$123+ Cheap flights from Jacksonville (JAX) 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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — MDW
Jun 4 — Jun 111
Round-trip
1 adult, Economy
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Cheapest flights from Jacksonville to MidwayExplore the most affordable flight options available from Jacksonville to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 5, 2026.
Explore the most affordable flight options available from Jacksonville to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 5, 2026.
This Frontier deal was found by Cheapflights users on 5/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/216:30 pm
JAX
- MDW
1 stop4h 32m
Frontier
Mon 5/256:00 am
MDW
- JAX
1 stop10h 35m
Frontier
Deal found 5/1![Frontier logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/166:28 pm
JAX
- MDW
1 stop4h 40m
Frontier
Sat 7/186:00 am
MDW
- JAX
1 stop10h 33m
Frontier
Deal found 5/1![Frontier logo]()
$241
This Southwest deal was found by Cheapflights users on 4/30. 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 5/233:05 pm
JAX
- MDW
Nonstop2h 30m
Southwest
Tue 6/26:00 pm
MDW
- JAX
Nonstop2h 15m
Southwest
Deal found 4/30![Southwest logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:28 pm
JAX
- MDW
1 stop17h 44m
Frontier
Wed 7/156:00 am
MDW
- JAX
1 stop10h 33m
Frontier
Deal found 5/3![Frontier logo]()
$243
This Frontier deal was found by Cheapflights users on 5/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/316:28 pm
JAX
- MDW
1 stop4h 40m
Frontier
Mon 8/106:00 am
MDW
- JAX
1 stop10h 33m
Frontier
Deal found 5/3![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/126:28 pm
JAX
- MDW
1 stop17h 36m
Frontier
Sun 6/146:00 am
MDW
- JAX
1 stop10h 33m
Frontier
Deal found 5/1![Frontier logo]()
$245
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:30 pm
JAX
- MDW
1 stop4h 32m
Frontier
Sun 6/76:00 am
MDW
- JAX
1 stop10h 35m
Frontier
Deal found 4/29![Frontier logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/256:30 pm
JAX
- MDW
1 stop17h 42m
Frontier
Tue 6/212:27 pm
MDW
- JAX
1 stop28h 08m
Frontier
Deal found 5/3![Frontier logo]()
$247
This Trip.com deal was found by Cheapflights users on 5/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:28 pm
JAX
- MDW
1 stop4h 40m
Frontier
Sat 7/1812:11 pm
MDW
- JAX
1 stop4h 22m
Frontier
Deal found 5/4![Frontier logo]()
$249
This Expedia deal was found by Cheapflights users on 5/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:28 pm
JAX
- MDW
1 stop4h 43m
Frontier
Fri 6/126:00 am
MDW
- JAX
1 stop10h 33m
Frontier
Deal found 5/1![Frontier logo]()
$250
This Frontier deal was found by Cheapflights users on 5/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:30 pm
JAX
- MDW
1 stop4h 32m
Frontier
Thu 5/286:00 am
MDW
- JAX
1 stop10h 35m
Frontier
Deal found 5/2![Frontier logo]()
$251
Best flights from Jacksonville to MidwayDiscover carefully curated flight deals from Jacksonville to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 5, 2026.
Discover carefully curated flight deals from Jacksonville to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 5, 2026.
This Southwest deal was found by Cheapflights users on 5/3. 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 7/16:45 pm
JAX
- MDW
Nonstop2h 25m
Southwest
Wed 7/1512:50 pm
MDW
- JAX
Nonstop2h 20m
Southwest
Deal found 5/3![Southwest logo]()
$269
This Delta deal was found by Cheapflights users on 5/1. 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 8/76:58 pm
JAX
- MDW
1 stop4h 17m
Delta
Tue 8/119:30 am
MDW
- JAX
1 stop7h 06m
Delta
Deal found 5/1![Delta logo]()
$300
This Southwest deal was found by Cheapflights users on 4/29. 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 9/165:25 pm
JAX
- MDW
Nonstop2h 25m
Southwest
Fri 9/186:45 pm
MDW
- JAX
Nonstop2h 15m
Southwest
Deal found 4/29![Southwest logo]()
$280
This Delta deal was found by Cheapflights users on 5/3. 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 8/65:34 pm
JAX
- MDW
1 stop6h 02m
Delta
Tue 8/119:59 am
MDW
- JAX
1 stop5h 53m
Delta
Deal found 5/3![Delta logo]()
$300
This Southwest deal was found by Cheapflights users on 4/29. 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 6/117:15 pm
JAX
- MDW
Nonstop2h 30m
Southwest
Tue 6/166:20 pm
MDW
- JAX
Nonstop2h 20m
Southwest
Deal found 4/29![Southwest logo]()
$280
This Southwest deal was found by Cheapflights users on 5/4. 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 6/47:15 pm
JAX
- MDW
Nonstop2h 30m
Southwest
Mon 6/87:20 pm
MDW
- JAX
Nonstop2h 15m
Southwest
Deal found 5/4![Southwest logo]()
$287
This KAYAK deal was found by Cheapflights users on 4/30. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/152:15 pm
JAX
- MDW
2 stops7h 05m
Southwest
Wed 6/1711:50 am
MDW
- JAX
1 stop8h 15m
Southwest
Deal found 4/30![Southwest logo]()
$316
This Southwest deal was found by Cheapflights users on 5/3. 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 6/211:50 am
JAX
- MDW
1 stop5h 25m
Southwest
Thu 6/47:20 pm
MDW
- JAX
Nonstop2h 15m
Southwest
Deal found 5/3![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 4/30. 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 7/137:15 pm
JAX
- MDW
Nonstop2h 30m
Southwest
Wed 7/158:10 am
MDW
- JAX
1 stop5h 05m
Southwest
Deal found 4/30![Southwest logo]()
$362
This Southwest deal was found by Cheapflights users on 5/1. 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 8/2911:15 am
JAX
- MDW
1 stop6h 25m
Southwest
Sat 9/1212:45 pm
MDW
- JAX
Nonstop2h 15m
Southwest
Deal found 5/1![Southwest logo]()
$365
Last-minute flights from Jacksonville to MidwayDiscover last-minute flight deals from Jacksonville to Midway. Data last updated May 5, 2026 and is based on user searches.
