Countryside Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 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
Top Flight + Hotel Deals in Countryside
Price found within the past 48 hours. Click for updated prices.
Top hotels in Countryside
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
€118
8 Sept - 9 Sept
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
€137
31 Aug - 1 Sept
includes taxes & fees
8/10 Very good! (2,125 reviews)
"Staff were amazing! Extremely helpful and accommodating, let us check in about 5 hours early. Definitely recommend"
Reviewed on 29 Aug 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
€264
30 Aug - 31 Aug
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
€21
per adult
90% of travellers recommend
Frequently asked questions
How much does a Countryside holiday package cost?
Offering great value package deals from €1,347 on Expedia, you'll be thrilled with how little a holiday to Countryside costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Countryside?
If you're hoping to score a cheap Countryside holiday package, consider visiting in January, February and April. You'll generally find lower rates on hotels and flights during these quieter months — ideal for travellers wishing to save money.
How many days is enough for Countryside?
Usually, a handful of days is enough to check out the top attractions during your Countryside holiday. But if you'd like to have time to rest or go on day trips, consider extending your itinerary.
How to find the best Countryside package deals?
Finding a cheap Countryside package deal is a breeze with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, add some filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most affordable Countryside 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 a Countryside holiday as a package?
An Expedia holiday package could land you great savings when compared to booking stays and flights separately. Better still, you can customise your Countryside escape to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a holiday package to Countryside?
Land incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Countryside trip.
How to plan a trip to Countryside?
- Choose your dates: What you plan to do in Countryside and your preferred season can help you decide when to go.
- Work out your budget: Ensure you have enough money to pay for everything from dining out and transportation to activities and airfares. Your accommodation will probably be the largest expense during your trip to Countryside.
- Work out your trip length: Think about how much time you'd like to spend discovering Countryside. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
- Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find a Countryside holiday package that brings all your bookings together.
Explore a world of travel with Expedia
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- Flights to Berkeley
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- Flights to Oak Lawn
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- Flights from Austin (AUS) to Chicago (MDW)
- Flights from Columbus (CMH) to Chicago (MDW)
- Flights from Grand Rapids (GRR) to Chicago (MDW)
- Flights from Jackson (JAN) to Chicago (MDW)
- Flights from New York (JFK) to Chicago (MDW)
- Flights from Kraków (KRK) to Chicago (MDW)
- Flights from Salt Lake City (SLC) to Chicago (MDW)
- Adventist GlenOaks Hospital
- Aon Center
- Berwyn Holidays
- Visit Broadview
- Canalport Riverwalk Park
- Centennial Beach
- Visit Bedford Park
- Chicago Place Mall
- Chicago Riverwalk
- Chicago Holidays
- Credit Union 1 Arena
- Daley Plaza
- Visit Downers Grove
- Edge Ice Arena
- Ernest Hemingway Museum and House
- Visit Forest Park
- Frank Lloyd Wright Historic District
- Garfield Park Conservatory
- Gregg House Museum
- Visit Hillside
- Hometown Holidays
- Hyde Park Holidays
- Visit La Grange Park
- Lisle Holidays
- Millennium Park
- Moser Tower and Millennium Carillon
- Norridge Holidays
- Visit Oak Brook
- Visit Oak Lawn
- Oak Park Holidays
- River Forest Holidays
- Riverdale Holidays
- Sunset Bridge Meadow
- Unity Temple
- University of Illinois Chicago
- Wheaton College
- Visit Willowbrook
- Wrigley Building
- Car hire in Budget 12232 Tesson Ferry Rd
- Car hire Burr Ridge
- Car hire Oak Lawn
- Car hire near PGN Jump N' Fun Entertainment
- Enterprise Rental Cars in Midway Intl.
- First Car Rental Rental Cars in Palos Park
- Hertz Rental Cars in Bedford Park
- Car hire in Sixt 41 Avenue Du Chateau
- Thrifty Car Rental Rental Cars in Downers Grove
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
