Wicker Park
Neighborhoods matter. As this post states, “you’re going to spend 1000x more time in your surrounding 5 blocks than you will in any other neighborhood in your city”.
I loved living in Chicago’s Wicker Park. It’s a wonderful and walkable neighborhood with lots to do. Though I recently left, during my time there I tried to explore as much as I could and Wicker Park was easy to explore when I was living in there. However, before I moved, when I would just come by for a few hours on a Saturday or something, I didn’t really know what to do or where to go. I certainly didn’t know how to spend a full day there. I was annoyed that I would feel befuddled as to where to go.
This lack of knowledge by non-residents was not unique to me. Many friends I talked to (typically living on the other side of the river and also a post-grad Chicago transplant) didn’t know what Wicker Park offered and rarely stopped by during their free time. This bummed me out a bit because, again, I enjoyed living there and I wanted everyone to understand why I found it so lovely.
So I’m solving that problem, hopefully.
I made the following neighborhood guide for anyone who wants to explore Wicker Park but craves more direction or wants to know what makes certain places special. The places featured in this guide are the places I returned to over and over.
There are three more sections of this post to follow. First, a link to the Google Maps list I made outlining everything good in Wicker Park. Second, individual overviews on every place featured on the Google Maps list. And lastly, my thoughts on how to spend an entire day doing great things all across Wicker Park.
Note 1: this post is a blatant rip-off of Alex Delany’s Everything Good series which provides guides, much more detailed than mine, to neighborhoods across Manhattan.
Note 2: Wicker Park differs from Manhattan neighborhoods in that it’s essentially a residential neighborhood with a few main business streets, namely Milwaukee Ave, Damen Ave, North Ave, and Division St. My recommendations are concentrated near these business streets. You can see the lack of recs on the right half of the map as those are strictly residential streets. I do, however, recommend strolling through those side streets, such as Hoyne Ave, because they’re tranquil and filled with pretty homes.
Note 3: I tried to avoid brands and chains as much as possible. Most of the places on my guide are small businesses unique to Wicker Park. Yes, I love the Iced Mint Mojito from Phil’z Coffee, and there’s a Phil’z Coffee in Wicker Park but that’s not very interesting to shout out. Similarly, Milwaukee Ave is filled with a lot of big brand name stores like Levi’s and Adidas that are not mentioned.
Note 4: this post is the first of several place/travel-oriented reflections that I’ve been thinking about for the last few months. Expect more soon.
Enough prefacing, here’s the meat and potatoes…
The Map
Here’s the map of my favorite spots. You can conveniently save it within Google Maps.
I inflated Wicker Park a little bit because I needed to capture a couple of places (favorite coffee, best steak, and best restaurant) that fall just outside the canonical boundaries of the neighborhood. So this is really a guide to Wicker Park+.
If you’ve lived in Wicker Park before then you’ve probably been to most of these places. There aren’t too many hidden gems on my list, but a lot of these places are overlooked by publications like Timeout or The Infatuation.
The list is likely missing some things, such as art galleries and stores tailored to women, but I’d prefer to leave things off than speak on them without any first-hand exploration. There are many other great things to do and places to eat within Wicker Park that are not on this list. I only lived there for two years and definitely didn’t get to see everything. Something not being on the list may be due to me never going there, but also maybe I didn’t like it ;). Leave a comment if there’s a place you feel I missed.
Cheers to Wicker Park, and if you find the map useful, feel free to share it with others.
Rundown on Each Spot
Restaurants
Category: Fine Dining
Slightly outside the bounds of Wicker Park, but I make exceptions for the best meal I ever ate in Chicago. It’s also easily most expensive restaurant in the area for dinner. 13-course Filipino tasting menu with a deserved Michelin star. I still think about the nilaga dish. Very pricey and reservations are tough to get.
Their Filipino-fusion brunch options and pastries are also exceptional, but, be wary, the line gets insanely long on the weekends. I recommend going just before they open at 9AM on a Winter weekday to avoid this.
Must try: Ube and Huckleberry Basque Cake
Category: Fine Dining
Best steak I’ve ever had. Cool ambience. Quite expensive. Go for a special occasion or celebration. Hard not to enjoy yourself if price isn’t a concern.
You need to sit at the bar to order their burger, which I highly recommend.
They also offer a butcher shop so you can purchase their quality meats and grill up at home.
Must try: Dry Aged Ribeye
Category: Fine Dining
Classy Asian fusion restaurant serving the food family style.
Like Boeufhaus, you need to sit at the bar to order their renowned burger.
