Deals on vacations and trips to Highland
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Highland flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Prospect Heights by IHG
Save 100% on your flight
Price was $775, price is now $510 per person
$510
per person
Jul 13 - Jul 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a 24-hour gym on site, and a 24-hour front desk and a fireplace in the lobby are also provided.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,945, price is now $1,167 per person
$1,167
per person
Jul 11 - Jul 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $2,116, price is now $1,334 per person
$1,334
per person
Jul 11 - Jul 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,007, price is now $646 per person
$646
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,179, price is now $765 per person
$765
per person
Jul 24 - Jul 27
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.
Top Highland hotels deals
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
$129 nightly
The price is $151 total per night
$151 total
Apr 29 - Apr 30
Total with taxes and fees
Free self parking is available and the hotel's multilingual staff can provide around-the-clock assistance. WiFi in public areas is free. Luggage storage is also provided.
Pet friendly
Parking included
Econo Lodge South Holland - Chicago Southland
17301 S Halsted St, Building B South Holland IL
Free Cancellation
Reserve now, pay when you stay
$59 nightly
The price is $66 total per night
$66 total
May 4 - May 5
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.
Parking included
Free WiFi
DoubleTree by Hilton Chicago - Alsip
5000 W 127th St Alsip IL
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $133 total per night
$133 total
May 14 - May 15
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like free self parking.
Pool
Free airport shuttle
Hilton Chicago/Oak Lawn
9333 S Cicero Ave Oak Lawn IL
Free Cancellation
Reserve now, pay when you stay
$126 nightly
The price is $145 total per night
$145 total
May 4 - May 5
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Pool
Free WiFi
Wind Creek Southland Casino and Hotel
17300 S Halsted St Hazel Crest IL
Free Cancellation
Reserve now, pay when you stay
$161 nightly
The price is $180 total per night
$180 total
May 4 - May 5
Total with taxes and fees
This resort features a casino, a full-service spa, and 4 restaurants. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Relax with a drink at one of the 3 bars/lounges and enjoy perks like free self parking.
Hot Tub
Spa
EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
18501 Convention Center Drive Tinley Park IL
Free Cancellation
$119 nightly
The price is $136 total per night
$136 total
May 10 - May 11
Total with taxes and fees
This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a picnic area, and express check-out are also offered.
Pet friendly
Parking included
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.
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