Exploring Chicago’s Vibrant Uptown Community
Exploring Chicago’s Vibrant Uptown Community
Published June 13, 2022
Are you interested in exploring a part of Chicago that’s rich in history and culture? If you are, consider a visit to Uptown! Almost a century ago, this community area on the city’s north side was one of the most lavish and influential entertainment districts in the country. Uptown’s grandeur is still on display, but it’s a more laid-back and accessible part of the city today.
Uptown is far enough away from the Loop (downtown Chicago) that it has its own unique vibe. However, it still feels like an urban center and is easy to get to on the CTA Red Line. The district is home to some of Chicago’s most extravagant music venues that had their heyday in the 1920s and 1930s. As such, the performing and visual arts are an integral part of Uptown.
Architecture enthusiasts will also enjoy Uptown’s art deco and gothic styles from that same era. Given that this is where Chicago’s wealthy and famous would go for a night on the town, the area has a distinctive “former glory” vibe to it. Some people might describe it as “run-down,” but I think Uptown maintains its historical roots and is still a dynamic community today.
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Five Parts of Uptown
1. Lawrence & Broadway
(Heart of Uptown)
The very center of Uptown is the intersection of West Lawrence Avenue and North Broadway. Many of the most iconic music venues are located here. In addition, there are lots of amazing places to eat within a block or two.
2. Asia on Argyle
(Uptown's North Side)
One of the coolest parts of Uptown is Asia on Argyle, a small but vibrant couple of blocks known for its Southeast Asian heritage. The CTA Argyle stop provides direct access to West Argyle Street, where you’ll find some of Chicago’s best Vietnamese and Thai cuisine.
Asia on Argyle was actually one of the first neighborhoods I explored in depth as part of my Chicago 360 blog series. If you’d like to learn more about this specific part of Uptown (including restaurant options), check out my separate blog post!
3. Wilson CTA Red Line Stop
A few blocks south of West Lawrence Avenue, you’ll find the Wilson CTA Red Line stop. This area has a lot to offer in terms of restaurants and shopping, especially along North Broadway. You’ll also find much of Uptown’s most prominent street art on display near Wilson.
4. Clark & Ashland
(Western Edge of Uptown)
On the western side of Uptown, North Ashland Avenue and North Clark Street run parallel to each other. Clark is more commercialized, and Ashland is more residential. If you travel north on either road, you’ll move from Uptown into Andersonville, another lively part of Chicago.
5. Buena Park
(Uptown's Southernmost Neighborhood)
This quiet, lakefront area has fewer attractions for visitors than other parts of Uptown. However, there are still some interesting bars and restaurants on North Broadway, which cuts diagonally through it. In Buena Park, you can find some historic homes and apartments, especially on West Hutchinson Street.
Points of Interest
Green Mill Cocktail Lounge
Address: 4802 N Broadway, Chicago, IL 60640
Website: https://greenmilljazz.com/
Facebook: https://www.facebook.com/greenmillcocktaillounge
This bar and jazz lounge is one of Uptown’s most amazing historical relics. It first opened in 1907 under a different name, and was both a speakeasy and a common hangout spot for famous mobsters such as Al Capone and Jack “Machine Gun” McGurn. Apparently, the bar is famous for its trapdoor and the network of tunnels underneath it, which at one time ran all the way to the other side of Broadway.
Today, the Green Mill is a lively bar that hosts jazz performances almost every night. The venue is cash only, and there may be a cover charge depending on the group. Visiting Green Mill is a lot of fun. Lots of people dress up because it really feels like a fancy night out, although the bar doesn’t have a dress code. The interior is also stunningly preserved. Old-fashioned nautical motifs and large painted murals on the walls make the Green Mill feel like it’s straight out of the 1920s.
Other Cool Uptown Bars
Given Uptown’s history as an entertainment district, it’s no surprise that there are many cool bars to check out here. Below are some other ideas beyond the Green Mill.
Fat Cat
Address: 4840 N Broadway, Chicago, IL 60640
Website: https://www.fatcatbar.com/
Facebook: https://www.facebook.com/FatCatBarChicago/
Instagram: https://www.instagram.com/fatcatchicago/
This popular bar and brunch spot offers lots of interesting sweet cocktail recipes. I’ve only been here for happy hour, but I need to go back to try some of their food items and their famous Bloody Mary!
