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.


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    Willis Tower.
  • 2
    Seadog's Lake and River Architecture Tour.
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    Jay Pritzker Pavilion in Millennium Park.
  • 4
    Lincoln Park Zoo carousel.
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    Lakeshore trails.
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    Adler Planetarium. Photo Courtesy of Adler Planetarium.
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    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. See reviews and ratings.  (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. See reviews and ratings. (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. See reviews and ratings.  (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. See reviews and ratings. (312) 922-3432;

Chicago City Pass See five attractions—the Shedd Aquarium, The Field Museum and Willis Tower Skydeck; the John Hancock Observatory 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;

DuSable Museum of African American History An upcoming exhibit showcases artwork from African-American museums. Browse the gallery of African art, too. (773) 947-0600;

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. See reviews and ratings. (312) 922-9410;

Garfield Park Conservatory A 3-acre world of plants under glass offers year-round enjoyment. Free. See reviews and ratings. (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. See reviews and ratings.  (312) 939-2438; 

John Hancock Observatory The five-state view from the 94th floor is spectacular and worth admission on a clear day. See reviews and ratings. (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. See reviews and ratings. (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. See ratings and reviews. 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. See reviews and ratings.  (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. See reviews and ratings. (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;

Willis Tower To experience the skydiving-esque rush of the Ledge, visit the Skydeck, located 1,353 feet above the street. See reviews and ratings. (312) 875-9696;

Wrigley Field The Chicago Cubs started playing at Wrigley Field in 1916, and the building still sports the original 1937 scoreboard. It’s also the last pro stadium to have ivy in the outfield. Tours available. (773) 404-2827;

Click ahead for where to eat and where to stay.


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