$114+ Cheap flights from Midway (MDW) to Jackson, MS (JAN)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JAN
Nov 25 — Dec 21
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Jackson with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midway to Jackson
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Best
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One-way
Cheapest flights from Midway to JacksonExplore the most affordable flight options available from Midway to Jackson. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 26, 2026.
Explore the most affordable flight options available from Midway to Jackson. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 26, 2026.
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:00 am -
1 stop4h 29m
Mon 11/165:06 pm -
1 stop5h 48m
Deal found 10/21![Delta logo]()
$242
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:35 am -
2 stops10h 00m
Thu 11/128:15 pm -
1 stop4h 55m
Deal found 10/22![Southwest logo]()
$253
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:40 am -
1 stop5h 50m
Mon 12/141:10 pm -
1 stop5h 55m
Deal found 10/23![Southwest logo]()
$257
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/77:35 am -
2 stops10h 00m
Thu 12/106:15 pm -
1 stop4h 55m
Deal found 10/22![Southwest logo]()
$268
This Southwest deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1410:15 am -
2 stops9h 00m
Mon 11/161:10 pm -
1 stop9h 35m
Deal found 10/21![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/185:10 am -
1 stop5h 45m
Mon 12/218:15 pm -
1 stop4h 45m
Deal found 10/24![Southwest logo]()
$325
Best flights from Midway to JacksonDiscover carefully curated flight deals from Midway to Jackson that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 26, 2026.
Discover carefully curated flight deals from Midway to Jackson that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 26, 2026.
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:40 am -
1 stop5h 50m
Mon 12/146:30 am -
2 stops9h 00m
Deal found 10/23![Southwest logo]()
$262
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/186:00 am -
1 stop5h 22m
Sat 2/205:45 am -
1 stop4h 07m
Deal found 10/21![Delta logo]()
$273
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:00 am -
1 stop4h 29m
Mon 11/165:06 pm -
1 stop5h 48m
Deal found 10/23![Delta logo]()
$312
This Southwest deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1410:15 am -
2 stops9h 00m
Mon 11/161:10 pm -
1 stop9h 35m
Deal found 10/21![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/65:14 pm -
1 stop5h 51m
Tue 2/912:13 pm -
1 stop4h 41m
Deal found 10/25![Delta logo]()
$325
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:25 pm -
1 stop9h 45m
Tue 11/101:10 pm -
1 stop5h 55m
Deal found 10/22![Southwest logo]()
$377
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2212:50 pm -
2 stops9h 35m
Sat 1/28:20 pm -
2 stops12h 00m
Deal found 10/26![Southwest logo]()
$461
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/94:00 pm -
1 stop3h 45m
Fri 11/138:15 pm -
1 stop4h 55m
Deal found 10/25![Southwest logo]()
$517
This Southwest deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/511:10 am -
2 stops8h 35m
Mon 11/98:15 pm -
1 stop4h 55m
Deal found 10/24![Southwest logo]()
$524
Last-minute flights from Midway to JacksonDiscover last-minute flight deals from Midway to Jackson. Data last updated October 26, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Jackson. Data last updated October 26, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:45 pm -
1 stop4h 50m
Mon 11/98:15 pm -
1 stop4h 55m
Deal found 10/21![Southwest logo]()
$374
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:25 pm -
1 stop9h 45m
Tue 11/101:10 pm -
1 stop5h 55m
Deal found 10/22![Southwest logo]()
$377
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:35 am -
2 stops10h 00m
Thu 11/128:15 pm -
1 stop4h 55m
Deal found 10/22![Southwest logo]()
$253
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:00 am -
1 stop4h 29m
Mon 11/165:06 pm -
1 stop5h 48m
Deal found 10/21![Delta logo]()
$242
This Southwest deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1410:15 am -
2 stops9h 00m
Mon 11/161:10 pm -
1 stop9h 35m
Deal found 10/21![Southwest logo]()
$313
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2012:25 pm -
1 stop9h 45m
Mon 11/238:15 pm -
1 stop4h 55m
Deal found 10/22![Southwest logo]()
$369
This Southwest deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2012:25 pm -
1 stop9h 45m
Sun 11/228:15 pm -
1 stop4h 55m
Deal found 10/21![Southwest logo]()
$385
One-way flights from Midway to JacksonSearch for one-way flight options from Midway to Jackson. Find affordable one-way fares based on user searches. Data last updated October 26, 2026.
Search for one-way flight options from Midway to Jackson. Find affordable one-way fares based on user searches. Data last updated October 26, 2026.
