Countryside Holidays from £1,034

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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.
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
per person
4 Sept - 9 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,037 reviews)
My favorite hotel in Chicago! Always a fabulous time and the staff are delightful!

Reviewed on 11 Jul 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
25 Aug - 29 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Nice property, very walkable. Front desk was great. Bar area nice & welcome drink nice. Concierge was not around. Got suite with 2 full baths which was awesome with teens. Great stay overall!

Reviewed on 12 Jul 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
23 Aug - 30 Aug
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Always love our stay at The Peninsula!

Reviewed on 29 Jun 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
25 Aug - 29 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
I didn’t like the staff insinuating that I couldn’t afford a bottle of Dom. I didn’t like the 3 calls to my room to make sure I understood what the price was. I didn’t like how Brandy told me the reason for doubting my ability to pay for a $700 bottle of champagne was because of what my “profile” said about me. I would love to see this profile they had on me. I did not appreciate being embarrassed in front of my wife. We spent close to 10K at this place for the 7 days we spent there. We chose to stay at Trump Intl in Chicago because we can afford to do so. I understood before checking in that it would be very expensive. I did not know that a profile would be built about me and I would be judged by the staff according to it. I will never stay at a Trump hotel again. There are too many hotels to chose from to have to deal with this kind of treatment.

Reviewed on 12 Jul 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
25 Aug - 29 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I love Virgin air and expected a 5-star experience. Hotel checkin was not all that welcoming, but efficientl. They had no valet service and basically told us we were on our own. Thought ok I need a drink so went to the rooftop bar. An afterthought at this hotel. Cushions were dirty and faded. Barely staffed. More like a rooftop bar in costs rica than downtown Chicago. Room was nice and stylish. The highlight of the stay tbh as was the coffee shop.

Reviewed on 13 Jul 2025

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
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £129 per night from 5 Aug to 6 Aug
£129
5 Aug - 6 Aug
includes taxes & fees
7.8/10 Good! (8,951 reviews)
"It was perfect for my family. Very close to the millennium Park"

Reviewed on 12 Jul 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
The price is £197 per night from 10 Aug to 11 Aug
£197
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (2,029 reviews)
"Clean, great location ."

Reviewed on 12 Jul 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £130 per night from 10 Aug to 11 Aug
£130
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (2,430 reviews)
"I always prefer staying in Hilton!"

Reviewed on 12 Jul 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,799 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Navy Pier

Navy Pier

4/5(125 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Magnificent Mile - River North which includes street scenes, signage and night scenes

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue

What to do in Countryside

River tour boat in Chicago

Architecture River Tour

£36
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£33
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Countryside

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.