Jazzin' at the Shedd

Jazzin' at the Shedd

1

Estate Ultra Bar

West Town
Average cocktail, $10; 1 foot from water

You practically need a map to get there, but once you’re out on the terrace over the Chicago River, it’s easy to see why clubby twenty-somethings bothered to find it. You’ll have to yell to be heard. 1177 N. Elston Ave.; 312-582-4777

2

Bridge House Tavern

River North
Average cocktail, $10; 3 feet from water

Outdoor seating is tucked along the lower level at this tavern, where plenty of snacks (popcorn, onion rings) round out a charmingly schizophrenic drink menu. Skip the cocktails and stick with whiskey, straight up: There’s a whole lot of it on this nicely edited list. 321 N. Clark St.; 312-644-0283

3

Japonais

River North
Average cocktail, $13; 4 feet from water

Sushi fanatics may have moved on to fizzier spots, but this glam destination restaurant on the fork of the North Branch still offers serene riverside lounging and delicious sake and shoshu cocktails. 600 W. Chicago Ave.; 312-822-9600

4

Chicago Cut Steakhouse

River North
Average glass of wine, $20; 10 feet from water

Observe the unholy high-roller schmoozing in the dining room as you make your way to the terrace—where you may drink without dining. The view will be worth the effort. 300 N. LaSalle St.; 312-329-1800

5

Smith & Wollensky

River North
Average cocktail, $13; 10 feet from water

Don’t even think of ordering anything other than a dry martini, except maybe a gin and tonic. You can sit on the terrace, one story above the water, unperturbed between 3 and 6 p.m.—or until the dinner crowd descends. 318 N. State St.; 312-670-9900

6

Waterfront Cafe

Edgewater
Average cocktail, $7; 15 feet from water

Join families with kids at this throwback seaside-style café, serving beer, wine, and sangría by the pitcher. 6219 N. Sheridan Rd.; 773-761-3294

7

Quay Restaurant & Bar

River East
Average cocktail, $10; 25 feet from water

Anchor yourself—alongside a sophisticated crowd of adults—on the 2,000-square-foot atrium patio overlooking a quiet inlet of the Chicago River. The classic cocktails, such as the Plymouth-based French 75, deserve a second round. 465 E. Illinois St.; 312-981-8400

8

North Pond

Lincoln Park
Average cocktail, $13; 38 feet from water

Pick your poison at this stately pondside spot, from a lush wine list or the locally driven cocktail menu, and then toast Bruce Sherman, who bagged this year’s James Beard award for best chef in the Great Lakes region. 2610 N. Cannon Dr.; 773-477-5845

9

Jazzin’ at the Shedd

Museum Campus
Average cocktail, $8; 100 feet from water

Straight-up jazz alternates with bossa nova on the museum’s beautiful lakefront terrace. This event kicks off Wednesdays at 5 p.m., plenty of time for drinks and appetizers before Navy Pier’s weekly fireworks show at 9:30. 1200 S. Lake Shore Dr.; 312-939-2438

10

Castaways

Gold Coast
Average cocktail, $8; 200 feet from water

There will come an afternoon when you’ll find yourself flip-flopping—sweaty and sunburned—toward this giant fake beached boat, and you’ll hear yourself order a Jamo (Jameson and soda) as you stumble into a seat amid the gaggle of brohams in board shorts, and you’ll enjoy it. No judgments. 1603 North Lake Shore Drive at North Avenue Beach, 773-281-1200

Photograph: John G. Shedd Aquarium