The Reservoir
Address: 844 W Montrose Ave, Chicago, IL 60613
Website: https://www.reservoirchicago.com/
Facebook: https://www.facebook.com/people/The-Reservoir/100040056895412/
Instagram: https://www.instagram.com/thereservoirchicago/
Like Fat Cat, The Reservoir seems to pay homage to Uptown’s history. The interior is a tasteful mix of older fixtures and more sleek, modern designs. I’ve also only been here for happy hour, but I like their classic and espresso martinis!
Street Art on North Clifton Avenue
Uptown is full of public art, but a lot of it is clustered on North Clifton Avenue. This short side street features dozens of different artists’ work. Although there isn’t much traffic on Clifton, you should remain alert for cars coming through here while admiring the various displays.
Montrose Beach
As we’ve already seen, Uptown’s defining features are its architecture and thriving arts scene. But this neighborhood really has a bit of everything, including a beautiful public lakefront on its eastern edge.
Here you’ll find wide open fields, walking trails, skyline views, concession stands, and more. It would probably take an entire afternoon to fully explore Uptown’s shoreline on a nice day.
The largest sandy beach in Uptown is Montrose Beach, which draws huge crowds in the summertime. The northern end serves as an off-leash dog park, while the south end is roped off as a nature preserve.
One unique attraction on this stretch of coastline is the Montrose Harbor Beacon. This eye-catching concrete pathway juts out into the lake and forms a hook shape. There are two structures that look like they might be old radio towers here. This path is open to the public, and walking to the very end of it takes a surprisingly long time! It offers unobstructed views of the Loop to the south and Edgewater to the north.
Montrose Point Bird Sanctuary
Not far from Montrose Beach, there is a wooded park where you’ll see lots of people with massive camera lenses and binoculars. They tend to keep their eyes on the tops of the trees, and groups speak in hushed tones. They’re all hoping to get clear views and photos of the beautiful birds in the Montrose Point Bird Sanctuary!
I’m no expert, but lots of colorful species seem to inhabit this nature preserve. I love that cardinals are pretty common here, although it may take some time to actually spot one.
Uptown's Diverse Food Scene
If you’ve browsed any other posts on Caffeinated Excursions, then you know that food is an integral part of my blog. Luckily, Uptown has a vibrant food scene that you won’t want to miss! The cuisines of Asia, Ethiopia, and Mexico are among the area’s specialties.
Asian Cuisine
Many of Uptown’s best Vietnamese, Thai, and other Asian restaurants are clustered around Asia on Argyle. I’ve written about this community in a separate blog post, so be sure to check that out for some delicious options! Be sure to also check out my Chicago Phở Guide, which features lots of restaurants in Uptown!
Ethiopian Dining
Some of Chicago’s most prominent and highly-rated Ethiopian restaurants can be found on Broadway. If Ethiopian food is something you’d like to try for the first time or become more familiar with, Uptown is the place to do just that!
Demera Restaurant
Address: 4801 N Broadway, Chicago, IL 60640
Website: https://demerachicago.com/
Facebook: https://www.facebook.com/DemeraEthiopian
Instagram: https://www.instagram.com/demerachicago/
I love this casual restaurant with friendly service and amazing food! I’ve eaten their yebeg wot (spicy lamb), doro wot (spicy chicken), and kitfo (steak tartare). Ethiopian food really has a full-bodied flavor complete with lots of spices and strong aromas. Demera is the perfect place to try some of these amazing flavors!
If you’d like to pair some drink options with Demera’s delicious food, they also offer some intriguing specialty cocktails. I had the pleasure of trying their Ethiopian hot toddy, house-made tej (honey wine), and a chocolate espresso martini as part of a Chicago Restaurant Week tasting menu. All three drinks were amazing, and the other cocktails on their menu sound equally delectable!
Selam Ethiopian Kitchen
Address: 4543 N Broadway, Chicago, IL 60640
Website: https://www.selamkitchen.com/
Facebook: https://www.facebook.com/selamkitchen/
Instagram: https://instagram.com/selamkitchen/
This is another great place to have an unforgettable feast! Selam specializes in organic food, and I highly recommend trying one of their combos: they offer a meat sampler (pictured below) and a vegetable sampler.
The meat sampler includes lamb, chicken, beef in a rosemary and jalapeño sauce, strips of steak, your choice of a veggie side, and a small serving of a crumbly, mild cheese. Everything was great, but the green sauce on the beef was especially unique. Their chicken, which included a whole leg and hard boiled eggs along with a delicious brown sauce, was probably my favorite part of the platter.
