Hi, friends. If you didn’t know, I live in Chicago’s Uptown neighborhood.
If you’re not familiar with where that is, it’s on the North Side, about halfway between downtown and the northern-most point of the city, right along the lakeshore.
It’s something I tried to downplay for the longest time, because Uptown isn’t really “trendy” or “cute.” It’s got a little bit of a bad rap for being unsafe (there’s a bit of a gang problem here) and it’s not really as hip of a place to live as… like, Lakeview or Old Town or Lincoln Park or… whatever.
But, after more than four years living in my little Uptown apartment (where has the time gone?) I’ve really come to love this neighborhood. I have a 25-minute door-to-door commute to my newsroom, I live mere blocks from Lake Michigan, there’s amazing Vietnamese food practically right outside my door, my yoga studio is just down the street, I am three skips away from some of the best live music venues in the city. It’s not uncommon to go for a 20-minute walk and hear at least six different languages and see a smattering of new street art. Uptown is really great.
It also has a really cool history! Back in the 1920’s, Uptown was designated as the city’s entertainment hub — hence all the theaters. Then the Great Depression hit, so the area tanked and, well, never really recovered.
However, Uptown’s been slooowwwllyyy (I say slowly because Chicagoans have been touting Uptown as “the next Wicker Park” for like 10 years now) coming back around. More and more new restaurants have been opening, and more entertainment options are moving into the area. Double Door is moving here, a First Ascent has opened up in the former Borders on Broadway, the CorePower Yoga chain deemed the neighborhood worthy of a studio… there’s a lot going on here.
I’ve always been adamantly opposed to creating guides of any kind because I’d hardly consider myself an expert on things to do or see or experience. However, after four-plus years of living in Uptown, I think I might almost be qualified to offer suggestions for things to do in my hood. Almost. Almost.
Without further ado, here are some of my favorite places in my neighborhood. Not all of them have photos, but since I frequent a lot of these places on the regular, I’ll add them as I take them!
Also, a quick note: This list includes Uptown proper: Not Andersonville… which may or may not have its own little neighborhood guide coming soon. We’ll see!
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The Aragon Ballroom and The Riviera Theatre. I love live music, so living walking distance from two of the best venues in Chicago is amazing. I’ve seen so many bands at both of these places: Cold War Kids, Andrew McMahon and flor, Quinn XCII, Death Cab, LANY… seriously, so many amazing bands.
Driftwood and Mr. Salsa. I love dive bars, and Driftwood is phenomenal. There’s a really nice pool table, a bar dog, $3 PBRs and street-facing windows that open in the summers. As an added bonus, you can go next door to Mr. Salsa to buy tacos, tortilla chips and guac, and then bring your food into the bar.
Tweet. This brunch restaurant probably has the best bloody marys in the city — and the food is amazing too! There’s an entire gluten-free menu, and the restaurant is attached to a phenomenal gay bar called Big Chicks. It’s cash-only, but there’s an ATM on-site. I’ve had close to everything (pescetarian) on the menu, and have yet to try anything bad.
Demera. I’d never had Ethiopian food before I moved here, but living so close to Demera is amazing! Ethiopian food is super vegetarian-friendly, and all the food here is so good. If you’ve never had Ethiopian food before, Demera is a great place to start. Ethiopian is traditionally eaten silverware-free, so you use pieces of spongy, sour bread called injera to scoop up stews and transfer them to your face. The food is served on massive platters, so it’s definitely a good place to go with a group.
Fat Cat. Fat Cat is a 1940’s-themed bar and restaurant located right on Broadway off the Lawrence stop. It’s a great place to grab food and drinks before a concert at the Aragon/ Riv, or, just a decent place to eat at in general if you want standard American fare.
Green Mill Cocktail Lounge. What would this list be without Green Mill? This destination is not just Uptown-famous, but also Chicago-famous. This is the oldest jazz club in the country, and is Al Capone’s old hangout. Check online in advance to see what’s going on before you pop in the doors — you might need to pay a cover fee, and this venue offers everything from live music to slam poetry.
