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 Belfry House

The Belfry House

3 out of 5
Save 100% on your flight
Price was $907, price is now $567 per person
$567
per person
Oct 22 - Oct 26
found 18 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
A restaurant, free self parking, and a terrace are among this hotel's amenities. WiFi in public areas is free. A lobby fireplace, a communal living room, and concierge services are also on offer.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,594, price is now $872 per person
$872
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, a business center, and a picnic area are also offered.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,747, price is now $1,046 per person
$1,046
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $965, price is now $599 per person
$599
per person
Oct 22 - Oct 26
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. WiFi in public areas is free. Valet parking, a coffee shop, and a snack bar/deli are also offered.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,282, price is now $822 per person
$822
per person
Oct 22 - Oct 25
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.

Top Highland hotels deals

Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

3 out of 5
4900 S Lake Shore Dr Chicago IL
$149 nightly
The price is $175 total per night
$175 total
Sep 10 - Sep 11
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
$85 nightly
The price is $100 total per night
$100 total
Sep 1 - Sep 2
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
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
$118 nightly
The price is $133 total per night
$133 total
Sep 7 - Sep 8
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.
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
17300 S Halsted St Hazel Crest IL
Free Cancellation
Reserve now, pay when you stay
$173 nightly
The price is $194 total per night
$194 total
Sep 8 - Sep 9
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
Quality Inn & Suites Orland Park - Chicago

Quality Inn & Suites Orland Park - Chicago

2.5 out of 5
8800 W 159th St Orland Park IL
Free Cancellation
$90 nightly
The price is $101 total per night
$101 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free English breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and dry cleaning are also provided.
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
$97 nightly
The price is $109 total per night
$109 total
Sep 7 - Sep 8
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
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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 $567. 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

Browse Highland vacation photos for more inspiration

A two-story brick building with a balcony, a front door, and steps leading up to the entrance.