Traveler: Get a Second Wind in Chicago

Here, 25 fresh ideas for the city’s regulars.

1.  You can see some amazing creatures at the Shedd Aquarium—but one of the most spectacular sights isn’t even inside. A big grassy hill behind the building faces a panoramic vista of Lake Michigan and the skyline, with the bonus of Lakefront Bike Trail people-watching at its foot. 1200 S. Lake Shore Dr., 312-939-2438,
2.  Willis Tower’s glass observation boxes that jut out over the city raised the stakes on sky-scraping gut checks (especially when the coating on one of the floors cracked this spring). But the John Hancock building answered in April with Tilt, daring visitors to stand in a windowed compartment while it slowly tilts forward until they’re leaning above the street—94 stories high. 875 N. Michigan Ave., 312-751-3681,
3.  The suave panache of Top Chef allstar Fabio Viviani may initially lure diners to his River North–sited Siena Tavern, but the tender pastas, 12-hour–braised osso buco, and coccoli—pockets of puff pastry accompanied by cheese, prosciutto di Parma, and truffle honey—are what they’re likely to Instagram. 51 W. Kinzie St., 312-595-1322,
4.  Devon Avenue, the nexus of Chicago’s Indian and Pakistani communities, might be the most exotic street in the Midwest. You’ll find everything from mystery meats to 220-volt appliances to oversized suitcases for sale here, but the best reason to go is the $3.49 lunch special at Annapurna. The service could be better, and you might have no idea what you’re ordering, but it always tastes good. 2608 W. Devon Ave., 773-764-1858,
5.  The “Mag” Mile might as well stand for magnet. Yes, it’s magnificent, but it’s also touristy and crowded. Lose the gawkers and take your spending money to downtown Evanston instead. The northern suburb, home to Northwestern University, is accessible by El and Metra trains. Hit The Mexican Shop (801 Dempster St.) for affordable jewelry and accessories, Uncle Dan’s Great Outdoor Store (901 W. Church St.) for ombre crochet Toms, Talia (1526 Chicago Ave.) for boutique European clothing labels, and Al’s Deli (914 Noyes St.) for the best iced butter cookie in the world.
6. We can’t say we’re surprised that one of Chicago’s top sweet spots has its roots in our state. Ranked among the country’s best bakeries of its kind by Food & Wine, Hoosier Mama Pie Company gets its name honestly—owner Paula Haney attended Brebeuf and IU before working in Chicago kitchens, once alongside celeb chef Grant Achatz. Try the banana cream. for locations
7.  Riding the crest of enthusiastic reviews for its 2013–2014 performances, the Goodman Theatre (which has premiered works by Tennessee Williams and David Mamet since the Art Institute of Chicago opened it in 1922) began its self-proclaimed theater “dream season” this year with Ask Aunt Susan in the Owen and is now showing Brigadoon in the larger Albert space (June 27–Aug. 3). Bravo, Goodman. 170 N. Dearborn St., 312-443-3800,
8.  The only bad thing about the addictive bacon-date-and–goat-cheese, sweet corn, and Malbec beef empanadas at the 5411 Store is that you’ll be three hours away from satisfying your next craving when you return to Indy. This is a great budget, BYOB dining option, but there are only a handful of tables, so consider going at off times. 2850 N. Clark St., 773-755-5411, 
9.  Some of the artifacts from the 1893 World’s Columbian Exposition (like preserved exotic animals) haven’t been seen by the public for 120 years, but now they’re on view, along with blown-up photos of the lavish White City, in the exhibit Opening the Vaults: Wonders of the 1893 World’s Fair. The display runs at The Field Museum through Sept. 7. 1400 S. Lake Shore Dr., 312-922-9410,
10.  You can pay big bucks to hear live music in Chicago, or you can hang out at one of the Old Town School of Folk Music’s free weekly jams, where you can listen to up-and-coming local talent—or pick up a guitar and sing along. Wednesdays and Thursdays at 4544 N. Lincoln Ave., Saturdays at 909 W. Armitage Ave.;
11.  Plenty of visitors check out Frank Lloyd Wright’s home and studio in Oak Park as well as some of the houses he designed in the neighborhood, but very few architecture tourists venture to the adjacent, just-as-walkable-and-classy River Forest, which has five lesser-known Wright homes, the FLW–designed River Forest Tennis Club, and dozens of other gorgeous, historic estates set along broad, tree-lined streets.
12.  If you can stand a bit of mansion envy, drive scenic Sheridan Road on a Sunday morning to see how Chicago’s 1 percent lives. Stop in North Shore burgs Winnetka, Glencoe, Highland Park, and Lake Forest, all of which have storied, walkable downtowns with plenty of independent shops and restaurants. Take Lake Shore Drive north until it ends, and immediately turn right onto Sheridan Road.
13.  The Thompson boutique hotel opened last fall to buzz about the modern decor (turquoise velvet sofas in each guest room) and hip amenities (reques room-service cookies and individual jugs of milk)—not to mention the on-site restaurant, Nico Osteria, an Italian seafood spot from the team behind Chicago standouts Blackbird, Avec, and The Publican. From $459/night; 21 E. Bellevue Pl., 312-266-2100,
14.  Why compete for a patch of sand with all the preening juiceheads and tourists at Oak Street and North Avenue beaches downtown when you can head up to the North Shore’s unspoiled, unpretentious Gillson Park beach in Mayberry-esque Wilmette? The broad expanse of sand is pristine and never too crowded. Rent a kayak or a stand-up paddleboard. 800 Gillson Park Dr.,
15.  There’s no signage to indicate you’ve arrived, but whiskey-centric River North speakeasy UNTITLED blooms into a posh multi-level drinks-and-dinner hotspot once you finally figure out where it is and how to get inside. (Look for the doorman between CVS and a parking garage.) 111 W. Kinzie St., 312-880-1511,

