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 Talbott, Autograph Collection
Downtown Chicago
Save 100% on your flight
Price was $592, price is now $403 per person
$403
per person
Nov 25 - Nov 28
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.
Four Seasons Hotel Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,341, price is now $791 per person
$791
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and laundry facilities.
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination
Save 100% on your flight
Price was $1,049, price is now $694 per person
$694
per person
Dec 25 - Dec 28
found 1 day 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.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $898, price is now $623 per person
$623
per person
Dec 19 - Dec 22
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.
Chicago Lake Shore Hotel
Kenwood
Price was $1,076, price is now $757 per person
$757
per person
Dec 21 - Dec 28
found 11 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
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.
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
$187 nightly
The price is $209 total per night
$209 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
$135 nightly
The price is $159 total per night
$159 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
$88 nightly
The price is $100 total per night
$100 total
Oct 15 - Oct 16
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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