Fourth in a series highlighting cities to which you can fly nonstop from Boston.
Said to be the birthplace of the skyscraper, this thriving metropolis, set on the shores of Lake Michigan and threaded by the Chicago River, boasts world-class museums, vibrant neighborhoods, lively urban parks, and a top-notch, continually-emerging culinary scene. Contemporary high rises and historic Beaux Art buildings spike the skyline as riverboats and water taxis cruise through the bustling downtown. It’s a fun-loving sports town too. “Fans here are crazy — maybe even more than in Boston,” says Adam Cooper, a New England native and Boston University graduate who moved to Chicago three years ago. Competitive and proud Chicagoans are also friendly and unpretentious, and eager to welcome visitors (even Bruins fans).
1.9 a.m. Take a look at the city’s most famous buildings on the Shoreline Sightseeing Architecture River Tour (600 East Grand Ave., 312-222-9328, www.shorelinesightseeing.com, adults $32, children ages 4-12 $18). You’ll see views of Trump Tower, Tribune Tower, Wrigley Building, Marina City, and others as you cruise the historic Chicago River.
2.10:30 a.m. Pop over to Millennium Park (201 East Randolph St., between Michigan and Columbus avenues, 312-742-1168, www.millenniumpark.org), a 24.5-acre urban oasis, with sprawling lawns, fountains, a reflecting pool, art and sculptures, including the 110-ton, 30-foot-high Cloud Gate (a.k.a. the Bean), designed by renowned British artist Anish Kapoor. The Frank Gehry-designed Jay Pritzker Pavilion hosts a variety of free concerts, movies, and events. For an insider look, join a free, guided tour of the park, offered by Chicago Greeters (meet at Chicago Cultural Center, 77 East Randolph St., 11:30 a.m. and 1 p.m. daily, mid-May-mid-October).
3. Noon Have lunch at hugely popular Gage (24 South Michigan Ave., 312-372-4243, www.thegagechicago.com, salads and sandwiches $9-$18, entrees $15-$38), a large, contemporary gastro pub, housed in a historic 1800s building, with dark woods, green subway tiles, and big banquettes. Classic comfort food gets updated twists, like the roasted turkey sandwich with dill havarti and alfalfa sprouts, smeared with a hot horseradish sauce, or the meatloaf sandwich with watercress and spicy mustard topped with an over-easy egg.
4. 1 p.m. Walk to the world-renowned Art Institute of Chicago (111 South Michigan Ave., 312-443-3600, www.artic.edu, adults $23, students $17), featuring one of the largest permanent collections in the country and one of the largest permanent Impressionist collections in the world. Don’t miss the Modern Wing, designed by Renzo Piano, with vivid displays of contemporary art.
5. 4 p.m. Hop on the Shoreline water taxi (all-day pass $23, 4-12 $11) to Navy Pier (600 East Grand Ave., 312-595-7437, www.navypier.com), the city’s most visited attraction, drawing more than 8.6 million people a year. The entertainment center on Lake Michigan is jam-packed with stores, restaurants, boardwalks, theaters, and family-friendly activities. Ride the 15-story Ferris wheel, stroll through Crystal Gardens, and watch a performance at one of the outdoor stages. The Chicago Children’s Museum and the Smith Museum of Stained Glass Windows are also located here.
6. 7 p.m. Steak is to Chicago what lobster is to New England, and one of the finest places to indulge your carnivore cravings is the upscale Chicago Cut Steakhouse (300 North LaSalle, 312-329-1800, www.chicagocutsteakhouse.com, $14-$59), located along the river. The classically-styled restaurant (dark woods, red velvet, linen table tops, and waiters in suits and ties) starts with prime beef, dry ages it onsite at least 35 days, and grills it on an 1800-degree broiler. The results are amazing. Our favorite is the bone-in ribeye, a perfectly charred, nicely-textured, intensely flavored piece of meat — perfect served with a side of truffled scalloped potatoes and grilled asparagus.
7. 9:30 p.m. Listen to local and world-touring musicians at the longstanding and beloved Andy’s Jazz Club (11 East Hubbard St., 312-642-6805, www.andysjazzclub.com, $5 before 7:30 p.m., $10 after). The intimate, friendly joint is known for its top-quality, live jazz.
8. 8 a.m. Start this busy day with one of the hefty breakfast platters at Wildberry (130 East Randolph St., 312-938-9777, www.wildberrycafe.com, $6.75-$11.25). Locals love their buttermilk pancakes (try the Berry Bliss, stuffed with blueberries and mascarpone and topped with strawberries, blackberries, and vanilla creme anglaise). But we like the sizzling skillets too, especially The Garden, loaded with veggies, melted cheeses, and two eggs.
