$139+ Cheap flights from Midway (MDW) to Jacksonville (JAX)
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 12/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JAX
Nov 29 — Dec 61
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Jacksonville with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midway to Jacksonville
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Cheapest flights from Midway to JacksonvilleExplore the most affordable flight options available from Midway to Jacksonville. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2026.
Explore the most affordable flight options available from Midway to Jacksonville. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2026.
This Trip.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:08 am -
1 stop11h 03m
Mon 11/167:03 pm -
1 stop5h 44m
Deal found 10/25![Frontier logo]()
$279
This Frontier deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:08 am -
1 stop11h 03m
Sat 11/147:16 pm -
1 stop5h 31m
Deal found 10/25![Frontier logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:08 am -
1 stop11h 03m
Wed 11/189:09 am -
2 stops9h 38m
Deal found 10/25![Frontier logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:09 am -
1 stop6h 58m
Tue 12/13:20 pm -
2 stops21h 13m
Deal found 10/25![Multiple Airlines logo]()
$286
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:40 pm -
Nonstop2h 30m
Wed 12/91:30 pm -
Nonstop2h 25m
Deal found 10/25![Southwest logo]()
$287
This Mytrip deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:08 am -
1 stop11h 03m
Mon 11/167:03 pm -
2 stops17h 19m
Deal found 10/26![Frontier logo]()
$288
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:08 am -
1 stop11h 03m
Wed 11/189:09 am -
2 stops9h 38m
Deal found 10/25![Frontier logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:15 am -
1 stop10h 16m
Tue 11/179:09 am -
2 stops9h 38m
Deal found 10/25![Frontier logo]()
$295
This Frontier deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:08 am -
1 stop11h 03m
Thu 11/198:08 pm -
1 stop4h 39m
Deal found 10/25![Frontier logo]()
$296
This Cheapflightsfares deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:16 am -
1 stop10h 52m
Mon 11/97:03 pm -
1 stop5h 44m
Deal found 10/26![Frontier logo]()
$298
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:40 pm -
Nonstop2h 30m
Sat 11/213:40 pm -
2 stops9h 45m
Deal found 10/26![Southwest logo]()
$302
Best flights from Midway to JacksonvilleDiscover carefully curated flight deals from Midway to Jacksonville that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 30, 2026.
Discover carefully curated flight deals from Midway to Jacksonville that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 30, 2026.
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/99:55 am -
1 stop6h 05m
Sun 12/137:20 am -
Nonstop2h 30m
Deal found 10/26![Southwest logo]()
$349
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/1210:47 am -
1 stop4h 55m
Fri 1/156:58 pm -
1 stop16h 02m
Deal found 10/25![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/265:45 pm -
1 stop5h 10m
Fri 1/297:59 pm -
1 stop15h 05m
Deal found 10/25![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/316:40 pm -
Nonstop2h 30m
Thu 1/76:30 am -
2 stops9h 25m
Deal found 10/28![Southwest logo]()
$366
This Southwest deal was found by Cheapflights users on 10/30. 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.
Fri 1/16:40 pm -
Nonstop2h 30m
Thu 1/75:55 am -
1 stop7h 25m
Deal found 10/30![Southwest logo]()
$367
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/255:45 pm -
1 stop4h 09m
Tue 1/2610:24 am -
1 stop7h 30m
Deal found 10/25![Delta logo]()
$368
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:00 am -
1 stop6h 23m
Sat 12/127:17 pm -
1 stop4h 37m
Deal found 10/30![Delta logo]()
$377
This Southwest deal was found by Cheapflights users on 10/30. 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.
Fri 12/1812:50 pm -
2 stops6h 45m
Thu 12/245:40 pm -
1 stop4h 50m
Deal found 10/30![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 10/30. 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.
Wed 12/29:40 am -
2 stops7h 40m
Tue 12/84:55 pm -
1 stop6h 45m
Deal found 10/30![Southwest logo]()
$382
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:12 pm -
1 stop4h 43m
Mon 12/75:45 pm -
1 stop6h 09m
Deal found 10/26![Delta logo]()
$393
This Southwest deal was found by Cheapflights users on 10/29. 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 11/196:40 pm -
Nonstop2h 30m
Fri 11/207:20 am -
Nonstop2h 30m
Deal found 10/29![Southwest logo]()
$395
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/297:00 pm -
Nonstop2h 15m
Wed 12/309:20 pm -
1 stop4h 00m
Deal found 10/26![Southwest logo]()
$402
Last-minute flights from Midway to JacksonvilleDiscover last-minute flight deals from Midway to Jacksonville. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Jacksonville. Data last updated October 30, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:16 am -
1 stop10h 52m
Mon 11/97:03 pm -
1 stop5h 44m
Deal found 10/26![Frontier logo]()
$298
This Trip.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:08 am -
1 stop11h 03m
Mon 11/167:03 pm -
1 stop5h 44m
Deal found 10/25![Frontier logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:08 am -
1 stop11h 03m
Tue 11/179:09 am -
2 stops9h 38m
Deal found 10/25![Frontier logo]()
$303
This Frontier deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:08 am -
1 stop11h 03m
Sat 11/147:16 pm -
1 stop5h 31m
Deal found 10/25![Frontier logo]()
$280
This Frontier deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:08 am -
1 stop11h 03m
Thu 11/198:08 pm -
1 stop4h 39m
Deal found 10/25![Frontier logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:15 am -
1 stop10h 16m
Tue 11/179:09 am -
2 stops9h 38m
Deal found 10/25![Frontier logo]()
$295
This Mytrip deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:08 am -
1 stop11h 03m
Mon 11/167:03 pm -
2 stops17h 19m
Deal found 10/26![Frontier logo]()
$288
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:08 am -
1 stop11h 03m
Wed 11/189:09 am -
2 stops9h 38m
Deal found 10/25![Frontier logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:08 am -
1 stop11h 03m
Wed 11/189:09 am -
2 stops9h 38m
Deal found 10/25![Frontier logo]()
$282
This Delta deal was found by Cheapflights users on 10/27. 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 11/176:00 am -
1 stop6h 20m
Tue 11/176:54 pm -
1 stop5h 00m
Deal found 10/27![Delta logo]()
$307
This Southwest deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:40 pm -
Nonstop2h 30m
Sat 11/213:40 pm -
2 stops9h 45m
Deal found 10/26![Southwest logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:09 am -
1 stop6h 58m
Tue 12/13:20 pm -
2 stops21h 13m
Deal found 10/25![Multiple Airlines logo]()
$286
One-way flights from Midway to JacksonvilleSearch for one-way flight options from Midway to Jacksonville. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
