Deals on vacations and trips to Countryside

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Countryside flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $875, price is now $517 per person
$517
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $881, price is now $529 per person
$529
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.
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 $1,764, price is now $1,098 per person
$1,098
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,876, price is now $1,179 per person
$1,179
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and laundry facilities.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,196, price is now $782 per person
$782
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, 2 restaurants, and a gym are all featured at this luxury hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. A business center, a terrace, and dry cleaning are also on offer.

Top Countryside hotels deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $130 total per night
$130 total
Sep 8 - Sep 9
Total with taxes and fees
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.
Free WiFi
Restaurant
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Free Cancellation
Reserve now, pay when you stay
$143 nightly
The price is $170 total per night
$170 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. A lobby fireplace, luggage storage, and wedding services are also on offer.
Pet friendly
Free WiFi
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Free Cancellation
Reserve now, pay when you stay
$248 nightly
The price is $291 total per night
$291 total
Sep 11 - Sep 12
Total with taxes and fees
This hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.
Free airport shuttle
Pet friendly
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Get rates
A gym, self parking, and a virtual front desk are featured at this aparthotel. WiFi in public areas is free. A convenience store and luggage storage are also provided.
Kitchen
Washer
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
$211 nightly
The price is $251 total per night
$251 total
Sep 1 - Sep 2
Total with taxes and fees
This hotel's 3 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and a coffee shop are also provided.
Free WiFi
Restaurant
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
$154 nightly
The price is $183 total per night
$183 total
Aug 17 - Aug 18
Total with taxes and fees
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-in, express check-out, and dry cleaning are also on offer.
Pet friendly
Free WiFi
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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 are vacation packages to Countryside?
Vacation packages, including flights and hotels in Countryside, start from just $517. Turn your travel fantasies into reality and book your dream trip with Travelocity today.
How long should my Countryside vacation be?
Many visitors spend around 3 nights in Countryside. But what's right for them mightn't be right for you. Whether you decide to stay for a matter of days or weeks, you'll love discovering everything that this place has to offer.
Where can I get the best vacation package deals for Countryside?
Look no further than Travelocity. With as many as 400 airlines and 1,000,000 properties worldwide, it's a piece of cake to find a Countryside package deal that fits your budget.
Why should I purchase my Countryside vacation package with Travelocity?
Because you'll never roam on your own if you book your vacation through us, and we offer round-the-clock customer support and excellent service to boot. Add to that our Price Match Guarantee and a huge range of destinations to pick from. It's our job to make your vacation as unforgettable as possible.
Can I save on my Countryside car rental if I combine it with a hotel or flight?
With a Countryside vacation package, you can combine your hotel, car and flight bookings and save a whole lot. If you can't wait to uncover the best of this wonderful area, why not make a beeline for Six Flags Great America? This top sight is 40 mi from Countryside. With your own set of wheels, you'll be there belong long.
Which airport is best for Countryside?
There's a high chance you'll be touching down at O'Hare Intl. Airport (ORD), which is 15 mi north of inner Countryside. Midway Intl. Airport (MDW) (7 mi away from central Countryside) and Lewis University Airport (LOT) (16 mi away from central Countryside) are your other options.
Where should I stay when visiting Countryside?
Many visitors choose to stay at the Holiday Inn Chicago SW-Countryside ConfCtr. It's sure to be a great base for your Countryside vacation.

Photos of local treasures

Browse Countryside vacation photos for more inspiration

A vast wheat field under a cloudy sky.
A rural landscape with rolling hills, a winding road, and a farmstead with silos.
A rustic barn in a lush green field with tall trees and a clear sky.
A snow-covered path with a lamppost and leafless trees in a foggy park.

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