If you follow me on Instagram and watch my stories, you may see that I travel...a lot. Most of the time, it’s for work and on occasion, it’s for pleasure.
Luckily, I like what I do and my work trips bring me to some incredible places in the United States. One of those is my faaaaavorite Midwestern city (sorry anywhere in Ohio!) and that’s Chicago, Illinois.
More often than not, I’m traveling to these cities for only one or two days with most spent either indoors at an office or a conference room. Alas, I really try to schedule some moments of R&R whenever I’m in a new place.
That being said, I know many people travel for work and if you’re headed to Chicago, well, this is the list damnit. For newcomers, old-comers (is that a thing?), and everything in between.
WHERE TO STAY:
I’ve stayed in MANY places throughout the city and here are a few favorites.
The Hoxton: The Hoxton is new (being built in May 2019!), sleek, and can I say chic? Well, I just did! It’s located in the West Loop (now known for being a HIP spot in town) and is home to one of my all-time favorite restaurants, Cira. The rooms are spacious, well designed, and the staff is incredibly friendly. Also, very walkable – especially to local favorites like Au Cheval, Girl & The Goat, and Bad Hunter (all great places to eat dinner alone...lol).
Chicago Athletic Association: This historic spot is located on Michigan Avenue and right across from Millennium Park! It’s old school, but born again with their sleek rooms and epic restaurants (aka: Cindy’s on the roof!) I’ve stayed here many times for its convenience and comfortable rooms. Their fitness center is top notch if you’re looking to squeeze a workout or two in before!
Hotel Lincoln: This bad boy is literally on Lincoln Park and the edge of that neighborhood and Old Town. Admittedly, one of my best friends lives nearby so it’s easy to get to her place but Hotel Lincoln also has an epic rooftop (expense that cocktail, girl! You’re working while you sip, mmk?), great bath products (sup Jonathan Adler), and even has a farmer’s market in front of it on Wednesday and Saturday in the Spring/Summer/Fall!
THE EATS:
Again, when I’m in town I usually am eating with my bestie or alone! That being said, here are some nomworthy eats.
Cira: This girl loves her Mediterranean and sometimes, you just wanna eat where you stay!! Luckily, The Hoxton has some of the best restaurants in town and Cira is it. They serve breakfast, lunch and dinner but dinner is where it’s at, y’all. The menu changes, but when I was there last I loved the burrata and beets, brown butter hummus, and grilled octopus!
Bad Hunter: I’ve been trying to eat less meat, so after a drink or two one night, I decided to head on over to Bad Hunter (also close to The Hoxton). I bellied up to the bar (I’ve always just wanted to say that), and the bartender immediately smiled and asked what I wanted to drink. After some time, he helped me pick a drink that was unique and funky, but also refreshing (it was August in Chicago!). It was the RnBeet which included orange wine, rhine hall plum brandy, beet, blanche armagnac, marigold honey, mint, genepy. TASTY. And speaking of tasty, the food at Bad Hunter is fireeee. The heirloom tomato salad was the freshest (literally) thing on the menu and I also couldn’t get enough of the pickled veggies, charred cucumbers and carrots.
Pacific Standard Time: Okay, so maybe I’m biased. But hell, I don’t care. PST as I’m affectionately calling it is B-O-M-B. It’s California cool brought to Chicago and since I’m a proud Californian, I had to see if the food lived up to the hype. First off, the branding is super cool (I’m a sucker for branding). And if you’re eating alone, suggest the bar (or overlooking the chefs!) since they’re high-top/counter seating. The produce is incredible, but also the seafood is to die for (lookin’ at chu Ahi Tuna Crudo).
WHAT TO DO:
This will be a short list so I’m always working (or eating). That being said, I have made time for some fun activities including…
Architectural River Tour: I did this the last time I was in town when I had a few hours to spare! I had low expectations, but since Tom is an architect, I thought I’d learn some new things! It exceeded my expectations and the tour host was incredibly informative and funny. It’s an inexpensive ticket and you can even buy hard seltzer (holla white claw!) or beer on board.
Millennium Park: I am obsessed with walking and whenever I go to Chicago I try to walk as much as possible (even in the winter!). One of my favorite things to do is see “The Bean” in Millennium Park, take a selfie and say hi OR run up and down the park. In the Summer you can also see a ton of shows, concerts that are perfect to hang out in and sip a beverage or two.
While we’re talking about walking, I’d say walking by the lake (Lake Michigan, y’all) on the lakefront trail is extremely fun and relaxing. I just Googled how long it is and it’s 18 miles (if you’re into that!!!).
Second City: What’s better than laughing with strangers?! NOTHING. Anyway, I’ve been to Second City a few times and whenever I’m on my own, I like to do something like this that’s unique to the city and a solo activity (with other people). If that makes sense. The shows change all the time and if comedy ain’t your thing, there’s a SoulCycle 10 minutes away. :)