Must try: Mott Burger
Category: Brunch
Besides the delicious Tex-Mex brunch, drinks, and upbeat staff, I love the interior design and triangular shape of the restaurant. Don’t skimp on dousing your food in their homemade condiments and spice mixes.
This is probably the place I miss the most since leaving.
Must try: Brisket Burnt Ends and a Bloody Maria
Category: Italian
Quaint restaurant with indoor and outdoor dining options and probably the best Italian food in the neighborhood. BYOB. Good place to take your parents.
Must try: Calabrian-style Calamari
Category: Vietnamese, Lunch, Take-out
Serves my favorite hot sandwich in all of Chicago, the Viet Dip. Think an Italian beef meets a Banh Mi. It’s incredible. They also have solid Pho and some tasty chicken-and-rice dishes which are great after workouts or a sauna (see below).
Cheap, fast, and always playing hip-hop. Pick up a punch card if you plan on going here often.
Must try: Viet Dip sandwich
Category: American, Fast Casual
A Chicago neighborhood staple for burger and fries. Small Cheval is a spin-off from the much-hyped Au Cheval, but I actually prefer Small Cheval’s burger and atmosphere. The burger is simple, think In-N-Out style, but tasty.
Go on a perfect Summer evening and sit outside.
Must try: Cheeseburger and fries
Category: Pizza
Lively spot for pizza with interesting toppings and a surprisingly strong beer list. A foolproof option for dinner with a big group. Central location.
Must try: Hot Doug's Atomic Sausage Pizza
Category: Fancy Mediterranean
Rooftop seating which transports you away from the bustling street corner a few feet away. Every dish is packed with spices. Their menu is not dumbed down to an American palette, feels authentic.
Must try: Anything involving lamb
Category: Sushi
Solid option for sushi. Nothing crazy but you can always get in and they have plenty of options to explore. Utilize their friendly BYOB policy.
Definitely go here instead of Sushi Taku. Sushi Taku always has lines because it’s all-you-can-eat but their sushi is “low-grade dog food”. Don’t be a sheep.
Must try: Tequila Roll
Category: Ramen
No-frills ramen joint that opened recently. Very flavorful broth and quick service. Say hello to the owner Rudy if you see him, he’s usually there.
Must try: Tonkotsu Ramen
Category: Ramen
I prefer the flavors at Oiistar more than Rudy’s but they venture into more innovative territories. These two restaurants compliment each other by serving different lanes. Are you feeling more adventurous? Try Oiistar.
Must try: Spicy Garlic Shoyumen
Category: Latin-American
One of the few Latin-American restaurants in Wicker Park, but their best item is actually a cocktail called the Holy Water. One of my favorite drinks in Chicago. It’s strong and prepared playfully. Worth going here just to drink it.
Must try: Yuka Fries and the Holy Water cocktail
Category: Italian
Old-school Supper Club interiors and a great wraparound patio. Food is solid but not incredible. It’s really about the vibe here. A neighborhood institution.
Must try: Some red wine and a classic Italian dish
Category: Italian
The pasta is made fresh in the window right in front of you so they get a lot of points on the aesthetics scale. Great for a date night. Small portions IMO.
Must try: Tortelli di Burrata
Category: Mexican
Marg pitchers, outdoor seating, friendly faces, always busy. Another great option for large groups having trouble deciding where to eat or drink. You order the tacos individually so everyone can be satisfied. Never a bad play.
Must try: Margarita Pitcher lol
Category: Pizza
One of the few places doing slices in the neighborhood. They aren’t reinventing the wheel, just making yummy, hot, and fresh pizza.
Must try: doesn’t really apply, whatever slice you’re feeling
Category: Pizza and Burgers(?)
Retro video game-inspired interiors and small but mighty menu. Both their pizza and their burgers are solid. The kind of place where it just feels right to order a Coke to drink.
Must try: Stop-In Burger
Category: Mexican
Quality, hole-in-the-wall Mexican joint. Great lunch option and you will probably have leftovers.
Must try: Super Burrito with Carne Asada, if you’re hungry
Category: Big Ass Lunch.
Solid Middle Eastern flavors and very generous portions. You are getting two meals for the price of one, which is what kept me coming back. Order some side sauces (tzatziki, spicy, etc.) otherwise the rice can be a bit dry.
Must try: Combination Meat Plate
Category: Big Ass Lunch Category
Is it the best food ever? No, definitely not. But you are going to walk out incredibly full for cheap and sometimes that’s what you need. Their generous lunch deal more than makes up for the lack of quality.
