Southwest Vacation Packages 2025/2026 from $491

Southwest flight + hotel vacation packages

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

Spark By Hilton Jackson Ridgeland

$491

per person

Dec 30 - Jan 5

found 1 day ago

Roundtrip non-stop flight included

Chicago (MDW) to Jackson (JAN)

This hotel features a gym and a seasonal outdoor pool. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Express check-in, express check-out, and laundry facilities are also on offer.

The Westin Jackson

Downtown Jackson

$767

per person

Dec 30 - Jan 5

found 1 day ago

Roundtrip non-stop flight included

Chicago (MDW) to Jackson (JAN)

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 business center, free WiFi in public areas, and valet parking. Enjoy the gym and perks like free self parking.

Hilton Garden Inn Jackson Downtown

Downtown Jackson

$563

per person

Dec 30 - Jan 5

found 1 day ago

Roundtrip non-stop flight included

Chicago (MDW) to Jackson (JAN)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free WiFi. Valet parking, a business center, and a coffee shop are also offered.

Wingate by Wyndham Jackson/Ridgeland

$576

per person

Dec 30 - Jan 5

found 1 day ago

Roundtrip non-stop flight included

Chicago (MDW) to Jackson (JAN)

This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Hilton Garden Inn Jackson/Madison

$669

per person

Dec 30 - Jan 5

found 1 day ago

Roundtrip non-stop flight included

Chicago (MDW) to Jackson (JAN)

This hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. Guests will appreciate free perks like free self parking and WiFi in public areas. A 24-hour business center, a grocery/convenience store, and a lobby fireplace are also on offer.

Top Southwest hotels deals

Baymont by Wyndham Jackson/Ridgeland

5709 I 55 N Jackson MS

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$85 total

Nov 23 - Nov 24

Total with taxes and fees

This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

Natchez Grand Hotel & Suites On the River

111 S Broadway Street Natchez MS

Free Cancellation

Reserve now, pay when you stay

$103 nightly

$116 total

Nov 23 - Nov 24

Total with taxes and fees

This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 5 conference rooms, 24-hour business center, and express check-out. Relax with a drink at the bar/lounge and enjoy the free buffet breakfast each morning.

Pool

Breakfast included

Woodspring Suites Jackson Pearl I-20

2 Mac and Bones Drive Pearl MS

Free Cancellation

Reserve now, pay when you stay

$79 nightly

$88 total

Nov 23 - Nov 24

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. Laundry facilities are provided for your convenience.

Pet friendly

Parking included

Prado Hotel

610 E County Line Road Ridgeland MS

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$103 total

Nov 23 - Nov 24

Total with taxes and fees

This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

Imperial Suites - Adults Only

3720 I-55 Jackson MS

$70 nightly

$78 total

Nov 23 - Nov 24

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Parking included

Free WiFi

Wingate by Wyndham Jackson/Ridgeland

6485 Frontage Road Ridgeland MS

Free Cancellation

Reserve now, pay when you stay

$76 nightly

$83 total

Dec 2 - Dec 3

Total with taxes and fees

Pool

Breakfast included

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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

Jackson Convention Complex

4/5(82 reviews)

View fascinating exhibitions, thrilling performances and interesting collectors’ tradeshows at Jackson’s leading convention complex.

Vicksburg National Military Park

4.5/5(170 reviews)

Explore the great outdoors at Vicksburg National Military Park, a lovely green space in Vicksburg. Stroll along the riverfront or visit the casinos in the area.

Mississippi State Capitol

4/5(229 reviews)

Admire the stunning beaux-arts architecture of this capitol building, take a tour through its stately interior or view a legislative session from a senate gallery.

Frequently asked questions

How much are vacation packages to Southwest?

With vacation packages available from just $491, there's no need to blow out the credit card for your visit to Southwest. Travelocity can help. Bundle experiences, hotels and flights into a convenient package and score exciting discounts. The more you book, the greater the savings.

Where can I get the best vacation package deals for Southwest?

It's hard to look past Travelocity when it comes to crafting your Southwest package deal. There are at least 400 air carriers and 1,000,000 worldwide properties to select from. Book your trip now and get ready to tick another place off your travel bucket list.

Why should I purchase my Southwest vacation package via Travelocity?

Whether you're in search of the ultimate unplugged getaway or after the fun and excitement that only a big city can provide, booking everything with Travelocity saves you time, money and hassle. No need to scour through hundreds of websites looking for the best deal — our Price Match Guarantee ensures you'll always score the lowest possible price, and our team of customer service experts are available for you round-the-clock.

Can I save on my Southwest car rental if I bundle it with a hotel or flight?

You can with our Southwest vacation packages. With one of these, there are loads of ways to make your travel budget go further. Bundle any two or more car, flight, hotel and tour bookings and watch the savings grow. With your own set of wheels, all the key sights in and around Southwest are within reach.

Which airport is best for Southwest?

Organizing where you step off the plane in Southwest is a piece of cake — most airlines jet in and out of Evers Intl. Airport (JAN).

What is there to do in Southwest?

A vibrant and impressive destination, Southwest is home to some terrific landmarks. Mississippi State Capitol and Mississippi Veterans Memorial Stadium are two of the most popular.