$112+ Cheap flights from Jacksonville (JAX) 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — MDW
Nov 7 — Nov 141
Round-trip
1 adult, Economy
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Find cheap flights from Jacksonville 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 Jacksonville to Midway
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Best
Last-minute
One-way
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 October 8, 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 October 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:20 pm -
1 stop6h 23m
Mon 10/266:15 am -
2 stops33h 11m
Deal found 10/7![Multiple Airlines logo]()
$253
This Southwest deal was found by Cheapflights users on 10/8. 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 10/296:30 pm -
1 stop7h 40m
Mon 11/212:50 pm -
Nonstop2h 15m
Deal found 10/8![Southwest logo]()
$255
This Southwest deal was found by Cheapflights users on 10/7. 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.
Fri 11/67:20 am -
Nonstop2h 30m
Mon 11/97:00 pm -
Nonstop2h 20m
Deal found 10/7![Southwest logo]()
$256
This Cheapflightsfares deal was found by Cheapflights users on 10/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:20 pm -
1 stop6h 23m
Mon 10/266:15 am -
1 stop11h 16m
Deal found 10/5![Frontier logo]()
$257
This Southwest deal was found by Cheapflights users on 10/5. 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.
Mon 11/27:05 pm -
Nonstop2h 30m
Wed 11/46:40 pm -
Nonstop2h 30m
Deal found 10/5![Southwest logo]()
$258
This Cheapflightsfares deal was found by Cheapflights users on 10/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:03 pm -
1 stop5h 44m
Mon 11/26:16 am -
1 stop10h 52m
Deal found 10/5![Frontier logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:03 pm -
1 stop5h 44m
Mon 11/308:42 pm -
2 stops17h 29m
Deal found 10/6![Frontier logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:46 pm -
1 stop4h 57m
Mon 10/266:15 am -
2 stops26h 30m
Deal found 10/6![Multiple Airlines logo]()
$261
This CheapOair deal was found by Cheapflights users on 10/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/235:59 pm -
1 stop15h 15m
Sat 11/288:28 am -
1 stop7h 39m
Deal found 10/6![Frontier logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:46 pm -
2 stops19h 49m
Wed 10/216:21 am -
1 stop11h 25m
Deal found 10/6![Frontier logo]()
$263
This Delta deal was found by Cheapflights users on 10/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:10 am -
1 stop5h 53m
Mon 11/24:19 pm -
1 stop4h 28m
Deal found 10/6![Delta logo]()
$264
This Southwest deal was found by Cheapflights users on 10/7. 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.
Thu 10/296:55 pm -
1 stop6h 35m
Sat 11/77:35 am -
1 stop7h 00m
Deal found 10/7![Southwest logo]()
$265
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 October 8, 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 October 8, 2026.
This Southwest deal was found by Cheapflights users on 10/5. 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.
Tue 11/101:30 pm -
Nonstop2h 25m
Thu 11/125:05 am -
1 stop6h 00m
Deal found 10/5![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 10/8. 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 12/412:00 pm -
1 stop7h 01m
Mon 12/75:12 pm -
1 stop4h 43m
Deal found 10/8![Delta logo]()
$313
This Southwest deal was found by Cheapflights users on 10/5. 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.
Wed 11/111:30 pm -
Nonstop2h 25m
Sun 11/157:00 pm -
Nonstop2h 20m
Deal found 10/5![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 10/5. 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.
Fri 11/67:05 pm -
Nonstop2h 35m
Sun 11/87:30 am -
1 stop5h 20m
Deal found 10/5![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 10/6. 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.
Thu 10/296:30 pm -
1 stop7h 40m
Mon 11/212:50 pm -
Nonstop2h 15m
Deal found 10/6![Southwest logo]()
$315
This Southwest deal was found by Cheapflights users on 10/3. 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.
Fri 10/301:30 pm -
Nonstop2h 20m
Tue 11/36:40 pm -
Nonstop2h 25m
Deal found 10/3![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 10/7. 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 11/174:55 pm -
1 stop6h 45m
Fri 11/207:00 pm -
Nonstop2h 20m
Deal found 10/7![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 10/7. 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 12/512:35 pm -
1 stop5h 50m
Wed 12/96:40 pm -
Nonstop2h 25m
Deal found 10/7![Southwest logo]()
$339
This Southwest deal was found by Cheapflights users on 10/8. 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 11/1910:45 am -
2 stops8h 40m
Sun 11/2212:25 pm -
2 stops10h 20m
Deal found 10/8![Southwest logo]()
$344
This Southwest deal was found by Cheapflights users on 10/3. 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 11/38:45 am -
2 stops11h 55m
Wed 11/411:30 am -
2 stops8h 50m
Deal found 10/3![Southwest logo]()
$357
Last-minute flights from Jacksonville to MidwayDiscover last-minute flight deals from Jacksonville to Midway. Data last updated October 8, 2026 and is based on user searches.
