Take in amazing views of the city’s architecture while sipping a glass of wine, eating local grub or just lounging around on this public walkway, which hugs the main branch of the Chicago River. Before you get a table at the Riverwalk’s array of restaurants and bars, you can hop aboard a boat tour or visit Urban Kayaks to rent a vessel that you can paddle yourself. Don’t leave without sitting on the steps of the River Theater (between the Clark and LaSalle bridges) and soaking up the sights.

This historic home was designed by famed architect Frank Lloyd Wright and is one of the most beautiful (and well-preserved) examples of his signature Prairie style. Looking out of the University of Chicago campus in Hyde Park, the Robie House has undergone an extensive renovation, restoring the property to its circa-1910 splendor. Step inside the home by booking a guided tour with the Frank Lloyd Wright Trust and see the art glass accents, restored furniture and a fireplace for yourself.

Immerse yourself in exhibits filled with dinosaur skeletons, ancient Egyptian mummies and an extensive collection of taxidermied animals at one of the world’s largest natural history museums. The Field Museum is packed with amazing artifacts, including a towering titanosaur skeleton (called Máximo) and a vial of nano-diamonds that came to Earth in a meteorite. Don’t forget to snap a photo with Sue, the most complete Tyrannosaurus rex skeleton ever found—it’s in the “Evolving Planet” exhibition.

Head to Lincoln Park to visit one of the only remaining zoos in the United States that offers free admission, providing a home to more than 1,100 animals. Popular Lincoln Park Zoo attractions include the Regenstein Macaque Forest, where you’ll see Japanese monkeys climbing through their habitat, and the Pritzker Penguin Cove, which contains plenty of waddling African birds. If you need a break, grab a burger, tacos or a cocktail on the Patio at Café Brauer, overlooking the Nature Boardwalk.

The cultural centerpiece of Chicago’s “front yard,” Millennium Park is stocked with public art, natural splendor and spectacular views of the city surrounding it. You’ll want to admire your reflection in the silvery Cloud Gate (a.k.a. “The Bean”), gaze at the Frank Gehry-designed Jay Pritzker Pavilion from the Great Lawn and take a stroll through the serene Lurie Garden. Spend an afternoon in Millennium Park or use it for a quick break on your journey through downtown Chicago.

Whether you love classic paintings or modern masterpieces, a visit to the Art Institute of Chicago will give you a peek at the museum’s collection of more than 300,000 artworks. Be like Ferris Bueller and see Georges Seurat’s iconic canvas A Sunday on La Grande Jatte or move on to the Modern Wing to spot the work of Andy Warhol and Jeff Koons. Don’t leave without admiring the Thorne Miniature Rooms—a collection of 68 scenes that incorporate hyper-detailed miniature architecture and furniture.

Encompassing prairies, lagoons, wide-open fields and some beautiful architecture, Humboldt Park is a sprawling green space that you can spend an entire day in. Stroll along the winding paths, admire the scenery from beneath the arches of the Humboldt Park boathouse or order some Puerto Rican food from one of the vendors along Luis Munoz Marin Drive. You can also pay your respects to the former home of Chance the Snapper, an alligator that was retrieved from one of the park’s lagoons in 2019.

A formerly abandoned stretch of elevated railway that has been transformed into a pathway for pedestrians and cyclists, the 606 is a quick and scenic way to experience multiple neighborhoods. Stretching from Humboldt Park to Bucktown, the 2.7-mile trail is packed with overlooks, public art and access to parks, coffee shops, bars and restaurants along the way. Go for a stroll, bring your roller blades or hop on a bike and experience some of Chicago’s Northwest Side from above.

If you have 90 minutes to spare, you have enough time for an entertaining crash course on the history of Chicago’s distinctive architecture, delivered from atop a boat. Operated by Chicago’s First Lady cruises and departing from the Chicago Riverwalk, each Chicago Architecture Foundations Center River Cruise is led by a trained docent who will regale you with stories about more than 50 buildings, from the Tribune Tower to Bertrand Goldberg’s River City apartment complex.

Step back in time while walking through this Chicago neighborhood, filled with historic buildings that were once a part of a community built around a railroad car company. While the Pullman Palace Car Company is long gone, you can still see vintage brick buildings like the Clock Tower and Administration Building and the Hotel Florence. Begin your visit at the Pullman National Monument Information Center, where you’ll find all the information you need for a self-guided tour.