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1411:27 am -
1 stop4h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Delta logo]()
$114
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/267:30 am -
1 stop3h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Southwest logo]()
$135
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2412:45 pm -
1 stop4h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Southwest logo]()
$163
This Southwest deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1410:15 am -
2 stops9h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Southwest logo]()
$179
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/74:19 pm -
1 stop5h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Delta logo]()
$184
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:35 am -
2 stops12h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Southwest logo]()
$185
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2212:50 pm -
2 stops9h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Southwest logo]()
$212
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/85:15 am -
1 stop5h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Southwest logo]()
$259
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2312:45 pm -
2 stops9h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Southwest logo]()
$274
Find flight deals from Midway to Jackson
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Jackson (JAN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $242 (Southwest) |
One-way from | $114 (Delta) |
Popular in | December |
Cheapest in | August |
Average price | $556 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Jackson that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 26, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Jackson that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoJackson
MDW Chicago Midway - JAN Jackson-Evers Intl
MDWJAN
Chicago Midway
Sat 11/14
11:27 am-4:21 pm
1 stop4h 54m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$114
Quickest round-trip
ChicagoJackson
MDW Chicago Midway - JAN Jackson-Evers Intl
MDWJAN
Chicago Midway
Thu 11/26
7:30 am-11:25 am
1 stop3h 55m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$135
ChicagoJackson
MDW Chicago Midway - JAN Jackson-Evers Intl
MDWJAN
Chicago Midway
Thu 12/24
12:45 pm-5:35 pm
1 stop4h 50m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$163
ChicagoJackson
MDW Chicago Midway - JAN Jackson-Evers Intl
MDWJAN
Chicago Midway
Sat 11/14
10:15 am-7:15 pm
2 stops9h 00m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$179
ChicagoJackson
MDW Chicago Midway - JAN Jackson-Evers Intl
MDWJAN
Chicago Midway
Sat 11/7
4:19 pm-9:37 pm
1 stop5h 18m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$184
ChicagoJackson
MDW Chicago Midway - JAN Jackson-Evers Intl
MDWJAN
Chicago Midway
Sat 11/7
6:35 am-7:15 pm
2 stops12h 40m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$185
ChicagoJackson
MDW Chicago Midway - JAN Jackson-Evers Intl
MDWJAN
Chicago Midway
Tue 12/22
12:50 pm-10:25 pm
2 stops9h 35m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$212
ChicagoJackson
MDW Chicago Midway - JAN Jackson-Evers Intl
MDWJAN
Chicago Midway
Mon 12/7
6:40 am-12:30 pm
1 stop5h 50m
Jackson-Evers Intl
Mon 12/14
6:30 am-3:30 pm
2 stops9h 00m
$262
ChicagoJackson
MDW Chicago Midway - JAN Jackson-Evers Intl
MDWJAN
Chicago Midway
Thu 2/18
6:00 am-11:22 am
1 stop5h 22m
Jackson-Evers Intl
Sat 2/20
5:45 am-9:52 am
1 stop4h 07m
$273
ChicagoJackson
MDW Chicago Midway - JAN Jackson-Evers Intl
MDWJAN
Chicago Midway
Wed 12/23
12:45 pm-10:25 pm
2 stops9h 40m
Jackson-Evers Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$274
Showing 1-10 of 18 resultsSorted by cheapest first
Compare providers for flights from Midway to Jackson
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Jackson in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Jackson, Mississippi flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Jackson, Mississippi flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Jackson, Mississippi flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Jackson, Mississippi flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Jackson, Mississippi flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Midway to Jackson
Have a flexible travel schedule? Discover the best time to fly to Jackson from Midway with our price prediction graph.
MDW-JAN
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Reviews of airlines servicing Jackson
Get insights into the airlines that provide service to Jackson. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Jackson. Reviews last updated October 26, 2026.
See what other customers who have flown with Southwest from Chicago Midway Airport to Jackson have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.4
Boarding
8.1
Comfort
8.0
Overall
7.9
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Boarding
8.1
Comfort
8.0
Overall
7.9
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Related info for your journey
Find useful and relevant information for your journey from Midway to Jackson. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Jackson?
Book flights to Jackson if you plan to visit one of these locationsVicksburg
Flowood
Clinton
Pearl
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Other flights to Jackson
Explore flights to Jackson departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 26, 2026.
Midway and Jackson flights
Browse other Midway and Jackson flight options. Last updated on October 26, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on October 26, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Midway to Jackson
Discover the top airline that operate flights from Midway to Jackson. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$308 | Average$502 | FlexibilityNo cancel fee | On-time63% |