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When I was 16, I came to Chicago on an art scholarship. I fell in love and knew in my heart that I’d live here someday. At age 30 (woof,) I finally did it, and I am so happy. Since I’m getting to explore the city more like a native and less like a tourist visiting the same spots over and over, I thought I’d start sharing some of the hidden gems that might be overlooked by people coming to visit for the first time. Today’s spotlight is on Wicker Park/Bucktown. It’s one of the trendiest “hipster”-ish parts of town, but that means there’s a lot of great food and drinks in addition to things to do and places to shop!

Gotta start with my favorite food group. I love Dimo’s (and Dimo’s loves me!) If you’re in the Six Points area and just need to grab something quick, this pizza is where it’s at. Pop in, drop my name, and grab a slice of the white pie or another monthly special – I promise you won’t be disappointed.

If you have more of a sweet tooth, head across the intersection to Stan’s Donuts. Stan’s began in LA and their popularity has spread here to the midwest with two locations in Chicago. There’s not a lot of space inside, so be prepared to eat your donut and get on out. Go on the weekend to get the biggest selection (the beignets, buttermilk bar, and chocolate sprinkles are my favorites.)

Wicker Park is home to many great bookstores, and one of my favorites is Volumes Bookcafe. Part bookstore, part coffee shop, part bar, this is a really cool spot. Browse for books and cozy up in the cafe with a cup of coffee, or come in later on, grab a beer, and borrow a board game with friends.

Mahalo is the most Instagram-worthy spot on the block. It’s Hawaiian-inspired, and begging to be photographed. The drink menu is fantastic (grab the daily daiquiri and thank me later) and I look forward to visiting again for a meal. We went a few months ago and weren’t bowled over, but the chef has changed since then, and both the menu and website look much better!

There are a lot of great spots in Wicker Park to grab a cup of coffee – hop off the Blue Line and head straight into La Colombe, or head around the corner to the Starbucks Roastery. (Yeah yeah, I know, Starbucks. It’s a roastery, though, and they have more creative drinks – the Coffee Malt is amazing!) If you’re looking for a spot to set up and work, I love Brü. Very freelance-friendly, and they accept Brewpass. Use the code DESI1 when you sign up for a free cup!

Quimby’s is another great bookstore in the neighborhood. They feature indie and underground books, comics, magazines and – best of all – zines. Growing up I was really into zines (I still have a few of my favorites kicking around my parents house) and I could spend hours browsing the shelves here. They have both local and national authors, as well as lots of fun gifts and notebooks. They also host shows from time to time – the great Sad13 played here last spring.

If you want a cinnamon roll the size of your head (and quite honestly if you don’t, there’s a great Urgent Care I can recommend in Wicker Park because something must be wrong,) head down to Kanela Breakfast Club. It’s my favorite one in the city so far, and the rest of the menu is equally great. They have a nice bar area and it’s bigger than it looks, so don’t let a line deter you. They turn it over quickly.

While it’s not a strictly local spot, I can’t visit Wicker Park without buzzing in to David’s Tea. Their summer collection is gorgeous and the iced tea press makes it easy to make single batches of iced tea in one tumbler – just grab and go. Pop in, grab a tea of the day, and try not to walk out with a pound of tea.

Don’t leave Chicago without a souvenir! Transit Tees have some of my favorite t-shirts and knick knacks. Ever since I saw Rachel on The Real World: Back to New York I’ve loved transit-inspired stuff, and there’s plenty of it here. Whether you want to rep a specific line or stop, they’ll have it. (Plus a lot of awesome Michigan stuff, too!)

Cabana Club

If you’re into records, stop over at Reckless Records. Wicker Park is just one of their three locations in the city. They have both new releases and used records, and their website has an up-to-date inventory search. I’ve found my one unicorn record by checking their website constantly! If there’s something you’re on the hunt for, head in. Actually, check them out anyway – the staff is always ready with recommendations.

Though it might not seem like it, there are a couple venues in Wicker Park where you can check out some shows. Subterranean features some of my favorite artists (including Doomtree in a few weeks!) and Chop Shop’s First Ward venue features some really great punk shows. (They also host the Pizza Summit where I attempted to eat my body weight in pizza against two competitive eaters in April, as pictured above.)

By the end of the day, you’ll be ready for some dessert. Jeni’s Ice Cream is a Midwestern classic (I highly recommend the salty caramel and brambleberry crisp combo) or head up on Damen to Mindy’s Hot Chocolate. Their whole menu is great, but I definitely recommend their namesake hot chocolates or cookies – chef Mindy even wrote a cookbook about cookies, so you know they’ve got to be great!

What are your favorite things to do on vacation? Any places in particular in Chicago you’re curious about? Let me know in the comments – I’d love to share the city with you!