Deals on vacations and trips to Highland

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Highland flight + hotel vacation packages

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Holiday Inn Chicago - Schaumburg by IHG

Holiday Inn Chicago - Schaumburg by IHG

3.5 out of 5
Price was $469, price is now $340 per person
$340
per person
Apr 27 - May 1
found 17 hours ago
Roundtrip flight included
Boston (BOS) 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 gym and perks like free self parking.
La Banque Hotel

La Banque Hotel

4 out of 5
Price was $934, price is now $575 per person
$575
per person
May 1 - May 6
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,893, price is now $1,205 per person
$1,205
per person
May 3 - May 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A business center, a picnic area, and luggage storage are also on offer.
Graduate by Hilton Evanston

Graduate by Hilton Evanston

4 out of 5
Downtown Evanston
Save 100% on your flight
Price was $1,098, price is now $727 per person
$727
per person
Apr 30 - May 3
found 16 hours ago
Roundtrip flight included
Boston (BOS) 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 communal living room, and luggage storage are also offered.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $906, price is now $635 per person
$635
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.

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
$110 nightly
The price is $126 total per night
$126 total
Mar 2 - Mar 3
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
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 8 - Mar 9
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
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
$88 nightly
The price is $101 total per night
$101 total
Mar 8 - Mar 9
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
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
Feb 24 - Feb 25
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
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
$113 nightly
The price is $128 total per night
$128 total
Feb 26 - Feb 27
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
Motel 6 Hammond, IN - Chicago Area

Motel 6 Hammond, IN - Chicago Area

2 out of 5
3840 179th St Hammond IN
$49 nightly
The price is $55 total per night
$55 total
Feb 25 - Feb 26
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A snack bar/deli and laundry facilities are also provided.
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 $340. 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.