$99+ Cheap flights from Midway (MDW) to Jacksonville (JAX)
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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JAX
Sep 13 — Sep 201
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
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 August 14, 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 August 14, 2026.
This Frontier deal was found by Cheapflights users on 8/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/311:50 am -
1 stop5h 20m
Sun 9/67:05 pm -
1 stop4h 42m
Deal found 8/10![Frontier logo]()
$202
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/302:45 pm -
1 stop7h 05m
Mon 11/27:20 am -
Nonstop2h 30m
Deal found 8/10![Southwest logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/96:25 am -
1 stop11h 36m
Fri 9/117:46 pm -
1 stop4h 58m
Deal found 8/13![Frontier logo]()
$205
This Southwest deal was found by Cheapflights users on 8/13. 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 9/511:45 am -
2 stops6h 55m
Sat 9/126:15 am -
1 stop6h 05m
Deal found 8/13![Southwest logo]()
$206
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/61:40 pm -
Nonstop2h 15m
Fri 9/113:50 pm -
1 stop6h 10m
Deal found 8/9![Southwest logo]()
$207
This Frontier deal was found by Cheapflights users on 8/13. 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 10/236:15 am -
1 stop11h 16m
Sat 10/247:46 pm -
1 stop4h 57m
Deal found 8/13![Frontier logo]()
$208
This Southwest deal was found by Cheapflights users on 8/13. 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 10/153:00 pm -
Nonstop2h 15m
Sat 10/174:55 pm -
Nonstop2h 20m
Deal found 8/13![Southwest logo]()
$210
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:45 am -
2 stops6h 45m
Sun 9/64:45 pm -
Nonstop2h 20m
Deal found 8/9![Southwest logo]()
$212
This Southwest deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/82:40 pm -
1 stop4h 05m
Sat 9/121:30 pm -
1 stop6h 45m
Deal found 8/13![Southwest logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 9/211:50 am -
1 stop5h 20m
Tue 9/88:44 pm -
2 stops22h 07m
Deal found 8/12![Multiple Airlines logo]()
$218
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 August 14, 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 August 14, 2026.
This Southwest deal was found by Cheapflights users on 8/13. 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 9/511:45 am -
2 stops6h 55m
Sat 9/128:00 am -
2 stops10h 05m
Deal found 8/13![Southwest logo]()
$211
This Delta deal was found by Cheapflights users on 8/11. 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 9/296:05 am -
1 stop6h 18m
Mon 10/55:34 pm -
1 stop6h 10m
Deal found 8/11![Delta logo]()
$241
This Southwest deal was found by Cheapflights users on 8/12. 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 9/266:45 am -
2 stops10h 20m
Sat 10/34:55 pm -
Nonstop2h 20m
Deal found 8/12![Southwest logo]()
$236
This Southwest deal was found by Cheapflights users on 8/13. 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 9/46:45 pm -
Nonstop2h 20m
Tue 9/85:25 pm -
Nonstop2h 30m
Deal found 8/13![Southwest logo]()
$242
This Southwest deal was found by Cheapflights users on 8/12. 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 9/2312:40 pm -
2 stops6h 10m
Mon 9/282:00 pm -
2 stops7h 10m
Deal found 8/12![Southwest logo]()
$252
This Southwest deal was found by Cheapflights users on 8/11. 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 10/23:00 pm -
Nonstop2h 15m
Mon 10/57:00 pm -
1 stop6h 25m
Deal found 8/11![Southwest logo]()
$264
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:45 pm -
Nonstop2h 20m
Fri 9/257:00 am -
Nonstop2h 25m
Deal found 8/10![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/53:00 pm -
Nonstop2h 15m
Thu 10/88:45 pm -
1 stop4h 10m
Deal found 8/13![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 8/11. 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 9/176:45 pm -
Nonstop2h 20m
Sun 9/205:35 pm -
Nonstop2h 25m
Deal found 8/11![Southwest logo]()
$324
Last-minute flights from Midway to JacksonvilleDiscover last-minute flight deals from Midway to Jacksonville. Data last updated August 14, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Jacksonville. Data last updated August 14, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 9/211:50 am -
1 stop5h 20m
Tue 9/88:44 pm -
2 stops22h 07m
Deal found 8/12![Multiple Airlines logo]()
$218
This Frontier deal was found by Cheapflights users on 8/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/311:50 am -
1 stop5h 20m
Sun 9/67:05 pm -
1 stop4h 42m
Deal found 8/10![Frontier logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 9/36:05 am -
1 stop11h 05m
Tue 9/88:44 pm -
2 stops22h 07m
Deal found 8/11![Multiple Airlines logo]()
$225
This Southwest deal was found by Cheapflights users on 8/11. 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 9/511:45 am -
2 stops6h 55m
Sun 9/66:10 pm -
1 stop5h 25m
Deal found 8/11![Southwest logo]()
$206
This Southwest deal was found by Cheapflights users on 8/13. 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 9/511:45 am -
2 stops6h 55m
Sat 9/128:00 am -
2 stops10h 05m
Deal found 8/13![Southwest logo]()
$211
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/61:40 pm -
Nonstop2h 15m
Fri 9/113:50 pm -
1 stop6h 10m
Deal found 8/9![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/82:40 pm -
1 stop4h 05m
Sat 9/121:30 pm -
1 stop6h 45m
Deal found 8/13![Southwest logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 9/96:25 am -
1 stop11h 36m
Fri 9/117:46 pm -
1 stop4h 58m
Deal found 8/13![Frontier logo]()
$205
This Southwest deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/235:55 pm -
Nonstop2h 25m
Wed 10/712:45 pm -
Nonstop2h 20m
Deal found 8/9![Southwest logo]()
$223
This Southwest deal was found by Cheapflights users on 8/12. 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 9/2612:45 pm -
Nonstop2h 15m
Sat 10/34:55 pm -
Nonstop2h 20m
Deal found 8/12![Southwest logo]()
$221
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 August 14, 2026.
