With colder temperatures lingering this February and March, it’s the best time to explore the many notable restaurants and local favorites in Chicago’s Old Town neighborhood. Wine and dine on elevated American comfort food, or pop in for a fun night of pizza and cocktails. Whether you are looking for something casual, celebratory or romantic, Old Town has it all! To help you choose the best restaurant for your night out, we’ve rounded up our top spots that are all located within minutes from our luxury apartment rentals.

Broken English Taco Pub (1400 N. Wells St.)



With three locations to boot, Broken English Taco Pub is a neighborhood go-to with daily menu specials including Taco Twosday! Located at the corner of N. Wells St and W Schiller, Broken English invites you in with colorful decor and convinces you to stay with their amazing menu featuring an array of Mexican street style tacos! Tip: If you have a craving for Huevos Rancheros and bottomless Mimosas, consider scheduling a brunch date.

tacopub.com | @brokenenglishtacopub

The VIG Chicago (1527 N Wells St.)



Inspired by a 1950s sports parlor, The VIG Chicago offers classic cocktails, craft beer, and a delicious gastropub menu. Perfect for catching up with friends, you can fulfill your craving for homestyle meals with any pick off The VIG’s menu, The Book.

We recommend the umami Chicken Wings topped with cilantro and sesame to start, followed by the Royal Isabela Roasted Corn salad. For the main event, a classic Steak & Fries or The VIG Burger with all of the fixings!

thevigchicago.com | @thevigchicago

Gibsons Bar & Steakhouse (1028 N Rush St.)



An iconic spot for classic American cuisine since 1989, Gibsons Bar and Steakhouse is a Chicagoan favorite for locals and celebrities alike including actress Kate Hudson, country star Cody Jinks, comedian Dave Chappelle, and more.

If you are seeking specialty steaks, Gibson’s is the place to be! The menu also features a variety of incredible side dishes, from Grilled Asparagus topped with Parmigiano and a Lemon Vinaigrette, to Butternut Squash with Chimichurri and Candied Sunflower Seeds, ensuring you’ll find something to satisfy everyone in your party.

gibsonssteakhouse.com | @gibsonssteakhouse

Happy Camper Pizzeria (1209 N Wells St.)



Good vibes and good pizza! Serving a delicious selection of pies and cocktails in a fun vintage park setting, Happy Camper is definitely a popular destination in Old Town.

From classic Pepperoni, to a Build-Your-Own Vegan pizza, to their Happytizers list, you are bound to find the perfect dish to pair alongside their cocktail menu. Our suggestion? The Pink Flamingo, made with Tequila, Pomegranate, Lime, Soda, & Jalapeño!

Looking to celebrate St. Patrick’s Day? Gather friends over great ‘za and drinks at Happy Camper. Tickets are now available.

happycamper.pizza | @happycamperchicago


Discover more of what Old Town has to offer. Explore our customized neighborhood guide and let us know your favorite spot over on Instagram.

For more details on Chicago’s newest luxury apartment rental building, TWO Old Town Park, contact us today!

Schedule a Virtual Tour ›