Countryside Vacations from $569

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Your Countryside Vacation

Book a Countryside vacation 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 vacation to Countryside now.

The Latest Countryside vacation packages

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $902, price is now $569 per person
$569
per person
Jul 8 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
we didn't have breakfast at the hotel

Reviewed on May 11, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,188, price is now $740 per person
$740
per person
Jul 8 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,070 reviews)
Wonderful experience, beautiful place. Breakfast on site was a huge plus!

Reviewed on May 13, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $963, price is now $624 per person
$624
per person
Jun 22 - Jun 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (472 reviews)
Really nice building with top-notch amenities in a fabulous location. Room was large, clean and well equipped with high end appliances, walk-in closet, floor to ceiling windows with lots of light. Overall, a great experience. Would stay again.

Reviewed on May 12, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,151, price is now $746 per person
$746
per person
Jul 8 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (471 reviews)
The rooms were very clean!

Reviewed on May 4, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,332, price is now $878 per person
$878
per person
Jul 8 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.

Reviewed on May 8, 2026

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Discover the most popular places to visit in Countryside

Wrigley Field

Wrigley Field

4.5/5(2,149 reviews)

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(461 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(4,925 reviews)

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

Navy Pier

What to do in Countryside

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$27
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

$38
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Countryside

Countryside Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$132 nightly
The price is $157 total per night from May 25 to May 26
$157 total
May 25 - May 26
Total with taxes and fees
8/10 Very Good! (10,222 reviews)
I didn't drive. Was close to public transit. Had construction going on in front of hotel, but wasn't given prior warning. Made getting in & out difficult. Came to check in & system was down, leading to a delay in getting our rooms.

Reviewed on May 13, 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $171 total per night from May 25 to May 26
$171 total
May 25 - May 26
Total with taxes and fees
8.8/10 Excellent! (5,162 reviews)
Friendly staff and excellent location. Loved our 2 bed suite with 2 bathrooms and a kitchen! Would absolutely stay again!

Reviewed on May 11, 2026

River Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $175 total per night from May 25 to May 26
$175 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (4,134 reviews)
Amazing

Reviewed on May 13, 2026

Hotel Riu Plaza Chicago
See all 5,013 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.

Find the Best Countryside Vacation Packages

Countryside Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
6,000
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Brookfield Zoo, Galloping Ghost and Lizzadro Museum of Lapidary Art

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Frequently asked questions

How much does a Countryside vacation package cost?
Offering great value package deals from $569 on Expedia, you'll be thrilled with how little a vacation to Countryside costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Countryside?
February, August and September are the best times to look for cheap Countryside vacation packages. Choosing to travel in less busy periods means you can usually find lower prices on flights and accommodations.
How many days is enough for Countryside?
Typically, a handful of days is enough to check out the main attractions during your Countryside vacation. But if you'd like to have more time to kick back or go on day trips, think about 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 vacation as a package?
An Expedia vacation package could land you great savings when compared to booking stays and flights separately. Better still, you can customize 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 vacation 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. Pick your dates: What you want to do in Countryside and your favorite season will help you decide when to get away.
  2. Plan your budget wisely: As well as the price of your hotel, you should factor in other expenses too. These include transportation, flights and food. Also, set aside some extra funds for unexpected costs that may crop up during your trip to Countryside.
  3. Explore Countryside with our trip planning tool: Gain insights into the top attractions and best stays for your trip to Countryside. You can also save your must-visit places, collaborate with your group and organize all your plans in one place.
  4. Decide how long to go for: Now that you're up to speed on Countryside, you can figure out the ideal length of your break. Create a draft itinerary and allocate enough time to cover everything you want to see.
  5. Combine your airfare and accommodations: Once you've nailed down your dates and duration, book the right Countryside vacation package for you.
  6. Book any day trips or activities: Now to the fun part — locking in everything you want to see and do. Browse some of the top things to do in Countryside and reserve your tickets in advance to save time (and maybe some spending money too!).

Does Expedia offer Book Now, Pay Later Countryside vacation packages?
If you're like us, you love going away but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the overall cost of your Countryside vacation over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.