What is the best way to see Chicago in a day?

Answers from Our Experts (4)

Start your a one-day sightseeing trip to Chicago with a cup of Chicago's own Intelligentsia coffee at the Monadnock Building, and then head to Millennium Park to see your reflection in the public artwork "The Beach" and check out the "spitting" faces at Crown Fountain (water appears to spout from projected images of faces on an oversized light installation). Next-door neighbor the Art Institute of Chicago will give you a chance to look at more works. See the man behind the sunflowers in Vincent van Gogh's Self-Portrait, and you'll notice the artist's seemingly mismatched dirty-blond hair and red beard. Also take a peak at Monet's Stacks of Wheat series, which depicts the eponymous wheat through different seasons. Be sure to leave time to explore the spectacular Modern Wing, which was completed in May 2009. If you are more interested in dinosaurs or diamonds than art, the Field Museum is also nearby, as is the Shedd Aquarium.

When you're ready for lunch, The Modern Wing has three eateries, including Terzo Piano, headed by Spiagga chef Tony Mantuano. Or grab some upscale pub grub at The Gage, located across from Millennium Park on Michigan Avenue. Head back north and stroll along the Magnificent Mile. Stop in the Hancock Center's Signature Room for a drink and some of the best views in the city before catching dinner in any of the Gold Coast restaurants.

Were it not for the Chicago River, the city of Chicago would likely not have risen to its Second City prominence. That said, there is no better way to spend a glorious Chicago day than on its river. River cruises that regale [tourists on] Chicago's architectural history abound. At certain points on the river, one can view over 100 years of architectural history. If a tour boat sounds pedestrian to you, consider a private excursion with your own docent.

If you only have one day in Chicago, split the day in two. Spend the morning on the river and the lake with an architectural boat tour along the city’s two beautiful bodies of water. These boat tours offer an incredible vantage point of the towering skyscrapers and historic buildings while also offering a great deal of history about the city in general. If it’s your first time to Chicago, the boat tour is an absolute must on your itinerary as the trip off the river and into Lake Michigan offers a view of the city that you simply cannot get anywhere else in Chicago.

For the second half of the day, spend the afternoon with a hop-on, hop-off tour courtesy of Chicago Trolley & Double Decker Company. The bus tour hits so many of the city’s important landmarks and is a wonderful way to see all of them. It takes visitors to spots like Millennium Park, the Art Institute of Chicago, the Field Museum Navy Pier, Water Tower center, and John Hancock Observatory. It also offers more narrow tours that go deeper into specific areas of the city.

Lauren Viera

The quick-and-easy answer? From the water.

Even if you’re not big on tours (neither am I), I cannot say enough good things about Chicago Architecture Foundation’s Architecture River Cruise. While floating down the Chicago River, a well-educated docent points out the city’s most beautiful and historic buildings, and all you have to do is sit back, relax with a cocktail or local beer and take a snapshot or two. The views are unparalleled and the experience is unforgettable. Be sure to book in advance, as this is one of the most popular tours in the city—and for good reason.

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