Highwood Vacations

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Top Hotel Deals

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
26.57 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
25.44 km from city center
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
5440 N River Rd Rosemont IL
25.83 km from city center
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove

4 out of 5
1200 N Mittel Blvd Wood Dale IL
28.38 km from city center
Book a stay at this business-friendly hotel in Wood Dale. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
6600 Mannheim Road, building 2 Rosemont IL
23.8 km from city center
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast ...
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road Chicago IL
24.74 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a free airport shuttle, and a 24-hour fitness center. Our guests praise ...
Comfort Suites Chicago O'Hare Airport

Comfort Suites Chicago O'Hare Airport

3 out of 5
4200 North River Road Schiller Park IL
28.17 km from city center
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
Four Points by Sheraton Chicago O'Hare Airport

Four Points by Sheraton Chicago O'Hare Airport

3 out of 5
10249 Irving Park Road Schiller Park IL
28.49 km from city center
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant ...
Sonesta Simply Suites Chicago O'Hare Airport

Sonesta Simply Suites Chicago O'Hare Airport

2 out of 5
4021 North Mannheim Rd Schiller Park IL
28.88 km from city center
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free WiFi, a free airport shuttle, and a 24-hour fitness center. Our guests praise the helpful ...
Hyatt Place Chicago/O'Hare Airport

Hyatt Place Chicago/O'Hare Airport

3 out of 5
6810 Mannheim Rd Rosemont IL
23.5 km from city center
Book a stay at this business-friendly hotel in Rosemont. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel

4.5 out of 5
5300 N River Rd Rosemont IL
26.21 km from city center
Book a stay at this luxury hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful ...
Hyatt Regency Deerfield

Hyatt Regency Deerfield

4 out of 5
1750 Lake Cook Rd Deerfield IL
7.48 km from city center
Book a stay at this business-friendly hotel in Deerfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
SpringHill Suites Chicago O'Hare by Marriott

SpringHill Suites Chicago O'Hare by Marriott

3 out of 5
8101 West Higgins Road Chicago IL
24.65 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport

2.5 out of 5
3939 N Mannheim Rd Schiller Park IL
29.18 km from city center
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Motel 6 Prospect Heights, IL

Motel 6 Prospect Heights, IL

2 out of 5
540 N Milwaukee Ave Prospect Heights IL
12.88 km from city center
Stay at this motel in Prospect Heights. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Wed, Dec 31 - Mon, Jan 5
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$188 Roundtrip, found 4 days ago
$188
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, Dec 31 from Los Angeles Intl. to O'Hare Intl., returning Mon, Jan 5, priced at $188 found 4 days ago
Frontier Airlines
Thu, Dec 18 - Thu, Jan 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$193 Roundtrip, found 11 hours ago
$193
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Thu, Dec 18 from Los Angeles Intl. to O'Hare Intl., returning Thu, Jan 1, priced at $193 found 11 hours ago
JetBlue Airways
Mon, May 18 - Thu, May 28
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$288 Roundtrip, found 5 hours ago
$288
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Mon, May 18 from Los Angeles Intl. to O'Hare Intl., returning Thu, May 28, priced at $288 found 5 hours ago
Delta
Wed, Dec 17 - Tue, Dec 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$347 Roundtrip, found 4 days ago
$347
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Dec 17 from Los Angeles Intl. to O'Hare Intl., returning Tue, Dec 23, priced at $347 found 4 days ago
Alaska Airlines
Sat, May 23 - Sun, May 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$411 Roundtrip, found 5 hours ago
$411
Roundtrip
found 5 hours ago
Select Alaska Airlines flight, departing Sat, May 23 from Los Angeles Intl. to O'Hare Intl., returning Sun, May 24, priced at $411 found 5 hours ago