Deals on vacations and trips to Highwood
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Highwood flight + hotel vacation packages
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Illinois Beach Hotel
Save 100% on your flight
per person
Aug 31 - Sep 5
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area is provided and the front desk is staffed around-the-clock.
Art Villa
West Town
Save 100% on your flight
per person
Sep 3 - Sep 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa and a hot tub are featured at this luxury aparthotel. Enjoy the a rooftop terrace and perks like free self parking and a free airport shuttle. Free WiFi in public areas, a garden, and a lobby fireplace are also on offer.
DoubleTree by Hilton Chicago Schaumburg
Save 100% on your flight
per person
Sep 3 - Sep 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy free perks like free self parking and an area shuttle.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
per person
Jul 31 - Aug 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A restaurant is on site and multilingual staff is available around-the-clock at the 24-hour front desk. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like buffet breakfast and WiFi in public areas. There's a 24-hour gym on site, and a coffee shop and a snack bar/deli are also provided.
Four Points by Sheraton Chicago O'Hare Airport
O'Hare
Save 100% on your flight
per person
Sep 3 - Sep 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. There's a gym on site, and concierge services and wedding services are also offered.
Top Highwood hotels deals
Hilton Chicago O'Hare Airport
O'Hare International Airport, Chicago, IL
This hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.
Free airport shuttle
Pet friendly
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave, Rosemont, IL
Free Cancellation
Reserve now, pay when you stay
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Self parking, a coffee shop, and limo/town car service are also offered.
Free airport shuttle
Pet friendly
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd, Rosemont, IL
Free Cancellation
This hotel features 3 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and free airport shuttle. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.
Pool
Free airport shuttle
Marriott Chicago O'Hare
8535 West Higgins Road, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. There's an indoor pool on site, and a 24-hour front desk and a coffee shop are also provided.
Pool
Free airport shuttle
Hyatt Regency Schaumburg Chicago
1800 East Golf Rd, Schaumburg, IL
Free Cancellation
Reserve now, pay when you stay
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking and a free area shuttle.
Hyatt Place Chicago/O'Hare Airport
6810 Mannheim Rd, Rosemont, IL
Free Cancellation
Reserve now, pay when you stay
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and free perks like buffet breakfast and a bus station shuttle.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Popular places to visit
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Frequently asked questions
Photos of local treasures
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