Everything to Know About Living in Chicago’s Old Town Neighborhood

The Old Town neighborhood is a wonderful mix of new modern and traditional Chicago. The neighborhood provides easy access to the business district of the Loop but also enough distance to give a community feel in a big city. Surrounded by Gold Coast, River North, and Lincoln Park, Old Town residents have attainable access to the lake and popular entertainment destinations. If you want to live in a historic environment with countless restaurants and bars, then Old Town is the neighborhood for you.

History of Chicago’s Old Town

Old Town Chicago is filled with many historical landmarks and buildings. The story of the neighborhood is visible through the tree-lined streets, old Victorian homes, and multi-generational restaurants and businesses. Take an afternoon and walk around to get a taste of this rich historic area. This includes one of the few buildings to survive the Great Chicago Fire, St. Michael’s Church. Old Town is also home to one of the first standing stations of the “El”, Sedgwick. Another interesting fact is that within the Old Town Triangle, the streets do not adhere to the Chicago street grid system since they predate the Chicago Fire. The triangle was formed by Clark, North, and Ogden streets. Knowing the history of the Old Town, Chicago neighborhood helps paint a picture of the overall community culture.

Chicago Old Town Neighborhood Today

Old Town is home to many new luxury apartments in Downtown Chicago. Old Town is also the best of both worlds. It’s walkable to the heart of the city, Michigan Avenue, and Lake Michigan, but also has a warm neighborhood feel with a lot of great restaurants, shops, green space, and areas to walk a dog. Old Town also makes for easy access to the Loop, River North, and Gold Coast neighborhoods too.

The neighborhood makeup is a mix between walk-ups, mid-rises, brownstones, and sleek, glass high-rise buildings. Anyone will be able to find something to love in Old Town apartments!

Things to do in Old Town

The Old Town neighborhood is home to some of Chicago’s top entertainment. If you are looking to laugh the night away, check out Second City. Known for its many famous alums, this storied spot hosts popular sketch shows & improv classes. Some iconic faces over the past 50 years include Dan Aykroyd, Chris Farley, Julia Louis-Dreyfus, Tina Fey, and Mike Meyers. Another top comedy club is Zanies. This comedy club hosts nationally known stand-up comedians seven nights a week. New City is a popular shopping, eating, and entertainment destination in Old Town. This neighborhood shopping area features Arclight Cinemas, Kings Bowling, Saks Fifth Ave Off 5th, Dick’s Sporting Goods, and restaurants like Earl’s Kitchen and Yard House. Steppenwolf Theater is Chicago’s premier ensemble theater exploring the new perspectives of acting and performance. This not-for-profit organization relies on community support to produce and present up to 16 plays and nearly 700 performances, readings, and other events on the three Steppenwolf stages. Old Town is a popular destination for top restaurants and nightlife. Next, we highlighted a few favorite dining options in Old Town.

Top Old Town Restaurants

To keep with the history of Old Town, Twin Anchors is an old-school tavern and barbecue restaurant opened in 1932. This historic restaurant gives off a bit of a gangster vibe and was once frequented by Frank Sinatra. They are best known for the ribs which are broiled, not smoked. If you’re looking for a great dining experience while still watching the games, check out Old Town Pour House. Locals order off their sizeable beer list and enjoy upscale pub food in an elegant wood-clad restaurant. The walls are covered with multiple TVs, so there is not a bad seat in the house for a game. Old Town also hosts Chicago’s first sushi restaurant (opened in 1967), Kamehachi. Make a reservation and enjoy the extensive menu of grilled seafood, steaks, salads and a variety of new maki and sashimi offerings. For more than 30 years, Topo Grigio has been an Old Town restaurant landmark for Italian-American cuisine. Whether you’re seated in the garden patio or the cozy dining room, the hearty Tuscan inspired dishes will have you wanting to return. Kick back with a plate of pasta or even just a glass of red wine and observe the vibrant Wells Street foot traffic. Broken English combines a unique take on Mexican street-style tacos, refreshing beverages, eclectic music, and vivid artwork created by local talent. The small plate tacos and margaritas always make for a great night!

Top Old Town Bars

Old Town is also a popular destination for patio drinks and nightlife gatherings. There are countless options for craft cocktails, exclusive beers, and expansive wine lists. We highlighted a few great locations for your weekend adventures.  Looking for a 44 oz vodka lemonade to kick off the weekend? Fireplace Inn is best known for its oversized drinks and the barbeque ribs. The bar is centrally located on Wells Street and has long communal styled tables for large parties and large drinks. Open since 1958, the Old Town Ale House has had plenty of time to establish itself as a prime dive bar for the Old Town neighborhood. This cash-only spot has a very laid back culture and plays the best of the jukebox tunes. Located just north of North Avenue on Wells Street, Corcoran’s Grill & Pub is a cozy pub with a great deals menu. Enjoy the weather on their large backyard patio or sit in the open air area of the new additional bar in the patio area. Declan’s Irish Pub provides bar-goers with the most authentic Irish bar experience in Old Town. The 140-year-old mahogany bar, decor, and menu will make you feel as if you were in Ireland. Patron’s can sip on Irish brews and Whiskey’s, inside or enjoy the large sidewalk seating on the lively street of Wells.

Where to Live in Chicago’s Old Town

Luxury Old Town apartments are a lovely escape from downtown, that also provides easy access to all of Chicago’s favorite spots. If you want to live in a historic environment with a plethora of places to try, then Old Town is the neighborhood for you.

Make sure to check out:

K Square:

Located in Chicago’s Old Town Triangle at 1749 N. Wells Street is a premier apartment community featuring unique floor plans ranging from studios to spacious two bedroom apartments. Community amenities at K Square feature on-site maintenance, package receiving, off street parking, pet area, dog run, lobby, laundry facilities, high-speed internet, heated garage, bike racks as well as newly renovated amenities including a new state-of-the-art fitness center, community lounge, and pool. Apartments at K Square feature efficient stainless steel appliances, central air and heat, spacious closets, extra storage, and unparalleled views of the city.

Old Town Park:

Old Town Park located at 1140 North Wells Street offers all the amenities of Chicago luxury apartment building. The property is located centrally close to dining, shopping, and nightlife right on Wells Street. This 32-story tower features studio, one, two and three bedroom floor plans. Enjoy an outdoor escape with a heated pool, hot tub, loungers, and daybeds.

The Scott Old Town Apartments:

The Scott Residences, at 211 W Scott Street, sits on bustling Wells Street, in the heart of Chicago’s popular Old Town neighborhood. The building features convertible, 1, 2, and 3 bedroom layouts. The Scott has a great amenity rooftop deck with panoramic views. Property highlights include a club lounge, demonstration kitchen, fitness center, rooftop sun deck with grills and fire pit, valet dry cleaning, billiards parlor, bike racks, storage lockers, package receiving, and a private dog run.

1225 Old Town on North Wells Street:

1225 Old Town is a vibrant luxury residence at 1225 N Wells Street. They offer convertible, 1, 2, and 3 bedroom layouts with gorgeous luxury finishes. It is a pet-friendly building and boasts stunning balcony views. Make sure to check out the roof deck pool during one of the gorgeous sunsets.

Living in the Old Town neighborhood of Chicago opens the door to luxury along with the historical past of this beautiful neighborhood. Reach out to your Luxury Living broker or contact us with any questions for setting up a showing.

*This post has been refreshed since the original published date of August 10, 2017.