$155+ Cheap flights from Jackson, MS (JAN) to Midway (MDW)
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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
JAN — MDW
Oct 10 — Oct 171
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
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 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 September 10, 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 September 10, 2026.
This Delta deal was found by Cheapflights users on 9/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/311:10 am -
1 stop4h 07m
Thu 11/511:38 am -
1 stop7h 06m
Deal found 9/8![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 9/8. 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 11/36:15 pm -
1 stop4h 50m
Thu 11/512:25 pm -
1 stop9h 40m
Deal found 9/8![Southwest logo]()
$314
This Southwest deal was found by Cheapflights users on 9/8. 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.
Sat 12/512:05 pm -
2 stops7h 30m
Mon 12/77:35 am -
2 stops10h 00m
Deal found 9/8![Southwest logo]()
$325
This Southwest deal was found by Cheapflights users on 9/9. 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.
Thu 10/15:55 am -
2 stops8h 15m
Wed 10/76:25 am -
1 stop5h 50m
Deal found 9/9![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 9/8. 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.
Sat 10/2412:30 pm -
2 stops8h 10m
Mon 10/264:30 pm -
1 stop3h 20m
Deal found 9/8![Southwest logo]()
$348
This Southwest deal was found by Cheapflights users on 9/8. 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 10/612:55 pm -
1 stop4h 00m
Tue 10/1312:15 pm -
2 stops7h 45m
Deal found 9/8![Southwest logo]()
$358
This Delta deal was found by Cheapflights users on 9/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3011:10 am -
1 stop5h 04m
Sun 11/16:04 am -
1 stop5h 45m
Deal found 9/8![Delta logo]()
$376
This Southwest deal was found by Cheapflights users on 9/5. 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 10/176:15 am -
1 stop4h 35m
Mon 10/194:30 pm -
1 stop3h 20m
Deal found 9/5![Southwest logo]()
$377
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 September 10, 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 September 10, 2026.
This Southwest deal was found by Cheapflights users on 9/8. 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.
Thu 11/58:15 pm -
1 stop4h 50m
Tue 11/1012:45 pm -
1 stop4h 50m
Deal found 9/8![Southwest logo]()
$309
This Delta deal was found by Cheapflights users on 9/9. 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.
Thu 10/15:14 pm -
1 stop5h 30m
Sun 10/46:05 am -
1 stop4h 18m
Deal found 9/9![Delta logo]()
$408
This Southwest deal was found by Cheapflights users on 9/8. 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 11/36:15 pm -
1 stop4h 50m
Thu 11/512:25 pm -
1 stop9h 40m
Deal found 9/8![Southwest logo]()
$314
This Southwest deal was found by Cheapflights users on 9/9. 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.
Thu 10/15:55 am -
2 stops8h 15m
Wed 10/76:25 am -
1 stop5h 50m
Deal found 9/9![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 9/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:30 pm -
1 stop7h 30m
Mon 10/261:10 pm -
1 stop6h 40m
Deal found 9/7![Southwest logo]()
$377
This Southwest deal was found by Cheapflights users on 9/5. 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 10/176:15 am -
2 stops9h 00m
Mon 10/194:30 pm -
1 stop3h 20m
Deal found 9/5![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 9/6. 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 10/265:55 am -
2 stops9h 10m
Fri 10/302:35 pm -
2 stops7h 20m
Deal found 9/6![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 9/9. 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.
Wed 10/146:35 pm -
1 stop4h 40m
Fri 10/1611:50 am -
1 stop10h 05m
Deal found 9/9![Southwest logo]()
$408
Last-minute flights from Jackson to MidwayDiscover last-minute flight deals from Jackson to Midway. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from Jackson to Midway. Data last updated September 10, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/9. 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.
Thu 10/15:55 am -
2 stops8h 15m
Wed 10/76:25 am -
1 stop5h 50m
Deal found 9/9![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 9/8. 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 10/612:55 pm -
1 stop4h 00m
Tue 10/1312:15 pm -
2 stops7h 45m
Deal found 9/8![Southwest logo]()
$358
This Southwest deal was found by Cheapflights users on 9/5. 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 10/176:15 am -
1 stop4h 35m
Mon 10/194:30 pm -
1 stop3h 20m
Deal found 9/5![Southwest logo]()
$377
This Delta deal was found by Cheapflights users on 9/9. 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.
