Countryside Vacations from ￥44,434

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The Latest Countryside Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3 out of 5
Downtown Chicago
per person
Dec 13 - Dec 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
8.8/10 Excellent! (1,165 reviews)
Very cozy beds and linens, immaculately clean, and friendly, professional staff. We’d stay here again!

Reviewed on Nov 3, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Dec 13 - Dec 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,390 reviews)
The hotel was beautiful, fabulous location , my only concern that I’m only giving 4 and not 5 is because we were not greeted on arrival, nothing was explained, boarding on rudeness. Bell man great

Reviewed on Nov 9, 2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Dec 13 - Dec 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (888 reviews)
The staff were all wonderful and really helpful. It was our first time in Chicago and they were more than wonderful for pointing us in the correct locations on where we needed to go and what to do

Reviewed on Nov 5, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Dec 13 - Dec 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9/10 Wonderful! (263 reviews)
Service was great, room was neat and very clean. Would stay again!

Reviewed on Oct 4, 2024

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
Dec 13 - Dec 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9/10 Wonderful! (809 reviews)
Very cool property. Easy access to shopping and dinning. Amazing room with nice shower and bed.

Reviewed on Nov 10, 2024

Find the Best Countryside Vacation Packages

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 ￥20,771 per night from Nov 21 to Nov 22
￥20,771
￥24,383 total
includes taxes & fees
Nov 21 - Nov 22
7.8/10 Good! (8,049 reviews)
"Perfect for travelers. Great hotel bar. Location ideal"

Reviewed on Nov 7, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥14,791 per night from Dec 11 to Dec 12
￥14,791
￥17,361 total
includes taxes & fees
Dec 11 - Dec 12
8.6/10 Excellent! (3,529 reviews)
"Pedro at check in was extremely helpful"

Reviewed on Nov 9, 2024

River Hotel
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
Fully refundableReserve now, pay when you stay
The price is ￥18,034 per night from Nov 24 to Nov 25
￥18,034
￥21,172 total
includes taxes & fees
Nov 24 - Nov 25
8.2/10 Very Good! (3,174 reviews)
"Very unique hotel layout, with a 10-story inner atrium that really opens up the interior of the hotel. Rooms are LARGE, very high quality and very clean. Great free breakfast, including a custom-order omelette bar. Location is great, just off Michigan Avenue, with Red Line subway station 1 block ..."

Reviewed on Nov 8, 2024

Embassy Suites by Hilton Chicago Downtown River North
See all 4,410 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.

Frequently asked questions

How much does a Countryside vacation package cost?
From as little as ￥44,434. Yes, you read that right. Our Countryside vacation packages are the easiest way to stretch your budget further. Bundle your hotels, flights and rental car and explore this destination your way.
How do I get a cheap travel package to Countryside?
Bundle your bookings with Expedia to save on your next exciting adventure. With more than 550 partner airlines and 1,000,000 hotel options worldwide, your Countryside vacation package can be tailored exactly to suit your budget. With all that extra money, why not add some fun activities and tours? It’s an easy way to unlock even more discounts. That vacation you’ve always dreamed of in Countryside is closer than you thought!
Where should I stay in Countryside?
A getaway to Countryside isn’t complete without checking out Burr Ridge Village Center, Adventist La Grange Memorial Hospital and Resurrection Cemetery & Mausoleums. Spend your evenings close to these attractions and make sightseeing simple.
What are the top hotels in Countryside?
If it’s comfort and convenience you’re after, you won’t beat Holiday Inn Chicago SW-Countryside ConfCtr. Spend your nights unwinding here and your days checking out Countryside’s finest sights.
How far in advance should I book my Countryside vacation?
It’s tricky picking the perfect time for airfares, but we normally say the earlier, the better. Most international flights on Expedia become available up to 12 months in advance. If you’re booking last minute, fear not. Cheap prices occasionally appear just weeks before departure dates.
What does an Expedia Countryside travel package include?
With Expedia, you can choose a combination of car rentals, hotels and flights to build your perfect Countryside travel package. Once you’ve made your booking, you can add on the fun things like tours and activities. Remember — the more you bundle, the more cash you’ll save!
What should I know before booking a Countryside travel package?
When you book your hotels, flights and car rentals together, you’ll be rewarded with awesome discounts. Whether you’re organizing a mountain getaway in a cabin or would rather stay in a ritzy city hotel, Expedia will make it happen for less.
Can I choose my airline with a Countryside Expedia vacation package?
With a vacation package, the choice is in your hands. Whether you’re eager to fly to Countryside in coach or business class, simply pick from the available airline options. Expedia has access to more than 550 partner airlines worldwide.
If I'm not able to travel, can I cancel my Countryside vacation package?
You can. We get that even the best-laid plans can go awry, so we’re happy to help if you have to make changes to your Countryside vacation package. It may be possible to amend or cancel your itinerary at no cost if you’ve booked within 24 hours. Your airline, hotel or car rental company may impose a fee if you booked more than 24 hours ago. Have a look at our Customer Service Portal for more information. Also, check your itinerary for the nitty-gritty on change fees.

Discover the most popular places to visit in Countryside

Image for Michigan Avenue

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
Image for McCormick Place

McCormick Place

4.5/5(1,805 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Image for Wrigley Field

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

What to do in Countryside

Image for Flyover in Chicago

Flyover in Chicago

￥5,732
Per adult
94% of travellers recommend
Flyover in Chicago
Image for Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

￥6,707
Per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Image for Chicago River Cocktail Cruise

Chicago River Cocktail Cruise

￥8,892
Per adult
90% of travellers recommend
Chicago River Cocktail Cruise
See all activities in Countryside
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.