Orangeville Vacations from $187

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The Latest Orangeville vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
West Lawn
Save 100% on your flight
Price was $317, price is now $187 per person
$187
per person
Feb 18 - Feb 21
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $635, price is now $355 per person
$355
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Great location, clean room and friendly staff!

Reviewed on Dec 14, 2025

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 $545, price is now $321 per person
$321
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,229 reviews)
The view of our king room was beautiful. However The bathroom had blue stains on the wall, the bathroom door looked as it was kicked in, and the seating area couch by the window had stains.

Reviewed on Dec 15, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $582, price is now $347 per person
$347
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.

Reviewed on Dec 14, 2025

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $746, price is now $451 per person
$451
per person
Feb 12 - Feb 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Absolutely fantastic hotel great service, you couldn’t ask for more.

Reviewed on Dec 3, 2025

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Orangeville Hotel Deals

Country Inn & Suites by Radisson, Freeport, IL

Country Inn & Suites by Radisson, Freeport, IL

2.5 out of 5
1710 South Dirck Drive Freeport IL
Fully refundable
$106 nightly
The price is $118 total per night from Jan 7 to Jan 8
$118 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
8.8/10 Excellent! (847 reviews)
Friendly, helpful staff, delicious coffee, Cookies in the lobby, a great full breakfast with lots of warm and easy-to-grab options, microwave in the room. We’ve stayed twice and enjoyed it b

Reviewed on Dec 9, 2025

Country Inn & Suites by Radisson, Freeport, IL
Super 8 by Wyndham Monroe WI

Super 8 by Wyndham Monroe WI

2 out of 5
500 6th St and Hwy 69 Monroe WI
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $81 total per night from Dec 22 to Dec 23
$81 total
Dec 22 - Dec 23
Total with taxes and fees
8.8/10 Excellent! (803 reviews)
The hotel was very clean. It is an older building but very neat and tidy. The bathroom is very small and the sink area isn't even in that area. Very close to restaurants and other businesses. Employees are friendly.

Reviewed on Dec 4, 2025

Super 8 by Wyndham Monroe WI
Baymont by Wyndham Freeport

Baymont by Wyndham Freeport

2.5 out of 5
1060 Riverside Dr Freeport IL
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $90 total per night from Dec 22 to Dec 23
$90 total
Dec 22 - Dec 23
Total with taxes and fees
7.8/10 Good! (709 reviews)
Stayed for a night, i must say the stay is nice. The place needs updating. Not today but in the future.

Reviewed on Nov 28, 2025

Baymont by Wyndham Freeport
See all 39 properties in Orangeville
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 Orangeville Vacation Packages

Orangeville Essential Information

Language
English
Currency
U.S dollars
Population
760
Top Sights
Lake Le Aqua Na State Park, Freeport Art Museum and Famous Fossil Winery

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Frequently asked questions

How much does an Orangeville vacation package cost?
You'll find cheap prices from $187 on Expedia for your Orangeville getaway. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Orangeville costs.
What are the cheapest months to go to Orangeville?
You can generally find lower prices and greater availability in December, January and February. Browse our cheap Orangeville vacation packages and you could land some excellent off-season deals.
How many days is enough for Orangeville?
With a well-organized schedule, you can easily visit the main Orangeville attractions in a few days. But if you want to discover hidden gems or go on day trips, think about booking your Orangeville vacation for longer.
How to find the best Orangeville package deals?
Landing a cheap Orangeville package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget range, apply a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most economical Orangeville package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book an Orangeville vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking stays and flights individually. Better still, you can customize your Orangeville getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Orangeville?
If you have your Orangeville travel dates confirmed, book early to grab some terrific deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for traveling on a whim.
Does Expedia offer Book Now, Pay Later Orangeville vacation packages?
If you're anything like us, you love traveling the world but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Orangeville trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.