We’re big fans of Chicago for many reasons, but mostly because it’s one of those places that never fails to inspire. How is it that a city that is not New York City can have so much style?! Just kidding – but not entirely.

In addition to loving the style of the city, we’re also going to be spending quite a bit of time there this summer because we have designed and furnished the spec apartment in Related Midwest’s newest luxury apartment complex, The Landmark West Loop. (Stay tuned for more on that!)

Since Shelby, our Head of Design, spent several years in Chicago, I picked her brain for her top go-to spots for a great day in the Windy City.


Design Shops

This list of stores had us searching for flights to Chicago, kid you not. Whether you’re looking for inspiration, wedding gifts for friends, or a pick-me-up just for you, these are sure to have exactly what you’re looking for.

Jayson Home – Impeccably curated shop of both modern and vintage furniture

Photo courtesy of The Everygirl

Interior Define – Modern upholstery shop in Lincoln Park (and Havenly vendor!)

Photo courtesy of The Everygirl

Humboldt House – Vintage shop with lots of mid-century modern finds

Photo courtesy of Humboldt House

Salvage One – Large showroom of salvaged artifacts that doubles as an event space

Photo courtesy of Salvage One

Brimfield – Repurposed furniture and decor store with a cabin-like feel

Photo courtesy of Brimfield

What to Do

Really, what you do in Chicago in the summer is: enjoy the beautiful outdoors, the art and, of course, the food. So, don’t overwhelm yourself with too many activities–as long as you’re outside as much as you can be, you’re soaking in the summer scene of Chicago.

Walk around Millennium Park – Beautiful park near Lake Michigan with The Bean (which is one of my favorite cheesy tourist attractions), Pritzker Pavilion, and Crown Fountain
Photo courtesy of Getty
Art Institute – Amazing collection, although I usually go for the gorgeous architecture of the modern wing and stroll to Millennium Park afterwards
Photo courtesy of Charles, Sparks + Co
Architecture Boat Tour – A cheesy tourist thing that is so awesome: see all the city’s iconic buildings by boat
Photo Courtesy of Shoreline Sightseeing

Where to Drink

Summertime is so beautiful in Chicago that it’s always fun to find a patio or rooftop to enjoy a cocktail. We have pulled together a list of both indoor and outdoor “must sip” drink stops.

Soho House – Hip social club in the West Loop with a beautifully designed lobby and bar that’s open to the public

Image courtesy of Soho House 
Billie Sunday – My favorite cocktail spot! Dark, great decor, and the best Old Fashioned I’ve ever had
Image courtesy of Billie Sunday
The Whistler – Small, dark space with live music and strong cocktails at a great price
Image Courtesy of The Whistler.
Lost Lake – Tiki bar in Logan Square with iconic banana leaf wallpaper
Image courtesy of The Chicago Tribune
Cindy’s – Rooftop bar on top of the Chicago Athletic Association with great views of Millennium park and delicious (although overpriced) drinks
Image courtesy of Cindy’s.
City Winery – If you find yourself downtown, this is a great spot overlooking the river to grab a glass of rosé on a sunny day
Image courtesy of City Winery

Where to Eat

We all know that Chicago is known for its delicious food. It would take several trips to really take a bite of the Chicago food scene (pun FTW). So, do yourself a favor and start with the list below.

Lula Cafe – In Logan Square cafe, best for brunch
Image courtesy of Chicago Mag
Parsons Chicken & Fish – Humboldt Park fried chicken and frozen Negroni joint – amazing patio, too!
Photo by Clayton Hauck for Parson’s / Longman & Eagle
Big Star – Taco spot in Wicker Park with killer margaritas and a great patio (if you don’t mind the wait)
Image courtesy of Eater Chicago
The Publican – beer and meat done right in a beautiful West Loop community-style space
Photo courtesy of The Publican
Little Goat – Sister location to Stephanie Izzard’s “Girl and the Goat” with great “fancy diner” brunch
Image courtesy of Little Goat

RH 3 Arts Club – A RH with a bar and dining experience in an amazing courtyard

Image courtesy of RH 3.

Where to Stay

With the endless fun activities on your itinerary, you need a cool (and comfortable) place to rest your head at night. Here are a few of our faves.

Public Hotel – Minimal design at it’s best in the heart of the Gold Coast
Image by Public Hotel
Longman & Eagle Inn – Six room inn above a Michelin star restaurant – go for brunch and sit at the bar to skip the lines
Photo by Clayton Hauck for Longman & Eagle
The Robey – Wicker Park flatiron style building with an outdoor pool, cocktail bar, and amazing rooftop views
Photo by The Robey

Also, Chicago is really, really humid in the summer so just mentally prepare for big hair and a lil’ sweat. It’s worth it, though, we promise.

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