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We love to travel - who doesn't? So we think some city guides are in order. We started with CTWF Nashville Favorites, because our city is simply a gem. But we're onto Chicago from which our fall intern Zoey hails. 

The city of Chicago is unique and strong. It's the 3rd most populated city in the U.S. so you can bet there's a whole lot more happening than wind and pizza. Skyscrapers and buildings with art deco façades stand tall side-by-side, and the high-energy Loop is balanced by the intentionality and creativity of the outer neighborhoods. Chicagoans themselves are passionate about every aspect of life (but especially their sports teams). It's getting cooler by the minute, yet it still remains true to itself above all. Let us be your guide, and see what Chicago is all about through our eyes. 

P.S. It's a seven-hour drive from Nashville. We're sensing a road trip. Don't forget to take our guide with you!

CTWF City Guide / Chicago Favorites

A few of our Chicago Favorites stand out from the rest. See the numbers above? We've elaborated a bit on those ten hot-spots for your traveling pleasure...

01 The Allis at Soho House

The luxurious color palate and tasteful furniture in this hotel-lobby-meets-cafe get us every time. Have a meeting here during teatime, and you'll be set to impress.

02 Gather Home + Lifestyle

This minimalistic general store holds a special place in our hearts - CTWF is sold here! And we can't get enough of the simple, natural, curated feel of the entire shop.

03 Penelope's

An adorable shop just down the street from The Winchester. If you come here post-lunch to browse their clothes and accessories, we promise that you'll walk away with a lovely new edition to your wardrobe.

04 Hopsmith Tavern

This pub has two levels, a great selection of beers on tap, and a lot of energy. We recommend it for a night out in the Gold Coast neighborhood.


05 The Winchester

This cafe is a quiet haven filled with delicious, natural light and even more delicious food. We recommend the smoked turkey sandwich for lunch or the PEI mussels for dinner.

06 Parson's Chicken & Fish

If you're in the mood for an upbeat place to enjoy some comfort food, you're in luck. Grabbing a chicken sandwich and a frozen cocktail here might be the best decision you make all afternoon.


07 Trenchermen

An effortlessly cool dining establishment in the heart of the Wicker Park neighborhood with an impressive wine list and some fun tile floors.

08 Heritage Bicycles 

Possibly Chicago's most well-known coffeehouse, this is the place to not only fuel up on coffee, but to also shop for beautiful bicycles as well. Don't forget to check out their sweet outdoor patio where you can enjoy your drink and some sunshine.

09 The Art Institute of Chicago

We just love slow strolls through rooms full of masterpieces, don't you?

10 Garfield Park Conservatory

Tranquil, lush, and free, this indoor conservatory is filled to the brim with beautiful plants and is a lovely place for a morning stroll no matter the season. 

Did we miss anything? Tell us your Chicago must-sees!

*Photos by Zoey Bloom

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