8 City Adventures in Chicago, Illinois

Explore the architecture of the Windy City on a Chicago Architecture Foundation Center River Tour and take in a Chicago Cubs game at the legendary Wrigley Field

Visit the United States’ third largest city for a multitude of downtown adventures. View planes taking to the sky at the Chicago Air and Water Show, explore the concrete jungle on segway or book a stay at the 21C Museum Hotel.

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. 

Absolutely Chicago Segway Tours’ Chicago Haunted Tour

Absolutely Chicago Segway Tours in Chicago Illinois (photo courtesy of Absolutely Chicago Segway Tours)

The Ghosts and Gangsters tour offers a fun way to explore Chicago while connecting with its history.

21c Museum Hotel

Inside the 21c Museum Hotel in Chicago Illinois (photo by Julie Soeffer)

This hotel in Chicago, Illinois, features more than 10,000 square feet of gallery space, including a 400-person capacity main gallery, that is free and open to the public. 

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. 

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.