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6 City Adventures in Chicago

Illinois

Chicago Area

History & Culture

It’s a breeze finding fun things to do in the Windy City, from an architectural river tour to taking in a game at one of baseball’s most famous fields.

If you want to catch Chicago from a fresh perspective, First Lady Cruises is a good place to start. Offering tours that navigate the river through the heart of the city, sightseers can learn about the Windy City’s architecture while gliding by it. Chicago is also home to the legendary Wrigley Field, fun finds like Maggie Daley Park and a Pizza City USA tour that offers a taste of some of the city’s best creations.

Chicago Air and Water Show

The Chicago Air and Water Show in Chicago, Illinois (photo by NAB Aerial)

Watch in wonder as planes take to the skies over Lake Michigan at this annual event in Chicago.

Wrigley Field

Baseball Fans at Wrigley Field in Chicago, Illinois (photo courtesy of choosechicago.com)

Visit the home of the Cubs in Chicago to take in the sights and sounds of one of the most famous sports venues in history.

360 Chicago Observation Deck

360 Chicago Observation Deck (photo by Nick Ulvieri)

Rising more than 1,000 feet over the Chicago’s Magnificent Mile, this spot provides panoramic vistas of skyscrapers, streets and vast blue of Lake Michigan.

Maggie Daley Park

Maggie Daley Park in Chicago, Illinois (photo courtesy of destination)

This 20-acre park along Lake Michigan in downtown Chicago welcomes travelers to escape the bustle of the city and enjoy the outdoors.

Pizza City, USA Tours

Pizza City, USA Tours in Chicago, Illinois (Labriola Chicago pizza photo courtesy of Pizza City, USA Tours)

James Beard Award-winning journalist Steve Dolinsky’s food tours show Chicago has much more to offer than deep-dish pies.

Chicago Architecture Foundation Center River Tour

Chicago Architecture Foundation Center River Tour in Chicago, Illinois (photo by Barry Butler)

See and learn about some of the most famous buildings in Chicago, Illinois, from the water during this Chicago River cruise.

Story: Kelly Powell
Issue: Weekend Guides

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Interior of The Henry Clay Estate in Lexington, Kentucky (photo courtesy of The Henry Clay Estate)

Ashland, The Henry Clay Estate

Explore the life of Speaker of the House and U.S Senator Henry Clay in Lexington, Kentucky, at an estate preserved by his children and grandchildren.

Ojibwe Spirit Horses at Madahoki Farm in Nepean, Ontario (photo courtesy of Madahoki Farm)

Madahoki Farm

This Indigenous farm in Nepean, Ontario, offers a glimpse into the lives of the region’s Native people by providing insight into their culture as well as the chance to see Ojibwe Spirit Horses.

Exterior of Mark Twain Study at Mark Twain Study and Gravesite in Elmira, New York (photo courtesy of Elmira College)

Mark Twain Study and Gravesite

The author behind The Adventures of Tom Sawyer did much of his work in Elmira, New York, in this octagonal study now located on the campus of Elmira College.

Vintage white Corvette on display at National Corvette Museum in Bowling Green, Kentucky (photo courtesy of National Corvette Museum)

National Corvette Museum

The Corvette earned its place in history as the first American sports car. That rich legacy is showcased today in Bowling Green, Kentucky.

Mural of Roberto Clemente outside The Clemente Museum in Pittsburgh, Pennsylvania (photo courtesy of The Clemente Museum)

The Clemente Museum

Roberto Clemente left his mark on Pittsburgh, Pennsylvania, as a player for the Pirates baseball team and as a humanitarian. His legacy lives on at this attraction that shares his story.

Third-floor gallery at the Country Music Hall of Fame and Museum in Nashville, Tennessee (photo by Diana Carniato Photography; Country Music Hall of Fame and Museum)

Country Music Hall of Fame and Museum

Learn about the legends of the genre at this Nashville, Tennessee, attraction where names like Hank Williams, Patsy Cline, Reba McEntire and Garth Brooks are honored.