Countryside Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Countryside Vacation
Book a Countryside vacation package and get set for a wonderful adventure. Known for its rural countryside and spectacular views, there's plenty to keep you on the move in this fascinating city. If your trip to Countryside includes a little sightseeing, take in famous attractions like Brookfield Zoo, SeatGeek Stadium and Chicago Ridge Shopping Mall. Browse Expedia's wide range of travel options and start planning your dream vacation to Countryside now.
Top Countryside Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
CA $729
per person
Nov 5 - Nov 8
found 2 days ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.2/10 Very good! (2,879 reviews)
This was such a great hotel. It’s in a wonderful neighborhood, and walking distance from the Riverwalk and Michigan Ave. I’m a solo female traveler, and I felt safe and comfortable here. The room was great and the bed was cozy. I would definitely stay here again.
Reviewed on Aug 11, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,569
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
The property waa clean and spacious
Staff were very nice and helpful. The location was perfect a short walk or drive to alot of places ans the best of all was that
A Garrett's popcorn shop waa right across the street!
Reviewed on Aug 11, 2026
Ready to book your vacation to Countryside?
Countryside Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $146
CA $173 total
Sep 8 - Sep 9
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $199
CA $237 total
Aug 30 - Aug 31
includes taxes & fees
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $320
CA $375 total
Sep 11 - Sep 12
includes taxes & fees
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.
What to do in Countryside
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
Frequently asked questions
How much does a Countryside vacation package cost?
You can grab a vacation package to this popular destination from CA $729 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 — ideal for budget-conscious travellers.
How many days is enough for Countryside?
We'd recommend booking a Countryside vacation for around 2 days. This will allow you plenty of time to check off top attractions including Burr Ridge Village Centre and Galloping Ghost, and explore neighbourhoods like Clearing and Indian Head Park. You could even slot in a day trip beyond Countryside.
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 favourite 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 travelling on a whim.
How to plan a trip to Countryside?
- Pick your dates: What you want to do in Countryside and your preferred season will help you decide when to travel.
- 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.
- 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.
- 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
