Cherry Vacations from $252

Book a Hotel + Flight or Car together to unlock savings

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.

The Latest Cherry vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $404, price is now $252 per person
$252
per person
Jan 27 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
Great staff and clean room, Coffee in the AM... can't ask for much more... Great job

Reviewed on Dec 4, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $651, price is now $379 per person
$379
per person
Jan 27 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Concierge not helpful and neither is was the door man, Neither would get me a cab, they said to just stand outside

Reviewed on Dec 4, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $562, price is now $336 per person
$336
per person
Jan 27 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
The room was beautiful and clean and a good city view of the city

Reviewed on Nov 26, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $548, price is now $332 per person
$332
per person
Jan 27 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
The staff was very responsive, the view nice, the location was great.

Reviewed on Dec 5, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $595, price is now $367 per person
$367
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.

Reviewed on Nov 26, 2025

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Cherry Hotel Deals

Grand Bear Resort at Starved Rock

Grand Bear Resort at Starved Rock

3 out of 5
2643 IL-178 Utica IL
$106 nightly
The price is $117 total per night from Dec 9 to Dec 10
$117 total
Dec 9 - Dec 10
Total with taxes and fees
7.2/10 Good! (1,000 reviews)
Very courteous staff, clean rooms, easy access to various activities both at Grand bear and in the surrounding area. Also surprisingly quiet considering the amount of families that were there. Better Sound insulation than expected.

Reviewed on Dec 2, 2025

Grand Bear Resort at Starved Rock
Days Inn by Wyndham Oglesby/ Starved Rock

Days Inn by Wyndham Oglesby/ Starved Rock

2 out of 5
120 N Lewis Ave Oglesby IL
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $79 total per night from Dec 9 to Dec 10
$79 total
Dec 9 - Dec 10
Total with taxes and fees
8/10 Very Good! (1,001 reviews)
Yes all was very good

Reviewed on Dec 3, 2025

Days Inn by Wyndham Oglesby/ Starved Rock
La Quinta Inn & Suites by Wyndham Peru Starved Rock St Park

La Quinta Inn & Suites by Wyndham Peru Starved Rock St Park

3 out of 5
4389 Venture Dr Peru IL
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $106 total per night from Dec 28 to Dec 29
$106 total
Dec 28 - Dec 29
Total with taxes and fees
7.6/10 Good! (155 reviews)
Amazing staff, great rooms

Reviewed on Dec 1, 2025

La Quinta Inn & Suites by Wyndham Peru Starved Rock St Park
See all 169 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.

Find the Best Cherry Vacation Packages

Cherry Essential Information

Language
English
Currency
U.S dollars
Top Sights
Illinois River Winery, August Hill Winery Tasting Room and LaSalle County Historical Society & Museum

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Frequently asked questions

How much does a Cherry vacation package cost?
You'll find cheap prices from $252 on Expedia for your Cherry escape. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Cherry costs.
What are the cheapest months to go to Cherry?
If you're looking to snag a cheap Cherry vacation package, consider planning a trip in December, January and February. You'll usually find better rates on airfares and hotels during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Cherry?
Usually, a handful of days is enough to visit the main sights during your Cherry vacation. However, if you prefer to have more time to unwind or go on day trips, consider extending your trip.
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 vacation package as soon as possible.
Is it cheaper to book a Cherry vacation as a package?
An Expedia vacation 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 vacation 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.
Does Expedia offer Book Now, Pay Later Cherry vacation packages?
Set off on your perfect escape to Cherry with help from our Book Now, Pay Later vacations. No need to save like crazy or hold off until your next payday — we've joined forces with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no hidden or late payment fees, you can easily stay on budget and snap up travel deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.