Your Ultimate City Guide to Chicago



The Windy City was where I spent my last fizzling moments (or was that the fizzling champagne? not sure) of 2015! Kicking off 2016 in Chicago, Illinois was even better than expected so I want to share with you! Here are my top Chi-Town things to do, see, and EAT during the Winter:

Starting with the most important...


Ok literally anything and everything.. this city is full of the classic favorites. Pizza, tacos, street foods, sushi, Thai, Italian.. yeah we ate a lot (oops! diet starts now). But to be specific:


{Ann Sather Swedish Diner} MUST TRY: homemade cinnamon rolls *mouth waters*


{Big and Littles - as seen on Diners Drive-Ins and Dives!} MUST TRY: Al Pastor Taco, Ahi Banh Mi po'boy, and ~extra must try!!~ Kimchi Fries

{Portillos} MUST TRY: Chicago Style Hotdog - I didn't know what I was ordering, I didn't love it, but I must admit you have to try it.. When in Chicago, right?! - Also this place is super cool and full of Chi-Town history and memorabilia!

Chicago Style


{Eataly} So this place is basically a two-story market with a bunch of mini restaurants that serve different Italian (get it - eataly.. eat Italy - don't wear tight pants) style foods! We chose the micro brewery, La Birreria, and tried the homemade beer and a plate of meats and cheeses.. let's just say it was 4 whole days of cheat meals on this little vaca. If meat isn't your thing, theres a pizza/pasta option, seafood/vegetable option, and of course gelato for those of us who skip dinner all together! 


{Old Town Social} My first semi-fancy New Year's Eve was spent in style here! Good food, strong drinks. If you're looking for a moderately upscale place to show off your new knee high boots (aka me) this is your place!

{Sluggers} Let's be real, one fancy night out per weekend is enough for those of us still under thirty. Moving on to somewhere more our speed - This place has an indoor batting cage.. in a bar.. um, can I come every weekend? It's basically a dive bar and we moved on after an hour, but skee-ball and arcade games on one floor and dancing on another? I was interested. Definitely the go to if you're with a big group of friends!

Late Night

(how am i still talking about food?!)

{Andy's Thai Kitchen} MUST TRY: Pineapple Fried Rice with cashews, raisins, egg and shrimp.. It almost sounds Open for delivery! (for a $3 charge -_-)

If you can pick yourself up after all that food...


Skydeck Chicago in the Willis Tower

Skydeck Chicago in the Willis Tower

FIRST! Buy a Chicago CityPASS

$96 for the pass gets you:

  1. Shedd Aquarium + VIP Entry (which you'll need, the line is so long) - Sea Otters, enough said.
  2. Skydeck Chicago in the Willis Tower + Fast Pass - 103 Stories High in the tallest building in Chicago! (14th Tallest in the World!)
  3. The Field Museum of Natural History + VIP Entry - there's a whole exhibit on gems of the world. Also, they have the largest and most put together T-Rex skeleton *nerd emoji face*
  4. Choice Between the Museum of Science and Industry (My Recommendation) OR the 360 Chicago Tour on the 94th floor in the John Handcock Building.
  5. Choice between Adler Planetarium + VIP Entry OR Art Institute of Chicago + Fast Pass (My Recommendation)

The CityPASS saves you over $100 if you were to pay for everything individually, so for us this was totally worth it!

WARNING! There is SO much to see in each place; fight that hangover and get there early!

American Gothic by Grant Wood - Art Institute of Chicago

American Gothic by Grant Wood - Art Institute of Chicago

Other Sites to See

Cloud Gate aka "The Bean" - A must see, obviously. Located in Millennium Park

Buckingham Fountain - Located in Grant Park

Sports Game if you can! - Chicago in the winter is home to the Bulls, Blackhawks, and Bears all playing at this time of year. 


Lessons Learned

Bring fashionable walking shoes, thank goodness for uber and lyft, the stretchier the jeans the better, the homeless people will take your $20 (season of giving i guess-_-), and once again, bring fashionable walking shoes.


Did I miss anything?! What's there to do during the summer in Chicago? - Let us know in the comments!