Countryside Vacations from $179

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $306, price is now $179 per person
$179
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,273 reviews)
Friendly staff with clean and basic amenities. Reasonable value for money.

Reviewed on Oct 20, 2025

The French Country Inn Lake Geneva

The French Country Inn Lake Geneva

3 out of 5
Save 100% on your flight
Price was $892, price is now $475 per person
$475
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
8.6/10 Excellent! (154 reviews)
The rooms are cozy with deck space overlooking Lake Como and the Getaway restaurant was on the property with a beautiful terraced patio. The food and service were great!

Reviewed on Oct 16, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $739, price is now $410 per person
$410
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
Beautiful rooms. Exceptional staff. An all around superior experience.

Reviewed on Oct 18, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $798, price is now $479 per person
$479
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Very gracious staff, impressive breakfast offerings/venue, cleanliness, location, Rooftop Bar, and seasonal (Halloween) decorations.

Reviewed on Oct 20, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $993, price is now $610 per person
$610
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
The front desk staff was super friendly and helpful. After waking up at 4am to catch an early flight, we were thrilled when they had a room ready for us for early check-in. Hyatt does a great job with room lay-outs. It was obvious that our room was recently renovated with a modern conveniences like motorized shades, a comfy window seat, hidden bar and Nespresso maker, and clean decor. Our friends were staying around the corner at the Ritz and liked our room better.

Reviewed on Oct 14, 2025

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Discover the most popular places to visit in Countryside

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

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

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy 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
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

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

Navy Pier

What to do in Countryside

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

$44
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

$45
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $170 total per night from Nov 2 to Nov 3
$170 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (9,498 reviews)
"The website for the gazebo restaurant within the hotel said there was an extensive menu. When you get down to the place it’s a small buffett set up which was similar to any other continental breakfast with some cereal, muffins, fruit, some biscuits, bacon and sausage etc. There was also a man at ..."

Reviewed on Oct 20, 2025

Congress Plaza Hotel
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
$116 nightly
The price is $136 total per night from Nov 16 to Nov 17
$136 total
Nov 16 - Nov 17
Total with taxes and fees
8.8/10 Excellent! (3,142 reviews)
"Nice location, rooms were nice size beds were comfortable water pressure was great"

Reviewed on Oct 20, 2025

Hilton Chicago/Magnificent Mile Suites
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $106 total per night from Nov 11 to Nov 12
$106 total
Nov 11 - Nov 12
Total with taxes and fees
7.8/10 Good! (2,498 reviews)
"Great Vibe!"

Reviewed on Oct 19, 2025

Freehand Chicago
See all 4,859 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 $179 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.