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
Sections
6
Hotels
Tour Options
Things to Do
Restaurants/Bars
Shopping
Etc Etc
Hotels
Amazing hotel in a prime location. Has a rooftop pool and one of the coolest examples of architecture in the city
Radisson Blu Aqua Hotel, Chicago
Also love this hotel- right near State Street and the Iconic Chicago Theatre. We stayed here most recently during the Christkindlmarket
Staypineapple, An Iconic Hotel, The Loop Chicago
Okay obviously if you want more options, check out Booking for more hotels (duh)
Booking.com: The largest selection of hotels, homes, and vacation rentals
Boutique hostel (private rooms also)
Freehand Chicago
Contains Cindys. Sooo cute. Overloooks Grant Park
Chicago Athletic Association - The Unbound Collection by Hyatt
Tour Options
An easy way to see a bunch of Chicago at once
Chicago Bus Tours
One of the few touristy stuff I genuinely recommend. The food is top tier
From Architecture to Food Guided Tour in Chicago - Klook Australia
a group tour option that also hits up NYC etc
North East Highlights
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.
Wrigley Field
I made a visual scrapbook of Chicago, check it out for inspo <3
Chicago | 5 days in the Windy City | Best Eats and Must Dos
As I said earlier, if you can swing it- DEFINITELY go to a Cubs Game. Even if youre not a baseball fan. its so fun
Chicago Cubs Game Tickets
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
Welcome — Drunk Shakespeare
Get an Iconic picture in front of this sign
The Chicago Theatre
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
360 CHICAGO
Anddd if you want to see the sights of Chicago without walking much
Chicago: Hop-on Hop-off Sightseeing Tour
Way more fun than it sounds, trust me
Chicago Architecture River Cruise
If you wanna knock out a bunch of touristy stuff
Go Chicago Card
Secret music shows every night in Chicago. They can be anywhere from inside museums after close to inside local's homes. I used to host them in my apartment!
Sofar Sounds
Unlock your inner Ferris Bueller and check it out
The Art Institute of Chicago: Home
I mean…do I even have to say anything else? Just LOOK AT IT
AIRE Ancient Baths Chicago
Easy 2 hour day trip to Milwaukee for a day trip if that's your vibe
Welcome to Amtrak Hiawatha | Milwaukee - Chicago
Nice lil walking trail on an old train track. Like the highline
The 606: Home
A Nature escape right there in the city
Northerly Island
The Art Institute is usually recommended- and for good reason. But I also love this museum. Right on Mag Mile
Museum Of Contemporary Art Chicago
A little different but very fun
Chicago Magic Lounge | Magic Bar and Theater | Andersonville
Usually around late July or early August
Lollapalooza Chicago
If you want to see the best bits of Chicago downtown in one go
Chicago: Millenium Park Self Guided Tour
Another great Museum- it has a whole ass submarine inside it
Chicago: Griffin Museum of Science and Industry Ticket
There is literally ALWAYS something going on Chicago, especially during summer. Check here to see what fests are on while you're there
Chicago Events Calendar For 2024 Including Concerts and Festivals
“Secret" park with a great view of Chicago skyline and Ohio st beach
Milton Lee Olive Park
The best bits of Chicago are not in the downtown. Theyre in the neighborhoods. Some more of my favorites- Lincoln Park, Logan Square, Pilsen, Andersonville, Lakeview, Ukranian Village.
Humboldt Park
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
Cafe Tola - Chicago
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
Cindy's Rooftop
The perfect restaurant for cocktails and nibbles. Even better on the roof in summer
Aba
Bespoke Cocktails
The Aviary - Chicago, IL
More Cocktails but a much more casual and fun Tiki vibe
Three Dots and a Dash
Iconic Obvi
Ralph's Coffee
Tapas and Sangria, perfect for sharing
Cafe Ba-Ba-Reeba!
Watch the Merchandise Mart Art Projections along the river with a glass of wine. Best viewing during summer obviously.
CITY WINERY RIVERWALK WINE GARDEN, Chicago
As seen on the Bear. Pro tip: you can order ahead!
Kasama
packed with locals and a fun night out
Kingston Mines – Chicago Blues Center Since 1968
one of my faves- one of Al Capones faves too. Thursday is big band night.
The Green Mill
So delicious
Longman & Eagle
Swedish brekkie with a side of the biggest cinnamon rolls you've ever seen
Ann Sather Restaurant
Usually always recommended and for good reason. Izard is Chicagos celebrity chef
Girl & The Goat | Los Angeles & Chicago | Chef Stephanie Izard
At one point this was the #1 burger in the USA
Au Cheval | Chicago
If youve got the time, dont skip Chinatown
Ken Kee Restaurant Hong Kong
Chicago has a thing for. “Food Halls” sort of like fancier cafeterias? This is an Italian one (sort of)
Eataly Chicago: restaurants, private dining and catering
My personal favorite Food Hall. Chicago has a ton of “food halls”- like fancy food courts. Its better then it sounds I swear
Revival Food Hall
One of our bougier brunch spots
3 Arts Club Cafe at RH Chicago
Another one of my favorite rooftop bars
LondonHouse Chicago, Curio Collection by Hilton
I wasnt going to, but I have had a request to add Deep Dish pizza. so FINE here it is. Lous > Giordanos
Lou Malnati's, the Best Chicago Deep Dish Pizza Restaurant
We used to go here as a special Christmas-time treat every year so it holds a special place in my heart
Russian Tea Time Restaurant
Black Owned business with tasty af breakfast. Im talking pancake flight. Very yum. Not diet friendly but who tf cares
Batter & Berries
Shopping
Much better than any typical “Chicago” souvenir. Get cute sweatshirts, hats, stickers or just other cute clothes
Alice and Wonder - Chicago Fashion Boutique
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
X.Style Chicago Flag T-Shirt ds569 T-Shirt
Unique store. IFYKYK
The Wicker Park Secret Agent Supply Co.
My fave thrift location in the city
The Salvation Army Family Store & Donation Center
Etc Etc
E-Sim for USA and Canada
4G eSIM card high-speed Internet access in the United States and Canada (buy now and get QR code) - Klook
Map for the “El”- Chicago's inner city train system
First bus All aboard! 'L' (rail) system map Detailed fare in for ...
Chicago's Metro Map. AKA The suburban train system
System Map | Metra
If you need an esim (or just buy a physical sim from Tmobile)
Frewie 3G/4G eSIM for USA - Klook Australia
Chicago also has “ferries” aka water taxis. Its not the most efficient system in the world but its a great way to see Chicago from the water on the cheap
