Highland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Highland Vacation
Spend less time travel planning and more time having exciting adventures with a Highland vacation package. The neighborhood of East Side, which is good for nature and walking, makes an excellent base for your city break. Like to get out and explore? Hard Rock Casino Northern Indiana, Purdue University Northwest and Hammond Sportsplex & Community Center are three of the leading places to visit during your trip to Highland. Don't delay your visit to this destination any longer. Your ultimate Highland vacation is only a few clicks away with Expedia.
Top Highland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was CA $5,407, price is now CA $2,968 per person
CA $2,968
per person
Jul 27 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
It was very pleasant and safe. I liked that you needed a room key to use the elevator which made us feel safe. The hotel is located very central and walking distance to everything. The staff was very friendly.
Reviewed on May 16, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,256, price is now CA $1,425 per person
CA $1,425
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (472 reviews)
Minimum effort. Pleasant stay. Very quiet. Enjoyed the 8th floor common area. Service at the front desk was really great. Convenient coffee shop / bakery in the lobby.
Reviewed on May 18, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $4,447, price is now CA $2,861 per person
CA $2,861
per person
Jul 27 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
The Sable was beautiful and peaceful. We enjoyed our stay and would definitely come back.
Thanks for the great customer service.
Reviewed on May 17, 2026
Highland Hotel Deals
DoubleTree by Hilton Chicago - Alsip
5000 W 127th St Alsip IL
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Jun 1 to Jun 2
CA $179
CA $203 total
Jun 1 - Jun 2
includes taxes & fees
8.4/10 Very Good! (1,054 reviews)
"Parking was very easy, the shower didn't get hot enough so we didn't say anything because we were rushing. Breakfast is good should be cheaper for $20 buffet. Kids under 13 shots eat for free is my opinion! Very nice people clean rooms! Should be at a cheaper price but I did enjoy my time"
Reviewed on May 18, 2026
Wind Creek Southland Casino and Hotel
17300 S Halsted St Hazel Crest IL
Fully refundableReserve now, pay when you stay
The price is CA $209 per night from May 19 to May 20
CA $209
CA $234 total
May 19 - May 20
includes taxes & fees
9.2/10 Wonderful! (378 reviews)
"Excellent property. We really our stay."
Reviewed on May 17, 2026
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
The price is CA $219 per night from May 19 to May 20
CA $219
CA $257 total
May 19 - May 20
includes taxes & fees
6.8/10 (1,009 reviews)
"Clean room and nice staff but no amenities ie: ice, adequate room lamps and plugs AND HOT WATER! Temperature was good enough to drink out of the faucet at 95 degrees, far short of heath code of 120 degrees!!"
Reviewed on May 17, 2026
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
