Chicago Trip Guide | Midwest Living

Chicago Trip Guide

On the western shore of Lake Michigan, the Midwest’s biggest city blends outdoor recreation and cosmopolitan luxuries. Millions visit each year to shop the Magnificent Mile, explore Millennium Park and cheer on one of the seven pro sports home teams. Jazz clubs and theaters keep the party going into the night.
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    Skydeck at Willis Tower
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    River cruise.
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    Millennium Park
    Millennium Park
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    Buckingham Fountain
    Buckingham Fountain
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    The Boarding House
    The Boarding House
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    Freehand Hostel
    Freehand Hostel

What to do

Adler Planetarium The exhibits get a little technical for a casual visitor, but the sky shows are stunning. If you go, splurge on a theater package to see a couple of them. (312) 922-7827;

American Girl Place The mecca for young girls anchors Water Tower Place along the Magnificent Mile. Shoppers find historical- and modern-theme dolls and clothing, plus a great cafe.  (877) 247-5223;

Andy’s Jazz Club This River North spot stands out for its  40-year history of excellent live music and for dinners of filet mignon and rack of lamb. (312) 642-6805;

The Art Institute of Chicago The Modern Wing showcases 20th- and 21st-century art. The renovated older galleries span 5,000 years and include some of the world’s major works of art. The museum’s website provides downloadable mini tours. (312) 443-3600;

Bobby’s Bike Hike Guided neighborhood biking or walking tours detail Chicago’s history. On the Lakefront Neighborhoods tour, pedal past Gold Coast mansions and the Lincoln Park Zoo; sample pizza, beer and more on the Bikes, Bites and Brews tour. (312) 915-0995;

Broadway in Chicago A source for tickets to shows in the theater district. (800) 775-2000;

Buckingham Fountain In Grant Park, one of the world’s largest fountains jets into action for 20-minute shows on the hour from 8 a.m. to 10 p.m. Starting at dusk, lights and music enhance the scene. (312) 742-7529;

Chicago Architecture Foundation River Cruise Entertaining 90-minute history lessons—covering the details of more than 50 buildings—are held on the decks of Chicago’s First Lady boats. (312) 922-3432;

Chicago City Pass See five attractions—the Shedd Aquarium, The Field Museum and Skydeck Chicago; 360 Chicago or Museum of Science and Industry; and the Adler Planetarium or the Art Institute—for about half the cost of the total for individual admissions. (888) 330-5008;

The Field Museum This treasure trove of science and anthropology is a Midwest must-see, if only to meet Sue, the resident T. rex. Thanks to reciprocity agreements, you might score free admission if you show a membership card from another science museum. (312) 922-9410;

Garfield Park Conservatory A 3-acre world of plants under glass offers year-round enjoyment. Free. (773) 638-1766;

Hot Tix Get last-minute, half-price tickets to direct-from-Broadway shows and other productions at three downtown locations or

John G. Shedd Aquarium See the beluga whale calf and other Pacific Northwest coast creatures at the Abbott Oceanarium exhibit and at aquatic shows.  (312) 939-2438; 

360 Chicago The five-state view from the 94th floor is spectacular and worth admission on a clear day. (312) 751-3681;

Lincoln Park Zoo This North Side zoo often prompts visitors to marvel, “This is free?” A nature boardwalk, the children’s zoo and the carousel are reliably entertaining. (312) 742-2000;

The Magnificent Mile More than 460 high-end stores, including boutiques, department stores and high-rise shopping malls, line North Michigan Avenue. (312) 409-5560;

Millennium Park Reflecting the skyline, the Cloud Gate sculpture also reflects the elevated mood in this center for cultural activities, such as free concerts at Jay Pritzker Pavilion. (312) 742-1168;

Museum of Contemporary Art Chicago A four-story, light-filled venue in the Streeterville neighborhood displays mod works from 1945 to the present, plus evening jazz concerts during the summer.  (312) 280-2660;

Museum of Science and Industry Visitors love programs about technology, transportation and more. The exhibit You! The Experience ages your face 30 years within minutes and makes a giant heart beat in time with your pulse.  (773) 684-1414;

Navy Pier The city’s most popular attraction turns 100 in 2016 and marks the occasion with a new (bigger) Ferris wheel. Other attractions include the Chicago Children’s Museum, Chicago Shakespeare Theater, restaurants, Imax movies and boat cruises. (800) 595-7437;

Oak Street Beach Potted palm trees, a life-size chess set and access to the 18-mile Lakefront Trail make this urban beach a must.

The Second City A training ground for big-name comics (including Jim Belushi, Mike Myers and Tina Fey), the theater stages smart shows that skewer current events. (312) 337-3992;

Skydeck Chicago To experience the skydiving-esque rush of the Ledge, visit the Skydeck, located 1,353 feet above the street. (312) 875-9696;

Wrigley Field The Chicago Cubs mark their 100th anniversary of playing at the field in 2016. Some $575 million worth of on-going renovations will add modern amenities while preserving retro charms. (773) 404-2827;

Where to eat

Atwood Restaurant Try a global spin on American classics, like pan-fried sweetbreads. (312) 368-1900;

Blackbird A small fine-dining restaurant in the West Loop serves inventive seasonal entrees, like leg of lamb with mushrooms, grapes and onion jam.  (312) 715-0708;

The Boarding House Owned by a master sommelier, the place sparkles under light fixtures made with thousands of wine bottles. An extensive wine list complements entrees like venison loin with rutabaga puree, bacon and currants.

