Countryside Vacation Packages 2026 from $339

Countryside flight + hotel vacation packages

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

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$339

per person

Apr 16 - Apr 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

Urban Chicago Oasis

Lakeview

Save 100% on your flight

$843

per person

Apr 24 - Apr 27

found 14 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features free WiFi in public areas, laundry facilities, and a virtual front desk.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$420

per person

Apr 17 - Apr 20

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.

Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

$414

per person

May 7 - May 10

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a gym, and a poolside bar. Enjoy the seasonal outdoor pool and perks like free WiFi. Self parking, a 24-hour business center, and a coffee shop are also offered.

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$381

per person

Apr 24 - Apr 27

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 free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.

Top Countryside hotels deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$109 total

Feb 16 - Feb 17

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

Hotel Riu Plaza Chicago

150 East Ontario Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$137 nightly

$161 total

Feb 16 - Feb 17

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

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Free Cancellation

Reserve now, pay when you stay

$196 nightly

$230 total

Mar 7 - Mar 8

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

Hilton Chicago

720 S Michigan Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$164 nightly

$192 total

Feb 21 - Feb 22

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

Pool

Hot Tub

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$94 nightly

$111 total

Feb 22 - Feb 23

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

Aloft Chicago Mag Mile

243 E. Ontario Chicago IL

Free Cancellation

Reserve now, pay when you stay

$90 nightly

$106 total

Feb 25 - Feb 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. Valet parking, a business center, and a snack bar/deli are also offered.

Pool

Pet friendly

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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

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.

Wrigley Field

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

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Frequently asked questions

How much are vacation packages to Countryside?

Vacation packages, including flights and hotels in Countryside, start from just $339. 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.