The Underrated Chicago Neighborhood Where Vintage Mansions And Trendy Breweries Coexist

Illinois has never had to shout about its string of cool things to do and cool places to do them in. From lesser-visited cities with eccentric shops and hard-to-ignore squirrels to lakeside neighborhoods that bring out your inner artist, you're always in close proximity to something unthinkably different. As you can imagine, the Windy City is no exception. And when it comes to vintage style house spotting, retro hang outs, and breweries that ooze cool, Old Irving Park absolutely takes the prize.

The buzz around Old Irving Park started to rise in the 1980s after a period of quiet following the Great Depression. As a neighborhood within the wider Irving Park community born between farming communities, this corner of Chicago offers the best of both worlds: suburban living with a growing number of exciting spaces to wander and slowly discover. Old Irving Park sits in the center of some exciting Chicagoan neighborhoods, with Montrose above it, Addison below it, Pulaski Avenue to the east, and the Milwaukee Road Railway to the west. 

The nearest international airport is Chicago O'Hare International Airport (ORD) which is about a 15-minute drive away. You can also use public transport by taking the Chicago Transit (CTA), which will get you into Irving Park-Blue in about the same amount of time. Midway International Airport (MDW) is roughly a 30-minute drive away. Once you arrive, walking the neighborhood is the best way to take in the historic architecture and trendy vibes. Even while underrated, this neighborhood draws in travelers with a love for elaborate homes from the past and craft beer far and wide.

Old Irving Park is renowned for its family-friendly environment, making it one of the best places to keep everyone entertained in a town that is as slow and cozy as it is interesting. One of the top things to do is to stroll through the neighborhood and take in the old-school Victorian extravagance of the architecture. One of the most iconic vintage homes to visit include the Race House, an elaborately designed brick Italianate, named after Stephen A. Race, who was one of the original members of the farmland community. Built in 1874 by an unknown architect, the house has had some minor preservation adjustments over the years but is worth visiting to see the last-standing house from the original Irving Park subdivision. Located at 3945 N. Tripp Avenue, this famous residence has had landmark status since 1988, making it a popular stop when visiting the neighborhood.

Another nearby mansion worth visiting is the John Gray House located at 4362 W. Grace St. The mansion, which speaks to the railroad suburb development era in Chicago, was built in 1856 and holds landmark status as of 2024. The home was originally founded by John Gray, the first Republican Cook County sheriff, giving it an added value to the fabric of the region that history lovers will appreciate. The mansion has sustained minimal changes which means that its original Victorian Italianate style hasn't been compromised.

If you're into craft beer and wood-fire meals, then it's worth stopping at the Old Irving Brewing Co. It has landed a spot on USA Today's list of best U.S. Brewpubs from 2018 to 2022 for a reason. Located on 4419 W. Montrose Ave., this restaurant and brewery is a staple that truly speaks to the community-oriented nature of the Old Irving Park area. Two years before opening its doors, the brewery really began in a garage before eventually opening and establishing itself as one of the neighborhood's most trusted spots for craft beer and a hearty plate of top quality food. Craft beer devotees will appreciate the range of offerings from year-round specials to seasonal beers. The fun and friendly atmosphere is also hard to pass up on to enjoy Chicagoan nights speaking with travelers and regulars alike.

 Smoque BBQ first opened in 2006 on 3800 N. Pulaski Rd, offering the neighborhood a chance to indulge in a smoky and unapologetically lavish BBQ shack in a family friendly environment. If the eateries' myriad awards for best BBQ across the country as well as within home Chicagoan ground isn't convincing enough, the long line of loyal regulars will seal the deal. The kid's menu options include mini pork and brisket sandwiches, macaroni and cheese, and a kid's fry. Otherwise, adults can enjoy sandwiches, platters, BBQ Gumbo and if you visit between Tuesday and Thursday you'll be able to get in line for a brisket taco kit bursting with the kind of flavors that make BBQ tacos top tier. Smoque BBQ is also BYOB so you can sip away on your favorite beer in true easy-going, home-from-home fashion. This is absolutely one of Old Irving Park's most trusted spots for a good time and a deeply satisfying meal.