Wrigley Field
Iconic Wrigley Field is arguably one of Chicago’s most storied landmarks, with millions of baseball fans flocking to the stadium just to get a photo in front of its famous ivy-covered exterior (whether they like the Cubs or not). The stadium anchors the Wrigleyville neighborhood, which has experienced a boon in development. A new outdoor plaza, luxury hotels, and an influx of restaurants/bars have boosted the area’s cultural cachet, so it’s worth hanging around before or after your stop at the stadium.

Shedd Aquarium

The entire marine world—from the Caribbean reef to Arctic waters—is on view on the banks of Lake Michigan. Some 32,000 animals live here. Big draws include Pacific white-sided dolphins, beluga whales, sharks, stingrays, and some awfully cute otters. The tours, which the Shedd calls “experiences” let you get up close and personal with most of them.
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Chicago Riverwalk

Located in the thick of Chicago’s downtown Loop, the Riverwalk is a lower-level path for pedestrians to enjoy an up-close-and-personal view of the Chicago River and the towering skyscrapers alongside it. The paths is straight-forward and manicured, with the major element being, well, the river. The twin corncob-esque Marina Towers are stunning from the river-level walkway, but the views also encompass Chicago greatest architecture hits, like an austere Mies Van Der Rohe (the former IBM building) and the grand Merchandise Mart.

The walking and running path follows the river’s natural curves, with different sections offering different experiences. One section features stadium-like seating, perfect for taking a break and watching the boats go by. Another area features seasonal restaurants and bars, including an outpost of City Winery, which fuels thirsty travelers with carafes of proprietary rosé and white wine during sweltering summer months.

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Museum of Contemporary Art, Chicago

The MCA, more than any other museum in town, is constantly morphing. Its relatively small permanent collection means it relies on special shows, from installations to video, and they always push boundaries. And while you might not have heard of the artists receiving solo shows at the MCA, go. Curators here have a crack eye for finding meaningful work by living artists and installing it in immersive ways. Besides the art Marisol from chef Jason Hammel (of Lula Cafe in Logan Square fame) is a distinct draw for farm-to-table fare, even for those who aren’t touring the museum.