Countryside Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 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 hotels in Countryside
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
S$252
20 Sept - 21 Sept
includes taxes & fees
8.8/10 Excellent! (5,458 reviews)
"Clean rooms"
Reviewed on 16 Sept, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
S$270
13 Oct - 14 Oct
includes taxes & fees
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
S$237
27 Sept - 28 Sept
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
Frequently asked questions
How much does a Countryside holiday package cost?
Offering great value package deals 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 Hillside
- Flights to Hometown
- Flights to Indian Head Park
- Flights from Downers Grove
- Flights from Mosinee (CWA) to Chicago (MDW)
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- Apollo Theater Chicago
- Art Institute of Chicago
- Visit Bellwood
- Blue Island Holidays
- Buckingham Fountain
- Centennial Beach
- Centennial Park Aquatic Center
- Visit Bedford Park
- Chicago Museum Campus Holidays
- Visit West Lawn
- Cicero Holidays
- Cna Center
- Visit Crestwood
- Downers Grove Holidays
- Elmhurst Holidays
- Frank Lloyd Wright Historic District
- Goose Island Holidays
- Grant Park
- Harvey Public Library
- Mccormick Place
- Melrose Park Holidays
- Visit Melrose Park
- Merchandise Mart
- Millennium Park
- Morton Arboretum
- Oakbrook Center Mall
- Palos Hills Holidays
- Pritzker Pavilion
- Shops at North Bridge
- Soldier Field
- Stone Park Holidays
- University of Illinois Chicago
- Walt Disney House
- Willis Tower
- Willowbrook Community Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
