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 – Old Town
Downtown Chicago
Price was CA $1,719, price is now CA $1,181 per person
CA $1,181
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (468 reviews)
Love the amenities. Great location too
Reviewed on May 3, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $2,882, price is now CA $1,972 per person
CA $1,972
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close.
The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.
Reviewed on May 6, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,723, price is now CA $1,886 per person
CA $1,886
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
Thank you to Javon who was super helpful in our check in . The staff was so nice and accommodating. Additional linens were delivered in less than 5 minutes and then even extended our check out to 1pm. I will definitely be back when I’m in Chicago to try to catch fireworks. Our corner room was outstanding and breathtaking
Reviewed on May 3, 2026
The Langham, Chicago
Downtown Chicago
Price was CA $2,147, price is now CA $1,518 per person
CA $1,518
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
This was THE BEST hotel we had ever stayed in.
Reviewed on May 4, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $3,360, price is now CA $2,425 per person
CA $2,425
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (3,670 reviews)
Amazing hotel and staff!
Reviewed on May 5, 2026
Chicago Heights Hotel Deals
Sleep Inn Midway Airport Bedford Park
6650 S Cicero Ave Chicago IL
Fully refundable
The price is CA $145 per night from May 19 to May 20
CA $145
CA $170 total
May 19 - May 20
includes taxes & fees
8/10 Very Good! (1,860 reviews)
Easy check in quiet
Reviewed on May 6, 2026
Econo Lodge South Holland - Chicago Southland
17301 S Halsted St, Building B South Holland IL
Fully refundableReserve now, pay when you stay
The price is CA $80 per night from May 20 to May 21
CA $80
CA $90 total
May 20 - May 21
includes taxes & fees
6/10 (772 reviews)
Really close to kfc
Reviewed on May 2, 2026
Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
The price is CA $176 per night from May 7 to May 8
CA $176
CA $206 total
May 7 - May 8
includes taxes & fees
6.8/10 (1,002 reviews)
No hangers and no drawers for clothes
Reviewed on May 3, 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.
