Uptown Neighborhood Guide

  |     |   The Bachelor, The Draper, The Lawrence House, The Synagogue


What originated as a summer resort town in the early 1900s, Uptown has long been a destination for entertainment and leisure on the lakefront at the expansive Montrose Beach. Neighborhoods within Uptown include Buena Park, Sheridan Park, Argyle Street (also known as Asia on Argyle or Little Vietnam), Margate Park, and the Uptown Square historic district. Theatres include the Riviera, the Aragon Ballroom, Green Mill Cocktail Lounge, and soon-to-be renovated historic Uptown Theatre. Access to the CTA red line, city buses, and Lake Shore Drive offer easy transportation options to the city at large.

Parks include the lakefront with trails, Cricket Hill (known for its annual kite festival), and the Clarendon Park Community Center. Montrose Beach has a corresponding dog park where your four-legged friends can run free and perhaps swim a few laps.

Lady Louise is our landlady and mascot. She also happens to be an adorable French BullDog. Uptown also has a special place in Lady Louise’s heart, read on for her essential guide to this historic neighborhood.


Meli Cafe | River North | FLATSLife
The fabric of the Uptown community is woven tight with many different cultures, and the food represents that. You’ll find both traditional American cuisine and innovative spins on the classics when walking through the neighborhood.
  1. 3 squares Diner 1020 W Lawrence Ave – A modern and refreshing take on classic diner food with crisp interiors. Chef Ian’s chicken and waffles doesn’t disappoint.
  2. Pho 888 1137 W Argyle St – Don’t let the simple interiors fool you, these flavorful packed dishes are a special treat for a casual lunch.
  3. Kal’ish 1313 W Wilson Ave Serving up delicious vegan dishes, Kal’ish also has yummy bakery treats and a grab n’ go section with salads, wraps, and pastas. Fan favourites include Mama’s Nachos and the Uptown Reuben. Both vegetarians and meat-eaters alike will find something tasty and enjoy the outdoor patio if weather permits.
  4. Wabi Sabi Rotary 4521 N Sheridan Rd – One of the few rotary sushi places in Chicago, and this one is a family run operation. Come hungry and for the all-you-can-eat option to take a taste of everything from sushi rolls, appetizers, and even ramen!
  5. Demera 4801 N Broadway St – Award winning Ethiopian food, perfect spot to share a rich and flavourful meal with friends. 


The Drifter | River North | FLATSLife
  1. Fat Cat 4840 N Broadway – Neighborhood staple with pub fare, games, and great music. It’s proximity to music venues makes it an easy choice for pre-show or after-show drinks. The menu has all comfort food staples like pork belly poutine, crispy mac and cheese bites, stacked burgers, and many more mouth-watering treats.
  2. Drink and Ink 4443 N Broadway – Do your friends ever ask you to tag along while they get a new tat? At Drink and Ink you can watch them get their new ink as you sip on a drink at the bar. Other perks include amazing artwork and a Nintendo 64!
  3. Larry’s 1020 W Lawrence Ave – Enjoy a variety of craft beer and cocktails in the historic art deco lobby of The Lawrence House. Bring your drinks out to the patio and lounge in the backyard, you can even catch a nighttime outdoor movie in the summer.
  4. Big Chicks 5024 N Sheridan Rd – This iconic northside gay bar is like a living art project. There is a vibrant unique energy in this legendary landmark, check it out.
  5. The Green Mill 4802 N Broadway St – Some of the most profound jazz musicians of the 20th century graced the modest stage at this infamous uptown bar. Go for an evening out at the same spot Al Capone used to frequent and catch music, poetry, or comedy.


Uptown isn’t short on local coffee shops with great brew and community centric environments for relaxing, working, or grabbing a drink when you’re on the run.
  1. Heritage Outpost 1020 W Lawrence Ave – Get your standard drip or go all out on a more dressed up coffee option like their lavender latte. Enjoy your beverage by the light-filled bar or venture into the art-deco Lawrence House lobby where there’s lounge seating and co-working tables.
  2. Emerald City Uptown 1224 W Wilson Ave – Lunch foods and pastries are always handmade from fresh ingredients, never process. Owner, Briano, wanted to create a welcoming space for the community to meet and enjoy delicious food and coffee. They also have puzzles and games for patrons to enjoy. Located a short jaunt from the Wilson CTA, stop by and try the fan favourite breakfast tacos.
  3. Everybody’s Coffee 935 W Wilson Ave – Committed to serving fresh and sustainable coffee by continually researching the best bean sources. Bright fresh space to work or meet and yummy lunch options like southern grits and bagel sandwiches. This spot has been featured in publications such as Time Out, The New York Times, and Conde Nast Traveler.
  4. First Sip Cafe 1057 W Argyle St – Rustic wooden floors, porcelain teacups, flowers, and vintage decor. Tucked into Argyle street, this cute coffee shop makes drinks so pretty that it will be hard to resist snapping a pic. They also host open mic nights, pop-up shops, and patio parties in the summer.

