Countryside Holidays from AU$1,839

Book a Hotel + Flight or Car together to unlock savings

Photo by Monica Ferro

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to AU$703 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Your Countryside Holiday

From its rural countryside to its spectacular views and beyond, there's a lot to love about Countryside. Discover the wonders of this awesome city with a Countryside holiday package that's tailor-made for you. Fill your days with visits to Brookfield Zoo, SeatGeek Stadium and Chicago Ridge Shopping Mall, some of the attractions you shouldn't miss during your trip to Countryside. Check out Expedia's wide range of travel options and start planning your perfect holiday to Countryside today.

The Latest Countryside Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Price was AU$3,931, price is now AU$1,839 per person
AU$1,839
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
8.8/10 Excellent! (1,617 reviews)
Would definitely book a stay again.

Reviewed on 16 Aug. 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was AU$4,291, price is now AU$1,977 per person
AU$1,977
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Great area: able to walk to many restaurants.

Reviewed on 18 Aug. 2025

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

4 out of 5
Downtown Chicago
Price was AU$4,182, price is now AU$1,929 per person
AU$1,929
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
9.6/10 Exceptional! (1,005 reviews)
The room was great The staff was very friendly free coffee in the morning was nice

Reviewed on 14 Aug. 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was AU$4,232, price is now AU$1,966 per person
AU$1,966
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
Check in and out was seamless! Got excellent help with bags and access to amenities! Great location it was about a 9 min walk to Riverwalk, Hop on Bus; felt safe and area was clean

Reviewed on 18 Aug. 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was AU$3,992, price is now AU$1,855 per person
AU$1,855
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
Terrible mattresses, old and crunchy or something; bad lumpy pillows. No coffee or water in the room. If you want free coffee, you gotta track to the lobby during coffee hours and pay a "resort" fee for the experience.

Reviewed on 17 Aug. 2025

Countryside Holiday

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 Madison Street Theatre

Our pick of the best Countryside Hotel Deals

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 AU$243 per night from 1 Sept to 2 Sept
AU$243
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (8,944 reviews)
"It takes around 20min for the hot shower to come out."

Reviewed on 17 Aug. 2025

Congress Plaza Hotel
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$272 per night from 3 Sept to 4 Sept
AU$272
3 Sept - 4 Sept
includes taxes & fees
8.2/10 Very Good! (1,187 reviews)
"Everything was great. Thanks for an awesome experience."

Reviewed on 15 Aug. 2025

The Wade
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
The price is AU$290 per night from 3 Sept to 4 Sept
AU$290
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,723 reviews)
"Kids really enjoyed the pool. Breakfast was good as well"

Reviewed on 17 Aug. 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,944 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
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in Countryside

Navy Pier

Navy Pier

4.5/5(64 reviews)

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

4.5/5(73 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Grant Park

Grant Park

4.5/5(47 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

What to do in Countryside

River tour boat in Chicago

Architecture River Tour

AU$63
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

AU$69
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Countryside

Frequently asked questions

How much does a Countryside holiday package cost?
Offering great value package deals from AU$1,839 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?

  1. Choose your dates: What you plan to do in Countryside and your preferred season can help you decide when to go.
  2. 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.
  3. 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.
  4. 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.