Countryside Holidays

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    Save up to S$134 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Countryside Flight & Hotel Packages

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

Hilton Chicago

4 out of 5
Downtown Chicago
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
8.4/10 Very Good! (1,387 reviews)
Beautiful hotel, quiet clean spacious rooms! Breakfast buffett to die for. Close to museums and Metro.

Reviewed on 24 Nov,2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
9.4/10 Exceptional! (888 reviews)
We had multiple issues with the locks on our door.

Reviewed on 24 Nov,2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
9/10 Wonderful! (263 reviews)
Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!

Reviewed on 11 Nov,2024

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
9/10 Wonderful! (809 reviews)
Lobby and shared space downstairs is beautiful and location is great in Fulton Market. We walked to many bars and restaurants and enjoyed the vibe. The rooms are underwhelming, no closet space, bathroom space lacking, and feel dated despite trying to go for a modern-industrial-chic vibe. The quality of the rooms do not match what the lobby area indicates. The hallways seem like they didn’t get touched in whatever remodel happened here. Overall I think it’s overpriced for what it delivers.

Reviewed on 20 Nov,2024

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
9/10 Wonderful! (1,378 reviews)
Location is very convenient And the hotel, the room and facilities are nice. I would stay again.

Reviewed on 25 Nov,2024

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Countryside

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 S$158 per night from 8 Dec to 9 Dec
S$158
includes taxes & fees
8 Dec - 9 Dec
7.8/10 Good! (8,182 reviews)
"Overall we liked the room we stayed at the only complaint was that the hallway leading to the room had an awful smell like lake dead fish or something when we arrived on 11/23 this morning the smell was less but it still smelled"

Reviewed on 25 Nov,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 S$153 per night from 25 Dec to 26 Dec
S$153
includes taxes & fees
25 Dec - 26 Dec
8.6/10 Excellent! (3,551 reviews)
"Is very close to everything"

Reviewed on 23 Nov,2024

River Hotel
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$152 per night from 25 Dec to 26 Dec
S$152
includes taxes & fees
25 Dec - 26 Dec
8.4/10 Very Good! (3,264 reviews)
"This is a go-to hotel for me near a yearly event I participate in. It's the best value of any of the hotels in its immediate surrounding area."

Reviewed on 21 Nov,2024

Club Quarters Hotel, Central Loop, Chicago
See all 4,484 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 holiday package cost?
From as little as S$757. Yes, you read that right. Our Countryside holiday 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 holiday 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 holiday 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 Centre, 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 holiday?
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 organising 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 holiday package?
With a holiday 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 holiday 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 holiday 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.

Popular places to visit

McCormick Place

McCormick Place

4.5/5(36 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
Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

4.5/5(147 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

What to do in Countryside

Flyover in Chicago

Flyover in Chicago

S$51
Per adult
94% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

S$65
Per adult
94% of travellers recommend
Architecture River Tour
Narrated by certified, local docent

Chicago Architecture Center River Cruise aboard Chicago's First Lady

S$73
Per adult
96% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.