Name: DoubleTree by Hilton Chicago - Alsip
Price range: CA $192
Rating: 8.4

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.

Hotel Felix River North/Magnificent Mile

Downtown Chicago

CA $667

per person

Sep 2 - Sep 5

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.2/10 Very good! (2,767 reviews)

Great location, we were able to walk everywhere we wanted to see. The red line is about a 10 minute walk if you are heading to Wrigley.

Reviewed on Jun 26, 2026

Level Chicago – Old Town

Downtown Chicago

CA $2,437

per person

Sep 12 - Sep 18

found 7 hours 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

The Talbott, Autograph Collection

Downtown Chicago

CA $793

per person

Sep 2 - Sep 5

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (126 reviews)

Always a pleasure and a great location

Reviewed on Jun 24, 2026

Level Chicago Fulton Market

Downtown Chicago

CA $2,125

per person

Aug 3 - Aug 8

found 9 hours 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

Level Chicago - River North

Downtown Chicago

CA $887

per person

Sep 5 - Sep 7

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,034 reviews)

Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.

Reviewed on Jun 19, 2026

Ready to book your vacation to Highland?

Choose your dates

Highland Hotel Deals

DoubleTree by Hilton Chicago - Alsip

5000 W 127th St Alsip IL

Fully refundableReserve now, pay when you stay

CA $192

CA $217 total

Jul 6 - Jul 7

includes taxes & fees

8.4/10 Very good! (1,106 reviews)

"Best cookies"

Reviewed on Jun 24, 2026

Wind Creek Southland Casino and Hotel

17300 S Halsted St Hazel Crest IL

Fully refundableReserve now, pay when you stay

CA $191

CA $214 total

Jun 30 - Jul 1

includes taxes & fees

9.4/10 Exceptional! (458 reviews)

"Loved the room beautiful hotel and great rooftop restaurant. Thanks Wind Creek!"

Reviewed on Jun 26, 2026

Motel 6 - Chicago, IL

10022 South Halsted Street Chicago IL

Fully refundableReserve now, pay when you stay

CA $140

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

See all 894 properties in Highland

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.