With a grand total of 77 neighborhoods, each with it’s own unique vibe, knowing exactly where to go and what to do when exploring Chicago can be a bit daunting. Local blogger, Lauren Wendt Bremer of Foxtail + Moss breaks down the coolest of the cool in eating, drinking, shopping, and checking out the latest must see spots in the Windy City.

Coffee /

Sawada Coffee 

The first U.S. coffee shop of world renowned barista and latte art expert Hiroshi Sawada, shares a space with Green Street Smoked Meats and perfectly embodies the industrial urban vibes of the West Loop. Get your morning going with a Military Latte (matcha + espresso) while you play pinball or admire the walls covered in street art and graffiti.

Heritage Bicycles General Store 

A mash-up of coffee house and bicycle shop, this Lincoln Park spot is heavy on charm. The perfect place to call office for the day or just sit and sip an iced lavender latte while you watch the bike mechanics work their magic. Whether or not you consider yourself an avid cyclist, it’s pretty cool that Heritage is producing the first completely Chicago-made bike since Schwinn left the city in the 70’s.

Eat /

Brunch:

Cindy’s Rooftop 

Cindy’s, the rooftop restaurant atop the Chicago Athletic Association, is a must for brunch. The elevated selection of breakfast mainstays are delish, but it’s the sweeping view of Millennium Park, the Art Institute, and the lakeshore that are not to be missed. Let resident spirit guide (yes, that’s her actual title) Nandini Khaund cure what ails you with her curated menu of potions, elixirs, apothecaries, and mocktails.

Lunch:

Big Star

Equal parts trendy taqueria and late-night honky tonk, Big Star boasts an extensive bourbon menu, killer pitchers of margaritas, and the best patio in town all set to a soundtrack of classic country and rock n roll spun by the bar staff. In the heart of Wicker Park, this spot operates on a first come, first serve basis so put your name on the waitlist and kill time by wandering around the super hip neighborhood.

Snack:

The Allis 

Not an elite member at the uber posh Soho House? No problem! With a come as you are vibe, The Allis is open to the public and serves an all day menu including light bites, coffee, wine, and craft cocktails. If you’re feeling just a little fancy, order Afternoon Tea service.

Dinner:

Bad Hunter 

New to the slew of bars and restaurants on West Loop’s Randolph Street, this veg-forward eatery stands out in a city that is all about it’s meat. Open brunch through dinner, Bad Hunter is best known for its creative take on vegetable dishes, but don’t worry, there’s plenty of offerings for the carnivores too. The sun drenched dining room feels more like an airy greenhouse with it’s white washed walls and plants aplenty, but I like to belly up to the bar for a low-ABV cocktail or two (definitely try the Spicy Carrot Cooler)!

Shop /

Una Mae’s 

This longstanding Wicker Park boutique offers an eclectic mix of hip menswear, contemporary women’s fashion, and a unique selection of apothecary + lifestyle goods. Don’t forget to check out the basement for a curated selection of some of the coolest vintage Chicago has to offer.

Humboldt House 

Tucked away in the Humboldt Park neighborhood, this “vintage modern” shop slangs seriously unique items for your home and body. Eclectic textiles, mid-century modern furniture, wall hangings, apothecary products, rocks and gems, and pieces from local and emerging Chicago makers and artists. This is where the cool kids shop!

Drink /

Moneygun 

Chicagoans love a good dive bar. Moneygun has all the low-key vintage neighborhood bar vibes (think distressed facade, big leather booths, extra low lighting) without the signature dive bar stench and creepy drunk old man sitting the next bar stool over. Enjoy a classic cocktail or get extra dive-y and order a Schlitz tall boy.

Green Mill Cocktail Lounge 

Famed for being Al Capone’s favorite haunt during Prohibition, this storied Uptown tavern hasn’t changed much in drinks or decor since the gangster’s heyday. Visit a little piece of Chicago history and catch a live performance any night of the week. The Mill has been open since 1907 and is one of the best known jazz clubs in the country.

Do /

Visit the MCA 

Soak up a little culture with a visit to the Museum of Contemporary Art Chicago. One of the world’s largest contemporary art venues, it never disappoints with edgy and current rotating exhibits, film screenings, and lectures. Admiring the architecture of the campus alone is worth the trip!

Skydeck Chicago 

Ok, so technically the Sears Tower was renamed the Willis Tower a few years back but you’ll be hard pressed to find a local willing to call it that. If you’re not shy about heights the Skydeck at Sears Tower is a totally unique way to view the city. Be ready to wait in line, the Skydeck is one of the more touristy things to do, but it’s so worth it for the Instagram shot!

Randolph Street Market 

Call it the Midwest’s version of the Rose Bowl Flea. You could spend a weekend digging for treasure at this sometimes outdoor, sometimes indoor monthly flea market. Over 200 vendors display antiques and vintage finds, handcrafted jewelry, art, and more, so you’re bound to find something outrageously unique to take home with you.  

Catch a show at City Winery 

Unlike any other music venue, catch an intimate concert at this fully functioning winery and restaurant. Or get your culinary arts learn on with a food or wine class. Good wine, good music, and good food. It doesn’t get much better!

All photos by Lauren Wendt Bremer unless noted. Header image by Rachel Bires.