$214+ Cheap flights from Jackson, MS (JAN) to Midway (MDW)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — MDW
Apr 12 — Apr 191
Round-trip
1 adult, Economy
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Find cheap flights from Jackson to Midway 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
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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 Jackson to Midway
Cheapest
Best
Last-minute
One-way
Cheapest flights from Jackson to MidwayExplore the most affordable flight options available from Jackson to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 13, 2026.
Explore the most affordable flight options available from Jackson to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 13, 2026.
This Southwest deal was found by Cheapflights users on 3/10. 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 4/76:30 am
JAN
- MDW
1 stop5h 10m
Southwest
Tue 4/147:25 am
MDW
- JAN
1 stop4h 55m
Southwest
Deal found 3/10![Southwest logo]()
$303
This Southwest deal was found by Cheapflights users on 3/11. 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 4/1812:20 pm
JAN
- MDW
1 stop5h 05m
Southwest
Tue 4/217:25 am
MDW
- JAN
1 stop4h 55m
Southwest
Deal found 3/11![Southwest logo]()
$315
This Delta deal was found by Cheapflights users on 3/9. 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.
Tue 5/55:36 am
JAN
- MDW
1 stop4h 20m
Delta
Tue 5/126:23 am
MDW
- JAN
1 stop6h 21m
Delta
Deal found 3/9![Delta logo]()
$317
This Southwest deal was found by Cheapflights users on 3/10. 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 4/2012:15 pm
JAN
- MDW
1 stop4h 45m
Southwest
Tue 4/217:25 am
MDW
- JAN
1 stop4h 55m
Southwest
Deal found 3/10![Southwest logo]()
$335
This Southwest deal was found by Cheapflights users on 3/12. 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 4/1112:20 pm
JAN
- MDW
1 stop5h 05m
Southwest
Sat 4/185:00 am
MDW
- JAN
1 stop6h 45m
Southwest
Deal found 3/12![Southwest logo]()
$337
Best flights from Jackson to MidwayDiscover carefully curated flight deals from Jackson to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 13, 2026.
Discover carefully curated flight deals from Jackson to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 13, 2026.
This Southwest deal was found by Cheapflights users on 3/11. 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 4/156:30 am
JAN
- MDW
1 stop5h 10m
Southwest
Tue 4/217:25 am
MDW
- JAN
1 stop4h 55m
Southwest
Deal found 3/11![Southwest logo]()
$303
This Delta deal was found by Cheapflights users on 3/10. 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.
Tue 5/510:58 am
JAN
- MDW
1 stop5h 28m
Delta
Tue 5/126:23 am
MDW
- JAN
1 stop6h 21m
Delta
Deal found 3/10![Delta logo]()
$303
This Southwest deal was found by Cheapflights users on 3/11. 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 4/86:30 am
JAN
- MDW
1 stop5h 10m
Southwest
Wed 4/158:15 am
MDW
- JAN
2 stops9h 15m
Southwest
Deal found 3/11![Southwest logo]()
$308
This Southwest deal was found by Cheapflights users on 3/8. 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 4/76:30 am
JAN
- MDW
2 stops8h 25m
Southwest
Tue 4/148:15 am
MDW
- JAN
2 stops9h 15m
Southwest
Deal found 3/8![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 3/7. 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.
Fri 4/175:02 pm
JAN
- MDW
1 stop5h 26m
Delta
Sun 4/196:00 am
MDW
- JAN
1 stop6h 08m
Delta
Deal found 3/7![Delta logo]()
$367
This Southwest deal was found by Cheapflights users on 3/11. 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 4/186:00 am
JAN
- MDW
2 stops8h 35m
Southwest
Tue 4/2111:35 am
MDW
- JAN
2 stops8h 45m
Southwest
Deal found 3/11![Southwest logo]()
$325
This Southwest deal was found by Cheapflights users on 3/12. 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 5/126:30 am
JAN
- MDW
2 stops8h 25m
Southwest
Fri 5/159:00 am
MDW
- JAN
2 stops10h 05m
Southwest
Deal found 3/12![Southwest logo]()
$385
This Southwest deal was found by Cheapflights users on 3/11. 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 5/812:15 pm
JAN
- MDW
1 stop8h 45m
Southwest
Mon 5/1811:40 am
MDW
- JAN
2 stops7h 25m
Southwest
Deal found 3/11![Southwest logo]()
$418
This Southwest deal was found by Cheapflights users on 3/8. 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 4/2412:15 pm
JAN
- MDW
1 stop4h 45m
Southwest
Sun 4/266:50 am
MDW
- JAN
1 stop5h 05m
Southwest
Deal found 3/8![Southwest logo]()
$421
This Southwest deal was found by Cheapflights users on 3/9. 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 4/195:55 am
JAN
- MDW
2 stops9h 35m
Southwest
Tue 4/218:15 am
MDW
- JAN
2 stops9h 15m
Southwest
Deal found 3/9![Southwest logo]()
$431
Last-minute flights from Jackson to MidwayDiscover last-minute flight deals from Jackson to Midway. Data last updated March 13, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Midway. Data last updated March 13, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 3/10. 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 4/76:30 am
JAN
- MDW
1 stop5h 10m
Southwest
Tue 4/147:25 am
MDW
- JAN
1 stop4h 55m
Southwest
Deal found 3/10![Southwest logo]()
$303
This Southwest deal was found by Cheapflights users on 3/12. 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 4/1112:20 pm
JAN
- MDW
1 stop5h 05m
Southwest
Sat 4/185:00 am
MDW
- JAN
1 stop6h 45m
Southwest
Deal found 3/12![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 3/9. 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.
