Countryside Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Countryside Vacation Packages

Countryside Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
The price is SARĀ 710 per night from Aug 6 to Aug 7
SARĀ 710
SARĀ 809 total
6 Aug - 7 Aug
includes taxes & fees
Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is SARĀ 728 per night from Jul 27 to Jul 28
SARĀ 728
SARĀ 866 total
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very Good! (1,775 reviews)
"The location is great, the cleanliness is appreciated and the staff are very helpful. The noise from AC was a bit annoying, but the overall experience was great."

Reviewed on 18 July 2026

The Chicago Hotel Collection Ambassador Gold Coast
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is SARĀ 1,123 per night from Aug 9 to Aug 10
SARĀ 1,123
SARĀ 1,335 total
9 Aug - 10 Aug
includes taxes & fees
8.6/10 Excellent! (1,927 reviews)
"Well... when we got there the rooms weren't ready and we had to wait over 4 hours until we finally got our rooms ready at 9 pm. There was no water in my room. And the room AC was very loud and the constant elevator noise while it moved up and down throughout the night... felt like sleeping next to ..."

Reviewed on 18 July 2026

The Wade
See all 4,819 properties in Countryside
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 Countryside vacation package cost?
You can grab a vacation package to this popular destination on Expedia. However, how much your vacation to Countryside costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Countryside?
If you're looking to score a cheap Countryside vacation package, consider visiting in January, February and April. You're likely to find lower prices on hotels and flights during these quieter months ā€” ideal for budget-conscious travelers.
How to find the best Countryside package deals?
Bagging a cheap Countryside package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply some filters and browse what's available. You can personalize your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most economical Countryside package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Countryside vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still get the freedom to create a customized Countryside vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Countryside?
If you have your Countryside travel dates locked in, book early to bag some incredible deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for traveling on a whim.
How to plan a trip to Countryside?

  1. Pick your dates: What you want to do in Countryside and your preferred season will help you decide when to travel.
  2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and meals to flights and activities. Your accommodations will likely be the largest expense during your trip to Countryside.
  3. Work out your trip length: Consider how much time you want to spend discovering Countryside. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a tailored Countryside vacation package.