Search for one-way flight options from Midway to Jacksonville. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This CheapOair deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/181:11 pm -
1 stop5h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Frontier logo]()
$139
This Priceline deal was found by Cheapflights users on 10/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/309:09 am -
1 stop6h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/210:21 am -
2 stops21h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$141
This Mytrip deal was found by Cheapflights users on 10/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/108:37 pm -
2 stops19h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Frontier logo]()
$142
This CheapOair deal was found by Cheapflights users on 10/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/281:11 pm -
1 stop5h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Frontier logo]()
$143
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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.
Sat 11/77:15 am -
1 stop10h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Frontier logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/75:02 pm -
2 stops22h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$145
This CheapOair deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected ” under the list of providers to see comparable flight deals.
Wed 11/46:16 am -
1 stop10h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Frontier logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/145:02 pm -
2 stops22h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$151
Find flight deals from Midway to Jacksonville
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Jacksonville (JAX). 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 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $279 (Trip.com) |
One-way from | $139 (CheapOair) |
Popular in | November |
Cheapest in | March |
Average price | $446 |
Good round-trip deal | $343 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Jacksonville 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 30, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Jacksonville that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Tue 12/8
6:40 pm-10:10 pm
Nonstop2h 30m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$144
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Tue 12/8
6:00 am-11:53 am
1 stop4h 53m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$154
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Tue 12/1
3:50 pm-9:15 pm
1 stop4h 25m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$154
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Mon 12/14
3:50 pm-9:15 pm
1 stop4h 25m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$154
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Sat 12/5
6:05 am-4:45 pm
1 stop9h 40m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$154
Quickest round-trip
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Fri 11/20
7:00 pm-10:20 pm
Nonstop2h 20m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$176
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Sat 11/28
8:28 am-5:07 pm
1 stop7h 39m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$179
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Thu 12/24
6:40 pm-10:10 pm
Nonstop2h 30m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$179
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Thu 12/31
3:10 pm-10:20 pm
1 stop6h 10m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$186
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Wed 12/30
12:45 pm-8:35 pm
2 stops6h 50m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$191
Showing 1-10 of 22 resultsSorted by cheapest first
Compare providers for flights from Midway to Jacksonville
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Jacksonville in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Jacksonville flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Jacksonville flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Jacksonville flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Jacksonville flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Jacksonville flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Midway to Jacksonville
Have a flexible travel schedule? Discover the best time to fly to Jacksonville from Midway with our price prediction graph.
MDW-JAX
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 Chicago Midway Airport to Jacksonville
What is the cheapest month to book a flight from Chicago Midway Airport to Jacksonville?
Currently, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Jacksonville (average of $238). Flying from Chicago Midway Airport to Jacksonville in November is currently the most expensive (average of $538). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from MDW to JAX?
Find hourly flight availability from Midway to Jacksonville. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2026.
It’s optimal to fly from Chicago Midway Airport to Jacksonville in the afternoon. By choosing this option you can save up to 5% on the cost of your flight, compared to a flight in the morning.
What is the cheapest day to fly from Chicago Midway Airport to Jacksonville?
Use this chart to determine the cheapest time to fly round-trip from Midway to Jacksonville. Price data was last updated on October 24, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Jacksonville flight should consider departing on Saturday afternoons when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Chicago Midway Airport to Jacksonville 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 Chicago Midway Airport to Jacksonville trip
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Reviews of airlines servicing Jacksonville
Get insights into the airlines that provide service to Jacksonville. 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 Jacksonville. Reviews last updated October 30, 2026.
See what other customers who have flown with Southwest and Frontier from Chicago Midway Airport to Jacksonville have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Related info for your journey
Find useful and relevant information for your journey from Midway to Jacksonville. 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 Jacksonville?
Book flights to Jacksonville if you plan to visit one of these locationsJacksonville Beach
Fernandina Beach
Orange Park
Kingsland
Waycross
Atlantic Beach
Yulee
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Top 2 airlines flying from Midway to Jacksonville
Discover the top 2 airlines that operate flights from Midway to Jacksonville. 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 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$160 | Average$288 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$238 | Average$391 | FlexibilityNo cancel fee | On-time63% |