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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $634, price is now $329 per person
$329
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
The Blackstone, Autograph Collection

The Blackstone, Autograph Collection

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $705, price is now $370 per person
$370
per person
Jan 16 - Jan 23
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. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a lobby fireplace, and express check-in are also offered.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $2,161, price is now $1,148 per person
$1,148
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was $1,079, price is now $605 per person
$605
per person
Jan 22 - Jan 26
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $886, price is now $500 per person
$500
per person
Dec 30 - Jan 4
found 2 days ago
Roundtrip flight included
Atlanta (ATL) 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
$127 nightly
The price is $146 total per night
$146 total
Nov 19 - Nov 20
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
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
$75 nightly
The price is $88 total per night
$88 total
Nov 13 - Nov 14
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
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
$111 nightly
The price is $124 total per night
$124 total
Nov 13 - Nov 14
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.
Parking included
Restaurant
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
$179 nightly
The price is $201 total per night
$201 total
Nov 13 - Nov 14
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
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 18 - Nov 19
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.
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
Nov 23 - Nov 24
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.
Don't see what you're looking for?
See all available properties in Highland
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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 $329. 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.

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Photo by Joe Farmer
Photo by Joe Farmer