Discover last-minute flight deals from Jacksonville to Midway. Data last updated May 5, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 5/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:30 pm
JAX
- MDW
1 stop4h 32m
Frontier
Mon 5/116:00 am
MDW
- JAX
1 stop10h 35m
Frontier
Deal found 5/3![Frontier logo]()
$256
This Frontier deal was found by Cheapflights users on 5/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:30 pm
JAX
- MDW
1 stop4h 32m
Frontier
Thu 5/286:00 am
MDW
- JAX
1 stop10h 35m
Frontier
Deal found 5/2![Frontier logo]()
$251
This Frontier deal was found by Cheapflights users on 5/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/216:30 pm
JAX
- MDW
1 stop4h 32m
Frontier
Mon 5/256:00 am
MDW
- JAX
1 stop10h 35m
Frontier
Deal found 5/1![Frontier logo]()
$240
This Southwest deal was found by Cheapflights users on 4/30. 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 5/233:05 pm
JAX
- MDW
Nonstop2h 30m
Southwest
Tue 6/26:00 pm
MDW
- JAX
Nonstop2h 15m
Southwest
Deal found 4/30![Southwest logo]()
$242
This Southwest deal was found by Cheapflights users on 4/30. 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 5/233:05 pm
JAX
- MDW
Nonstop2h 30m
Southwest
Tue 5/267:00 am
MDW
- JAX
1 stop5h 40m
Southwest
Deal found 4/30![Southwest logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/256:30 pm
JAX
- MDW
1 stop17h 42m
Frontier
Tue 6/212:27 pm
MDW
- JAX
1 stop28h 08m
Frontier
Deal found 5/3![Frontier logo]()
$247
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:30 pm
JAX
- MDW
1 stop4h 32m
Frontier
Sun 6/76:00 am
MDW
- JAX
1 stop10h 35m
Frontier
Deal found 4/29![Frontier logo]()
$246
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:28 pm
JAX
- MDW
1 stop4h 43m
Frontier
Thu 6/186:00 am
MDW
- JAX
1 stop10h 33m
Frontier
Deal found 4/29![Frontier logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/126:28 pm
JAX
- MDW
1 stop17h 36m
Frontier
Sun 6/146:00 am
MDW
- JAX
1 stop10h 33m
Frontier
Deal found 5/1![Frontier logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/126:28 pm
JAX
- MDW
1 stop17h 36m
Frontier
Tue 6/1612:27 pm
MDW
- JAX
2 stops25h 37m
Frontier
Deal found 4/29![Frontier logo]()
$254
One-way flights from Jacksonville to MidwaySearch for one-way flight options from Jacksonville to Midway. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
Search for one-way flight options from Jacksonville to Midway. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/298:36 pm
JAX
- MDW
1 stop18h 00m
Allegiant Air
Deal found 5/1![Allegiant Air logo]()
$123
This Super.com deal was found by Cheapflights users on 4/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/256:30 pm
JAX
- MDW
1 stop4h 52m
Frontier
Deal found 4/30![Frontier logo]()
$134
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:30 pm
JAX
- MDW
1 stop4h 32m
Frontier
Deal found 4/30![Frontier logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/269:03 pm
JAX
- MDW
2 stops25h 59m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:34 pm
JAX
- MDW
2 stops25h 28m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$138
This Trip.com deal was found by Cheapflights users on 5/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/56:30 pm
JAX
- MDW
1 stop4h 32m
Frontier
Deal found 5/3![Frontier logo]()
$139
This Southwest deal was found by Cheapflights users on 4/30. 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 5/233:05 pm
JAX
- MDW
Nonstop2h 30m
Southwest
Deal found 4/30![Southwest logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/249:40 pm
JAX
- MDW
2 stops25h 28m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/156:28 pm
JAX
- MDW
1 stop17h 44m
Frontier
Deal found 4/30![Frontier logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1010:14 pm
JAX
- MDW
2 stops41h 13m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$152
Find flight deals from Jacksonville to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Jacksonville (JAX) 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 May 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $240 (Priceline) |
One-way from | $123 (Kiwi.com) |
Popular in | November |
Cheapest in | August |
Average price | $337 |
Good round-trip deal | $402 or less |
Good one-way deal | $195 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Jacksonville 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 May 5, 2026.