Many Ethiopian dishes are served atop injera: a soft, spongy, slightly sour bread that’s used to fill the base of the large metal platters the food is served on. You’ll often get two or three additional pieces of injera rolled up in a basket on the side.
Injera is integral to Ethiopian cuisine because everything is traditionally eaten by hand. This might sound difficult seeing as veggies, meats, and stews with ample sauce are common. I like to rip small pieces of the injera and use them to pick up the food on the plate. Plus, it tastes great!
Occasionally, Ethiopian restaurants will provide silverware unprompted (e.g. at Demera, where the yebeg wot is more of a soup than a sauce if you order it individually). However, many will not. I would invite everyone to try Ethiopian food by hand! It’s definitely part of what makes this dining experience so special.
Recommended Mexican Restaurants
Uptown is a great place to get Mexican food! Below are a few noteworthy places to eat that all have their own special vibe.
Fiesta Mexicana Restaurant
Address: 4806 N Broadway, Chicago, IL 60640
Website: https://www.fiestamexicanachicago.com/
Facebook: https://www.facebook.com/fiestamexicanauptown/
Instagram: https://www.instagram.com/fiestamexicanauptown/
Fiesta is a colorful, cozy restaurant that serves delicious Mexican food and margaritas at reasonable prices. I suggest ordering one of their combo plates, especially if you’re really hungry!
Kie-Gol-Lanee
Address: 5004 N Sheridan Rd, Chicago, IL 60640
Website: https://kiegol.com/
Facebook: https://www.facebook.com/kiegolchicago
Instagram: https://instagram.com/kiegolchicago/
I really love that this Mexican restaurant specializes in food from Oaxaca! According to their website, their name is a phonetic spelling of their hometown in Oaxaca (Santa María Quiegolani). Kie-Gol-Lanee feels a little more upscale than some of the other places on this list, but that’s part of what makes this dining experience unique!
Oaxaca is a state in Southern Mexico that is known for its regional cuisine. It is pretty distinctive from other types of Mexican food. At Kie-Gol-Lanee, I’ve tried a few house cocktails, plus their guisado de conejo: stewed rabbit in a yellow mole sauce with veggies and salad. The sauce it came in was phenomenal, and the meat itself was very tender. If you’re interested in trying Oaxacan food in Chicago, this is the perfect place to do it!
Carmela's Taqueria
Address: 1206 W Lawrence Ave, Chicago, IL 60640
This small taco shop sort of feels like a hole in the wall, but that’s never a bad thing in my book! I tried three of their tacos when I went: al pastor, lengua, and cachete beef. All of them were very tasty and authentic!
Other Delicious Uptown Eats
Lucy's
Address: 4570 N Broadway Ave, Chicago, IL 60640
Website: https://hangry.io/lucys-uptown
Facebook: https://www.facebook.com/lucyschicago/
Instagram: https://www.instagram.com/lucyschicago/
If you’re craving a mouth-watering spicy fried chicken, Lucy’s is the place to go! Their sandwiches are massive, with giant pieces of juicy chicken that are twice as big as the bun. I’ve tried some of the sides at Lucy’s, including fries and mac-and-cheese, but I’d recommend going with their deep fried pickles! These crispy spears are just as tasty as the fried chicken!
Ragadan
Address: 4409 N Broadway, Chicago, IL 60640
Website: https://ragadan.com/
Facebook: https://www.facebook.com/Ragadanrestaurant
Instagram: https://www.instagram.com/ragadanrestaurant/
Ragadan is a relative newcomer that has been making waves in Chicago’s culinary world. It’s really added some flair to this stretch of Broadway that connects the Wilson CTA Station to Buena Park. According to their website, Ragadan serves falafel and American classics that are infused with Jordanian spices and flavors.
I’ve tried their burgers, hummus plate, and two of their amazing milkshakes. I would highly recommend all of these! I still need to try one of their famous sandwiches, which have captured the attention of amateur food bloggers and big name critics alike!
Go Explore Uptown for Yourself!
I’ll be the first to admit that I haven’t seen or done everything Uptown has to offer. With that said, I hope this blog post provides a sense of what makes this neighborhood so special. Its arts and architecture, multiculturalism, and culinary scene make it one of Chicago’s finest areas to explore!
Have you been to Uptown before? Are there any attractions or restaurants here that I didn’t mention? Leave a comment below and let me know! Be sure to also check out my other Chicago 360 posts to learn more about local communities throughout the Windy City!
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This post was published on June 13, 2022
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