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.
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Price was $449, price is now $289 per person
$289
per person
May 19 - May 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area is provided and the front desk is staffed around-the-clock.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,238, price is now $712 per person
$712
per person
May 22 - May 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.
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,868, price is now $1,172 per person
$1,172
per person
May 13 - May 20
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 2 bars/lounges and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.
Hilton Chicago/Oak Brook Suites

Hilton Chicago/Oak Brook Suites

3.5 out of 5
Yorkfield
Save 100% on your flight
Price was $493, price is now $325 per person
$325
per person
Jun 1 - Jun 6
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was $945, price is now $625 per person
$625
per person
May 13 - May 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.

Top Highland hotels deals

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
$102 nightly
The price is $115 total per night
$115 total
Mar 29 - Mar 30
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
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
$114 nightly
The price is $131 total per night
$131 total
Mar 16 - Mar 17
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.
Pool
Free WiFi
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
$152 nightly
The price is $170 total per night
$170 total
Mar 10 - Mar 11
Total with taxes and fees
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.
Hot Tub
Spa
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
Reserve now, pay when you stay
$99 nightly
The price is $113 total per night
$113 total
Mar 19 - Mar 20
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.
Pet friendly
Parking included
Wingate by Wyndham Tinley Park

Wingate by Wyndham Tinley Park

2.5 out of 5
18421 N Creek Drive Tinley Park IL
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $120 total per night
$120 total
Mar 10 - Mar 11
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Enjoy the hot tub and free perks like on-the-go breakfast and free self parking. A 24-hour business center, free WiFi in public areas, and express check-out are also on offer.
Pool
Hot Tub
Quality Inn & Suites Matteson near I-57

Quality Inn & Suites Matteson near I-57

2.5 out of 5
21050 Matteson Avenue Matteson IL
Free Cancellation
Reserve now, pay when you stay
$68 nightly
The price is $78 total per night
$78 total
Mar 29 - Mar 30
Total with taxes and fees
A gym, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. There's luggage storage and multilingual staff can provide around-the-clock assistance.
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 $289. 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

Al Capone's old Prairie avenue home before and today, 7244 South Prairie Avenue. Built by it's original owners in 1914 at a cost of $5,000. With their roots still in New York , Al Capone and family began to move into the place on August 8, 1923. The ownership was under Mae and Theresa Capone. Frank Capone's funeral was held here. Theresa Capone passed away in this house in 1952. On November 26,1947, the ownership was transferred to Mafalda Maritote. (Al's sister). After Theresa's death, she sold the house on January 15,1953, to a William B. Petty. It has changed hands since then and is currently for sale.
Al Capone's old Prairie avenue home before and today, 7244 South Prairie Avenue. Built by it's original owners in 1914 at a cost of $5,000. With their roots still in New York , Al Capone and family began to move into the place on August 8, 1923. The ownership was under Mae and Theresa Capone. Frank Capone's funeral was held here. Theresa Capone passed away in this house in 1952. On November 26,1947, the ownership was transferred to Mafalda Maritote. (Al's sister). After Theresa's death, she sold the house on January 15,1953, to a William B. Petty. It has changed hands since then and is currently for sale.