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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $290, price is now $164 per person
$164
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Houston (IAH) 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 Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,051, price is now $562 per person
$562
per person
Feb 13 - Feb 17
found 19 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $773, price is now $432 per person
$432
per person
Feb 13 - Feb 17
found 16 hours ago
Roundtrip flight included
Denver (DEN) 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.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $424, price is now $240 per person
$240
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. Valet parking and dry cleaning are also offered on site.
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
East Hazel Crest
Save 100% on your flight
Price was $440, price is now $271 per person
$271
per person
Jan 13 - Jan 16
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (MDW)
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.

Top Highland hotels deals

Hilton Chicago/Oak Lawn

Hilton Chicago/Oak Lawn

3.5 out of 5
9333 S Cicero Ave Oak Lawn IL
Free Cancellation
Reserve now, pay when you stay
$130 nightly
The price is $150 total per night
$150 total
Dec 3 - Dec 4
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.
Baymont by Wyndham Chicago/Alsip

Baymont by Wyndham Chicago/Alsip

2.5 out of 5
12801 South Cicero Alsip IL
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $85 total per night
$85 total
Nov 30 - Dec 1
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
Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

2 out of 5
10022 South Halsted Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$80 nightly
The price is $94 total per night
$94 total
Nov 27 - Nov 28
Total with taxes and fees
Free self parking is available and the motel's front desk is staffed around-the-clock. Laundry facilities are provided for your convenience.
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4 out of 5
777 Ameristar Blvd. East Chicago IN
Free Cancellation
Reserve now, pay when you stay
$107 nightly
The price is $120 total per night
$120 total
Nov 30 - Dec 1
Total with taxes and fees
This Art Deco hotel features a casino, a marina, and 5 restaurants. Enjoy the 24-hour gym and perks like free self parking. A bar/lounge, a 24-hour front desk, and a snack bar/deli are also provided.
EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG

EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG

3.5 out of 5
18501 Convention Center Drive Tinley Park IL
Free Cancellation
$92 nightly
The price is $105 total per night
$105 total
Dec 1 - Dec 2
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.
DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
5000 W 127th St Alsip IL
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $129 total per night
$129 total
Dec 3 - Dec 4
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
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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.

Frequently asked questions

How much are vacation packages to Highland?
Packages, which provide both flights and hotels in Highland, are priced from as little as $164. Make your daydreams a reality and secure your dream vacation with Travelocity today.
Where can I get the best vacation package deals for Highland?
For an amazing package deal to Highland, turn to Travelocity. Take your pick from as many as 400 air carriers and 1,000,000 properties across the globe to create your ideal escape — you're spoiled for choice!
Why should I book my Highland vacation package with Travelocity?
Travel should be about making cherished memories and forgetting all your worries — which is why we have a friendly team of customer service experts available 24/7 should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best deal available on our terrific range of destinations. So what are you waiting for? There's no time like the present to lock in the vacation you've always dreamed of.
Will I save money on my Highland car rental if I combine it with a hotel or flight?
With a Highland vacation package, you can combine your car, hotel and flight bookings and save a nice amount. If you can't wait to discover the best of this fabulous location, why not make tracks to Six Flags Great America? This top sight is 60 mi from Highland. With your own wheels, you'll be there in no time.
Which airport is best for Highland?
For plenty of travelers, a stay in Highland means stepping off the plane at O'Hare Intl. Airport (ORD). This popular airport sits 35 mi northwest of the downtown area. You could also choose to jet into Midway Intl. Airport (MDW) (20 mi away from central Highland) or South Bend Intl. Airport (SBN) (60 mi away from central Highland).
Where should I stay when visiting Highland?
If you're looking for someplace comfortable to spend your nights, have a look at the Quiet & Comfortable 2 Bed Corporate Near 80/94 A Richard St Main Floor. It's the top choice for many travelers.

Photos of local treasures

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Photo by Joe Farmer
Photo by Joe Farmer