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Highlights of Andersonville, Chicago

A walk down the coolest street in Chicago's coolest neighborhood.

street art in Chicago's Andersonville neighborhood

Chicago's Andersonville neighborhood has gotten some attention in recent years when it came in second on a list of amazing city neighborhoods in Time Out. And honestly, that ranking is pretty hard to argue with. Andersonville is amazing! And the heart of Andersonville is Clark Street. Lined with shops, cafes, bars, restaurants, and some truly amazing street art, you can easily spend a whole afternoon ducking in and out of the establishments here. Here are my favorites!

The Understudy

Move over NYC! Chicago has a drama bookstore too!

The Understudy popped up in Andersonville post-pandemic, and it’s an artist’s dreamscape. It’s half bookstore, half cafe, and all amazing. It’s stacked with play scripts, books about art and theatre, and a few small sections of fiction and queer lit and social justice reads and… it’s everything you want in a creative hangout.

a tea latte and a book on a table

Eli Tea Bar

This place is a hidden gem and a proper local treasure! It’s a wonderful local tea shop, with cozy tables and couches for working or relaxing. They have a huge menu of loose leaf tea, and they can prepare many of them as tea lattes and beautiful bubble tea combinations. They also have a little shop section full of trendy teaware, unique trinkets, and a whole wall of tarot and oracle decks. It’s a wonderful cozy cafe. They're also regularly open late, catering to the crowd that wants to be social without having to go to a bar. It's a true community gem.

Enjoy Andersonville

unique Chicago souvenirs

This cute little kitschy shop perfectly embodies everything that makes Andersonville charming. This shop is full of quirky, smart, creative, and just glorious treasures and gifts. I’ve found many a holiday gift in this charming little place. And if you’re visiting the city, it’s a great place to get a Chicago memento without having to pick up something mass-produced for a downtown souvenir shop.

Jeni's Ice Cream

For a sweet treat on Clark Street, look no further than Jeni’s! 

Full disclosure, Jeni’s is a global chain and not necessarily a Chicago specialty. But I can’t list my favorite Clark Street locales without mentioning Jeni’s Ice Cream. And if you don’t have Jeni’s in your city -and they are a major metropolis centric chain- this is your chance!

For me, Jeni’s is the be-all-end-all of ice cream chains. They pride themselves on creative ingredients and unique flavors. They have a long list of amazing classics and regularly changing specialties. And best of all, their “basic” serving includes two flavors and a waffle wedge!

Sample away, but trust me on the salted peanut butter with chocolate chips.

Lady Gregory's

This cozy pub is my favorite spot on Clark Street for a beautiful sit down meal. It’s a cozy Irish Pub with a menu full of classics. It has an impressive draft list and some of the best cocktails in the city. Come for the Irish whiskeys, and stay for the shepherd’s pie.

The Andersonville Galleria

The Andersonville Galleria brands itself as “your year round art fair,” and that is precisely what it is. It’s a twisting and turning building with multiple floors, stuffed with shelves and booths dedicated to local artists. Everything at the Galleria was made by a local artisan. The items on offer range from stunningly gorgeous to properly unhinged, and everything in between. You can -and should- get lost in here for an hour. You’ll leave with a Chicago treasure that was actually made by a Chicago artist, and you can’t beat that.

Women and Children First

This is my favorite indie bookstore in the whole of Chicago. The kind of community-first, Amazon-bashing, social-justice-campaigning bookstore that you just can’t help but support. 

They’ve got a huge selection, incredibly knowledgeable and helpful staff, and robust sections of literature that queer, BIPOC, and disabled voices, among others. This is the kind of shop that goes out of the way to make sure that everyone feels not just accepted, but welcomed and valued.

Keep indie bookstores in business! Buy your new books from places like Women and Children.

a pint from Hopleaf on a bar next to a book of poetry


For a cozy drink on a chilly Chicago day - or a refreshing one on a hot day - Hopleaf is the place. The full restaurant at Hopleaf is nothing to sneeze at, but my favorite place to hang out here is the front room around the bar. This area doesn’t take reservations, and all orders there have to be placed at the bar, but that makes it the perfect place to relax with a few friends, or on your own with a book, and sample a delicious brew. Or two. Or three.

The draft list here is truly massive, which means something for everyone! If the plethora of choices is a little baffling, feel free to ask the bartender for recommendations. Every single one of them is friendly, knowledgeable, and usually happy to pour samples until you find the one you want. It’s an amazing place with the best atmosphere.

a wooden chair in a used bookstore

Uncharted Books

Charming local used bookstore with a haunted painting and a resident bookshop dog.


Ok, here’s a little more info. This is a glorious used bookstore and an Andersonville treasure. The space is well organized and beautifully decorated, and yes, one of the paintings at the back is allegedly haunted. And, depending on who’s working the desk on the day of your visit, you might get to meet Ramona! That’s the bookshop dog.

That's the Best of Chicago's Andersonville Neighborhood!

This whole neighborhood in quintessentially Chicago, and I hope you enjoy your time exploring it. You’ll probably find your own list of gems! Enjoy!

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Love and Shenanigans,


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