Wheeling Vacations

Favored for its convenient access to Chicago, this small town seems a world away from the nonstop action of the Windy City.

Wheeling has easy access to the Windy City of Chicago via the Metra rail system. Explore Chicago’s Sears Tower, Navy Pier and Millennium Park by day and head north to the quiet serenity of Wheeling for the evening. 

A family-friendly town, Wheeling is sprinkled with parks offering playgrounds and walking trails. Bring children to the Outdoor Family Aquatic Center, which features splash pools, water slides and other water activities. The Community Recreation Center offers an Olympic-sized indoor pool and state-of-the-art facilities ideal for visitors of all ages. 

Explore the walking trails of Potawatomi Woods Preserve. Named after the Native American tribe of the region, the wetland habitat is an ideal bird-watching setting. Wheeling is known for Chevy Chase Country Club. Built in 1927, the historic Tudor-style club facilities complement an 18-hole course. 

In the mid-19th century, Wheeling was a popular overnight stop for people journeying from Chicago to the Wisconsin Territory. Travelers often spent several days in the small village, leading entrepreneurs to open strings of inns and restaurants to feed and house visitors. Today, those cafés continue their prominence as Restaurant Row. Visit the 5-mile (8-kilometer) stretch of Milwaukee Avenue which features diverse cuisine. Italian, Asian Fusion, steakhouses, and more provide a culinary delight for any visitor. 

Drive 9 miles (14 kilometers) outside the village center to Chicago Botanic Garden. With 26 stunning gardens lined with trails and benches, the park is an ideal place to relax for a few hours. Head a few minutes farther east to Millard Park for waterfront access to Lake Michigan. 

Located less than 30 miles (48 kilometers) north of Chicago, Wheeling is a popular commuter town that maintains its own identity. Wheeling is most convenient to get around by car. Chicago Executive Airport is located in Wheeling, and O’Hare International Airport is less than 15 miles (24 kilometers) from the village. The Metra offers a commuter rail that runs to Chicago throughout the day. 

Read less

Top Hotel Deals

See all Wheeling hotels
1.0 out of 5 stars
1.5 out of 5 stars
2.0 out of 5 stars
2.5 out of 5 stars
3.0 out of 5 stars
3.5 out of 5 stars
4.0 out of 5 stars
4.5 out of 5 stars
5.0 out of 5 stars
Most popular package deals found by our travelers
Most popular package deals found by [originCity] travelers

Top Flight + Hotel Deals

See all Wheeling packages

Top Deals on Flights

See all Wheeling flights

Book a Vacation to Wheeling