Stay Here: Chicago, IL 🍕
This newsletter is a special one for us — we wrote it in person together in Los Angeles for the first time since Stay Here began. Ophelia’s currently taking a 5-week break in between jobs, and the days and weeks have blended together. Carving out time to write this newsletter has re-established a bit of routine and normalcy, so we’re grateful you’re here. This week, we’re headed to the midwest and going to Chicago! Ophelia’s dear friend, Alice, and her boyfriend, David, both spent 4 years living in this city, so it’s a city close to her heart. We’re both overdue for a visit!
As always, you can browse through all our newsletters if you're looking for other cities to travel to. Thank you for being a subscriber!
The Publishing House
West Loop, Chicago, IL
Starts at $249/night
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Owned by a husband and wife team, this bed & breakfast is an 11-room inn that was originally built in 1909. According to their Wallpaper feature, “each room has been individually furnished and named after notable Chicago authors or a place or characters from books that take place in the Windy City.”
We love the exposed brick walls, and the cozy, eclectic furniture.
How beautiful is this minimal library?
Grand Avenue
West Loop, Chicago, IL
Starts at $227/night, sleeps 4
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We love all of the cool tones and funky light fixtures in this West Loop apartment.
Those brass knobs are amazing!
Freehand Chicago
River North, Chicago, IL
Starts at $122/night
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We included the New York outpost of Freehand in our NYC newsletter and had to include the beautiful Chicago location as well. Designed by famed NYC firm Roman and Williams, Freehand is “comforting, inspirational, and communal.”
Honorable mentions
This 89 room hotel in an Art Deco skyscraper that was originally designed as an office building (starts at $315/night).
A European style hotel that is a tribute to Northwestern, with an eclectic mix of textures and patterns (starts at $188/night).
This Sonder apartment building in Near North filled with earth tones (starts at $109/night).
Do this
We really trust Alice and David who were kind enough to provide us with their best local recs!
From Alice:
For incredible views, walk the Lakefront Trail along the lake — Alice says looking back to see the skyline is unbeatable.
Visit Frank Lloyd Wright houses in Chicago! You can see some while walking in Oak Park (where Ernest Hemingway & Walt Disney’s birth homes were too). If you visit Robie House, don’t forget to drop by Plein Air Cafe for pastries and coffee.
For entertainment, Second City is the best for comedy shows or classes, and for cocktails, The Aviary is legendary.
And of course, it’s not a visit to Chicago without dropping by The Bean and The Art Institute of Chicago (there’s currently a Cézanne exhibition on until September).
From David:
You can’t miss these well-loved local favorites: Purple Pig, Pequod’s pizza, Girl and the Goat, & Au Cheval.
For less touristy, affordable options that have less of a wait: Cafe Babareeba for the best Spanish tapas), Little Goat Diner (from Stephanie Izard of Top Chef fame, who also owns Girl and the Goat), Small Cheval (fast food version of Au Cheval, but burgers are better), and of course Jeni’s ice cream and Molly’s cupcakes. David says these two dessert spots are Midwest staples, and “the greatest deserts to ever exist.”
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If you enjoy reading this content, please share it with your friends, family, neighbors, colleagues, and more. As always, let us know if you have any feedback or had a chance to check out one of our stays and we just might feature your review in our next newsletter! We love hearing from you. 🙂
Next up on Stay Here: Washington, D.C.! Let us know if you have any recs or favs from the area (reply to stayhere@substack.com). We'll be sure to give you a shout-out. :)
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