Above:Green Mill Photo: Chris Sweda/Chicago Tribune
If Chicago’s neighborhoods could talk, once-regal Uptown might tell the best tales. The intersection of Broadway and Lawrence, for instance, used to be an entertainment epicenter anchored by several opulent theaters—the Aragon, Riviera, and Uptown—that brought in Hollywood’s biggest names. Uptown even had a film studio, and stars such as Charlie Chaplin, Bob Hope, and Gloria Swanson lived in the area. Though the old-school glitz has faded, the streets are now lined with eclectic shops and ethnic restaurants (including some of the city’s best pho spots). Look for Uptown to perk up—dare we say, regain some of its splendor—when the CTA wraps up its massive revamp of the Wilson station later this year.
1. Claude Seymour House
This 12,000-square-foot beauty takes up five—five!—city lots and showcases classic Prairie elements such as horizontal features and ornate stained glass windows.
2. Graceland Cemetery
Famous Chicagoans—among them Ernie Banks, Daniel Burnham, and Roger Ebert—are buried here. Don’t miss the Louis Sullivan–designed Getty Tomb, a designated city landmark built in 1890.
3. Margate Park
Settle in with a book while the kids hit the modern playground, custom-designed with sculptures, mosaics, and interactive art. Bring Fido—there’s a dog park here, too.
4. St. Mary of the Lake Church
Dedicated in 1917, the Renaissance-style church is an amalgamation of three Roman cathedrals, with marbled pillars, coffered ceilings, and stunning paintings.
5. West Argyle Street
This city experiment—a “shared” street that gives equal preference to bikes, cars, and pedestrians—is still working out the kinks. Its shops, bakeries, and Vietnamese eateries are worth a stroll anyway.
6. Ace Fashion Trading Company
It’s not exactly Michigan Avenue, but if you need a scarf for less than $4 or a string of costume-caliber pearls, look no further.
7. Nearly New Bikes
Come in with $100, leave with a stylin’ used bike—hello, summertime cruising—that’s been expertly repaired. Hit the ATM first, though: It’s cash only.
This cute family-run shop sells locally made jewelry, gift-worthy candles, and adorable stuffed animals to rival any toy store’s.
You’ll find everything from live bamboo to waving gold kitties (you know what we mean), plus some crazy good deals on unusual kitchenware.
10. Woolly Mammoth
One man’s creepy is another’s eccentric (yet oddly cool) collection of doll parts, taxidermied squirrels, and vintage surgical tools.
Eat & Drink
11. 42 Grams
This relative newcomer to fine dining has two Michelin stars thanks to its Charlie Trotter–trained chef, Jake Bickelhaupt.
12. Baker & Nosh
Here’s some karma: The always-packed indie coffee shop serving flaky croissants and rich scones recently took over a former Starbucks.
13. Demera Ethiopian Restaurant
Step 1: Order No. 16, a choose-your-own-meat bonanza. Step 2: Wrap it in spongy injera bread. Step 3: Wash it down with Castel, an Ethiopian lager. Step 4: Repeat.
14. Green Mill Cocktail Lounge
Once frequented by Al Capone, this iconic gin joint still reels in the top jazz players in town. The martinis are expertly mixed, and the plush velvet booths are old-school swank in the best way.
15. Uptown Pho
If you’re not feeling the pho (pronounced fuh)—a belly-warming broth teeming with beef, scallions, cilantro, and spice—the banh mi is solid. But seriously: Get the pho.
16. Uptown Underground
You literally have to go underground to find this old-timey “retrotainment”: cabaret, burlesque, magicians, acrobats, and more.
Throughout May:City Lit Theater’s comedy Forty-Two Stories explores the dynamics of a colorful Lake Shore Drive high-rise and its motley crew of residents.
Throughout May:Watch the tale of a legendary chanteuse unfold in Black Ensemble Theater’s Black Pearl: A Tribute to Josephine Baker.
May 1:At Uptown Underground, the Skivvies play eclectic tunes on the cello and ukulele—in their underwear, naturally.
May 10:Alt-rock heroes the Jesus and Mary Chain bring their feedback-drenched pop and shoegazing angst to the Riviera Theatre.
May 19 to 20:Catch the drumming and elegant jazz of the Dave King Trio at the Green Mill Cocktail Lounge.
Did You Know?
The J. Geils Band played the last show at the now-shuttered Uptown Theatre on December 19, 1981.