Chicago is one of my favorite cities. If I could move there, I probably would. (Holler if anyone is hiring.) My favorite neighborhood is West Loop, but I don’t discriminate. I covered a lot of territory with this city guide. There’s a sprinkling of things to do, eat and see from all over the city.
eat
The Chicago food scene is excellent! I spent a lot of my time in West Loop but these recs are spread out all over the city.
The Chicago food scene is excellent! I spent a lot of my time in West Loop but these recs are spread out all over the city.
3 Arts Club Café
1300 N Dearborn Pkwy
Chicago, IL 60610
3artsclubcafe.com
This restaurant is GORGEOUS. Nestled inside Restoration Hardware, 3 Arts is a great weekend spot to curl up and have a boozy brunch. They don’t take resies so go early, put your name in and grab a glass of something and hang out in all the cozy nooks of the store.
La Sirena Clandestina
954 W Fulton Market
Chicago, IL 60607
lasirenachicago.com
La Sirena Clandestina is an awesome Brazilian restaurant. Grab a sammy, a pisco sour, and enjoy the low key vibes in this West Loop spot.
GT Fish & Oyster
531 N Wells St
Chicago, IL 60654
gtoyster.com
GT Fish is an amazing seafood restaurant. If you’re craving oysters and shrimp cocktail (*ahem* me always *ahem*), this place will be your new fave.
Beatrix
519 N Clark St
Chicago, IL 60654
beatrixrestaurants.com
A SOLID breakfast/brunch option. With a couple of locations in the city, Beatrix has you covered. With a mix of healthy and not-so-healthy dishes, I actually had brunch here twice the last time I was in town.
Lou Malnati’s Pizzeria
439 N Wells St
Chicago, IL 60654
loumalnatis.com
If you haven’t experienced Chicago deep dish, you’re missing out. I don’t have strong feelings for or against deep dish pizza, but it’s worth trying the next time you’re in the Windy City. Lou Malnati’s was my first deep dish experience, and I thought it was delish. It’s not pizza, but it’s still delish. Ok, maybe I do have strong feelings about it.
Summer House
1954 N Halsted St
Chicago, IL 60614
summerhousesm.com
Summer House is the kind of place where I would meet some of my girlfriends for brunch and not leave until it’s dark out. They have a hip vibe AND a rose cart.
The Digest
COFFEE & BREAKFAST
drink
The cocktail and bar scene in Chicago is just as good as the food scene. Not going to lie, I made some serious rounds in Chicago, so don’t judge. Anyway, here are my faves.
The cocktail and bar scene in Chicago is just as good as the food scene. Not going to lie, I made some serious rounds in Chicago, so don’t judge. Anyway, here are my faves.
Cindy’s
12 S Michigan Ave
Chicago, IL 60603
cindysrooftop.com
Cindy’s has THE view of Millenium Park. Located on the roof of the Chicago Athletic Club, Cindy’s overlooks the famous Chicago bean while serving a fab array of cocktails and wine. (Well, they had Scribe in a can so that’s pretty fab to me.) Worth a visit just for the views.
The Allis
113-125 N Green St
Chicago, IL 60661
theallis.com
The “lobby” bar inside the Chicago Soho House is low key fab. With gorgeous interiors, Allis is a great place to grab happy hour or drinks before dinner.
Fox Bar
113-125 N Green St
Chicago, IL 60607
foxbar.com
I could probably spend all night at Fox Bar. Another bar located inside Soho House, Fox Bar is a bougie dive bar that serves mean cocktails. Snap a pic of you and your friends for the wall and then hang as long as you can. Big fan.
Broken Shaker
19 E Ohio St
Chicago, IL 60611
freehandhotels.com/chicago/broken-shaker
Broken Shaker a pop-up bar of sorts inside the Freehand hotel. During the day, it’s part of the coffee shop and lobby, and at night it’s a bustling party with great cocktails and chic people.
The Digest
stay
Chicago has some incredible hotels. It depends on where you want your home base to be, but here are some solid options for your next trip.
Chicago has some incredible hotels. It depends on where you want your home base to be, but here are some solid options for your next trip.
Soho House Chicago
113-125 N Green St
Chicago, IL 60607
sohohousechicago.com
It’s pretty obvious but I love Soho House. The atmosphere, the community, and the amenities – it’s the perfect home base where ever you’re traveling.
Chicago Athletic Association
12 S Michigan Ave
Chicago, IL 60603
chicagoathletichotel.com
Located in an amazing building with amazing decor and amazing views, the Chicago Athletic Association is an amazing hotel for your next visit to the Windy City.
The Digest
see
The history in Chicago is WILD. From Obama to mobsters to stunning architecture, there is so much to see and do.
The history in Chicago is WILD. From Obama to mobsters to stunning architecture, there is so much to see and do.
Wendella Boats
400 N Michigan Ave
Chicago, IL 60611
wendellaboats.com
You have to go on an architectural boat tour while in Chicago. Do not go with any boat tours except for Wendella. Groupon and discount may be attractive, but trust me, Wendella is legit and worth the price.