Thu 10/223:33 pm -
1 stop7h 00m
Sun 10/256:04 am -
1 stop6h 10m
Deal found 9/9![Delta logo]()
$353
This Delta deal was found by Cheapflights users on 9/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2411:10 am -
1 stop4h 07m
Mon 10/265:09 pm -
1 stop6h 00m
Deal found 9/8![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 9/8. 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.
Sat 10/2412:30 pm -
2 stops8h 10m
Mon 10/264:30 pm -
1 stop3h 20m
Deal found 9/8![Southwest logo]()
$348
This Southwest deal was found by Cheapflights users on 9/6. 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 10/265:55 am -
2 stops9h 10m
Fri 10/3011:50 am -
1 stop10h 05m
Deal found 9/6![Southwest logo]()
$388
This Delta deal was found by Cheapflights users on 9/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3011:10 am -
1 stop5h 04m
Sun 11/16:04 am -
1 stop5h 45m
Deal found 9/8![Delta logo]()
$376
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 September 10, 2026.
Search for one-way flight options from Jackson to Midway. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
This Delta deal was found by Cheapflights users on 9/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/133:33 pm -
1 stop7h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Delta logo]()
$155
This Southwest deal was found by Cheapflights users on 9/9. 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.
Sat 10/2412:30 pm -
2 stops8h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Southwest logo]()
$160
This Delta deal was found by Cheapflights users on 9/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3011:10 am -
1 stop5h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Delta logo]()
$178
This Southwest deal was found by Cheapflights users on 9/8. 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 10/305:55 am -
2 stops9h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Southwest logo]()
$194
This Southwest deal was found by Cheapflights users on 9/6. 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 10/1612:00 pm -
1 stop5h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 9/8. 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.
Mon 10/125:55 am -
2 stops9h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Southwest logo]()
$214
This Southwest deal was found by Cheapflights users on 9/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:40 pm -
1 stop4h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Southwest logo]()
$239
This Southwest deal was found by Cheapflights users on 9/5. 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 9/206:55 pm -
1 stop5h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Southwest logo]()
$249
This Delta deal was found by Cheapflights users on 9/7. 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.
Wed 9/2311:08 am -
1 stop5h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Delta logo]()
$255
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 September 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $309 (Delta) |
One-way from | $155 (Delta) |
Popular in | May |
Cheapest in | November |
Average price | $426 |
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 7,457,451 searches. Data last updated September 10, 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 Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Sat 12/5
3:48 pm-10:55 pm
1 stop7h 07m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$155
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Tue 10/13
3:33 pm-10:33 pm
1 stop7h 00m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$155
Quickest round-trip
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Sat 10/24
11:10 am-3:17 pm
1 stop4h 07m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$155
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Sat 10/24
12:30 pm-8:40 pm
2 stops8h 10m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$160
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Sat 12/5
12:05 pm-7:50 pm
2 stops7h 45m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$160
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Fri 10/30
5:55 am-3:05 pm
2 stops9h 10m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$194
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Fri 10/16
12:00 pm-5:55 pm
1 stop5h 55m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$209
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Mon 10/12
5:55 am-3:05 pm
2 stops9h 10m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$214
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Tue 9/22
6:40 pm-11:15 pm
1 stop4h 35m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$239
JacksonChicago
JAN Jackson-Evers Intl - MDW Chicago Midway
JANMDW
Jackson-Evers Intl
Wed 9/23
7:05 am-3:20 pm
2 stops8h 15m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$244
Showing 1-10 of 19 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 September.
| 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 September 10, 2026.
Get a feel of what it's like to fly with Southwest 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.
Crew
8.6
Overall
8.0
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Overall
8.0
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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 locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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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 September 10, 2026.
Jackson and Midway flights
Browse other Jackson and Midway flight options. Last updated on September 10, 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 September 10, 2026.
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Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Jackson to Midway
Discover the top airline 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 7,457,451 searches. Data last updated September 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$308 | Average$426 | FlexibilityNo cancel fee | On-time63% |