Chicago Trip Guide | Midwest Living

Chicago Trip Guide

Soaring observation decks and winding park trails show the Midwest’s biggest city in a whole new light.
+ enlarge
1 of 9
Pause »
  • 1
    Skydeck at Willis Tower
  • 2
    Seadog's Lake and River Architecture Tour.
  • 3
    Jay Pritzker Pavilion in Millennium Park.
  • 4
    Lincoln Park Zoo carousel.
  • 5
    Lakeshore trails.
  • 6
    Adler Planetarium. Photo Courtesy of Adler Planetarium.
  • 7
    The Field Museum.
  • 8
    Wrigley Field.
  • 9
    Atwood Cafe. Photo Courtesy of Atwood Cafe.

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 and their moms anchors Water Tower Place along the Magnificent Mile. Shoppers will find plenty of historical-theme dolls and clothing, plus a great cafe to enjoy lunch. (877) 247-5223;

Andy’s Jazz Club In a city full of live-music clubs, this River North spot has a sophisticated menu and an almost 40-year history of drawing crowds. (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 bike tours are a lively way to learn more about Chicago’s history. The “Historic Hyde Park and Kenwood Mansion Tour” is a pleasant, well-paced ride culminating with a stop near President Obama’s house. Politics are kept to a minimum. (312) 915-0995;

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

Buckingham Fountain One of the world’s largest fountains puts on a daily 20-minute water shows in Grant Park on the hour from 8 a.m. to 10 p.m. Free. (312) 742-7529;

Chicago Architecture Foundation River Cruise Aboard Chicago’s First Lady cruises, these colorful 90-minute history lessons—covering more than 50 buildings—depart daily, April through November. (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 theater shows at booths in the theater district and at Water Works Visitors Center.

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 The Jay Pritzker Pavilion hosts free outdoor concerts throughout the year; Crown Fountain and the Cloud Gate sculpture fascinate visitors. (312) 742-1168;

Museum of Contemporary Art An edgy, fun venue offers 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 A 150-foot Ferris wheel, the Chicago Children’s Museum, the Chicago Shakespeare Theater, restaurants and boat cruises draw visitors to the lakefront. (800) 595-7437;

Seadog Cruises Funny tour guides offer a dose of Windy City history. (888) 920-2600;

The Second City A training ground for big-name comics, the storied theater features 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 started playing at Wrigley Field in 1916. Though the park is undergoing $575 million worth of renovations, you can still enjoy some of the ballpark's 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 tiny fine-dining restaurant in the West Loop serves inventive seasonal entrees, like leg of lamb with mushrooms, grapes, onion jam and burnt cinnamon. (312) 715-0708;

The Bongo Room The funky Wicker Park cafe is known for great breakfast dishes, fist-thick breakfast burritos and seasonal flapjacks. (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 steaks are fantastic—from 20-ounce sirloins to lighter flank cuts—at the steak house at The James Chicago in River North. Try fill-your-own doughnuts for dessert. (312) 660-6000;

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 Enjoy upscale pub food and top-notch whiskey and beer close to Millennium Park. Camembert cheese and melted onion marmalade top the Gage burger. (312) 372-4243;

Lockwood Restaurant and Bar Located just off the Palmer House Hilton’s lobby, Lockwood is known for freshness. Pork belly, wild black bass and farm-raised venison are all possibilities on the dinner menu, which changes frequently. Reservations recommended. (312) 917-3404;

Mercat a la Planxa Spanish tapas star on the seasonal menu in the fine-dining restaurant adjacent to the historic 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;

Pizzeria Uno Eating deep-dish gooeyness in the little River North spot where the chain started makes the pie taste even better.  (312) 321-1000;

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;

Table Fifty-Two Chef Art Smith of Top Chef Masters fame serves Southern-influenced entrees in an elegant Gold Coast dining room. Meals start with goat cheese biscuits. (312) 573-4000;

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;

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

Hotel Allegro A renovated landmark in the Loop’s theater district blends vibrant colors with original Art Deco design. (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 A $128 million renovation breathed new life into the South Michigan Avenue hotel that once hosted 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 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;


Add Your Comment