Cherry Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to ฿4,531 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Cherry Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 1 day ago
Return flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
The servers and bartenders at the property were amazing! Gentleman who stored our luggage was polite and extremely attentive!

Reviewed on 16 Jul 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 1 day ago
Return flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
There was an odd odor. My room was not ready for several hours after check in.

Reviewed on 17 Jul 2025

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 1 day ago
Return flight included
Calgary (YYC) to Chicago (ORD)
8.6/10 Excellent! (1,795 reviews)
The hotel was a little above average. You get a room credit for certain areas of the hotel with your stay which was appreciated as we utilized for breakfast before heading out for the day. The staff was friendly and courteous. Our room had a nice view however we had to get our sheets changed the first day we got there because one of the beds had obvious stains and the other was full of hair (not just one or two here and there). We ran out of shampoo, conditioner and body wash by our last day because they weren’t refilled. When I checked out, I was told I’d get an email with my receipt. I didn’t. I called the hotel twice a few hours later to confirm my email address and still haven’t received it. I just expected a little from a Fairmont hotel. Not sure I’d stay again.

Reviewed on 19 Jul 2025

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 1 day ago
Return flight included
Calgary (YYC) to Chicago (ORD)
8.4/10 Very Good! (1,986 reviews)
The hotel was beautiful and historic. Not a lot of upgrades so be prepared for the classic style rooms.

Reviewed on 19 Jul 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 1 day ago
Return flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Comfortable beds and nice breakfast. Close to parking. Recommend.

Reviewed on 19 Jul 2025

Top hotels in Cherry

Grand Bear Resort at Starved Rock

Grand Bear Resort at Starved Rock

3 out of 5
2643 IL-178, Utica, IL
The price is ฿5,474 per night from 21 Jul to 22 Jul
฿5,474
฿6,257 total
21 Jul - 22 Jul
includes taxes & fees
7.2/10 Good! (859 reviews)
"It was amazing! The waterpark was clean and everyone was friendly."

Reviewed on 16 Jul 2025

Grand Bear Resort at Starved Rock
Quality Inn Peru near Starved Rock State Park

Quality Inn Peru near Starved Rock State Park

2.5 out of 5
5240 Trompeter Road, La Salle, IL
Fully refundableReserve now, pay when you stay
The price is ฿2,884 per night from 3 Aug to 4 Aug
฿2,884
฿3,259 total
3 Aug - 4 Aug
includes taxes & fees
7.8/10 Good! (623 reviews)
"na"

Reviewed on 12 Jul 2025

Quality Inn Peru near Starved Rock State Park
Best Western Oglesby Inn

Best Western Oglesby Inn

2.5 out of 5
900 Holiday Street, Oglesby, IL
Fully refundableReserve now, pay when you stay
The price is ฿3,531 per night from 20 Jul to 21 Jul
฿3,531
฿3,918 total
20 Jul - 21 Jul
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"Clean Quite Good Location Plenty of Parking Parked Pickup with Camper & Motorcycle with no issues"

Reviewed on 14 Jul 2025

Best Western Oglesby Inn
See all 161 properties in Cherry
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.

Frequently asked questions

How much does a Cherry holiday package cost?
You'll find cheap prices from ฿14,240 on Expedia for your Cherry escape. However, factors like the season, choice of hotel and length of stay will determine how much your holiday to Cherry costs.
What are the cheapest months to go to Cherry?
If you'd like to snag a cheap Cherry holiday package, consider travelling in January, February and November. You'll generally find lower rates on accommodation and flights during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Cherry?
With a well-planned schedule, you can easily visit the top Cherry attractions in a few days. But if you want to discover hidden spots or take day trips, consider booking your Cherry holiday for longer.
How to find the best Cherry package deals?
Use Expedia's filters to help you find some tempting Cherry package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Cherry package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your holiday package as soon as possible.
Is it cheaper to book a Cherry holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging hotels and flights separately. Better still, you can tailor your Cherry trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a holiday package to Cherry?
Land fantastic discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu Cherry adventure.
How to plan a trip to Cherry?

  1. Pick your dates: The things you plan to do in Cherry and your favourite season can help you decide when to go.
  2. Set a budget: Factor in costs like flights, food and transportation when calculating how much to set aside for your trip to Cherry. Then, select a hotel that matches your budget, whether that's an economical option or a high-end getaway.
  3. Set the duration of your trip: Start by making a list of all the activities and sights you want to experience in Cherry. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to pick a Cherry holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.