aren’t worth your money).
  • Magnificent Mile: the largest shopping district with various mid-range and high-end shops lined on Michigan Avenue.
  • The 606 (kind of like The Highline in NYC): great for an evening stroll, jog or bike ride; a 2.7-mile elevated pedestrian path that connects Logan Square, Humboldt Park, Bucktown and Wicker Park.
  • Explore neighborhoods:
    • River North (fine dining, mainstream clubs, bars & lounges; vibe: basic bros and tourists).
    • West Loop (top restaurants, brunch, bars, coffee shops, murals; vibe: young professionals).
    • Wrigleyville (a neighborhood built around its baseball stadium, sports bars; vibe: baseball enthusiasts).
    • Wicker Park & Logan Square (great restaurants, independent boutiques, coffee shops & bars; vibe: hipsters and gentrifiers).
    • Lincoln Park (free zoo, Lincoln Park, “beach;” vibe: residential & relaxing)
    • Hyde Park (U Chicago, Museum of Science and Industry, Obama’s house, Renaissance Society, Promontory Point; vibe: multicultural, students, residential, young professionals).
    • Pilsen (historically Mexican neighborhood with a variety of food options, murals, shops and museums; vibe: diverse).



  • Top Deep Dish Restaurants ($$): Lou Malnati’s Pizza, Giordano’s & Pequot’s Pizza; be wary of long lines.
  • Chicago Dogs ($): UB Dogs, Portillo’s, Fatso’s Last Stand & Wieners Circle
  • Au Cheval ($$): “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


  • Rooftops: Cindy’s, LondonHouse Chicago, Raised, Cerise, Apogee, The Up Room.
  • Speakeasies: The Violet Hour (super cool), The Library, Blind Barber, Booze Box, The Office, Room 13.
  • Activities & Drink: 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).
  • Cocktails: The Violet Hour, Scofflaw, Bangers & Lace, Three Dots and Dash (tiki bar), The Heavy Feather (on top of Slippery Slope), The Barrelhouse Flat, Moneygun.


  • Mainstream clubs: Underground, Studio Paris, Celeste, DISCO
  • Techno & EDM clubs: 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 🙂

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