Old Town

A walker’s paradise and features dozens of diverse restaurants, shops, and housing options. 

Welcome to Old Town

A tiny, walkable neighborhood of Chicago that packs a punch
Charming and exciting, the Old Town community of Chicago is home to endless opportunities to enjoy a high quality of life among the neighboring skyscrapers. Private and quiet during the day, Old Town is a walker’s paradise and features dozens of diverse restaurants, shops, and housing options. 
Escape the chaotic city center and venture to the tree-lined streets and cozy pockets of Old Town to appreciate the natural beauty of the local parks and Lake Michigan views in the distance. Old Town offers something for everyone among the stately Victorian buildings and mellow, pleasant streets.

What to Love

  • Home to the best comedy clubs in the city and a thriving nightlife scene
  • Peaceful and private residential streets
  • Scenic backdrops along the lake

Local Lifestyle

Residents of Old Town enjoy a quiet lifestyle during the day and a vibrant nightlife scene when the sun sets. Bursting with opportunities to experience quality restaurants, parks, and annual festivals, there is no shortage of things to do in this historic neighborhood of Chicago. Choose from high-rise apartments or condominiums or renovated walk-ups on quiet residential streets. Something for everyone from all walks of life, Old Town may be one of Chicago’s smallest neighborhoods, but it’s loaded with thriving entertainment experiences in a lively and inviting community.

Dining, Entertainment, and Shopping

Offering a huge pizza menu and an extensive cocktail list, Happy Camper Pizza fills the void for creative pizzas and meals in Old Town. Combining great pizza, booze, vibes, and happiness, Happy Camper Pizza is a fun destination to gather with friends in a hip and unique space adorned with camper decor to complete the experience.  
If you’re craving authentic Mexican street tacos, visit Broken English Taco Pub for unique creations and refreshing drinks in an upbeat and welcoming space. Bursting with flavor and loaded with fun toppings, the tacos at Broken English will surely satisfy your cravings and leave you coming back for more! Try the “Oh My Cod” with fried pescado and tarragon mayo or the cauliflower al pastor for a healthy vegan option. 
A never-ending rooftop party, Utopian Tailgate is the ideal destination for “friends, wanders, and adventurers.” A playground for grownups with an elevated menu of traditional American fare and extensive drinks, Utopian Tailgate is the place to be if you’re looking for a nontraditional bar and party experience in the heart of Old Town. Situated above Second City and offering gorgeous views, Utopian Tailgate offers interactive games, a 10,000-square foot dance floor, and themed evenings for the ultimate party experience. 
Serving a stripped-down menu of the essentials in a casual atmosphere, Small Cheval is a fast-paced joint for quality burgers, fries, shakes, and shots. Offering quality condiments to accentuate the already delicious burgers, Small Cheval is a fun destination for a quick bite and an excellent craft beer with friends.
The best dive bar in Chicago, Old Town Ale House is a neighborhood landmark and community staple since 1958. A pub you don’t want to miss and a place where you may never leave, Old Town Ale House has a deeply rooted history in the culinary scene of Chicago and rave reviews from nationally-ranked magazines and leading gastropub experts. If you’re looking for the quintessential, neighborhood bar, you’ve found the best spot at the Ale House!

Things to Do

The world’s premier school of comedy, Second City is also a comedy club and theater space hosting improv performances and shows almost every evening. Attend a class, which are open for all ages, and grab tickets to a hilarious show to appreciate why Second City is the world’s leading comedy destination. 
With over eight acres to explore, Seward Park offers pristine green spaces for athletic games and parties. With beautiful lawns to enjoy and an indoor facility with basketball courts, a fitness center, and dance studio, Seward Park is the hub of the Old Town community and offers activities and classes for all ages. Relax outside during the summer for the anticipated Summer Concert Series or attend a Movie in the Park or take advantage of the dozens of amenities provided by the park’s community center. 
Held in the Old Town Triangle Historic District, the Old Town Art Festival brings over 200 artists to the community every summer for exhibits, workshops, presentations, and juried contests. With activities for kids, live music stages, and a large food court featuring local eateries, the Old Town Art Festival is the place to experience magnificent works of art across all genres during the beautiful summer season in Chicago.


There are several high-achieving schools in the Old Town neighborhood. Some include:

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