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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $313, price is now $144 per person
$144
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Limo/town car service, WiFi in public areas, and express check-out are also on offer.
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,621, price is now $605 per person
$605
per person
Dec 24 - Dec 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.
The Blackstone, Autograph Collection

The Blackstone, Autograph Collection

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $668, price is now $334 per person
$334
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a lobby fireplace, and express check-in are also offered.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $384, price is now $196 per person
$196
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $351, price is now $187 per person
$187
per person
Jan 23 - Jan 26
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.

Top Countryside hotels deals

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
Free Cancellation
Reserve now, pay when you stay
$95 nightly
The price is $112 total per night
$112 total
Nov 25 - Nov 26
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.
Pool
Breakfast included
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $115 total per night
$115 total
Dec 7 - Dec 8
Total with taxes and fees
A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.
Pet friendly
Free WiFi
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
$110 nightly
The price is $129 total per night
$129 total
Dec 8 - Dec 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
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $134 total per night
$134 total
Nov 20 - Nov 21
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, a communal living room, and express check-in are also on offer.
Free WiFi
Restaurant
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$86 nightly
The price is $100 total per night
$100 total
Nov 25 - Nov 26
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. Express check-out, luggage storage, and concierge services are also on offer.
Pool
Pet friendly
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $139 total per night
$139 total
Dec 8 - Dec 9
Total with taxes and fees
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.
Breakfast included
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.

Popular places to visit

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

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

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
McCormick Place showing a high rise building and a city

McCormick Place

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

Frequently asked questions

How much are vacation packages to Countryside?
Vacation packages, including flights and hotels in Countryside, start from just $144. 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

Photo by Monica Ferro
Photo by Monica Ferro

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