Countryside Vacation Packages 2025/2026 from $229

Countryside flight + hotel vacation packages

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

DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove

$229

per person

Nov 16 - Nov 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking and a free area shuttle.

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$767

per person

Dec 2 - Dec 8

found 16 hours 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.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$327

per person

Nov 10 - Nov 13

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.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$683

per person

Dec 5 - Dec 7

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.

Fairmont Chicago at Millennium Park

Downtown Chicago

Save 100% on your flight

$453

per person

Nov 10 - Nov 13

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 eco-certified hotel. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Top Countryside hotels deals

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$179 total

Oct 26 - Oct 27

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

Freehand Chicago

19 East Ohio Street, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$134 nightly

$158 total

Oct 21 - Oct 22

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a coffee shop, and a snack bar/deli are also offered.

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$186 nightly

$219 total

Oct 5 - Oct 6

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.

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$161 nightly

$189 total

Oct 20 - Oct 21

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

citizenM Chicago Downtown

80 East Wacker Place, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$218 nightly

$255 total

Oct 30 - Oct 31

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

10 E Grand Ave, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$187 nightly

$220 total

Oct 1 - Oct 2

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

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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

4.5/5(2,128 reviews)

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

4.5/5(332 reviews)

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

4.5/5(4,870 reviews)

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 $229. 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.