Use the filters below to find and compare flights from Jacksonville to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
JacksonvilleChicago
JAX - MDW
JAXMDW
Jacksonville
Wed 7/1
6:45 pm-8:10 pm
Nonstop2h 25m
Chicago Midway
Wed 7/15
12:50 pm-4:10 pm
Nonstop2h 20m
$269
Quickest round-trip
JacksonvilleChicago
JAX - MDW
JAXMDW
Jacksonville
Wed 9/16
5:25 pm-6:50 pm
Nonstop2h 25m
Chicago Midway
Fri 9/18
6:45 pm-10:00 pm
Nonstop2h 15m
$280
JacksonvilleChicago
JAX - MDW
JAXMDW
Jacksonville
Thu 6/11
7:15 pm-8:45 pm
Nonstop2h 30m
Chicago Midway
Tue 6/16
6:20 pm-9:40 pm
Nonstop2h 20m
$280
JacksonvilleChicago
JAX - MDW
JAXMDW
Jacksonville
Thu 6/4
7:15 pm-8:45 pm
Nonstop2h 30m
Chicago Midway
Mon 6/8
7:20 pm-10:35 pm
Nonstop2h 15m
$287
JacksonvilleChicago
JAX - MDW
JAXMDW
Jacksonville
Fri 8/7
6:58 pm-10:15 pm
1 stop4h 17m
Chicago Midway
Tue 8/11
9:30 am-5:36 pm
1 stop7h 06m
$300
JacksonvilleChicago
JAX - MDW
JAXMDW
Jacksonville
Thu 8/6
5:34 pm-10:36 pm
1 stop6h 02m
Chicago Midway
Tue 8/11
9:59 am-4:52 pm
1 stop5h 53m
$300
JacksonvilleChicago
JAX - MDW
JAXMDW
Jacksonville
Mon 6/15
2:15 pm-8:20 pm
2 stops7h 05m
Chicago Midway
Wed 6/17
11:50 am-9:05 pm
1 stop8h 15m
$316
JacksonvilleChicago
JAX - MDW
JAXMDW
Jacksonville
Tue 6/2
11:50 am-4:15 pm
1 stop5h 25m
Chicago Midway
Thu 6/4
7:20 pm-10:35 pm
Nonstop2h 15m
$324
JacksonvilleChicago
JAX - MDW
JAXMDW
Jacksonville
Mon 7/13
7:15 pm-8:45 pm
Nonstop2h 30m
Chicago Midway
Wed 7/15
8:10 am-2:15 pm
1 stop5h 05m
$362
JacksonvilleChicago
JAX - MDW
JAXMDW
Jacksonville
Sat 8/29
11:15 am-4:40 pm
1 stop6h 25m
Chicago Midway
Sat 9/12
12:45 pm-4:00 pm
Nonstop2h 15m
$365
Showing 1-10 of 21 resultsSorted by cheapest first
Compare providers for flights from Jacksonville 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 Jacksonville to Midway in May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Jacksonville-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 Jacksonville-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Jacksonville-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Jacksonville-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 Jacksonville-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 Jacksonville to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Jacksonville with our price prediction graph.
JAX-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.
Cheapflights Insights
Everything you need to know about your flight from Jacksonville to Chicago Midway Airport
What is the cheapest time of day to fly from JAX to MDW?
Find hourly flight availability from Jacksonville to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 5, 2026.
It’s optimal to fly from Jacksonville to Chicago Midway Airport at noon. By choosing this option you can save up to 40% on the cost of your flight, compared to a flight in the morning.
How much does it cost to fly round-trip from Jacksonville to Chicago Midway Airport?
The best insider tips for Jacksonville to Chicago Midway Airport flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Jacksonville to Chicago Midway Airport trip
Our travel experts
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 May 5, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andFrontier from Jacksonville to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Food
7.0
Comfort
8.0
Overall
7.9
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Jacksonville 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
Lansing
Merrillville
Hammond
Porter
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Other flights to Midway
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Jacksonville and Midway flights
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Top 3 airlines flying from Jacksonville to Midway
Discover the top 3 airlines that operate flights from Jacksonville 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 May 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$129 | Average$296 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$136 | Average$225 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$202 | Average$347 | FlexibilityNo cancel fee | On-time63% |