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.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
Save 100% on your flight
Price was $342, price is now $224 per person
$224
per person
Dec 10 - Dec 13
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. A hair salon, express check-in, and express check-out are also on offer.
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination
Save 100% on your flight
Price was $1,048, price is now $618 per person
$618
per person
Dec 11 - Dec 18
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features 3 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, express check-out, and luggage storage are also on offer.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $565, price is now $346 per person
$346
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The Talbott, Autograph Collection
Downtown Chicago
Save 100% on your flight
Price was $567, price is now $354 per person
$354
per person
Dec 10 - Dec 13
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 business center, free WiFi in public areas, and valet parking. Dry cleaning, luggage storage, and wedding services are also on offer.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $724, price is now $482 per person
$482
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
The Cardinal Hotel
2205 Main St Highland IN
Free Cancellation
Reserve now, pay when you stay
$219 nightly
The price is $246 total per night
$246 total
Oct 11 - Oct 12
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including pet-sitting services. A restaurant, a 24-hour front desk, and a coffee shop are also provided.
Breakfast included
Pet friendly
Wind Creek Southland Casino and Hotel
17300 S Halsted St Hazel Crest IL
Free Cancellation
Reserve now, pay when you stay
$199 nightly
The price is $223 total per night
$223 total
Oct 13 - Oct 14
Total with taxes and fees
This luxury resort features a casino, a full-service spa, and 8 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 4 bars/lounges and enjoy perks like free self parking.
Hot Tub
Spa
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
$159 nightly
The price is $187 total per night
$187 total
Nov 1 - Nov 2
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
DoubleTree by Hilton Chicago - Alsip
5000 W 127th St Alsip IL
Free Cancellation
Reserve now, pay when you stay
$121 nightly
The price is $136 total per night
$136 total
Nov 1 - Nov 2
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
Ameristar Casino Hotel East Chicago
777 Ameristar Blvd. East Chicago IN
Free Cancellation
Reserve now, pay when you stay
$134 nightly
The price is $150 total per night
$150 total
Oct 18 - Oct 19
Total with taxes and fees
A casino, 5 restaurants, and a 24-hour gym are all featured at this Art Deco hotel. Business travelers can take advantage of the 24-hour business center. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Parking included
Restaurant
Baymont by Wyndham Chicago/Alsip
12801 South Cicero Alsip IL
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $105 total per night
$105 total
Oct 14 - Oct 15
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Pet friendly
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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