Southwest Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
2.5-star property
Holiday Inn Express Clinton by IHG
8.6/10 Excellent! (1,005 reviews)
May 22 - May 25
3 night stay
Chicago (MDW) to Jackson (JAN)
Delta • Non-stop • Coach
Jackson (JAN) to Chicago (MDW)
Southwest Airlines • Non-stop • Coach
Price was $590, price is now $568 per person
$568
per person
found 1 day ago
Elevator wonky… made being on the 4th floor less than desirable. Comfy sleep, good breakfast.
Reviewed on Oct 25, 2024
2.5-star property
Holiday Inn Express Jackson - Ridgeland by IHG
9.6/10 Exceptional! (464 reviews)
May 22 - May 25
3 night stay
Chicago (MDW) to Jackson (JAN)
Delta • Non-stop • Coach
Jackson (JAN) to Chicago (MDW)
Southwest Airlines • Non-stop • Coach
Price was $642, price is now $612 per person
$612
per person
found 1 day ago
I liked everything.
Reviewed on May 28, 2025
3.0-star property
Staybridge Suites Flowood Nw Jackson by IHG
9/10 Wonderful! (400 reviews)
May 22 - May 25
3 night stay
Chicago (MDW) to Jackson (JAN)
Delta • Non-stop • Coach
Jackson (JAN) to Chicago (MDW)
Southwest Airlines • Non-stop • Coach
Price was $645, price is now $616 per person
$616
per person
found 1 day ago
The hotel was amazing and family friendly. The staff was very accommodating.
Reviewed on Aug 19, 2025
3.0-star property
Holiday Inn Jackson Southeast - Pearl by IHG
8.6/10 Excellent! (668 reviews)
May 22 - May 25
3 night stay
Chicago (MDW) to Jackson (JAN)
Delta • Non-stop • Coach
Jackson (JAN) to Chicago (MDW)
Southwest Airlines • Non-stop • Coach
Price was $645, price is now $616 per person
$616
per person
found 1 day ago
Property was very convenient to our travel route Friendly and helpful staff. Food at on-site restaurant was great!
Reviewed on May 5, 2024
2.5-star property
Holiday Inn Express Hotel & Suites BYRAM by IHG
9/10 Wonderful! (588 reviews)
May 22 - May 25
3 night stay
Chicago (MDW) to Jackson (JAN)
Delta • Non-stop • Coach
Jackson (JAN) to Chicago (MDW)
Southwest Airlines • Non-stop • Coach
Price was $628, price is now $601 per person
$601
per person
found 1 day ago
Fast check in and easy access to dining.
Reviewed on Apr 19, 2025
Top rated hotels for your Southwest vacation package
Natchez Grand Hotel & Suites On the River
111 S Broadway Street Natchez MS
Free Cancellation
Reserve now, pay when you stay
58.35 mi from city center
$110 nightly
The price is $123 total per night
$123 total
Apr 2 - Apr 3
Total with taxes and fees
Natchez Grand Hotel & Suites On the River offers a 24-hour gym, conference space, and a 24-hour business center. Front-desk staff can answer questions 24/7, and assist with dry cleaning/laundry, securing valuables, and luggage storage. Additional amenities include a seasonal outdoor pool, coffee/tea in a common area, and a microwave in a common area.
Pool
Breakfast included
Imperial Suites - Adults Only
3720 I-55 Jackson MS
32.71 mi from city center
$70 nightly
The price is $78 total per night
$78 total
Apr 1 - Apr 2
Total with taxes and fees
At Imperial Suites - Adults Only, guests have access to free WiFi in public areas. If you drive, take advantage of free parking. Front-desk staff are standing by 24/7 to assist with any requests.
Parking included
Free WiFi
Hyatt Place Jackson/ Ridgeland
1016 Highland Colony Pkwy Ridgeland MS
Free Cancellation
Reserve now, pay when you stay
38.31 mi from city center
$101 nightly
The price is $111 total per night
$111 total
Apr 19 - Apr 20
Total with taxes and fees
Guests staying at Hyatt Place Jackson/ Ridgeland enjoy an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The front desk is staffed 24/7 to help secure valuables, and answer any questions about the accommodations. Additional amenities include a business center, free newspapers, and a banquet hall.
Pool
Breakfast included
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.
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