9. and 10. 9 a.m. Rent bikes (Bike and Roll, 239 East Randolph St., 312-729-1000, www.bikechicago.com, $8-$20 an hour) to pedal the 18-mile-long Lakefront Trail, flanked by beaches, parks, gardens, and concession stands. Bike to Lincoln Park Zoo (Cannon Drive at Fullerton Parkway, 312-742-2000, www.lpzoo.org); the 49-acre lakefront property has an award-winning Nature Boardwalk and more than 1,000 animals — and it’s free.
11. Noon “Cheese, Swine & Wine” is the logo for the trendy Purple Pig (500 North Michigan Ave., 312-464-1744, www.thepurplepigchicago.com, $5-$21), with an impressive wine list and menu of small plates, including house-made charcuterie, cheeses from around the world, and signature “smears,” like the house-cured lardo Iberico, roasted bone marrow with herbs, and the creamy whipped feta cheese with cucumbers. Yes, there are pig’s ears and tails and pork jowls on the menu, but also an impressive milk-braised pork shoulder and Wagyu sirloin tip.
12. 1:30 p.m. Time to go shopping! The Magnificent Mile, stretching from the Michigan Avenue Bridge to Oak Street, is chock-a-block with top fashion houses, specialty boutiques, and major department stores, including Nordstrom, Neiman Marcus, and Saks Fifth Avenue.
13. 4 p.m. Zoom up 103 floors in the Willis Tower (formerly the Sears Tower) to the Skydeck (233 South Wacker St., 312-875-9696, www.theskydeck.com, adults $18, 3-11 $12), where you’ll have stunning, bird’s-eye views of the city. If you’re feeling adventurous (and are not the least bit squeamish about heights), step out on the Ledge, a glass box suspended 1,353 feet in the air.
14. 6 p.m. The culinary scene in this vibrant city is hotter than ever, and Embeya (64 West Randolph, 312-612-5640, www.embeya.com, $9-$38) is at the forefront of creativity and innovation. The contemporary, polished restaurant is under the helm of young Vietnamese chef Thai Dang, who creates artful and thoughtful interpretations of traditional Asian fare. The menu is divided into cold and hot small plates — which are big enough to share — and larger entrees. Don’t pass up the green papaya salad with cilantro, crispy shallots, and house-made beef jerky, the mussels swimming in coconut broth with a bit of Thai chili heat, and the crispy soft-shell crab. The standout rabbit leg is tenderized in a duckfat confit for 24 hours and served with garbanzo beans and royal trumpet mushrooms, and the honeyed, grilled quail is meant to be dunked in a fresh lime salt made tableside, for a perfect pairing of tastes and textures.
15. 9 p.m. End your evening with laughter at the famous The Second City comedy club (1608 North Wells St., 312-664-3959, www.secondcity.com, prices vary), training grounds for some of the world’s top comedians, including Steve Carell, Tina Fey, Stephen Colbert, and the late John Belushi and Gilda Radner.
16. and 17. 9 a.m. Spend today museum-hopping at Museum Campus, a 57-acre park on Lake Michigan linking the city’s top museums. Start at the Shedd Aquarium (1200 South Lake Shore Drive, 312-939-2439, www.sheddaquarium.org, Total Experience Pass with access to all exhibits and aquatic show, adults $37.95, 3-11 $28.95), the largest indoor aquarium in the world. Don’t miss the Stingway Touch Tank and the Jellies exhibit. At the Field Museum (1400 South Lake Shore Drive, 312-922-9410, www.fieldmuseum.org, all access pass adults $30, 3-11 $21), you can see the largest, most complete Tyrannosaurus ever discovered, stroll a re-created African marketplace, enter the Native American Pawnee Earth Lodge, walk along a replicated stretch of the Nile River, and explore a three-story Egyptian tomb. The Adler Planetarium (1300 South Lake Shore Drive, 312-922-7827, www.adlerplanetarium.org, Premium Pass adults $28, 3-11 $22) has three high-tech domed theaters showing an array of stunning light shows.
18. Of course, you can’t leave the Windy City without trying its famous deep-dish pizza. It’s worth a cab ride back to the Lincoln Park area for the pies at Pequod’s Pizza (2207 North Clybourn Ave., 773-327-1512, www.pequoidspizza.com, $6.95-$17.50, plus toppings), baked and served in a hot cast-iron pan. The cheesy crust is slightly charred, the sauce is nicely flavored, and the toppings are fresh.