Countryside Vacation Packages 2026 from $244

Countryside flight + hotel vacation packages

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

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$244

per person

Mar 20 - Mar 22

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.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$502

per person

Mar 22 - Mar 27

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.

Trump International Hotel & Tower Chicago

Downtown Chicago

$876

per person

Mar 12 - Mar 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Hilton Chicago

Downtown Chicago

Save 100% on your flight

$435

per person

Mar 12 - Mar 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

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.

Palmer House a Hilton Hotel

Downtown Chicago

Save 100% on your flight

$455

per person

Mar 12 - Mar 17

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 business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and limo/town car service.

Top Countryside hotels deals

Hilton Chicago

720 S Michigan Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$155 nightly

$182 total

Feb 1 - Feb 2

Total with taxes and fees

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$94 total

Jan 25 - Jan 26

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-out, dry cleaning, and luggage storage are also on offer.

Club Quarters Hotel Wacker at Michigan, Chicago

75 E Wacker Dr Chicago IL

Free Cancellation

Reserve now, pay when you stay

$88 nightly

$103 total

Jan 30 - Jan 31

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. A snack bar/deli, express check-in, and express check-out are also on offer.

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$168 nightly

$192 total

Jan 23 - Jan 24

Total with taxes and fees

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$126 total

Jan 19 - Jan 20

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.

Hyatt Regency Chicago

151 East Wacker Dr Chicago IL

Free Cancellation

Reserve now, pay when you stay

$182 nightly

$214 total

Feb 8 - Feb 9

Total with taxes and fees

This smoke-free hotel's 4 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A terrace, a snack bar/deli, and express check-in are also on offer.

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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

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

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.

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Frequently asked questions

How much are vacation packages to Countryside?

Vacation packages, including flights and hotels in Countryside, start from just $244. 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.