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.
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.
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.
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.
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.
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.
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.
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.
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.