Two-Day Chicago Getaway | Midwest Living

Two-Day Chicago Getaway

One Chicago CityPass ($96) grants holders access to up to five attractions in addition to sweet perks (go ahead, skip the line). Interested? Here’s how we’d make the most of a weekend in Chicago with a pass.
The Ledge is part of the Skydeck at Willis Tower; it hangs 1,353 feet above Wacker Drive.
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The Field Museum
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North Michigan Avenue
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Navy Pier.
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Day 1

The Museum Campus conveniently encompasses a trio of CityPass attractions within its 57 acres of rolling hills, open green spaces and wide paved paths.

The Field Museum is home to Sue, the world’s largest T. rex skeleton, plus the stunning Grainger Hall of Gems.

At Shedd Aquarium, dolphins and beluga whales live in the Oceanarium.

Inside the Adler Planetarium, the impressive Grainger Sky Theater gives viewers a tour of the solar system.

Grab dinner on South Wabash at Buddy Guy’s Legends, where soul food (jambalaya and po’ boys) and live music restore weary travelers. Nearby, relax in freshly styled rooms at the Essex Inn (from $75).

Day 2

Impressionist paintings and American classics such as American Gothic are just a few of the collections at the Art Institute of Chicago. (CityPass grants access to either the Art Institute or Adler Planetarium.) Don’t overlook the fantastic dining options; upscale Terzo Piano’s menu stars Italian classics.

Seven blocks away, visitors thrill to the views from the Ledge, a clear-glass case jutting out from the 103rd floor of Willis Tower.

Still have time? Visit either the Museum of Science and Industry or the 360 Chicago (formerly the John Hancock Observatory).

For dinner, Sepia in the West Loop entices diners with artisanal wines and entrees like duck breast with beets. 

For information: Choose Chicago (312) 567-8500; City Pass

More Chicago favorites

Navy Pier It’s easy to spend an entire day at Navy Pier and still not do it all. Stroll the nearly mile-long pier and take in stunning views of Lake Michigan and the skyline. Speedboat tours show off the scenery, as do lively dinner cruises. The Chicago Children’s Museum encourages hands-on learning, and an Imax theater presents the latest big-thrill flicks. Harry Caray’s serves solid pub and Italian fare, and in the summer, twice-a-week fireworks over the lake cap it all off. (312) 595-5282;

Magnificent Mile We can’t count how many times we’ve walked up and down North Michigan Avenue. But it felt even more magical one night during the holiday season when we slid into a horse-drawn carriage and saw the Magnificent Mile in a whole new way. We gazed up at the gorgeous light displays, listened to the clip-clop of hooves on the streets and admired tony window displays in the Gold Coast. Even the cold couldn’t dim our sense of wonder. (312) 567-8500;

Grant Park The Art Institute of Chicago, the Museum Campus, Millennium Park—these famous landmarks all live in Grant Park. Visitors can also stroll through the Lurie Gardens, catch free concerts at Jay Pritzker Pavilion, explore art installations, or picnic on a grassy hill and admire beautiful azure blue Lake Michigan. (312) 742-3918;

Chicago Architecture Foundation River Cruise These colorful tours explore the city’s history as told through its classic and brand-new buildings. Cruises depart daily, April through November. (312) 922-8687;

Night out It’s not fancy, but bowling at the neon-spangled Waveland Bowl in Northcenter certainly is fun ( In the evenings, Cosmic bowling has you aiming for the pins amid black lights, fog machines and classic rock. After a game or two, dig into a burger accompanied by a craft brew at The Fountainhead, an award-winning gastropub in nearby Ravenswood (

5 Great Places to Get Vintage

1 Wrigley Field The life of a Cubs fan is one of highs and lows. But for the past 101 years, Wrigley has remained a constant, welcoming fans with the same ivy-covered outfield and manual scoreboard (since 1937). Though the park started $575 million worth of renovations in 2014, you can still enjoy some of the ballpark’s retro charms. (866) 800-1275;

2 Gene and Georgetti A meal at Gene and Georgetti, Chicago’s oldest steakhouse, is like a scene from The Godfather. Frozen in 1941, its wood-paneled walls shelter velvety red chairs where regulars knock back the stiff martinis and slabs of prime rib that made this restaurant a standard. Steaks range from $40 to $54. (312) 527-3718;

3 Green Mill Cocktail Lounge Founded in 1907, this nightclub gained notoriety when it became the haunt of Prohibition gangsters. Still known as Chicago’s best jazz club, it fills up fast. (773) 878-5552;

4 Brimfield Browse 1950s and ’60s Americana ranging from $1 to $25,000. The shop is among the 20-plus vintage stores centered around North Clark Street. (773) 271-3501;

5 Hotel Lincoln Contemporary rooms, mod chandeliers and a reception desk of drawer fronts give the 1928 building in the Old Town Triangle flair. From $199. (855) 514-8112;

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