An Insider’s Guide: 48 Hours in Chicago

If you ask New Yorkers why Chicago is called Second City, they might say (with a side-eye and a huff) that it’s because it doesn’t compare to NYC.

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If you ask New Yorkers why Chicago is called Second City, they might say (with a side-eye and a huff) that it’s because it doesn’t compare to NYC. But ask anyone from Chi-Town, and you’ll find that there’s nothing second rate about this amazing city.

Showy and dazzling, Chicago offers plenty of razzmatazz, but you might not see it if you spend your quick trip here elbowing your way through crowds. Make the most of the time you have by shying away from tourist traps in favor of spots you might visit if you were a lifelong Cubs and Bears fan.

Millennium Park

OK, OK. This one is a little touristy. But there’s so much to do and see in Millennium Park that you really wouldn’t want to miss it. Plus, it’s within easy walking distance of many other downtown hotspots, so it’s pretty convenient. Don’t miss the opportunity to snag a selfie by The Bean or take a self-guided tour of Lurie Garden — pretty in all four seasons. Check out the public art, including exhibits at the chapel or the sculptures and fountains throughout the park. If you’re lucky, you might even make it for a free concert at the Jay Pritzker Pavilion.

Female tourist standing outside in Millenium Park in front of The Bean smiling in Chicago during daytime

Source: Adobe Stock

Maggie Daley Park

If Millennium Park is a little too crowded for you, then try Maggie Daley Park instead. There’s a great playground for kids and a sweet rock-climbing wall set below towering skyscrapers. Go ice skating at the skating ribbon, where you can also catch killer views of the skyline.

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Chicago Cultural Center

While everybody else is heading to the Art Institute of Chicago or the Museum of Contemporary Art, why not explore the Chicago Cultural Center instead? Free admission is the first perk you’ll experience. After entering this historic building, you’ll see some incredible architecture, including the largest Tiffany stained-glass dome in the world. Catch a free concert, and browse the rotating exhibits.

sign for the Chicago Cultural Center on the outside marble wall of the building, next to the entry with flowers in the background

Source: Shutterstock

The Driehaus Museum

Although it’s located near the famed Miracle Mile, the Driehaus Museum is still off the beaten path. It gives you a good look at how Chicago’s better half lived during America’s Gilded Age, which lasted from the 1870s through the early 20th century. This refurbished home has a gorgeous stained-glass dome, 17 types of marble in the main hall, lavish furniture, and tons of artwork.

Big Monster Toys

Wanna feel like a kid again? Step through the oversized door at Big Monster Toys, and you’ll think you’ve arrived at Santa’s workshop. You’re greeted by a giant purple monster — very friendly, not to worry — and you can shop or tour the studio where some of the most famous toys were invented. Its oversized decorations, such as a 25-foot giraffe and a full-size caboose, are enough of a reason to get your rear in gear to check it out. If you have kids along with you, this stop is an absolute must.

Garfield Park Conservatory

Welcome to the jungle! No, not the concrete jungle. In addition to 12 acres of outdoor gardens, Garfield Park Conservatory also has a real-life, honest-to-goodness indoor jungle. No matter what time of year it is, you might work up a sweat while you stroll through the Palm House, the Conservatory’s largest room, with its perfect tropical landscape and plenty of warm-weather plants.

A daytime view of the exterior of the Garfield park conservatory in Chicago with green trees and shrubbery and a clear, blue sky

Source: Adobe Stock

Do these tips get you excited for your next trip to the Windy City? Share your travel photos of Chicago with us on Facebook.

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