1929 indoor pool at the InterContinental hotel, Chicago
1929 indoor pool at the InterContinental hotel

16.  Dive into the same ornate 1929 indoor pool where actor/Olympian Johnny Weissmuller once competed. Located in the InterContinental hotel on the Mag Mile, the showy 25-meter-long swimming hole still looks resplendent with Spanish Majolica tile, fish-scale-design windows, and a terra cotta Neptune fountain. From $359/night; 505 N. Michigan Ave., 312-944-4100,
17.  If you found the BODIES exhibit more fascinating than gruesome, check out the International Museum of Surgical Science in Lincoln Park. Some of the exhibits are a little creepy (death masks, amputation saws), but the medical paintings and bone sculptures are works of art. 1524 N. Lake Shore Dr., 312-642-6502,
18.   EVENTS
Summer shows in Chicago can be as crowded as the beach, but these three July happenings will be worth elbowing your way into.
Sheffield Garden Walk & Music Festival
July 19–20,
Buy a program and take a self-guided walking tour of more than 80 private residential gardens, many of them nestled around stately Victorians and row houses in this historic district.
The Last Ship
Through July 13,
Sting created an original score for this musical, inspired by his childhood in an English shipyard town. After its debut run at Bank of America Theatre, it’s heading to Broadway.
Chicago SummerDance
Fridays through Sundays,
The city’s biggest dance floor covers 4,900 square feet outdoors in Grant Park. A free dance lesson precedes two hours of random strangers jiving together to live music. Bueller? Bueller?
Chicago2819.   EATALY CHICAGO
You can’t possibly eat your way through Mario Batali and Joe Bastianich’s 63,000-square-foot temple of Italian gastronomy (43 E. Ohio St., 312-521-8700, But you can buy the goods to cook something delizioso at home.
Giraudi chocolate bars with wrappers by Italian artist Georgia Galanti. $7.80 and up
Antica Dispensa Paglia & Fieno spinach and egg tagliolini pasta nests. $5.80 for 8.8 ounces
Villa Manodori lemon olive oil. $21.80 for 8.45 ounces
Tassoni Cedrata soda, made in Italy since 1956. $2.48 for 6.3 ounces
Niasca Portofino pesto-and-tomato sauce. $14.80 for 10.6 ounces
20.  For the baseball purist, there’s no better way to soak up the pastoral charm of Wrigley Field, 100 years young this season, than a midweek day game, a tradition that’s become endangered in recent seasons as the Cubs have moved toward an evening schedule. Tickets for those rare Wednesday and Thursday afternoon match-ups are dirt-cheap and fill the place with hardcore bleacher bums. 1060 W. Addison St., 773-404-2827,
21.  But if you’ve come to the old ballpark in search of a different kind of ball, you might consider the rooftops along Sheffield and Waveland avenues, which compensate for a distant view of the action with all-you-can-eat-and-drink packages. The revelry doesn’t come cheap, but Cubs fans have good things to say about the 3639 Wrigley Rooftop. All-inclusive tickets start at $125.
22.  It’s no Canyon Ranch, but Chicago boasts several destination spas in downtown hotels, most notably The Peninsula. Some of the Asian-based luxury chain’s signatures take a little getting used to—like the way housekeepers deferentially stand against the wall when a guest passes by—but at the spa, there’s no tinge of culture shock. The wood-walled sanctuary smells of eucalyptus and offers a full menu of treatments, including a massage performed with bamboo rods. From $460/night; 108 E. Superior St., 312-337-2888,
23.  Doesn’t the lake look pretty? Remember, it’s not just for show—it’s actually navigable. And the view gets better offshore from the deck of the Red Witch, a double-masted wooden ship. Choose a two-hour evening cruise on Wednesday or Saturday night to watch fireworks over Chicago’s skyline, and be ready to volunteer if you want to help hoist a sail. Feel free to bring snacks aboard, too, but this isn’t the right time or place for deep-dish pizza. (Drinks—wine, beer, soda, and water—are available for purchase on the ship.) $110 per person. Burnham Harbor, 599 E. Waldron Dr., 312-469-0233,
A savory-sweet pop-tart at 2 Sparrows
A savory-sweet pop-tart at 2 Sparrows

24.  Though the chic Merchandise Mart design showrooms sell only to the trade, any decorating junkie looking for inspiration can wander freely through DreamHome on the ground floor. Celebrating its 10th anniversary this summer, the display currently includes six poshly decked-out rooms (through Dec. 7) and has previously featured the work of famed Chicago decorator Nate Berkus. 222 W. Merchandise Mart Plaza, 312-527-7058,
25.  Chicagoans do not mess around when it comes to inventive brunch. And perhaps no eatery better proves the point than Lakeview’s 2 Sparrows, where toques bang out sweet and savory housemade pop-tarts (foie gras cherry!) alongside a Bloody Norseman made with locally distilled aquavit and garnished with a hunk of beef jerky. 553 W. Diversey Pkwy., 773-234-2320,
Photos by Travis Roozee; 5411 Store photo by Anna Knott

This article appeared in the July 2014 issue.