Things To Do in Uptown

Uptown has been a hotspot for live entertainment since the turn of the century, catch your favorite artists or discover someone new! Uptown’s proximity to the lakefront means access to beautiful beaches and recreation like rollerblading, biking, or team sports.
  1. See a show. Venues span down Broadway street with plenty of food and drink options for before and after the performance. Choose from The Aragon ballroom ,The Riviera Theatre, or The Green Mill.
  2. Soak up the sun at Montrose Beach 4400 North Lake Shore Dr
  3. Enjoy tasty food and live performances at Argyle Night Market – Drawing almost 5,000 people every Thursday summer night, this market has plenty of tasty food offerings, live entertainment, and local craft vendors.
  4. Check out the Haitian American Museum of Chicago. Founded in 2012, the museum was created to hold programs and exhibits that would add to the rich multicultural tapestry of the city. Not only do they display art, but they also have a rotating selection of films as well as community-driven small group conversations to discuss issues in Uptown. 
  5. Visit famous Chicagoans at the expansive Graceland Cemetery. These sacred grounds are home to the resting place of famous architects like Ludwig Mies van der Rohe and the “father of skyscrapers”, Louis Sullivan. Other notable Chicagoans include Jack Johnson, the first African American World Heavyweight Boxing Champion and Scottish American spy, Allan Pinkerton.

Shopping in Uptown

While Uptown might not come to mind for shopping in Chicago, there are certainly some very unique local shops to explore.

  1. Uptown Bikes 4653 N Broadway – This full service bicycle shop located right by the L tracks is a neighborhood favorite. What makes this shop truly special is the knowledgeable, friendly, and welcoming staff.
  2. Foursided 5061 N Clark St – Longtime custom framing and gift store. Foursided is one of the shops that’s hard to pass by without wanting to take a peek at what’s inside. They offer antique trinkets, local art, unique gifts, framing services, and more.
  3. XHT Gifts 1110 W Argyle St – Unique finds located right on the main street of Argyle. They don't have a website to check out beforehand, but they're worth a stop in to discover things like rare Hello Kitty items before or after grabbing a bite to eat.

Keep it Fresh with Dry Cleaners in Uptown

Uptown has plenty of options for cleaning and tailoring with great reviews and reasonable pricing.

  1. JS Cleaners 3704, 4820 N Sheridan Rd – Friendly and quick service.
  2. Tae Cleaners 4411 N Hazel St – Nice staff with reasonable prices.
  3. Princess Cleaners 4136 N Broadway – Wonderful customer service at a good price point.

Working out in Uptown

Any way you like to move, you’ll find a gym or studio in Uptown to do it! If outdoor recreation is more your thing, head east to the lakefront to walk, jog, run, or bike on scenic paths.
  1. The Lawrence House 1020 W. Lawrence Ave – Whether your thing is cardio, weights, or a mix of both you’ll challenge yourself to surpass new goals in the gym adjacent to the restored art deco pool in the Lawrence House basement. There’s even a boxing ring to practice your jabs and kicks.
  2. The Draper 5050 N Broadway St – Two story fitness center with cardio, weights, circuit training and everything in between. All FLATS residents are encouraged to take advantage of the free weekly group fitness classes led by top trainers.
  3. First Ascent Uptown 4718 N Broadway St – On top of standard training equipment First Ascent has a full scale bouldering gym to climb your way to your next fitness goal. Sound fun? Take a beginners climbing classes from encouraging instructors.
  4. Primary CrossFit & Yoga 5050 N Sheridan Rd – Committed to inclusive training for all ages and fitness experience. CrossFit classes are combo workouts that hit cardio, strength, agility, balance, and flexibility. If that doesn’t sound your like thing they also offer yoga, rowing, and private one-on-one training sessions.
  5. Bodi Shak 4704 N Broadway – Community-oriented gym dedicated to being more than just a place to get a workout in. Their fitness offerings range from HIIT to boxing to yoga and more. They also host private events and are invested in giving back to local charities.

Co-Working in Uptown

  1. The Lawrence House 1020 W. Lawrence Ave – The restored art deco lobby is the perfect place to settle in to get some work done whether you prefer a communal table, swivel chair, leather couch, or outdoor lounger. Perks include a Heritage Outpost coffee shop and vending machine when you need some libations!
  2. Human Citizen Workplace 4101 N Broadway – Local option for individuals, teams, and small businesses with the amenities of a downtown coworking office. They offer professional development working as well a community of driven people that represent many industries.


Convenient and walkable options to grab your basic kitchen staples or all ingredients for that fancy new recipe you’ve been meaning to try.

  1. Aldi 4500 N Broadway St
  2. Jewel-Osco 4355 N Sheridan Rd
  3. Mariano’s 1800 W Lawrence Ave and 5201 N Sheridan Rd
  4. Target 4466 N Broadway St

University and College

  1. Harry S. Truman College 1145 W Wilson Ave


You won't have to search far and wide to find top-notch healthcare for your furry companions.

  1. Duke Animal Hospital 3941 Ashland Ave



World-class medical care is never far away.

  1. Weiss Memorial Hospital 4646 N Marine Dr

2 thoughts on “Uptown Neighborhood Guide

  1. Why didn’t you mention a favorite restaurant in the neighborhood is Fiesta Mexicana? A good place for the local as well for the concert goers and other visiting our Uptown area.


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