24 Hours In… Chicago

Uncovering the secrets of the Windy City with Doug from Dusty Groove record store.

Glance down any side street in Chicago and you’re guaranteed to find something to tempt you—particularly if you’re a lover of beer, bourbon and blues. To help you get off the beaten track and explore the city’s lesser known haunts, we hooked up with Doug Arnold from the legendary Dusty Groove record store for a whistlestop tour through his hometown’s underbelly.

1. Shop

Dusty Groove

Record store

From jazz and blues to hip-hop and house, music runs in Chicago’s blood. And anyone seriously into rare records and vintage vinyl will know our guide Doug Arnold, buyer at Dusty Groove records on Ashland Ave. Opening for business in 1996, Dusty Groove—which has a vintage soul, funk and jazz niche—has been recognised by Rolling Stone as one of America’s best record stores. Starting as a part-time hobby selling vinyl out of an apartment on the south side, it’s now a thriving online destination and a store that opens seven days a week. “Chicago is one of the best cities on the planet for record diggers and music lovers”, says Doug, “because every record store in the city and nearby ’burbs has its own personality, its own identity, niche and style. We're not competitors, we're a community. We survive recessions, we're immune to passing trends; we're as honest and real as they come. Just like the city itself.”

2. Bike

Divvy Bike Rental

Chicago Divy bikes

“Chicago is a very bike-friendly city,” explains Doug. “If you're fit and willing, there are few better ways to take it all in, especially if you can escape the most congested downtown areas. Chicago Complete Streets is a good resource for potential routes, and you'll spot Divvy Bike rental stands all over town."

How Divvy works: This bike sharing system features thousands of bikes at hundreds of stations from Andersonville to Hyde Park, available 24/7. Each station has a touchscreen kiosk, station map, and a docking system that releases bikes using a member key or ride code. There’s no better way to explore the side streets and back alleys. 


Humboldt Park

Humboldt Park hike

A little sweaty after all that cycling? No problem. "Humboldt Park is an inner-city gem.” says Doug. “The beaches and lakefront public park spaces are well known to many, but I’d encourage visitors to the city to venture inland to some of the many other beautiful spots. Humboldt Park is a diverse neighborhood, but its heart is the park itself. If you’re not local, you'll be surprised it's such a big, lush, forest-y oasis."

Where to find it: Humboldt Park is located on the West Side of Chicago. Despite being inner city and not as well-known as some of Chicago’s other green spaces, it actually totals 219 acres and offers gyms, an inland beach, soccer fields, a lagoon, tennis courts and a replica of the Wrigley Field.

4. EAT

Big Star

Big Star tacos

"Chicago is a great town for bars, there are wonderful spots all around. Where to start?” muses Doug. “Well, Big Star in Wicker Park is great for food and drinks."

Chow down: Big Star refers to itself as "a bourbon and beer-focused, taco-slinging, late-night honky-tonk"; housed in a defunct 1940s gas station (you'll find it at 1531 N Damen), you'll party to classic country and rock & roll spun by the bar staff. The taco menu is extensive, but we'd advise starting with a couple of Taco De Panza - that's crispy, braised pork belly, tomato guajillo sauce, queso fresco, onion and cilantro.


Maria’s Packaged Goods & Community Bar

“It has an unruly name, but one of my favorite drinking spots is Maria's Packaged Goods & Community Bar in the Bridgeport neighborhood. It’s a really a great spot, and they spin music we love, so it's a natural choice.

Where it's at: Located at 960 W 31st Street in the beautiful Bridgeport, Maria's has been operating since 1986. It's half liquor store, half neighborhood tavern, providing locals with artisanal and craft beers (in bottles, cans and tap) and spirits. There are over 400 beers on offer, so you’re going to need more than one visit.