Southwest Vacation Packages 2026 from $442

Southwest flight + hotel vacation packages

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

Studio 6 Suites Jackson Ridgeland MS

$442

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

Chicago (MDW) to Jackson (JAN)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A safe deposit box and laundry facilities are also provided.

Ameristar Casino Hotel Vicksburg

$626

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

Chicago (MDW) to Jackson (JAN)

The casino and nightclub are among the highlights at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at one of the 2 bars/lounges and enjoy perks like free self parking.

Relax Inn By Oyo Jackson MS Hwy 80/I-20

$466

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

Chicago (MDW) to Jackson (JAN)

Staff at the 24-hour front desk can provide around-the-clock assistance. Take advantage of the free self parking.

Hyatt Place Jackson/ Ridgeland

$535

per person

Nov 6 - Nov 9

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. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and free perks like on-the-go breakfast and free self parking.

Hilton Jackson

$523

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

Chicago (MDW) to Jackson (JAN)

This hotel features 2 restaurants, an outdoor pool, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Top Southwest hotels deals

Hilton Jackson

1001 E County Line Rd Jackson MS

Free Cancellation

Reserve now, pay when you stay

$79 nightly

$88 total

Aug 30 - Aug 31

Total with taxes and fees

Baymont by Wyndham Jackson/Ridgeland

5709 I 55 N Jackson MS

Free Cancellation

Reserve now, pay when you stay

$79 nightly

$90 total

Aug 23 - Aug 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 business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.

Pool

Breakfast included

Prado Hotel

610 E County Line Road Ridgeland MS

Free Cancellation

Reserve now, pay when you stay

$85 nightly

$93 total

Aug 23 - Aug 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

Natchez Grand Hotel & Suites On the River

111 S Broadway Street Natchez MS

Free Cancellation

Reserve now, pay when you stay

$102 nightly

$114 total

Aug 23 - Aug 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.

Tru By Hilton Ridgeland Jackson

6934 I-55 E. Frontage Rd Ridgeland MS

Free Cancellation

Reserve now, pay when you stay

$94 nightly

$103 total

Sep 13 - Sep 14

Total with taxes and fees

A gym is featured at this hotel, along with free WiFi in public areas. Enjoy the free buffet breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.

Breakfast included

Free WiFi

Imperial Suites - Adults Only

3720 I-55 Jackson MS

$70 nightly

$78 total

Aug 23 - Aug 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.

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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.

Stay near popular Southwest attractions

A modern building with reflective glass windows and a geometric design.

Jackson Convention Complex

8.0/10 (450 reviews)

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

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Frequently asked questions

How much are vacation packages to Southwest?

With vacation packages available from just $442, 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.