Must try: nothing really qualifies here, whatever you are craving
Coffee Shops
My favorite coffee drink in all of Chicago is here: the Ipsento Latte. Coconut milk, dairy, honey, cayenne pepper, and espresso. It’s delicious and gets you wired. This is also a good spot to do some work. Lots of seats and outlets.
Specialty: Ipsento latte
Scandinavian minimalist aesthetic here at the expansion of the Andersonville powerhouse with the same name. I’m demanding you order both a drink and a pastry when you go.
Specialty: Swedish pastries
Funky coffee and funky interiors. A solid option right on Milwaukee Ave. They are open late if you need somewhere to do work in the evening.
Specialty: Lattes with interesting flavors
Your favorite yuppie’s favorite coffee shop. They have locations across Chicago and Milwaukee which are usually filled with white girls working on Macbooks. That being said, there’s a reason people like to go here. The coffee and food exceed expectations and it’s a great place to work.
Specialty: Cozy spaces to work
A good option just north of Wicker Park. Part of the Dark Matter Coffee network. Dark Matter takes pride in sustainability sourcing the best coffee beans and featuring local Chicago artists on their bags of coffee.
Specialty: Quality beans
Bars
My personal favorite bar. It has everything I’m looking for (and I happened to live close by): indoor or outdoor seating options, never a line/wait, dapper-yet-divey decor, astounding and ever-changing beer list, fridges stocked with only Miller High Life, and really tasty food. I am glad this became my local watering hole and can’t recommend it enough. Good for any sort of group.
Specialty: Rotating draft list and Chicago-style hot dogs
Many people are saying they have the best martinis in the city. I don’t like martinis so I wouldn’t know. I tried theirs a few times and my main takeaway was, “wow, that’s a strong drink”. Still felt worthy to mention in case you do like martinis. The interior seems like it hasn’t changed since the ‘50s.
Specialty: Martinis
This cocktail bar sits on top of the Robey Hotel and provides great views of the Chicago skyline and the sunset. Their drinks are phenomenal as well.
Specialty: Cocktails with a view
A hopping approachable bar filled with people under 30. The demographics of Wicker Park skew older than Lakeview, Lincoln Park, or Old Town so this is a great place to party with younger people. Always busy. Always playing music from middle school that is somewhat cringey but you still know all the lyrics to. Bring your friends to Lottie’s, get some drinks, mingle, enjoy. Shout-out to their merch too — probably the most worn bar merch in Chicago.
Specialty: Getting drunk with a big group of friends
A speakeasy-style spot where you walk through a “record store” to enter. A variety of live music is always on from local performers. Inventive cocktail list and a moody atmosphere to accompany the music.
Specialty: Cocktails
Phyllis’ Musical Inn (No website either, Instagram page)
Live music from local performers as well, often doing rock covers it seems. Cash only and very affordable drinks. Their patio really surprised me. Homey space with benches and trees. If I owned a bar, I would try to mimic their patio space.
Specialty: Live music
Great dive bar with a big outdoor space in the back. It feels like you walked into a small town in Wisconsin when you enter, but the house cocktails are anything but simple Midwestern options. Lots of spirits and beers too.
Specialty: Cocktails
Chic wine bar with charcuterie plates. I don’t know that much about wine, but the servers (idk if they were sommeliers) were quite helpful in providing enjoyable pours. Not many other wine bars within Wicker Park.
Specialty: Wine
If you want to drink and play pool at a laid-back bar this is your spot.
Specialty: Pool table that’s never overly crowded
Rite Liquors (No official website but read this instead)
They both sell liquor and serve liquor here. Please read the article above. A unique bar experience. Often a rougher crowd. The kind of place that doesn’t like yuppies like me moving into Wicker Park. Cash only. Worth checking out.
Specialty: Cheap beers
Sometimes you are in the mood for an overwhelming amount of TVs, sports, and beers with your boys. Go here if that’s the case. Not the best place to take a girl or a co-ed friend group.
Specialty: Day drinking for college football
Run-of-the-mill bar which packs people in for anything related to MMA or wrestling. Lively atmosphere on these nights and the bartenders are very nice.
Specialty: UFC Fight Night
Sweet Treats
Urban Japanese energy radiates throughout this ice cream shop. They offer normal ice cream, soft serve and interesting toppings. Very sweet flavors.
Specialty: Ice cream and cereal mixed together
Hole-in-the-wall ice cream and fast food store that is only open in the Summertime. A true neighborhood joint. The calories don’t count when you enjoy some ice cream or gelato from here.
