Chicago Heights Vacation Packages
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Your Chicago Heights Vacation
When you book a vacation package to Chicago Heights, you can relax and enjoy your escape knowing your travel plans are in order. Discover the many gems of this vibrant city while staying in a neighborhood like Glenwood, which is great for golfing. There's plenty to put on your itinerary during a trip to Chicago Heights, beginning with popular attractions such as Coyote Run Golf Course and Ravisloe Country Club. No matter your travel plans or the size of your budget, putting together the ultimate tailored Chicago Heights vacation is simple with Expedia.
Top Chicago Heights Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $1,769, price is now CA $1,257 per person
CA $1,257
per person
Aug 10 - Aug 15
found 21 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (1,006 reviews)
Great place to stay and excellent breakfast choices
Reviewed on May 14, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,271, price is now CA $1,438 per person
CA $1,438
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (478 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 $3,275, price is now CA $2,074 per person
CA $2,074
per person
Jul 31 - Aug 5
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,507 reviews)
Beautiful views and amazing amenities
Reviewed on May 25, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,988, price is now CA $1,971 per person
CA $1,971
per person
Jul 31 - Aug 5
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (3,727 reviews)
Super location, good crowd of staff and fellow travellers. Smells great!
Reviewed on May 24, 2026
ENVITAE Hotel 4 Bedroom Luxury Apartments
Near North Side
Price was CA $3,341, price is now CA $2,376 per person
CA $2,376
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (16 reviews)
⭐⭐⭐⭐⭐
We had a fantastic stay in this 4-bedroom apartment hotel. Looks exactly like the pictures. The unit was spotlessly clean and perfectly appointed — it truly felt like a home away from home. The kitchen had every amenity you could possibly need, which made cooking and relaxing with family incredibly easy.
The bedding was beautiful and very comfortable, and having a washer and dryer in the unit was a huge bonus, especially for a longer stay.
The building itself felt very secure, including the parking area, which gave us great peace of mind. We also loved the amenities — the gym and lounge area were excellent and well maintained.
Overall, this was one of the best apartment-style stays we’ve had. Comfortable, convenient, and thoughtfully set up. We would absolutely stay here again.
Reviewed on Mar 5, 2026
Chicago Heights Hotel Deals
Sleep Inn Midway Airport Bedford Park
6650 S Cicero Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $160 per night from May 28 to May 29
CA $160
CA $188 total
May 28 - May 29
includes taxes & fees
8/10 Very Good! (1,882 reviews)
"This property needs renovation bad and upgrading . I took pictures and for this brand and for Expedia to be affiliated this really should be corrected ."
Reviewed on May 24, 2026
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundable
The price is CA $213 per night from May 27 to May 28
CA $213
CA $264 total
May 27 - May 28
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
"Nice place and good price"
Reviewed on May 23, 2026
DoubleTree by Hilton Chicago - Alsip
5000 W 127th St Alsip IL
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Jun 14 to Jun 15
CA $175
CA $198 total
Jun 14 - Jun 15
includes taxes & fees
8.6/10 Excellent! (1,061 reviews)
"Always a nice stay."
Reviewed on May 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.
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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.
