Deals on vacations and trips to Highland

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Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $454, price is now $336 per person
$336
per person
Jan 21 - Jan 23
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This smoke-free hotel includes 3 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a terrace are also offered.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $705, price is now $490 per person
$490
per person
Jan 20 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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.
Wyndham Garden Schaumburg Chicago Northwest

Wyndham Garden Schaumburg Chicago Northwest

3 out of 5
Price was $518, price is now $377 per person
$377
per person
Jan 15 - Jan 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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, free WiFi in public areas, and airport drop-off service. You'll appreciate the area shuttle, free self parking, and terrace.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $680, price is now $496 per person
$496
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $1,104, price is now $819 per person
$819
per person
Jan 9 - Jan 13
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Top Highland hotels deals

The Cardinal Hotel

The Cardinal Hotel

3 out of 5
2205 Main St Highland IN
Free Cancellation
Reserve now, pay when you stay
$224 nightly
The price is $251 total per night
$251 total
Dec 8 - Dec 9
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 Chicago Southland Casino and Hotel

Wind Creek Chicago Southland Casino and Hotel

4.5 out of 5
17300 S Halsted St Hazel Crest IL
Free Cancellation
Reserve now, pay when you stay
$179 nightly
The price is $200 total per night
$200 total
Dec 1 - Dec 2
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.
Pool
Hot Tub
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
Nov 22 - Nov 23
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and a free airport shuttle. A business center, free WiFi in public areas, and express check-out are also on offer.
Pool
Free airport shuttle
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
$84 nightly
The price is $95 total per night
$95 total
Nov 15 - Nov 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
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

3 out of 5
4900 S Lake Shore Dr Chicago IL
$143 nightly
The price is $168 total per night
$168 total
Nov 24 - Nov 25
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
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
$86 nightly
The price is $101 total per night
$101 total
Nov 8 - Nov 9
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.
Pet friendly
Parking included
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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 $336. 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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A two-story brick building with a balcony, a front door, and steps leading up to the entrance.