Specialty: Vinny Spinny
Recreation
Run, walk, bike, or rollerblade along this elevated old trail. There isn’t a ton of green space in Wicker Park so this highly vegetated trail supplements that nicely. You don’t get interrupted by any cars or intersections, just you and the pavement. Hop on/hop off wherever you want. 2.7 miles in total.
An authentic Eastern European bathhouse experience. Sauna, steam room, hot tub, cold plunge. Get whacked by the branches (platza) if you want. This is the hottest sauna I’ve ever experienced along with the coldest cold plunge. Pro tip: if you are going to eat at the restaurant upstairs between cycles, just wear your robe up there, no need to change. Fun to go with friends.
Small garden cared for by the neighbors. Has a few benches and seats. Nice place to go if you are craving alone time for meditation or contemplation.
Wicker Park (the actual park)
The Farmer’s Market is hosted here, there are “fun-sized” basketball courts, a dog run and a large open field for picnics. Only large-ish park in Wicker Park.
Relatively affordable local yoga studio offering a wide variety of classes. Very welcoming environment to try new types of yoga.
Shops (from a guy who doesn’t really like shopping’s perspective)
Lots of high-quality denim and cool jackets in here. They will also patch holes in any of your garments. The style is very 2010s hipster, but in the best way possible.
Boutique clothing, footwear, and accessories store on the first floor and military surplus reseller in the basement. I never needed any military gear, but I did really like the normal clothes they carried.
Iconic book store with a great aesthetic. Lots of used books for sale at a good price. Easy to get lost in here. The one downside is they don’t stock many of the new bestsellers.
Sometimes you need a cute little gift or card for something. This place is the place to go when that’s the case.
Vintage and streetwear shop. Lots of hyped-up sneakers on the first floor (not my style, but maybe yours) and vintage stuff upstairs. I found a cool Cubs hat and Minnesota Vikings shirt here.
The highest quality menswear store in the area. All the pieces are expensive so I never actually purchased anything from them but I would have loved to have swapped my wardrobe with their store. If you are into menswear, this is the only place to find brands like Kapital, Engineered Garments, and Drake’s.
Overpriced home goods and accessories but the owner does curate a beautiful selection. I would say the aesthetic they offer is farmhouse chic. If you would rather support a local business than saving money using Amazon, consider checking this store out.
Yes, it’s a brand, but there are not many other bike shops nearby. They conduct repairs on your bike speedily and carry any kind of cycling accessory you might need.
Grocery and Liquor
Big, cheap chain supermarket. Always has a BOGO deal on meats. Stocks basically everything you would ever need.
However, one time I needed pine nuts and this way the only store that carried them. Small market with a good selection of upscale ingredients and fresh produce.
Best craft beer selection in the neighborhood, carries some really excellent options. One man show (I think). Not the best prices, but a great shop name.
Best spirits collection in the area, especially for whiskeys. Solid selection of craft and foreign beers. Also a place to get any sort of cocktail accouterment like bitters and shakers. A one-stop shop for anything alcohol-related.
One Great Day in Wicker Park
Inspired by the New York Times’ 36 Hours in … series, here’s how I would structure one absolutely fantastic, and perhaps gluttonous, day in Wicker Park. Consider these places the best of the bunch, my top recommendations.
I would be remiss if I did not mention that you can take the train from O’Hare directly to the center of Wicker Park, which is not something most fun neighborhoods in American cities can claim. This is another perk of the neighborhood.
So, let’s say you arrive at the Damen Blue Line stop in the morning and are looking to spend a whole day in Wicker Park. Here’s how I would do that:
Walk up Milwaukee Ave from the “Six Corners” to Ipsento 606. Order the Ipsento Latte, the best specialty latte in the city.
Walk along the 606 Trail and enjoy your drink for a while, then find your way back to the Six Corners.
Eat brunch at Dove’s Luncheonette.
Walk through Wicker Park, either the park or side streets, to Chicago Bath House.
Enjoy an authentic Eastern European spa experience. The Sauna is really hot and the cold plunge is really cold so be prepared.
Grab the Viet Dip sandwich next door at Phodega for lunch.
Start happy hour early at Bangers and Lace with some great beers.
Do some shopping along Milwaukee Ave.
For dinner, get a burger from one of many great options. Small Cheval, Mott St. and Beaufhaus get my vote. You must sit at the bar for the burgers at the last two.
End the night with a cocktail, or several, back near the Six Corners at The Up Room (city views), Violet Hour (very posh), or Dorian’s (speakeasy with live music).
Thanks for reading.
So helpful, thank you! You should make these for all Chicago neighborhoods!