Eat, Drink, Explore, & Shop: Chicago City Guide

Modern Vintage Life readers, allow us to introduce you to our newest contributor, Crista Funk. If you’re wondering about either travel or music, Crista is the one to ask. Today she’s kicking off our series of detailed City Guides with one city on everyone’s bucket list: Chicago. Read below and tell us you aren’t ready to book a flight, STAT…

One of my favorite cities in the United States is Chicago. It could be because I spent a good part of my youth in the Midwest, but I like to think it’s because the city has a magic and warmth unlike any other. In over 15 years of trips to Chicago, I’ve never once ran out of adventure. And since fall is one of the best times to visit, I figured we’d start off our series with the Windy City. There are more delectable restaurants and exciting activities than you can count, but I’ll tackle some of my favorites that will give you just a taste of what the City has to offer… Even if you only have 48 hours to take it all in.


Little Goat Diner

Little Goat [West Loop] Sister restaurant to Girl & The Goat (which also has a pristine reputation), Little Goat Diner has an adorable mod meets modern vibe that’s as unique as some of their American-Asian inspired breakfasts. And their cinnabuns – lets’ just say these are the only cinnabuns I’ll eat, EVER. If your table wait has you desperate for a morning latte, explore the attached bakery and swoon over the mini pies and scones.

Antique Taco [Wicker Park] Living in Los Angeles you’d think I’d skip the tacos in other cities, but Antique is a can’t-miss. They’re not your run of the mill tacos. Each is a piece of mouth watering goodness (my go-to being Pork Carnitas), and even better when washed down with a refreshing Rosemary’s Margarita. Bonus: The interior is crisp and cute, and the surrounding stores are worth a post-meal stroll.

Pequod’s Pizzeria [DePaul] People gush that Lou Malnati’s and Giordano’s are the best Chicago-style pizza in the city, but I challenge that. For straight forward, deep-dish pizza, try Pequod’s. It’s not fancy and the only way to take down a whole slice is in a mode of ravenous hunger, but they make some of the finest pies around.

Sunda [River North] One of my absolute favorite restaurants in the city, the food at Sunda is to die for. I honestly can’t tell you what I think of the decor, but I can tell you that for weeks after eating at this Asian fusion restaurant I was still lusting after their Pork Belly Buns and Brussels Sprout Salad. The menu is pricey so I’d suggest going the shared plates route and don’t forget to make a reservation. 

Do-Rite Donuts [The Loop] Their offerings satisfy any sweet tooth. They don’t get carried away with a million different flavors, instead they’ve mastered the art of complementary tastes and taken the chocolate donut to a whole new level. The Valrhona Chocolate Cake is a must, but a personal favorite is Blueberry Crumb.


June and Henry

The Violet Hour [Wicker Park] There’s no shortage of Speakeasy style lounges in the City, but one of the best is The Violet Hour in Wicker Park. The entrance is highlighted by a single glowing light and the facade of the building changes regularly. The interior is only outdone by the unique libations their mixologists concoct. Think post dinner drinks for a tasty late night cap.

Ipsento 606 [Bucktown] Part coffee shop, part bar, Ipsento 606 never disappoints. It has a minimalistic interior that’s perfect for those who need to do a little work while they travel, and the open air windows make it ideal for a warm weather day. Atmosphere aside, the coffee is touted as being some of the best whether you try their chilled Nitro Coffee or savor one of their specialty espresso drinks. Cardamom Rose latte, yes please! 

Sawada Coffee [West Loop] Attached to Green Street Smoked Meats, Sawada is a tiny, industrial coffee joint known for their bitter Military Latte (green tea + espresso). They have Matcha and chai lattes as well, each ready for its Instagram debut. If you can’t make Do-Rite Donuts, nibble on their Doughnut Vault cake doughnuts.

Green Mill [Uptown] Green Mill is definitely more about the music than the drinks, but it’s a great spot to enjoy a cocktail and experience the jazz and blues of Chicago. The location’s interior screams 1920s speakeasy, while the live music immerses you even further into the era. There are Poetry Slam nights for an even more unique Chicago experience. It’s cash only though, so come prepared!


Garfield Park

Walk through Pilsen Because Chicago’s beauty is unmatched during fall, the foliage starts to change and the city’s crisp air is refreshingly inviting, you should take a stroll through Pilsen. The neighborhood is rich with colorful murals not much different from those seen in New York. There are shops to explore and streets to admire and if you have an appreciation for local art, you can breathe it all in without a museum fee. 

Garfield Park Conservatory [East Garfield Park] Apparently you can’t keep me away from the plant life, because GPC is another incredible Chicago location to take in flowers, palms, cacti and more. A silent stroll through each of the houses will settle the mind and remind you of all of the simple beauties our world has to offer. When you need a break from the bustle of the city, Garfield Park is your answer.

Use the Pedway [The Loop] The Pedway is made up of underground tunnels that take you to different parts of the city within the business district without having to endure the elements on bad weather days. The pathways aren’t bare though, there are shops, restaurants and public art along the way. You may not spend all day down here, but how many cities do you know with underground tunnels to explore? 

Architecture Boat Tour [The Loop] Any Chicagoan will attest that the architecture boat or kayak tours are worth every penny. In just two hours you’ll learn about over 50 stunning Chicago buildings rich in history and unique in design. If you do the Twilight cruise, you’ll marvel at the way light hits each exterior.  

The Art Institute [The Loop] Take your exploration in doors at the Art Institute, one of the oldest museums in the US. It’s also one of the largest, with over 300,000 pieces and curation like you’ve never seen. They have classic works and changing installations from all over the world, and the Institute is often the first US museum to unveil works from emerging artists. A peek at their upcoming exhibits is enough to solidify a visit.


Moon Voyage

Moon Voyage [Wicker Park] I despise digging through racks of cluttered clothes to find what I want, which is just one of the reasons Moon Voyage makes the list. It’s airy, minimal and just about every piece they carry is something I want in my closet. They carry designers from all over the world with prices to accommodate anyone’s budget. 

Art Effect [DePaul] This store has it all. A slightly kitchy vibe with endless options for magnificent finds. Their vintage wares, jewelry, clothing…you could get lost in here for hours. They too have Chicago centric pieces and enough variety to lock down a gift for just about any type of friend you’re buying for. 

Modern Cooperative [Pilsen] You might not leave with new furniture but Modern Cooperative is what modern vintage dreams are made of. There are handmade goods, mid-century pieces, and housewares you never knew existed. It doesn’t hurt that the prices are reasonable and the staff complete sweethearts. 

Verdant Matter [Pilsen] This quaint nursery meets gift shop houses succulents, ferns and a vibrant array of other table plants. The store has tons of affordable pottery options guaranteed to keep you in a state of indecision for hours. After a day of exploring Pilsen, this is an excellent stop to enjoy more plant life.

Foursided Cards & Gift [Lakeview] Foursided has everything you don’t actually need. Pretty stationery (a guilty pleasure of mine), candles, Chicago-centric art, jewelry, knick knacks, pins, cute cards…need I go on? I stop by when I want unique paper goods to take home or gifts for friends who love the city as much as I do.  

Do you have a favorite place to eat, drink or shop in Chicago?

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