Fri 4/175:02 pm
JAN
- MDW
1 stop5h 26m
Delta
Mon 4/205:21 pm
MDW
- JAN
1 stop5h 54m
Delta
Deal found 3/9![Delta logo]()
$347
This Southwest deal was found by Cheapflights users on 3/11. 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 4/1812:20 pm
JAN
- MDW
1 stop5h 05m
Southwest
Tue 4/217:25 am
MDW
- JAN
1 stop4h 55m
Southwest
Deal found 3/11![Southwest logo]()
$315
This Southwest deal was found by Cheapflights users on 3/10. 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 4/2012:15 pm
JAN
- MDW
1 stop4h 45m
Southwest
Tue 4/217:25 am
MDW
- JAN
1 stop4h 55m
Southwest
Deal found 3/10![Southwest logo]()
$335
One-way flights from Jackson to MidwaySearch for one-way flight options from Jackson to Midway. Find affordable one-way fares based on user searches. Data last updated March 13, 2026.
Search for one-way flight options from Jackson to Midway. Find affordable one-way fares based on user searches. Data last updated March 13, 2026.
This Southwest deal was found by Cheapflights users on 3/12. 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 4/265:55 am
JAN
- MDW
1 stop4h 40m
Southwest
Deal found 3/12![Southwest logo]()
$214
This Delta deal was found by Cheapflights users on 3/11. 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.
Mon 3/165:35 am
JAN
- MDW
1 stop4h 21m
Delta
Deal found 3/11![Delta logo]()
$389
This Southwest deal was found by Cheapflights users on 3/11. 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 3/1612:20 pm
JAN
- MDW
2 stops5h 30m
Southwest
Deal found 3/11![Southwest logo]()
$394
Find flight deals from Jackson to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Jackson (JAN) to Midway (MDW). 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 March 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $303 (Southwest) |
One-way from | $214 (Southwest) |
Popular in | December |
Cheapest in | August |
Average price | $484 |
Cheapflights Fare Finder
Customize your flight search to find flights from Jackson to Midway 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 2,558,603 searches. Data last updated March 13, 2026.
Use the filters below to find and compare flights from Jackson to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Wed 4/15
6:30 am-11:40 am
1 stop5h 10m
Chicago Midway
Tue 4/21
7:25 am-12:20 pm
1 stop4h 55m
$303
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Tue 5/5
10:58 am-4:26 pm
1 stop5h 28m
Chicago Midway
Tue 5/12
6:23 am-12:44 pm
1 stop6h 21m
$303
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Wed 4/8
6:30 am-11:40 am
1 stop5h 10m
Chicago Midway
Wed 4/15
8:15 am-5:30 pm
2 stops9h 15m
$308
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Tue 4/7
6:30 am-2:55 pm
2 stops8h 25m
Chicago Midway
Tue 4/14
8:15 am-5:30 pm
2 stops9h 15m
$313
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Sat 4/18
6:00 am-2:35 pm
2 stops8h 35m
Chicago Midway
Tue 4/21
11:35 am-8:20 pm
2 stops8h 45m
$325
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Fri 4/17
5:02 pm-10:28 pm
1 stop5h 26m
Chicago Midway
Sun 4/19
6:00 am-12:08 pm
1 stop6h 08m
$367
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Tue 5/12
6:30 am-2:55 pm
2 stops8h 25m
Chicago Midway
Fri 5/15
9:00 am-7:05 pm
2 stops10h 05m
$385
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Fri 5/8
12:15 pm-9:00 pm
1 stop8h 45m
Chicago Midway
Mon 5/18
11:40 am-7:05 pm
2 stops7h 25m
$418
Quickest round-trip
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Fri 4/24
12:15 pm-5:00 pm
1 stop4h 45m
Chicago Midway
Sun 4/26
6:50 am-11:55 am
1 stop5h 05m
$421
JacksonChicago
JAN - MDW
JANMDW
Jackson-Evers Intl
Sun 4/19
5:55 am-3:30 pm
2 stops9h 35m
Chicago Midway
Tue 4/21
8:15 am-5:30 pm
2 stops9h 15m
$431
Showing 1-10 of 15 resultsSorted by cheapest first
Compare providers for flights from Jackson to Midway
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 Jackson to Midway in March.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Jackson, Mississippi-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Jackson, Mississippi-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Jackson, Mississippi-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Jackson, Mississippi-Chicago Midway Airport 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 Jackson, Mississippi-Chicago Midway Airport 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 Jackson to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Jackson with our price prediction graph.
JAN-MDW
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 Midway
Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated March 13, 2026.
Get a feel of what it's like to fly with Southwest and Delta from Jackson to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Related info for your journey
Find useful and relevant information for your journey from Jackson to Midway. 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 Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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Complete your trip
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Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on March 13, 2026.
Jackson and Midway flights
Browse other Jackson and Midway flight options. Last updated on March 13, 2026.
Other flights from Jackson
Browse through other flights departing from Jackson. Flights are based on user searches made on Cheapflights and were last updated on March 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Jackson to Midway
Discover the top 2 airlines that operate flights from Jackson to Midway. 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 2,558,603 searches. Data last updated March 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$196 | Average$350 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$234 | Average$406 | FlexibilityNo cancel fee | On-time63% |