Larry’s/ 3 Squares Diner/ Heritage Outpost/ Lawrence Hotel. So, love them or hate them, Cedar Street’s FLATS is sloowwwlllyyy buying out ALL of Uptown. One of the developer’s latest projects was the Lawrence Hotel: A micro-apartment building complete with Larry’s (bar), 3 Squares (diner) and Heritage Outpost (coffee shop). This whole building is kind of a one-stop shop for pretty much any social outing you can imagine.
Bar on Buena. BoB is a cute and convenient little pub located in Buena Park. It’s probably my go-to spot when friends want to grab drinks in my neighborhood. There’s a dog-friendly patio, and a pretty decent beer selection on tap. Also, the attached North Buena Deli and Wine is a great place to grab a sandwich or pick up a bottle of wine or specialty food item if you’re in need of a last-minute gift.
First Sip. This airy and quaint coffeeshop is a relatively new addition to Little Vietnam, and it quickly became one of my favorites along Argyle Street. The Pearl Noir and Mary’s Rose are two of my favorite iced drinks.
Cafe Hoang. So, I know Tank Noodle is kind of the go-to default place for pho in Uptown, but one of our food writers at the Trib tipped me off to Cafe Hoang, and honestly? I like it better than Tank. It’s almost always empty so I’m not entirely sure how it stays in business… but as long as it’s open, I’ll continue frequenting it.
Immm Rice & Beyond. I love this Thai restaurant! The menu focuses more on street food and serves dishes found in stalls and carts in Thailand, which also makes this place a perfect fit for the annual Argyle Night Market that happens ever summer. (Tip: Make it up to Argyle at least once for the night market. It’s held every Thursday during summers, and is a good way to eat your way through Asia on Argyle without spending a small fortune!)
Longacre. I’ve been pretty vocal about my love of Detroit-style pizza, so the fact that there’s an independently-owned Detroit-style pizza place (that also serves vegan pizza!) walking distance from my apartment is amazing. Plus, it serves cans of Vernor’s on-site! You can’t get much more Michigan than that.
Ka’lish. Ka’lish is an entirely plant-based restaurant right next to Longacre. It’s a little pricey, but it’s so delicious that it’s totally worth it. Also, the baked goods are some of the best dairy-free treats I’ve ever had.
Reservoir. This restaurant is open all day, but tbh, I’ve only ever been for brunch. You can get $18 bottomless mimosas, and the stuffed french toast is sooooooo good!
Montrose Beach. Pretty much every lake-adjacent neighborhood in the city has a really great beach, and Uptown’s is Montrose. The whole beach is super accessible via walk, bike or public transit. There’s also a dog beach, a boat harbor, a skate park, a bird sanctuary, Cricket Hill, the Peace Garden, a public park and a little bar/ restaurant.
Chiu Quon Bakery. OK, this might be cheating because there’s a Chiu Quon down in Chinatown, but I love this Asian bakery. My favorite was Luck’s, which sadly closed down last year, but Chiu Quon is also amazing. The cheese buns are my absolute favorite!
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OK, there you have it! Some of my favorite places in Uptown. Remember, this list is in no way extensive — and there are tons of other great places in Uptown, like VN Tofu, Sun Wah, Klein’s, Loving Heart, Ba Le, Baton, Everybody’s Coffee, Nick’s on Wilson… I could go on and on. These are just some of my absolute favorites!
I’m also always discovering new places, and even though Uptown is small in comparison to the rest of the vast Chicagoland area, the neighborhood itself is still more than two times larger than the last city I lived in. So even after four years, I still haven’t tried everything this neighborhood has to offer!
And, like I said, I’ve never felt comfortable doling out travel guides because I am in no way an expert and everyone’s tastes and interests are different… but after almost half a decade in Uptown, I figured it was time to share some of my favorites with the general internet.
Anyway, happy exploring!
