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.
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,758, price is now CA $1,194 per person
CA $1,194
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (498 reviews)
This location is primarily a place where people live as in an apartment complex. The hotel part of it seems to be more for people doing longer stays. That means you’re not get the normal amenities or service you would get with a more traditional hotel. It is not a bad location, but I would try not to stay here again.
Reviewed on Jun 20, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,439, price is now CA $1,687 per person
CA $1,687
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
The people at the front desk were extremely helpful. Everyone was super kind & you never really have to leave the hotel.. plenty of shops and restaurants right there in the hotel!
Breakfast was not included, but there is breakfast on site.. there’s cheap breakfast and expensive breakfast all depends on what you are in the mood for. Wonderful stay over all!!!
Reviewed on Jun 22, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,746, price is now CA $1,217 per person
CA $1,217
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
The Emily Hotel
Downtown Chicago
Price was CA $1,740, price is now CA $1,285 per person
CA $1,285
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
Great location, great space in the rooms!!
Reviewed on Jun 21, 2026
Chicago Heights Hotel Deals
Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $194 per night from Jul 15 to Jul 16
CA $194
CA $241 total
Jul 15 - Jul 16
includes taxes & fees
8.2/10 Very good! (1,010 reviews)
"it was okay"
Reviewed on Jun 21, 2026
Sleep Inn Midway Airport Bedford Park
6650 S Cicero Ave Chicago IL
Fully refundable
The price is CA $164 per night from Jul 5 to Jul 6
CA $164
CA $193 total
Jul 5 - Jul 6
includes taxes & fees
8/10 Very good! (1,928 reviews)
"Everything was great but the the smell the first day we got out on Friday inside the room was very bad. I had to go buy some plug-ins besides that I must say a hotel was excellent clean. Customer service was wonderful. Very professional. Breakfast was good room service was wonderful. I will stay ..."
Reviewed on Jun 21, 2026
DoubleTree by Hilton Chicago - Alsip
5000 W 127th St Alsip IL
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Jul 6 to Jul 7
CA $167
CA $189 total
Jul 6 - Jul 7
includes taxes & fees
8.4/10 Very good! (1,100 reviews)
"Terrible smell on Hallways and the room Room have every item broken and old I feel I waste my money,"
Reviewed on Jun 20, 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.
