The Instagram Travel Guide to ... Chicago - OZY | A Modern Media Company

The Instagram Travel Guide to ... Chicago

The Instagram Travel Guide to ... Chicago

By Katie Pisa


Because the Windy City’s Instagrammers are putting the “chic” in Chicago.

By Katie Pisa

This is the second article in a multipart travel series. OZY tasks the rising stars of Instagram to share their favorite, little-known spots to eat, drink, shop and sightsee.

A handful of super chic Chicagoans are out to prove there’s more to the Windy City than baseball caps and pizza. Just look to the city’s most-loved Instagram accounts to discover a city that is artsy, fashionable, delicious and on the rise. OZY connected with three of Chicago’s top Instagrammers to uncover the city’s secret side.


Nathan Michael started taking photographs of his favorite places and sharing them on Instagram as a fun way to connect with different communities around the world. Now his nearly 99,000 followers come to him for alluring shots of Chicago and several big brands seek his help with their own social media content.   

Where to eat: “Last year I stumbled upon Mott St with a few friends. When I first tasted their miso butter oyster mushrooms, it was game over. The menu is a flavor bomb to the senses,” says Michael. As well, Thrillist recently named Mott St the Best Burger in Chicago, he notes.

View this post on Instagram

My kind of "super" bowl party. @MottStreetChi

A post shared by Nathan Michael (@nathanmichael) on

Where to drink: A little tiki spot in the heart of Logan Square, Lost Lake Tiki offers more than vintage hula skirts and bamboo-lined walls. “They serve the most legit daiquiris and rum punch bowls you can dream of. My personal favorite is the Bunny’s Banana Daiquiri,” Michael says. Plus, the drinks are served flaming!

Where to shop: For home goods and lifestyle accessories, Michael loves Scout in Andersonville, a northern suburb of Chicago. Its owner, Larry Vodak, has dedicated the last 10 years of his business to finding the most timeless, one-of-a-kind pieces to adorn people’s homes. “His sense of style is always charming, classic and, at times, a little quirky,” says Michael. 

View this post on Instagram

Morning Light Filed Under: #NMhomelife

A post shared by Nathan Michael (@nathanmichael) on

Where to visit: “When I’m needing an extra dose of inspiration, I love visiting the Art Institute of Chicago. It’s packed with visual eye candy to awaken anyone’s senses to being alive.”


Jena Gambaccini is the creative director for Giuliana Rancic’s fashion label G by Giuliana. She joined Instagram as a way to support the fashion blog she started seven years ago: chicityfashion. Gambaccini, whose followers number 25,000, looks stylish posed against the backdrop of urban Chicago streets. Her feed is also dotted with pretty sunsets and beaches, as well as some envy-inducing shoes and clothes.

Where to eat: Avec is consistently good and has been around since before Chicago’s Randolph Street became oversaturated with restaurants, says Gambaccini, who admits she eats out “way more than I should.” It’s always packed, but worth the wait, she says, adding, “You can’t leave without trying the focaccia.”

View this post on Instagram

Last night…the calm before the truffle focaccia

A post shared by Jena Gambaccini (@chicityfashion) on

Where to drink: There are a lot of great places to drink in Chicago, but California Clipper is Gambaccini’s favorite. “I just love the vibe there — great drinks, live music and the red lights inside give it this vintage feel that I adore.”

Where to shop: Gambaccini’s favorite store in Chicago is “hands down” space519, she says. “It’s very well curated with a bit of everything — clothing, accessories, apothecary and home. The owners have impeccable taste and it shows in the merchandise.” She also cites it as her go-to spot for buying gifts.

Where to visit: Though Chicago’s Riverwalk is touristy, it has some of the best views of the city, says Gambaccini. It’s just been expanded and has many new restaurants and bars, so there’s plenty to eat and drink along the way.


Emily Weinstein has been exploring Chicago’s food and bar scene for six years — ever since she moved to the city to do a master’s in journalism at Northwestern University. She started her food blog and then followed it up with an Instagram account, which now has over 4,500 followers. Her full-time job is overseeing the marketing and communications for a wine and spirits distributor, which comes in handy for her Instagram feed.

Where to eat: “As a Chicago foodie, I get asked several times a day what my favorite restaurant is,” says Weinstein, and Asian-fusion Mott St is her top pick, as every dish is “jam-packed with flavor.” Their cocktail menu is also pleasing, with several Malört-centric drinks — made with the bitter liqueur every Chicagoan has a love-hate relationship with, she says. Her tip: Order the everything wings and the burger.

View this post on Instagram

How I cure my Monday blues. Actually, the burger from @mottstreetchi remedies all of my woes. Stacks on stacks on stacks of meat, cheese and sweet potato straws, with a little hoisin aioli, pickled jalapeños, dill pickles and miso butter. Oh, and a fried egg, too 🍳 le duh. Note: You've gotta sit at the bar to order this beauty 🍔 Where are some of y'alls favorite burgers from? I am the burger queen 👸🏼 so I'm always looking for my next patty to chow down on! #🍔 #🍳 #mondayblues #burger #cheeseburger #devourpower #tryitordiet #doublepatty #mottst #chicago #instafood #f52grams #friedegg #doublecheeseburger #312food #everythingerica #fabfoodchicago #eatmunchies #yougottaeatthis #burgerorder

A post shared by Emily Weinstein (@weinanddine) on

Where to drink:Parson’s Chicken & Fish may lure folks in for its fried goodness, but people definitely stay for the drinks and the ambiance,” says Weinstein. Most popular drink? The frozen negroni, which pairs perfectly with a hot summer day.

Where to shop: Weinstein’s favorite shopping area is not one store but the whole area where North Avenue and Clybourn Avenue intersect. It’s much less crowded than Chicago’s most popular shopping areas, she says, and has all the essentials from Nordstrom Rack to Crate and Barrel. It also sits next to New City, a district filled with restaurants, shops, bowling and nightlife.

Where to visit: Go to the Signature Lounge, a bar on the 96th floor of the John Hancock Tower where the views of the entire city of Chicago and Lake Michigan can’t be beat. “Drinks are expensive, so I’d recommend only going for one or two,” she advises.

Sign up for the weekly newsletter!

Related Stories