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Your perfect weekend: Hyde Park

Looking to have an amazing weekend in Chicago? Here's how you can accomplish that in a single neighborhood: Hyde Park.

Photograph: Martha Williams
By Clayton Guse |

Chicago is a city of neighborhoods. Every corner of the city brings a new adventure. From hip new restaurants to free museums, conquering a single neighborhood in a weekend can feel impossible. Lucky for you, we're here to tell you exactly how to do that. This month's 'hood: Hyde Park.

RECOMMENDED: A complete guide to the Hyde Park neighborhood


Restaurants, Coffee shops

11am: Plein Air Cafe

icon-location-pin Hyde Park

Kick your weekend off with a breakfast at the University of Chicago–adjacent Plein Air Cafe. Grab a croissant sandwich or the quiche of the day, and get ready to take in one of the city’s most gorgeous neighborhoods.

Osaka Garden at Jackson Park
Photograph: Steven Kevil/Wiki Commons
Things to do, Literary events

1pm: Jackson Park

icon-location-pin Woodlawn

You can get a great taste of Chicago’s rich history at Jackson Park, the site of the World’s Columbian Exposition in 1893. It’s now home to a golf course, basketball courts and a Japanese garden that is sure to make your jaw drop.

Photograph: Krystal Thibault
Restaurants, American

4pm: Medici on 57th

icon-location-pin Hyde Park

At this point, it’s time to start drinking. Stop by Kimbark Beverage Shoppe and peruse the bounty of beer and wine. Then head to Medici on 57th Street, BYOB and have a burger and a shake. Be sure to bring a Sharpie to contribute to the rants and messages that have been left on the restaurant’s booths since the ’60s.

Court Theatre
Photograph: Martha Williams

7pm: Court Theatre

icon-location-pin Hyde Park

The Court Theatre was nominated for eight 2015 Equity Jeff Awards and took home one. The theater has a stacked winter lineup that includes Aeschylus’s Agamemnon (November 5 to December 6) and Satchmo at the Waldorf (January 7 to February 7), which was written by Wall Street Journal theater critic Terry Teachout.


Restaurants, Mediterranean

11am: Nile Restaurant

icon-location-pin Hyde Park

Start your day by stuffing your gut full of falafel and hummus at Nile Restaurant. Get there when it opens, because a swarm of U of C students will pack the place before noon.

Photograph: Josh S. Jackson
Things to do

1pm: Promontory Point

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Promontory Point (enter at E 55th St and S Shore Dr), a man-made peninsula that juts out into the lake, is a hot spot for weddings and tourists in the summer. But in the winter, you can walk along it in isolation and feel like you’re in a goddamned Carl Sandburg poem. It also has one of the best skyline views in the city.

Restaurants, Italian


icon-location-pin Hyde Park

A10 is the name of a road that travels through Italy and France. It’s also the name of a spectacular Hyde Park restaurant that straddles the cuisines of the two countries. Make a reservation in advance for Saturday dinner, and expect to spend a good chunk of change. But it’s worth it. 

Time Out says
Seven Ten Lanes
Photograph: Grace Wiley
Bars, Lounges

Seven Ten Lanes

icon-location-pin Hyde Park

Cap off your night by kicking it back to the analog age at Seven Ten Lanes. You’ll have to keep score by hand at the eight-lane bowling alley, which can be a bit perplexing, but always fun, after a few beers.


Museum of Science and Industry
Photograph: J.B. Spector
Museums, Science and technology

11am: Museum of Science and Industry

icon-location-pin Hyde Park

The Museum of Science and Industry—which you visited, what, 27 times as a kid?—still holds interest for the adult you. The historic institution is home to some of the most mind-blowing exhibits in town, from robots to a simulated coal mine.

Shopping, Lifestyle

3pm: Hyde Park Cigars and Lounge

icon-location-pin Hyde Park

Whether or not you’re a smoker, Hyde Park Cigars can turn you into a tobacco aficionado for an afternoon. It’s BYOB, and with more than 1,500 brands of cigars and an indoor smoking lounge, it’s a great setting to float off into a hazy, whiskey-ridden oblivion.

Bars, Dive bars

6pm: Woodlawn Tap

icon-location-pin Hyde Park

Just off the U. of C. campus, Jimmy’s (as it’s affectionately called by those in the know, after dearly departed original owner Jimmy Wilson) is the favored spot for the scholars to rub elbows with undergrads and working-class neighborhood regulars. Grab a cheap burger and an even cheaper beer and reminisce on a perfect weekend in Hyde Park.

More to explore