Search for one-way flight options from Midway to Jacksonville. Find affordable one-way fares based on user searches. Data last updated August 14, 2026.
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:45 pm -
Nonstop2h 15m
Deal found 8/8![Southwest logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 8/10. 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
Deal found 8/10![Frontier logo]()
$100
This Super.com deal was found by Cheapflights users on 8/11. 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.
Fri 9/411:50 am -
1 stop5h 20m
Deal found 8/11![Frontier logo]()
$103
This Frontier deal was found by Cheapflights users on 8/11. 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 10/912:03 pm -
1 stop4h 48m
Deal found 8/11![Frontier logo]()
$104
This Trip.com deal was found by Cheapflights users on 8/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:05 am -
1 stop11h 05m
Deal found 8/10![Frontier logo]()
$105
This Trip.com deal was found by Cheapflights users on 8/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/211:50 am -
1 stop5h 20m
Deal found 8/10![Frontier logo]()
$106
This Trip.com deal was found by Cheapflights users on 8/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:25 am -
1 stop11h 36m
Deal found 8/10![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 10/141:12 pm -
2 stops27h 13m
Deal found 8/13![Frontier logo]()
$108
This Delta deal was found by Cheapflights users on 8/11. 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 9/1111:35 am -
1 stop3h 53m
Deal found 8/11![Delta logo]()
$109
This Southwest deal was found by Cheapflights users on 8/13. 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 9/1212:45 pm -
Nonstop2h 15m
Deal found 8/13![Southwest logo]()
$111
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:55 pm -
Nonstop2h 25m
Deal found 8/10![Southwest logo]()
$112
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 August 14, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $202 (Frontier) |
One-way from | $99 (Southwest) |
Popular in | July |
Cheapest in | March |
Average price | $317 |
Good round-trip deal | $316 or less |
Good one-way deal | $195 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 2,558,603 searches. Data last updated August 14, 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
Sat 9/5
11:45 am-7:40 pm
2 stops6h 55m
Jacksonville
Sat 9/12
8:00 am-5:05 pm
2 stops10h 05m
$211
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Sat 9/26
6:45 am-6:05 pm
2 stops10h 20m
Jacksonville
Sat 10/3
4:55 pm-6:15 pm
Nonstop2h 20m
$236
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Tue 9/29
6:05 am-1:23 pm
1 stop6h 18m
Jacksonville
Mon 10/5
5:34 pm-10:44 pm
1 stop6h 10m
$241
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Fri 9/4
6:45 pm-10:05 pm
Nonstop2h 20m
Jacksonville
Tue 9/8
5:25 pm-6:55 pm
Nonstop2h 30m
$242
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Wed 9/23
12:40 pm-7:50 pm
2 stops6h 10m
Jacksonville
Mon 9/28
2:00 pm-8:10 pm
2 stops7h 10m
$252
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Fri 10/2
3:00 pm-6:15 pm
Nonstop2h 15m
Jacksonville
Mon 10/5
7:00 pm-12:25 am
1 stop6h 25m
$264
Quickest round-trip
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Fri 9/18
6:45 pm-10:05 pm
Nonstop2h 20m
Jacksonville
Fri 9/25
7:00 am-8:25 am
Nonstop2h 25m
$287
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Mon 10/5
3:00 pm-6:15 pm
Nonstop2h 15m
Jacksonville
Thu 10/8
8:45 pm-11:55 pm
1 stop4h 10m
$296
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Thu 9/17
6:45 pm-10:05 pm
Nonstop2h 20m
Jacksonville
Sun 9/20
5:35 pm-7:00 pm
Nonstop2h 25m
$324
Cheapest one-way
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Mon 9/28
6:45 pm-10:05 pm
Nonstop2h 20m
$99
Showing 1-10 of 20 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 August.
| 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 August 14, 2026.
It’s optimal to fly from Chicago Midway Airport to Jacksonville at noon. By choosing this option you can save up to 19% 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 August 14, 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
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Crew
8.6
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
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 August 14, 2026.
Midway and Jacksonville flights
Browse other Midway and Jacksonville flight options. Last updated on August 14, 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 August 14, 2026.
Popular flight searches
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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 2,558,603 searches. Data last updated August 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$160 | Average$272 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$238 | Average$382 | FlexibilityNo cancel fee | On-time63% |