The 7 Most Old-School Spots in Chicago to Eat, Drink or Just Instagram

Most days, it seems we can’t get where we’re going fast enough. The “L” is delayed, so order a Via and when it finally arrives ten minutes later, we hit traffic. Maybe it’s a sign we need to stop rushing toward the future and slow down. What better way to do that than to spend some time at a place that hasn’t changed since Prohibition? Here are seven of our favorite spots that are stuck in time…in a good way.

5 Old-Fashioned Ice-Cream Shops That Take You Back in Time

The Green Mill Cocktail Lounge

Opened in 1907, this Uptown jazz bar was once a haunt of none other than Al Capone. In fact, you can still snag a seat in his favorite booth on the bar’s west side. Just think twice before you start hatching any schemes.

4802 N. Broadway Ave.; 773-878-5552 or

The Berghoff

Back in 1898 when this German restaurant opened, you could get a beer and a sandwich for a nickel. Those prices have inflated over the years, but you can’t put a price on dining at what is easily the Loop’s most iconic restaurant.

17 W. Adams St.; 312-427-3170 or

The Richard H. Driehaus Museum

This museum, located in the former mansion of Samuel M. Nickerson, a prominent 19th-century banker, really puts the phrase “Gilded Age” in context. Seventeen types of marble as well as onyx, alabaster, carved and inlaid wood cover practically every surface. And we haven’t even touched on the collection of art and antiques.

40 E. Erie St.; 312-482-8933 or

Gene & Georgetti

Chicago’s not short on great steakhouses, so why not choose by seniority? Gene & Georgetti is the city’s oldest, having opened in 1941. While it's perfected the chops and pastas, it hasn’t messed with the ambiance: Expect a cozy vibe that takes you back.

500 N. Franklin St.; 312-527-3718 or

The Rookery

Construction of this early skyscraper was completed in 1888, but Frank Lloyd Wright redesigned the two-story skylit lobby in 1905. What remains is a prestigious Chicago landmark, listed on the National Register of Historic Places. Best of all, it’s free to just pop in and gawk.

209 S. LaSalle St.; 312-553-6100 or

Club Lucky

Club Lucky’s Formica-topped bar is an exact replica of the original, from when the spot opened in 1938. Queue your favorite Rat Pack tune on the jukebox, then sidle up to a barstool for a martini. We don’t usually say this, but ring-a-ding-ding.

1824 W. Wabansia Ave.; 773-227-2300 or

Cafe Brauer

This Prairie-style landmark boasts soaring ceilings with Tiffany-style lamps that date back to 1908. Oh, and the terrace views of surrounding Lincoln Park ain’t bad either.

2001 N. Clark St.; 312-742-2000 or

amanda nyren
Amanda Nyren

Writer, yogi, mom to about a dozen houseplants

A lifelong Chicago resident, Amanda started covering the local scene for PureWow in 2016. She's a freelance writer and content strategist.
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