Countryside Holidays from £969
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Your Countryside Holiday
Book a Countryside holiday 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 holiday to Countryside now.
Top Countryside Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
£1,528
per person
19 Nov - 24 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
We had the most memorable time… we flew out from California to see my 5 yr old granddaughter for the weekend . Thank you Sharon and staff for making my weekend with her a day she will always remember. I have highly recommended this hotel to all my law enforcement partners. Thank you and we will be back.
Reviewed on 7 Oct 2026
Countryside Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 6,000 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 27ºC |
Top Sights | Brookfield Zoo, Galloping Ghost and Lizzadro Museum of Lapidary Art |
Top hotels in Countryside
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£114
1 Nov - 2 Nov
includes taxes & fees
8/10 Very good! (10,212 reviews)
"When I first walked in to the hotel, I was impressed by the beautiful lobby. But that was it. The rooms are extremely dated, the bathtub has rust all over, and the door frames have huge dents. Yes, they do have nice high ceilings, but the furniture needs to be updated, and the windows need room darkening ..."
Reviewed on 7 Oct 2026
River Hotel
75 East Wacker Drive Chicago IL
£150
1 Nov - 2 Nov
includes taxes & fees
8.8/10 Excellent! (5,483 reviews)
"Clean and very helpful staff. Great location!"
Reviewed on 7 Oct 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
£128
1 Nov - 2 Nov
includes taxes & fees
8/10 Very good! (2,429 reviews)
"N/A"
Reviewed on 7 Oct 2026
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
Skydeck Chicago at Willis Tower
£32
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
£30
per adult
94% of travellers recommend
Frequently asked questions
Why should I book my Countryside holiday with Expedia?
Expedia has you covered for every detail of your next Countryside holiday. You'll always get the best deals, but when you bundle your accommodation, airfares and/or hire car into a holiday package, you can save even more. Want to truly make the most of your escape? Add a few fun tours and activities to your package. Expedia offers flexible cancellation policies on most bookings, so there's no need to stress if you have to change your plans. Visit our Customer Service Portal link to find out more.
When is the best time of year to holiday in Countryside?
Countryside is a busy place in March, May and June. If you don't like large crowds and prefer a quieter pace, lock in your escape for February, August and September. With daytime average temperatures of -4ºC, January is the coolest period in Countryside. The warmest month is July, when you can experience averages of 23ºC throughout the day. Whatever the temperature, you'll discover plenty of things to keep you entertained here.
What is the top hotel for my holiday in Countryside?
Offering plenty of amenities and home comforts, LondonHouse Chicago, Curio Collection by Hilton will make an ideal base for your Countryside holiday.
How do I get a cheap holiday to Countryside?
One of the easiest ways to save money (and time) is to combine your bookings with Expedia. Hotels, flights, hire cars and activities — we've got them all. Pick and choose a combination that suits you and see your savings stack up. We know holidays are never a one-size-fits-all. That's why we offer over 400 air carriers and 321,000 hotels across the world, so you can customise your Countryside holiday your way. Learn more about how you can save money on your next holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my Countryside holiday?
There are plenty of places to check out during your holiday in Countryside. Brookfield Zoo, SeatGeek Stadium, Oakbrook Centre Mall and Drury Lane Theatre are just a few of this city's major attractions.
Do I need a visa for my Countryside holiday?
Look up the latest information on official government websites. Your nationality and whether you're visiting for study, business or leisure will determine if you need a visa for Countryside. Familiarise yourself with the application process, including the required documentation, fees and turnaround times. Start your application well in advance to allow enough time for processing. Some visas can take weeks or even months to go through, depending on the country.
What should I wear on my Countryside holiday?
Consider the types of activities you'll be doing during your Countryside trip and travel with pieces that you can easily mix and match. For fashion inspiration or even information on dress codes, browse style blogs or social media accounts. Take a look at the local weather forecast so you can pack your bags accordingly. The warmest time of year in Countryside is July, with average daily temperatures of 23ºC. If you're on holiday during the coolest month of January, the mercury averages -4ºC during the day.
What does an Expedia Countryside holiday include?
With Expedia, you can select any combination of flights, hotels and car hires to create your perfect Countryside package. Once you've made your booking, simply add on the fun things like tours and activities. Remember, the more you bundle, the more pounds you'll save! Explore a wide range of property types and select one that suits your group size and travel needs. The most popular holiday rentals here are private holiday homes and apartments. With Expedia, it's easy to tailor your Countryside retreat just the way you like.
Does Expedia offer Book Now, Pay Later Countryside holidays?
We do. Expedia has joined forces with online lender Klarna to help you easily pay for your holiday in instalments. Simply select the payment plan that suits you best during the checkout process and take away the stress of budgeting for your trip. Make sure you bundle your accommodation, car hire and flights with Expedia to get the biggest bang for your buck. Check out our flexible payment options below:
- Pay monthly holidays: Make your holiday dreams a reality sooner with Klarna's manageable monthly instalment plans. If paying over multiple transactions sounds right for you, pick this option during the checkout process.
- No-deposit holidays: When you stumble on an unbeatable deal but your budget doesn't quite cover it yet, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to lock in your getaway.
Can I choose my airline with a Countryside Expedia holiday?
Yes — and it's simple too. Expedia has access to more than 400 partner airlines worldwide. Our packages give you the freedom to pick from available flights, hotels and activities that suit you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
