Travel Guide: Chicago

Ah, the Windy City. My love for this city grows with every visit. If it wasn’t for the harsh winters, I could definitely see myself living in Chicago during my young adult years. It reminds me of New York City, but not as hectic. The scenery is gorgeous with skyline views of buildings and Lake Michigan bordering the city. The food is amazing, which is always a plus for me. I’ve been to this wonderful city five times so far and I’m never opposed to flying out there again (if the price is right). There’s plenty to do, see, and eat. Below are a few that I’ve been able to check out during my visits.

Things to Do

  • Skydeck Chicago at Sears (Willis) Tower: 233 S Wacker Drive
    • Purchase tickets in advance and go early to avoid the crowd
    • Get the infamous photo of the Chicago skyline all around you
  • John Hancock Center: 875 N Michigan Ave
    • Less crowded than Willis Tower to get amazing view of the city
  • Chicago Lakefront Path: 1600 N Lake Shore Dr
    • Gorgeous path to go for a run near by the water
  • Millennium Park: 201 E Randolph St
    • Beautiful park with tons of sculptures
    • The Bean
    • Amphitheater
  • Navy Pier: 600 E Grand Ave
  • Attend a Cubs game at Wrigley Field
  • Attend a Bears game at Soldier Field



  • Longman & Eagle: 2657 N Kedzie Ave
    • Pork Belly Benedict
  • Wildberry Pancackes and Cafe: 130 E Randolph St
    • Cinnmon Roll Pancake (or any pancake, really)
  • Hash House a Go Go: 1212 N State Pkwy
    • Chicken and Waffles
  • Little Goat Diner: 820 W Randolph St
    • Anything!
  • The Bongo Room: 1152 S Wabash Ave


  • Intelligentsia Coffee: Various Locations 
  • Goddess and The Baker: 33 S Wabash Ave


  • Sweet Mandy B’s: 1208 W Webster Ave
  • Molly’s Cupcakes: 2536 N Clark St


  • High Five Ramen: 112 N Green St
    • Ramen at full spice (or half spice)
  • 90 Miles Cuban Cafe: 2540 W Armitage Ave
    • Ropa Vieja and BYOB
  • The Silver Palm: 768 N Milwaukee Ave
    • Three Little Piggy Sandwich
  • Lou Malnati’s Pizzeria: Various Locations
    • Deep dish pizza


  • Frontera Fresco: 111 N State St (located inside Macy’s)
    • Steak Torta and tacos
  • Xoco: 449 N Clark St
    • Same owner as Frontera Fresco, so delicious tortas here too!
  • Portillo’s: 100 W Ontario St
    • Polish Hot Dog or Italian Beef
  • Wow Bao: Various Locations
    • Mongolian Beef Bao

Things to Know

  • Easy access to city from both O’Hare and Midway Airport by CTA “L” Train
  • Driving around Chicago is fairly easy, but having a car isn’t necessary
  • The “L”, Uber, and of course walking are available for transportation
  • Chicago is based off a grid system, so it’s easy to navigate around
  • Logan Square is my favorite neighborhood to drink



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