Highland Vacation Packages
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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.
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination
Price was CA $1,084, price is now CA $784 per person
CA $784
per person
Sep 11 - Sep 14
found 4 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.6/10 Excellent! (1,024 reviews)
Clean large room. Friendly helpful staff. Garage parking with covered bridge to hotel and casino. Highly recommend.
Reviewed on Jun 25, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $3,635, price is now CA $2,437 per person
CA $2,437
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,544, price is now CA $1,096 per person
CA $1,096
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
The property is convenient but they need to do a refresh on lobby carpet and the rooms carpet. The showers are dated and need a refresh. Also they need a better stocked bar and they need a kitchen.
Reviewed on Jun 27, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,991, price is now CA $2,125 per person
CA $2,125
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!
Reviewed on Jun 25, 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 $192 per night from Jul 6 to Jul 7
CA $192
CA $217 total
Jul 6 - Jul 7
includes taxes & fees
8.4/10 Very good! (1,107 reviews)
"Great stay, quiet and staff was very friendly. Also, the breakfast buffet was good."
Reviewed on Jun 27, 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 $191 per night from Jun 30 to Jul 1
CA $191
CA $214 total
Jun 30 - Jul 1
includes taxes & fees
9.4/10 Exceptional! (460 reviews)
"It was clean, the staff was nice for the most part, my biggest complaint would be there isn’t a single posted sign anywhere saying there’s a deposit and when we got there already paying almost $400 for our room for a couple nights they charged us $100/night which brought our total way higher than ..."
Reviewed on Jun 27, 2026
Motel 6 - Chicago, IL
10022 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $141 per night from Jun 28 to Jun 29
CA $141
CA $165 total
Jun 28 - Jun 29
includes taxes & fees
7.4/10 Good! (373 reviews)
"One of the most comfortable and affordable Motel 6s I’ve stayed at! Room had everything you need (fridge, microwave, TV) and quiet/peaceful. A bit of a trek from Chicago downtown, but not bad (15-20 minutes). Highly recommended!"
Reviewed on Jun 23, 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.
What to do in Highland
Chicago Pass: Save up to 50 Percent - Includes 360 CHICAGO
CA $186
per adult
82% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
