Chicago is one of those unsung cities that deserves all the praise in the world. We often hear folks say they’d love to live there if it weren’t for the Chicago winters. To which we say: Hello from Bozeman.
It’s one of those cities that feels Midwest-friendly and simultaneously like a cool little sister (or brother) of New York. But that’s almost unfair — Chicago is, and has always been, its own city with a unique style and vibe. That’s infinitely clear whenever we stop into our favorite Chicago shops or grab a bite.
Here’s our team guide.
Eat & Drink:
RL Restaurant - We have come here for years and will keep coming for years more, yet it somehow never gets old — which, come to think about it, sums up why we love Ralph Lauren, the brand. Order the Lobster Bisque, RL Burger with Hand-Cut French Fries, and Ralph's famous Coconut Cake (fun fact: we recreated this cake for our grand opening at Men's when we had our Ralph Lauren ambassador in store for our event). Make sure to book a reservation!
Avec - Avec was prominently featured in The Bear, so you know it’s good. Please, for us, order the short-rib hummus. There are two locations, and both are popular, so make a reservation!
Au Cheval - Great burger and even better vibes! There’s also a location in New York.
Doma - The. Best. Breakfast. The line is always out the door, but it’s worth it, we promise.
Judson & Moore Distillery - A whiskey distillery owned by good friends of Haley’s. Elise is also the co-owner and designer of Jeune Otte.
Le Colonial - Make a reservation and add a request in the notes to see if you can get prime seating. Our marketing manager, Tess, loves sitting in the back room in the evening, but if you are dining at lunchtime, try to reserve a table by the windows. Do not sleep on the pan-seared chicken dumplings and chilled vegetable roll!
Shop:
Notre - A beautifully curated selection of men's and women’s clothing.
Jeune Otte - A women’s sustainable clothing line designed and made in Chicago using high-end deadstock fabrics from brands like Theory and Khaite. We’re cheating a little here because they do not have a brick-and-mortar location but are online! This is a brilliant Chicago business to support.
Shopping on Randolph & Armitage - Incredible women’s shops. Take a stroll to see what you find!
Independence - A drool-worthy men’s store for the guy who allegedly has it all (trust us, he’s going to want something here).
Good Form Vintage - Some of the best vintage in the city. You never know what you’ll find, but guaranteed, it will feel like something you’d like to hand down to future generations.
Do:
Architecture River Tour - Amazing history and a fun way to see the different eras of architecture around the city!
Art Institute of Chicago - Their exhibits are not to be missed.
Soho House Chicago - Haley and Josh viewed Rag and Bone's Spring 24 collection here, then had mocktails on the rooftop. The first floor is open to the public, and it’s a great spot to work — cozy and delicious with a great coffee bar selection. There are also incredible massages at Cowshed Spa.
Chicago Athletic Club + Cindy’s (Rooftop Bar) - Great spot to work from and/or grab a drink with clients or colleagues. The best views of Millenium Park.
Stay:
The Hoxton - Perfect location in the heart of the Fulton Market District, with mid-century modern decor and floor-to-ceiling windows for taking in the city.
The Chicago Athletic Association - Also on our list of things to do (Cindy’s for the views!), the rooms strike the perfect balance between historic and modern. The views don’t hurt either.
Ambassador Hotel Chicago - A historic hotel near Lincoln Park and all sorts of iconic landmarks.
