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Westchester Vacation Packages

Westchester is a popular destination within Chicago. It makes up part of an important city that is home to 2,700,000 inhabitants. Westchester is about 13 miles (21 kilometers) from Chicago’s downtown area. If you are flying in, Westchester is approximately 8 miles (13 kilometers) away from Midway International Airport.

Many of Chicago’s highlights can be found within easy driving distance of Westchester, so it is a great place to base yourself while you are in town. Stevenson Park and the Oak Brook Golf Course are just two of the best places to explore here. Two other interesting attractions you’ll find within a short distance of Westchester are Brookfield Zoo and the York Woods County Forest Preserve.

Chicago’s heart is also filled with interesting places to visit, like Willis Tower and McCormick Place. Don't return to Westchester without a stop at Millennium Park and Hancock Tower.

Those interested in exhibits and shows will find some interesting cultural attractions in and around Westchester. Step inside the many inspiring exhibit spaces such as the Graue Mill and Museum in Oak Brook.

If you are ready to indulge in some retail therapy, amble through the boutiques, stores and stalls that are part of the Oakbrook Center Mall in Oak Brook.

When you’re ready to relax after a long day exploring the charming streets of Westchester, check in to one of the many local accommodation options. Check out the rooms and rates at the DoubleTree by Hilton Chicago - Oak Brook, the Best Western Plus Chicago Hillside, or the Hampton Inn Chicago/Westchester (Oak Brook).


Top Hotel Deals

See all 682 Hotels in Westchester
C$100
Hampton Inn Chicago/Westchester (Oak Brook)

Hampton Inn Chicago/Westchester (Oak Brook)

2222 Enterprise Drive, Westchester
4.1
of 5, from 155 reviews
2.5 out of 5.0

Situated in the business district, this hotel is within 3 mi (5 km) of Oak Brook Golf Course, York Woods County Forest Preserve, and Oakbrook Center Mall. Drury Lane Theater is 3 mi (4.9 km) away.

C$96
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago
3.4
of 5, from 465 reviews
3.0 out of 5.0

Built in 1893, this downtown Chicago hotel offers a convenient location across from Grant Park and close to Lake Michigan.

C$89
Inn of Chicago

Inn of Chicago

162 E Ohio St, Chicago
3.6
of 5, from 1,938 reviews
3.0 out of 5.0

Inn of Chicago is a half-block from the Magnificent Mile and 2 blocks from the landmark Tribune Tower. Millennium Park, Navy Pier, and the Art Institute of Chicago are among the many attractions within 1 mile.

C$163
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

17 E Monroe St, Chicago
4.2
of 5, from 2,581 reviews
4.0 out of 5.0

This 1925 Beaux Arts-style Chicago hotel is steps from Millennium Park, 2 blocks from Macy's and the Art Institute, and 1 mile from Lake Michigan, Magnificent Mile shopping, and Wrigley Tower.

IHSP Chicago Hostel

IHSP Chicago Hostel

1616 North Damen Avenue, Chicago
3.1
of 5, from 8 reviews
2.0 out of 5.0

Located in West Town, this hostel is within 3 mi (5 km) of Humboldt Park, United Center, and Merchandise Mart. Lincoln Park Zoo is 3 mi (4.9 km) away.

C$100
Edward Hotel Chicago

Edward Hotel Chicago

6600 N. Mannheim Rd, Rosemont
3.8
of 5, from 449 reviews
3.0 out of 5.0

Situated near the airport, this hotel is 0.4 mi (0.6 km) from Allstate Arena and within 3 mi (5 km) of Rivers Casino and Donald E. Stephens Convention Center. Rosemont Theatre and MB Financial Park at Rosemont are also within 3 mi (5 km).

C$111
Chicago's Essex Inn

Chicago's Essex Inn

800 S Michigan Ave, Chicago
3.6
of 5, from 1,374 reviews
3.5 out of 5.0

Across from the greenery and attractions of Grant Park, the Essex Inn is 3 blocks from the Loop business district and Lake Michigan, 4 blocks from the Art Institute, and a mile from Loop theaters.

C$126
Warwick Allerton Hotel Chicago

Warwick Allerton Hotel Chicago

701 North Michigan Avenue, Chicago
4.0
of 5, from 2,543 reviews
4.0 out of 5.0

Located on Michigan Avenue in the middle of Chicago's Magnificent Mile, this 1920s Italian Renaissance hotel is surrounded by fashionable shops, 1 mile from Lake Michigan and the Art Institute.

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