Countryside Holidays from £897

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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.
Kinzie Hotel

Kinzie Hotel

Downtown Chicago
£897
per person
13 Nov - 19 Nov
found 5 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (2,200 reviews)
My boyfriend, pup, and I recently stayed at the Kinzie for his birthday. We had stayed here a few years ago and remembered it being a much nicer experience, so unfortunately this visit was disappointing. The location is great, but once you factor in the additional fees, I think there are much nicer options in Chicago for the price. For example, the Kimpton Gray is a great dog-friendly hotel with no additional pet fee. I’m not opposed to paying a pet fee, but between that and the other extras here, we could have stayed somewhere nicer. Also, what exactly is the $34.95 nightly service fee for? This is not a resort. The biggest frustration was our room temperature. The room was extremely warm and we could not get it to cool down, so we called the front desk for help. We were told to flip off a switch that had a metal barrier covering it, turn it back on, and then hold the “cool” button. Why is appropriately cooling a hotel room this much of an obstacle? Even after doing that, the system repeatedly timed out, so we kept waking up hot and having to adjust it again. Overall, this just isn’t the Kinzie I remember. What previously felt like a nice hotel now feels much more like a budget hotel experience where you’re being nickel-and-dimed with added fees. Unfortunately, we won’t be staying again.

Reviewed on 22 Aug 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£1,814
per person
26 Oct - 31 Oct
just found
Return flight included
London (LON) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Level Chicago - River North

Level Chicago - River North

Downtown Chicago
£1,212
per person
27 Sept - 1 Oct
found 20 hours ago
Return flight included
London (LGW) to Chicago (ORD)
9.2/10 Wonderful! (1,043 reviews)
First time staying here and we were not disappointed at all. We were upgraded to a two room suite and the view was spectacular! Beds were super comfortable with soft bedding and the room had everything we needed. The staff were all really friendly and helpful as well. Would definitely stay again.

Reviewed on 21 Aug 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,271
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Amazing stay! Perfect location. Staff were incredibly helpful and friendly. Will definitely stay again next time I’m in Chicago!

Reviewed on 22 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,163
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
They charge a facilities fee which is about 20 bucks a night for the amenities. I generally don't have a problem with that as it includes breakfast. BUT, I was annoyed that in the hotel gym (which isn't bad), the bikes had some problems. It's a slight nitpick, admittedly, but that's what it is. The hotel is very close to transit and the LOOP which is the main area of Chicago. Staff were amazing and helpful, the breakfast was very filling. The gym has weights that go up to 20KG, which is pretty nice and they do have those gymbro slogans on the walls which is kind of fun.

Reviewed on 22 Aug 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

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£90
8 Sept - 9 Sept
includes taxes & fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
£125
30 Aug - 31 Aug
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
£216
11 Sept - 12 Sept
includes taxes & fees
Hilton Chicago O'Hare Airport
See all 4,854 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.

What to do in Countryside

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

£35
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.