The Bongo Room The funky Wicker Park cafe is known for great breakfast dishes, fist-thick breakfast burritos and hotcakes with seasonal fruits and fillings. (773) 489-0690;

Buddy Guy’s Legends You’ll find more than great soul food and live music at the new South Wabash location. It’s especially fun to visit during Chicago’s Blues Festival in summer and when the Rock and Roll Hall of Fame guitarist and owner plays 16 shows of his own in January. (312) 427-1190;

David Burke’s Primehouse All dry-aged steaks are fantastic at The James Chicago hotel in River North. Try fill-your-own doughnuts for dessert. (312) 660-6000;

Eataly Think of this place as a multistory celebration of Italian edibles. Counter-service stations offer puttanesca-filled panini and Nutella crepes; elegant sit-down restaurant Baffo serves a six-course tasting menu; and aisles stock imported olive oils and cheeses for home cooking.

Eleven City Diner Old-school jazz washes over patrons at a South Loop destination known for its breakfasts. Try the Lincoln Park location, too. (312) 212-1112;

Frontera Grill Celeb chef Rick Bayless owns the 2007 James Beard Award-winning restaurant specializing in seasonal Mexican flavors in River North.  (312) 661-1434;

The Gage Top-notch whiskey and beer pair with meals like the Gage venison burger, with smoked Gouda, fried jalapeños, mushrooms and pickled onions, at a gastropub near Millennium Park.  (312) 372-4243;

Little Goat Diner Top Chef winner Stephanie Izard’s  casual sister of fine-dining Girl and the Goat (across the street in the West Loop) serves snacks like goat cheese chili fries and “sammiches” of braised beef.

Mercat a la Planxa Catalan-inspired tapas star on the seasonal menu in the fine-dining restaurant adjacent to the Blackstone Hotel in the South Loop. (312) 765-0524;

North Pond Farm-to-table philosophy fuels the Lincoln Park spot with pretty Chicago skyline views. (773) 477-5845;

Oiistar Get your authentic ramen fix in Wicker Park. A bowl of savory broth swims with fresh-made noodles, pork belly, mushroom, egg and garlic. Also delicious: buns stuffed with duck and wasabi.

Pizzeria Uno The deep-dish pizza craze began at this little River North spot. Pies feature crispy-edged crust, gooey cheese, toppings and a chunky tomato sauce—layered on in that order.  (312) 321-1000;

The Purple Pig Getting a spot at one of the communal tables may take an hour, but patience pays off. Linger over small plates (like the milk-braised pork) and a well-curated wine and cheese list.

Sepia A former printing house in the West Loop serves rustic food with a contemporary twist, plus throwback cocktails such as the Sepia Mule, with ginger-infused vodka, fresh lime juice and ginger beer. (312) 441-1920;

Stan’s Donuts and Coffee The double-chocolate old-fashioned doughnut is decadent on its own but even better sliced with a thin layer of fresh gelato in the middle.

Topolobampo A sleek Mexican restaurant owned by chef Rick Bayless connects to his Frontera Grill in River North and serves organic and heirloom produce. (312) 661-1434;

Where to stay

The Allerton Hotel Chicago Beyond its 1920s redbrick Renaissance exterior, the Allerton is contemporary. Rooms at this Magnificent Mile spot are comfortable with calming aesthetics. (877) 701-8111;

Embassy Suites Chicago—Downtown/Lakefront A 10-minute walk from Navy Pier, the River North hotel recently completed a multimillion upgrade. (312) 836-5900;

Freehand Hostel Aimed at social travelers, room options include a shared dorm with bunk beds, the lobby sports a craft-cocktail bar, and staff arranges group tours and runs.

Hard Rock Hotel Chicago Music fans love this salute to rock in the 1929 Carbide and Carbon Building on Michigan Avenue (musician memorabilia on display throughout the building). (866) 966-5166;

Holiday Inn Chicago Mart Plaza The affordable chain hotel in River North completed a $20 million ecofriendly renovation. Every room has a view and free Wi-Fi, and a skywalk connects to the Merchandise Mart  (312) 836-5000;

Hotel Allegro Touches of shimmering fabric echo original Art Deco design in this renovated landmark in the theater district. (866) 672-6143;

Hotel Felix The River North hotel combines a 1927 Beaux Arts building with contemporary furnishings. Sensors reduce energy usage when rooms are unoccupied. (312) 447-3440;

Hotel Chicago The high-energy, upscale hotel with a nightclub just off the lobby stands alongside the House of Blues in Marina City. (312) 245-0333;

Inn of Chicago Magnificent Mile You can walk just about anywhere from this hip boutique hotel in Streeterville. The 1920s facade complements sleek furnishings. Soak in the view from the 22nd-floor deck. (312) 787-3100;

JW Marriott Chicago A $396 million project has transformed a historical Burnham building into a luxe hotel. The property includes a 20,000-square-foot spa. (312) 660-8200;

Renaissance Blackstone Hotel Spend a bit to get a room overlooking Lake Michigan at this South Michigan Avenue hotel that has hosted 12 presidents. (312) 447-0955;

Trump International Hotel and Tower Chicago Standard rooms at this pricey (but oh-so-luxurious) hotel have soaking tubs, a kitchen, fireplace and 10-foot window wall. Sixteen, on the 16th floor, serves dinner with a view.  (312) 588-8000; 

The Virgin Hotel Ergonomic headboards support you while sitting in bed, sliding partitions create private areas in the room, and a smartphone app lets you adjust the heat and order room service.

The Wit Check-in includes a warm chocolate chip cookie, and throughout the hallways, you’ll hear the chirping of birds and crickets. In the Loop’s theater district. (312) 467-0200;

More information: Choose Chicago (312) 567-8500;


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