Cherry Holidays from £1,308

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Your Cherry Holiday

Entertainment, food, art and more … There's so much to immerse yourself in with a Cherry holiday package. And with the ability to customise 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 holiday is just clicks away with Expedia.

Top Cherry Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,959, price is now £1,308 per person
£1,308
per person
4 Sept - 11 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Location

Reviewed on 10 Jul 2026

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 £2,703, price is now £1,644 per person
£1,644
per person
12 Sept - 19 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
I thoroughly enjoyed my stay at Hotel Felix! While it may not technically be a five-star luxury chain, it definitely gave us five-star hotel vibes thanks to the incredible staff and the fantastic extra perks.The location is absolutely awesome. It puts you about a mile or so from all the major hotspots, including Navy Pier, the Riverwalk, and the Magnificent Mile. There are tons of excellent places to eat right nearby, and having a Divvy bike rental station right down the street made exploring the city incredibly easy.The service from the staff was top-notch from start to finish. I highly recommend this hotel for anyone looking for a stylish, perfectly located, and highly accommodating place to stay in Chicago!

Reviewed on 13 Jul 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,642, price is now £1,672 per person
£1,672
per person
12 Sept - 19 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Clean rooms, nice pool, location great

Reviewed on 12 Jul 2026

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Save 100% on your flight
Price was £2,363, price is now £1,503 per person
£1,503
per person
13 Sept - 20 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (635 reviews)
Great location and amazing AC in the room

Reviewed on 12 Jul 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,733, price is now £1,806 per person
£1,806
per person
12 Sept - 19 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Booked this stay for my husband Birthday. Wanted to make sure he enjoyed himself as well as me. I spent over $800 for the corner room, check in is at 4pm and we arrived about 430ish. Got to the room and the Amenities I purchased wasn’t there which was $100(they stated it would be at 4pm) which is why I want to arrive later. I noticed that the bed sheets were ripped, small stains on the couch in front of bed and the seat in the corner by the window that creeped me out. So we left and via Hilton app I contacted the Hotel to find out why my paid Amenities wasn’t there and they sat them in there while we were gone to dinner. We got back and the chocolate covered strawberries were melted. The best part about the stay was the firework show. My husband and I enjoyed ourselves as best we could after noticing these issues it was disgusting seeing the stains and the ripped sheets especially paying what was over $1000 for one night

Reviewed on 13 Jul 2026

Cherry Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Illinois River Winery, August Hill Winery Tasting Room and LaSalle County Historical Society & Museum

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 £153 per night from 2 Aug to 3 Aug
£153
2 Aug - 3 Aug
includes taxes & fees
7.2/10 Good! (1,025 reviews)
"This place needs a serious deep clean!! The base boards of our beds had stains that looked like dried blood. There was nasty yellow stains on the sheets. When asked if I can change rooms I was told no that I need to speak to a manager but there was no manager on property. I'm a single mom of five ..."

Reviewed on 12 Jul 2026

Grand Bear Resort at Starved Rock
Super 8 by Wyndham Peru Starved Rock State Park

Super 8 by Wyndham Peru Starved Rock State Park

2 out of 5
1851 May Rd La Salle IL
The price is £56 per night from 5 Aug to 6 Aug
£56
5 Aug - 6 Aug
includes taxes & fees
7/10 Good! (912 reviews)
"We got in late in the evening and it had been 100 outside - the AC had not been turned on in the room and it took several hours before it cooled down to a comfortable temp. Breakfast was just waffles and a few other carbs. Wasn't a horrible experience, but not as good as the Super 8 stays I've had ..."

Reviewed on 7 Jul 2026

Super 8 by Wyndham Peru Starved Rock State Park
Days Inn by Wyndham Oglesby/ Starved Rock

Days Inn by Wyndham Oglesby/ Starved Rock

2 out of 5
120 N Lewis Ave Oglesby IL
The price is £74 per night from 21 Jul to 22 Jul
£74
21 Jul - 22 Jul
includes taxes & fees
8.2/10 Very good! (1,011 reviews)
"I was afraid we had made a mistake when the side door key readers was broken and the door propped open, but inside was well taken care of. Newer clean carpets, paint, the bed was clean and comfortable, nice towels, quiet away from busy highways."

Reviewed on 12 Jul 2026

Days Inn by Wyndham Oglesby/ Starved Rock
See all 158 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Cherry travel package cost?
Be ready to book, because a getaway to Cherry starts from an affordable £1,308. When you bundle your hotels, flights and car rentals into a travel package, you'll enjoy the best bargains.
If I'm not able to travel, can I cancel my Cherry travel package?
Yes, you can cancel your Cherry booking if your plans have changed. Whether you'll be charged a fee or not depends on your hotel, airline or car rental company. You may be able to cancel or change for free if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.
How do I get a cheap travel package to Cherry?
One of the simplest ways to save dollars (and time) is to combine your bookings with Expedia. Flights, hotels, activities and rental cars — we've got them all. Choose a combination that suits you and see your savings stack up. Of course, a travel package is never a one-size-fits-all. That's why Expedia offers over 550 air carriers and 1,000,000 hotels throughout the world, which lets you customize your Cherry holiday.
Does Expedia offer Book Now, Pay Later Cherry holidays?
Your bank balance shouldn't stop you from escaping on holiday, so Expedia has worked out a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book an incredible getaway without draining your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your trip. Check out these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month is what works best for you, Klarna can help. Paying in easy monthly instalments will make that dream holiday possible.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay for your holiday in multiple transactions.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the full total upfront) makes it easier to click that "book now" button, consider a low deposit holiday payment plan with Klarna.

What are the top hotels in Cherry?
Hyatt Regency Chicago and The Godfrey Hotel Chicago are among the most well-known hotels in Cherry. Why not look up the rates and amenities at each and then make up your mind?
How far in advance should I book my Cherry holiday?
While prices change frequently, we generally advise reserving your seat as soon as possible. Most international fares are found on Expedia up to a year in advance. If you're booking last minute, you might still be in luck. Cheap journeys to Cherry sometimes occur only weeks before departure.
What does an Expedia Cherry travel package include?
Flights, rental cars and hotels — we have them well covered. With Expedia, you can create your Cherry package your way. All you have to do is work out what you need. Once you've made your booking, you can add on fun things like experiences and activities. The more you bundle, the greater the savings!
What should I know before booking a Cherry travel package?
So many places to explore, so many things to do. With a package, you'll be able to tick more of them off your list. Combine your flights, rental cars and hotels and get set to save.
Can I choose my airline with a Cherry Expedia travel package?
With a travel package, you're the boss. Whether you want to fly to Cherry in coach or first class, simply choose from the available airline options. Expedia has access to over 550 partner airlines across the world.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.