Discover last-minute flight deals from Jacksonville to Midway. Data last updated October 8, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:46 pm -
2 stops19h 49m
Wed 10/216:21 am -
1 stop11h 25m
Deal found 10/6![Frontier logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:20 pm -
1 stop6h 23m
Mon 10/266:15 am -
2 stops33h 11m
Deal found 10/7![Multiple Airlines logo]()
$253
This Cheapflightsfares deal was found by Cheapflights users on 10/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:20 pm -
1 stop6h 23m
Mon 10/266:15 am -
1 stop11h 16m
Deal found 10/5![Frontier logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:46 pm -
1 stop4h 57m
Mon 10/266:15 am -
2 stops26h 30m
Deal found 10/6![Multiple Airlines logo]()
$261
This Southwest deal was found by Cheapflights users on 10/8. 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 10/296:30 pm -
1 stop7h 40m
Mon 11/212:50 pm -
Nonstop2h 15m
Deal found 10/8![Southwest logo]()
$255
This Cheapflightsfares deal was found by Cheapflights users on 10/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:03 pm -
1 stop5h 44m
Mon 11/26:16 am -
1 stop10h 52m
Deal found 10/5![Frontier logo]()
$259
This Delta deal was found by Cheapflights users on 10/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:10 am -
1 stop5h 53m
Mon 11/24:19 pm -
1 stop4h 28m
Deal found 10/6![Delta logo]()
$264
This Southwest deal was found by Cheapflights users on 10/7. 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.
Thu 10/296:55 pm -
1 stop6h 35m
Sat 11/77:35 am -
1 stop7h 00m
Deal found 10/7![Southwest logo]()
$265
This Southwest deal was found by Cheapflights users on 10/5. 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.
Mon 11/27:20 am -
Nonstop2h 30m
Tue 11/36:40 pm -
Nonstop2h 25m
Deal found 10/5![Southwest logo]()
$258
This Southwest deal was found by Cheapflights users on 10/7. 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.
Fri 11/67:20 am -
Nonstop2h 30m
Mon 11/97:00 pm -
Nonstop2h 20m
Deal found 10/7![Southwest logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:03 pm -
1 stop5h 44m
Mon 11/308:42 pm -
2 stops17h 29m
Deal found 10/6![Frontier logo]()
$260
This CheapOair deal was found by Cheapflights users on 10/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/235:59 pm -
1 stop15h 15m
Sat 11/288:28 am -
1 stop7h 39m
Deal found 10/6![Frontier logo]()
$262
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 October 8, 2026.
Search for one-way flight options from Jacksonville to Midway. Find affordable one-way fares based on user searches. Data last updated October 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:55 pm -
2 stops27h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Frontier logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/68:10 pm -
1 stop28h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Frontier logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:03 pm -
2 stops17h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/153:20 pm -
2 stops21h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$122
This Southwest deal was found by Cheapflights users on 10/8. 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 11/27:05 pm -
Nonstop2h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Southwest logo]()
$123
This Mytrip deal was found by Cheapflights users on 10/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/27:03 pm -
2 stops17h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/93:56 pm -
2 stops26h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/65:55 pm -
2 stops27h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:45 pm -
1 stop23h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Allegiant Air logo]()
$130
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 October 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $253 (Kiwi.com) |
One-way from | $112 (Kiwi.com) |
Popular in | November |
Cheapest in | December |
Average price | $358 |
Good round-trip deal | $409 or less |
Good one-way deal | $188 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 7,457,451 searches. Data last updated October 8, 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 Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Fri 11/6
7:03 pm-5:47 pm
1 stop23h 44m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$119
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Thu 1/7
1:30 pm-3:00 pm
Nonstop2h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$123
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Wed 1/6
1:30 pm-3:00 pm
Nonstop2h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$123
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Sat 1/9
5:05 pm-10:10 pm
1 stop6h 05m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$133
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Fri 11/20
5:59 pm-1:45 pm
1 stop20h 46m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$135
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Mon 12/14
3:45 pm-10:40 pm
2 stops7h 55m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$139
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Sun 11/1
7:03 pm-11:47 pm
1 stop5h 44m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$146
Quickest round-trip
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Tue 11/3
1:30 pm-2:55 pm
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$164
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Thu 10/29
6:10 am-10:03 am
1 stop4h 53m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$165
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Tue 11/10
1:30 pm-2:55 pm
Nonstop2h 25m
Chicago Midway
Thu 11/12
5:05 am-12:05 pm
1 stop6h 00m
$257
Showing 1-10 of 19 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 October.
| 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 October 8, 2026.
It’s optimal to fly from Jacksonville to Chicago Midway Airport in the evening. By choosing this option you can save up to 14% 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?
Airfare is below average for this route at the moment.
Jacksonville to Chicago Midway Airport flights typically cost between $328 and $469 in October.The cheapest round-trip price found within the last 5 days was $253 on Multiple Airlines (Oct 22-Oct 26).
The best insider tips for Jacksonville to Chicago Midway Airport flights
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Cheapflights partnered with top experts to bring you the best recommendations for your Jacksonville to Chicago Midway Airport trip
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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 October 8, 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.
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
7.9
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
7.9
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
7.9
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
7.9
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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
Valparaiso
Hammond
Saint Joseph
Porter
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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 7,457,451 searches. Data last updated October 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$129 | Average$295 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$134 | Average$259 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$197 | Average$389 | FlexibilityNo cancel fee | On-time63% |