
Cherry Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Cherry Vacation
Entertainment, food, art and more … There's so much to immerse yourself in with a Cherry vacation package. And with the ability to customize your city adventure, you know it'll be one that's tough to forget. Can't wait to sightsee but not sure where to begin? Any trip to Cherry should include Spring Creek Golf Course. Whoever you're taking a break with and whether your budget is big or small, your dream Cherry vacation is just clicks away with Expedia.
Top Cherry Vacation Deals
Price found within the past 48 hours. Click for updated prices.

The Whitehall Hotel, BW Premier Collection
Downtown Chicago
Price was CA $1,258, price is now CA $947 per person
CA $947
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
8.4/10 Very Good! (3,926 reviews)
Overall a great stay, staff was friendly and bed was comfy.
Reviewed on Jun 6, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,852, price is now CA $1,331 per person
CA $1,331
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,519 reviews)
Loved the location. Fitness room was a little disappointing because it’s small and the there are only 2 peloton bikes, but one was out of commission.
Reviewed on Jun 4, 2026

Level Chicago – Old Town
Downtown Chicago
Price was CA $1,876, price is now CA $1,378 per person
CA $1,378
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (481 reviews)
Very clean and loved the location and amenities with the store on the first floor was fantastic
Reviewed on Jun 3, 2026

Pendry Chicago
Downtown Chicago
Price was CA $2,295, price is now CA $1,689 per person
CA $1,689
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,121 reviews)
I absolutely loved it! I little bit noisy but close to literally everything!
Reviewed on Jun 2, 2026

Omni Chicago Hotel
Downtown Chicago
Price was CA $1,332, price is now CA $986 per person
CA $986
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,784 reviews)
Booked a room - got a suite! Enjoyed the extra space. A separate living room for watching TV or working at a desk. Staff at the hotel was very helpful. Enjoyed the breakfast too.
Reviewed on Jun 3, 2026
Cherry Hotel Deals

Grand Bear Resort at Starved Rock
2643 IL-178 Utica IL
The price is CA $182 per night from Jun 8 to Jun 9
CA $182
CA $209 total
Jun 8 - Jun 9
includes taxes & fees
7.2/10 Good! (1,005 reviews)
"The breakfast was good. Room service doesn't come into your room or deliver items like towels/toilet paper. If you need resupply of towels etc, you must pick them up at the front desk. The room didn't have a coffee maker."
Reviewed on Jun 7, 2026

La Quinta Inn & Suites by Wyndham Peru Starved Rock St Park
4389 Venture Dr Peru IL
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Jul 6 to Jul 7
CA $161
CA $181 total
Jul 6 - Jul 7
includes taxes & fees
7.6/10 Good! (226 reviews)
"Staff was friendly. Pool and hot tub were nice. The room was big. Comfy bed. Breakfast was good. Windows were always open in pool room which I felt was unsafe being next to an expressway. My room window had a big crack in it, luckily I was on 2nd floor. The fan in my bathroom was so loud it sounded ..."
Reviewed on Jun 1, 2026

Super 8 by Wyndham Peru Starved Rock State Park
1851 May Rd La Salle IL
Fully refundableReserve now, pay when you stay
The price is CA $88 per night from Jul 5 to Jul 6
CA $88
CA $99 total
Jul 5 - Jul 6
includes taxes & fees
7/10 Good! (895 reviews)
"Breakfast was minimal with waffles about the only choice. Syrup was in a big bottle that had a pump that didn't work. There was also a slice or two of bread available for toast."
Reviewed on Jun 4, 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.







