A Cool Girls Guide to Chicago
Some of the coolest, most unique or best things to do in Chicago for the gal (or guy) with discerning taste. I lived there for years before moving to Europe and Australia, trust me. My favorite US city.
Map
Hotels
Amazing hotel in a prime location. Has a rooftop pool and one of the coolest examples of architecture in the city
Also love this hotel- right near State Street and the Iconic Chicago Theatre. We stayed here most recently during the Christkindlmarket
Okay obviously if you want more options, check out Booking for more hotels (duh)
Boutique hostel (private rooms also)
Contains Cindys. Sooo cute. Overloooks Grant Park
Tour Options
An easy way to see a bunch of Chicago at once
One of the few touristy stuff I genuinely recommend. The food is top tier
a group tour option that also hits up NYC etc
Things to Do
Okay even if youre not a baseball fan, Wrigley is worth checking out. Theres cute little markets just outside, plenty of bars and restaurants or of course, concerts held there.
You may have been told to check out Second City (and I don't disagree) but if you want some comedy that's a bit different check out Drunk (and improvised) Shakespeare. Youll cry from laughing
I mean…do I even have to say anything else? Just LOOK AT IT
Get an Iconic picture in front of this sign
Okay normally I'd recommend the bar thats at the top of the John Hancock, but at the time of writing its closed. So instead, fork up the $$ and go to the Observation Deck. Its a better view than Willis Tower. I recommend going just before Sunset
Restaurants/Bars
There are like 5 location so check which is closest to you but I love, love, love the empanadas. Also the Horchata Latte
Cindy's is no longer a hidden secret (in fact you'll find it on plentyyy of Chicago Must Dos) but its famous for a reason okay
The perfect restaurant for cocktails and nibbles. Even better on the roof in summer
Bespoke Cocktails
More Cocktails but a much more casual and fun Tiki vibe
Shopping
Much better than any typical “Chicago” souvenir. Get cute sweatshirts, hats, stickers or just other cute clothes
The design on this is the Chicago Flag. You'll see it EVERYWHERE. People literally have tattoos of it. I like to rock a subtle souvenir with the deisgn on it
If you need an esim (or just buy a physical sim from Tmobile)
Unique store. IFYKYK
My fave thrift location in the city
Etc Etc
E-Sim for USA and Canada
Map for the “El”- Chicago's inner city train system
Chicago's Metro Map. AKA The suburban train system