$98+ 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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JAX
Oct 10 — Oct 171
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
Best
Last-minute
One-way
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 September 10, 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 September 10, 2026.
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:25 am -
1 stop11h 36m
Tue 10/137:46 pm -
1 stop4h 57m
Deal found 9/8![Frontier logo]()
$215
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:21 am -
1 stop10h 04m
Tue 10/137:46 pm -
1 stop4h 57m
Deal found 9/9![Frontier logo]()
$216
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:21 am -
1 stop11h 25m
Tue 10/207:46 pm -
1 stop4h 57m
Deal found 9/7![Frontier logo]()
$217
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:25 am -
1 stop11h 36m
Sun 10/47:46 pm -
1 stop4h 57m
Deal found 9/5![Frontier logo]()
$219
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/126:15 am -
1 stop11h 16m
Sat 10/247:46 pm -
1 stop4h 57m
Deal found 9/9![Frontier logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:21 am -
1 stop11h 25m
Sat 10/1711:32 am -
2 stops13h 11m
Deal found 9/10![Frontier logo]()
$224
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:25 am -
1 stop11h 36m
Sun 10/116:20 pm -
1 stop6h 23m
Deal found 9/5![Frontier logo]()
$225
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:52 am -
1 stop10h 39m
Mon 10/127:46 pm -
1 stop4h 57m
Deal found 9/8![Frontier logo]()
$230
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:25 am -
1 stop11h 36m
Mon 10/58:07 pm -
1 stop4h 36m
Deal found 9/8![Frontier logo]()
$231
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:16 am -
1 stop10h 52m
Sun 11/87:03 pm -
1 stop23h 44m
Deal found 9/9![Frontier logo]()
$234
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 September 10, 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 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.
Tue 10/136:00 pm -
Nonstop2h 20m
Thu 10/151:30 pm -
Nonstop2h 20m
Deal found 9/8![Southwest logo]()
$357
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/411:39 am -
1 stop4h 04m
Mon 11/96:59 pm -
1 stop4h 55m
Deal found 9/5![Delta logo]()
$411
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.
Wed 10/76:00 pm -
Nonstop2h 20m
Tue 10/1312:45 pm -
Nonstop2h 20m
Deal found 9/6![Southwest logo]()
$371
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.
Wed 10/79:40 am -
2 stops6h 40m
Thu 10/227:00 am -
2 stops7h 25m
Deal found 9/8![Southwest logo]()
$373
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.
Wed 9/306:05 am -
1 stop4h 51m
Tue 10/136:10 am -
1 stop4h 53m
Deal found 9/8![Delta logo]()
$423
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 10/139:40 am -
2 stops6h 40m
Tue 10/201:30 pm -
2 stops9h 30m
Deal found 9/7![Southwest logo]()
$401
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 10/310:30 am -
Nonstop2h 15m
Sat 10/101:50 pm -
1 stop5h 55m
Deal found 9/5![Southwest logo]()
$403
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 10/13:00 pm -
Nonstop2h 15m
Sun 10/47:45 am -
Nonstop2h 20m
Deal found 9/8![Southwest logo]()
$405
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.
Fri 11/612:50 pm -
Nonstop2h 15m
Sun 11/87:20 am -
Nonstop2h 30m
Deal found 9/5![Southwest logo]()
$409
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.
Thu 11/196:40 pm -
Nonstop2h 25m
Sun 11/229:00 pm -
1 stop4h 05m
Deal found 9/5![Southwest logo]()
$419
Last-minute flights from Midway to JacksonvilleDiscover last-minute flight deals from Midway to Jacksonville. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Jacksonville. Data last updated September 10, 2026 and is based on user searches.
