Deuce's and The Diamond Club

Deuce's and The Diamond Club

Start your tour of the neighborhood at Belmont Harbor (3158 Lakefront Tr.). Sail right past the dog beach, make your way to the south harbor, and look up. That’s where you’ll find people learning to fly on the outdoor trapeze rig operated by TSNY Chicago (773-484-8861,; two-hour classes from $47), a New York–based school that runs this waterfront facility all summer, through mid-October, weather permitting. A short trot north, Waveland Park (3500 N. Recreation Dr.) has ten first-come, first-served tennis courts. Grab a court with a friend or take lessons through Tennis on the Lake (3650 N. Recreation Dr.; 773-278-8877). After a grueling third-set tiebreaker, flop onto a deck chair and sip an electrolyte-replacement drink from Tennis on the Lake’s pro shop, called the Racket Shack, which sells energy bars, salty snacks, and hot dogs; this season, the shack is whipping up Jamba Juice smoothies and making barbecue Fridays through Sundays from 9 a.m. to 9 p.m. On June 30 and July 1, throw some gel in your hair and be one of the first to experience the new Wavefront Beachfront Music Festival ( at Montrose Beach, which celebrates electronic dance music. Near the fest site, check out The Dock at Montrose Beach (200 W. Montrose Harbor Dr., 773-704-8435; entrées from $9)—it opened last summer—for dog-friendly waterfront dining on burgers and margaritas.

Heading west, work up an appetite with a walking tour. First, traverse Alta Vista Terrace (two blocks west of Sheffield Avenue between Byron and Grace Streets), a gem of a block that was developed by Samuel Gross in 1904 as a replica of a charming row-house-lined street in London’s Mayfair area. To the west on Irving Park Road, ramble through Graceland Cemetery (enter at 4001 N. Clark St.; 773-525-1105). Seek out the grand memorials of famous Chicagoans such as Potter and Bertha Palmer, Marshall Field, Ludwig Mies van der Rohe, Daniel Burnham, and Cyrus McCormick. But don’t forget to notice Graceland’s beautiful landscaping, chronicled earlier this year in Graceland Cemetery: A Design History, a new book by Christopher Vernon.

Affirm life with a seat on one of the neighborhood’s many charming restaurant patios. On the weekends, grab a tree-shaded spot for brunch at Café 28 (1800 W. Irving Park Rd., 773-528-2883; entrées from $17), a Cuban-Mexican bistro that’s good for superspicy Bloody Marys and a rich asparagus and Serrano ham Benedict. At Café Orchid (1746 W. Addison St., 773-327-3808; entrées from $11), a quirky Turkish BYO, free parking, flower-draped outdoor tables, and top-notch hummus are the draws. Top Chef lovers should visit Frog n Snail (3124 N. Broadway, 773-661-9166; entrées from $14) to see what Dale Levitski is up to (hint: something about mussels, frites, and profiteroles); grab one of the four sidewalk tables.

The June 24 Pride parade may be over when you read this, so get the full Boystown experience by hanging out on the patio of the legendary Sidetrack nightclub (3349 N. Halsted St., 773-477-9189; cocktails from $5) or sipping frozen cocktails at D.S. Tequila (3352 N. Halsted St., 773-697-9127; cocktails from $5), a buzzy recent addition to the scene (hightail it straight to the outdoor seating). In Wrigleyville, peer out at the drunk baseball fans from the civilized patio at Deuce’s and The Diamond Club (3505 N. Clark St.; 773-644-5554). Indulge in some less-overt people watching when you pick up an ice-cream cone at Windy City Sweets (3308 N. Broadway, 773-477-6100; cones from $3) and enjoy it on a sidewalk bench. We recommend playing the game Guess Who’s on a First Date among the many couples occupying the outdoor two-tops at PingPong (3322 N. Broadway, 773-281-7575; entrées from $10) and Wakamono (3317 N. Broadway, 773-296-6800; entrées from $9).

Photography: Neil Burger/ of Deuce's and the Diamond Club