It Might Be the Second City, but Chicago’s First on Our List of Healthy Hotspots in the Midwest—Here’s Why

Gazing up the skyline of Chicago a few years ago, still claiming my East Village apartment in Manhattan as home, I gasped and muttered aloud, “It’s so clean, it’s blue.” And truly, after making these sparkling streets my own for the last two years, Chicago's stunning eco-certified architecture and dialed train system (imagine signs that tell you how many minutes away your train is before you even descend the steps) are just a tiny glimpse of the multifaceted gem some call the Second City.

With an underground music scene that rivals the best of New York and Austin (not to mention festivals like Pitchfork, Lollapalooza, and Riot Fest), Chicago’s low-key atmosphere is ripe with friendly baristas, understanding fitness instructors, and well-versed Uber drivers ready to give you the scoop on its varied offerings—including the vegan spot that Beyoncé’s been known to hit up when she’s in town.

Keep reading for a city guide of Chicago’s healthiest places to sleep, eat, and play.

Good Sleep

The Robey

The landmark Art Deco Northwest Tower was built in 1929 and transformed by Belgian design duo Nicolas Schuybroek Architects and Marc Merckx Interiors into this contemporary hotel equipped with breathtaking 180-degree views, not to mention a rooftop pool. It's little wonder why it's become a hub for cool-kid locals and artists. Take a business meeting or draft some emails in its airy second-floor lounge bedecked with endless and comfy sectional couches, or wander down to the sun-drenched Café Robey for a plate of spicy avocado toast.

The Langham

Ethereal and elegant. This forward-thinking, ultra-luxe escape just off of the river is also a LEED-certified green hotel that touts one of the most breathtaking (and award-winning) wellness destinations in the country, Chuan Spa (think Traditional Chinese Medicine meets magical pink salt saunas and Bioenergetic-Shen Touch massages). Even its indoor pool is outfitted with an overwater lighting installation that makes every backstroke seem like you’re looking up at a softly lit constellation of stars.

The Gray

Hoping to pack light but still break a sweat during your stay? Located in a historic building in Chicago’s Financial District, the newly upgraded fitness center also touts a unique partnership with Lululemon that allows travelers to borrow workout gear during their stay to keep up their fitness routine without the hassle of carrying around an extra duffel of dirty laundry.

Ace Hotel

Of course, the Ace has officially made its way to the Windy City. Just opened last August, the brand’s first property in the Midwest collaborated with local artisans and artists to capture the city’s modernist design history. The interactive electric blue Jonathan Nesci “dome” sculpture was recently installed on its garden rooftop space, Prairie, while indoors, its signature restaurant City Mouse decreases its foodprint through composting, using the soil it fertilizes to landscape its pretty patio.

Good Food

Lyfe Kitchen

Short for Love Your Food Everyday, locally sourced ingredients are top of menu for regulars that love LYFE for taking the guesswork out of their meals (no MSG, corn syrup, or trans fats allowed). Enjoy a farm-fresh salad and baked sweet potato fries with a grass-fed burger, or go for its infamous “unfried” crispy baked chicken and cashew-cream pasta sauce, not to mention a plethora of gluten-free, nut-free, vegetarian and vegan dishes.


Thanks to patrons like Beyoncé and Stevie Wonder, this vegan bistro has become a wellness landmark for in-the-know locals. Lauded for her customized meal plans for celebs like Tasha Smith, Taraji P. Henson, and Angela Bassett, holistic expert Karen Calabrese reopens her beloved restaurant to the public next month with a wholesome new menu of raw, conscious comfort foods.

Enoteca Roma

Easily one of the most ethereal back patio setups in the city with twinkling lights strung between giant trees, this is an easy spot for a romantic date or group gathering where you won’t feel like you’re touching elbows while you dine. Light bites like an array of tasty bruschetta options and braised gnocchi only make the affordably priced wines even more delicious, while the soundtrack (regularly playing LCD Soundsystem and indie-leaning outfits like Widowspeak) will soothe your social anxiety.


Part of the buzzy Boka Restaurant Group, Somerset’s interior boasts a country club-chic attitude and easy menu of American cuisine, like roasted peach salad, chilled corn soup, and summer squash dumplings. Chef Lee Wolen’s attitude about making “food people like to eat” is a nice match with the friendly interior that begs for another cup of oolong tea to take in its bustling clientele and glistening 1920s interior.

Good Sweat


This studio embodies the wide-open spaces of the Midwest while still feeling like a cozy, dimly lit retreat that’s faintly scented with lavender. Next-level total fitness offerings like barre and power yoga are just steps away from soothing spa therapies that combine traditional Eastern practices with modern Western services like acu-healing (think acupuncture, acu-organ detox, and Reiki). For a fancy treat, try a Hammam Detox Therapy session, or simply wrap up your workout with a languid lounge in the steam room for a full-body detox.

Page One Pilates

Page Barker’s intimate studio featuring eight intuitive reformer machines is more like a personal retreat than an icy fitness setup—immediately apparent with the warmth of fig-scented Tatine candles and supportive instructors. As for the workout, Barker is known for her fresh take on the Pilates method that incorporates tailored music and surprising sequences to better facilitate a brain/body connection. Even the cleaning methods tout an earth-focused connection, meaning the equipment you lounge on is kept up with organic, non-toxic cleansers and all workout gear is washed in Guppyfriend bags to keep microplastic fibers from entering the water supply.


Just opened last spring, its founder Laura Sage dreamed up the yoga-meet-meditation hot spot when she was in search of her own meditative escape. Part of the ClassPass program, guests can stop in for a gentle movement and stretching class that can be followed by meditation and even an out-of-this world chair massage. Thanks to Sage’s other passion project, a breast cancer research non-profit, a complimentary Thrivers class is available to cancer patients and their caregivers each month.

The 606

For a scenic (and free!) run or bike ride, this 12-mile stretch repurposed the old Bloomingdale train line into a community space for outdoor fitness at your own pace. This “rails-to-trails” project makes taking in the city even easier with elevated views and a pet-friendly strolling environment.

Good Times


Owned by the only local womenswear designer on the city’s famous Magnificent Mile, this see-now-buy-now luxury boutique offers zero-waste fashion thanks to hand-cut patterns and repurposing scraps from the cutting room floor. The atelier space doubles as a showroom, meaning Azeeza is often on premises to providing advice or even design a new garment in customized fabric and colors with the final product available to deliver or ship to your home base in just a few weeks. Since it’s the label’s creative hub, you can walk in and witness the team patterning the upcoming season's collection samples or shooting their next lookbook.

Schubas Tavern

A favorite music venue for indie bands and local songwriters, the intimate theater setting feels as appropriate for an ambient punk show as it does for an electro dance party. Grab a drink at the storied bar in the old Schlitz Brewery during soundcheck, or a kale salad in its retro kitchen to make an entire night of it with just one stop.

The Occult Bookstore

Looking for energetic stones, herbs, and possible mystery circles? This neighborhood landmark is filled with almost 100 years of history offering books, classes, and esoteric wares with a homespun appeal. Even those that aren’t actively practicing woo-woo arts will appreciate the welcoming (and highly knowledgeable) staffers who prove quick to share their tips on cleansing crystals and organic gardening.

Kokorokoko Vintage

Satiating your sustainable shopping needs, owners Ross Kelly and Sasha Hodges have pulled together a technicolor array of finds from the “post-hip-hop, pre-Internet era” that feel like a time capsule-preserved dream for the past decade. Everything from cassette tapes to retro candies is on display, with prices that make cramming an extra ice dancer-inspired leotard or high-waisted ski legging into your suitcase an easy decision.

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