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:25 am -
1 stop11h 36m
Sun 10/47:46 pm -
1 stop4h 57m
Deal found 9/5![Frontier logo]()
$219
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:25 am -
1 stop11h 36m
Sun 10/116:20 pm -
1 stop6h 23m
Deal found 9/5![Frontier logo]()
$225
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:25 am -
1 stop11h 36m
Mon 10/58:07 pm -
1 stop4h 36m
Deal found 9/8![Frontier logo]()
$231
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:25 am -
1 stop11h 36m
Tue 10/137:46 pm -
1 stop4h 57m
Deal found 9/8![Frontier logo]()
$215
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:21 am -
1 stop10h 04m
Tue 10/137:46 pm -
1 stop4h 57m
Deal found 9/9![Frontier logo]()
$216
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:52 am -
1 stop10h 39m
Mon 10/127:46 pm -
1 stop4h 57m
Deal found 9/8![Frontier logo]()
$230
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:52 am -
1 stop10h 39m
Sun 10/116:20 pm -
1 stop6h 23m
Deal found 9/9![Frontier logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:21 am -
1 stop11h 25m
Sat 10/1711:32 am -
2 stops13h 11m
Deal found 9/10![Frontier logo]()
$224
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/126:15 am -
1 stop11h 16m
Sat 10/247:46 pm -
1 stop4h 57m
Deal found 9/9![Frontier logo]()
$220
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:21 am -
1 stop11h 25m
Tue 10/207:46 pm -
1 stop4h 57m
Deal found 9/7![Frontier logo]()
$217
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 September 10, 2026.
Search for one-way flight options from Midway to Jacksonville. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:53 am -
1 stop7h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$98
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:21 am -
1 stop11h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$102
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:16 am -
1 stop10h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$107
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:21 am -
1 stop10h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$108
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:25 am -
1 stop11h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:25 am -
1 stop11h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$113
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/82:04 pm -
1 stop22h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$114
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:25 am -
1 stop11h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$119
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/26:46 pm -
1 stop23h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$120
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:42 pm -
1 stop22h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$123
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 September 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $215 (Kiwi.com) |
One-way from | $98 (Priceline) |
Popular in | July |
Cheapest in | March |
Average price | $352 |
Good round-trip deal | $251 or less |
Good one-way deal | $198 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 September 10, 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
Quickest round-trip
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Thu 10/1
3:00 pm-6:15 pm
Nonstop2h 15m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Fri 10/9
2:55 pm-6:15 pm
Nonstop2h 20m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Mon 11/9
12:50 pm-4:05 pm
Nonstop2h 15m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Thu 10/15
2:55 pm-6:15 pm
Nonstop2h 20m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$172
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Wed 10/28
6:00 pm-9:20 pm
Nonstop2h 20m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$172
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Tue 12/8
6:40 pm-10:05 pm
Nonstop2h 25m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$172
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Thu 12/24
9:58 am-3:57 pm
1 stop4h 59m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$182
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Thu 3/4
8:35 am-12:00 pm
Nonstop2h 25m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$186
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Thu 11/19
6:40 pm-10:05 pm
Nonstop2h 25m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$186
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Wed 10/7
8:05 am-5:20 pm
2 stops8h 15m
Jacksonville
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$187
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 September.
| 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 |
- 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 July is currently the most expensive (average of $470). 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 September 10, 2026.
It’s optimal to fly from Chicago Midway Airport to Jacksonville at noon. By choosing this option you can save up to 10% on the cost of your flight, compared to a flight in the evening.
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
Our travel experts
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 September 10, 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.
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Comfort
8.0
Overall
8.0
Crew
8.6
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Jacksonville flight routes
Other flight options
Other flights from Midway
Popular flights
Alternative routes for Midway to Jacksonville
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Jacksonville by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Jacksonville by cabin class
Find flights from Midway to Jacksonville, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Jacksonville
Explore flights to Jacksonville departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 10, 2026.
Midway and Jacksonville flights
Browse other Midway and Jacksonville flight options. Last updated on September 10, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on September 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 September 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$160 | Average$288 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$238 | Average$389 | FlexibilityNo cancel fee | On-time63% |