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$88+ 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 7/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JAX
Jul 16 — Jul 231
Thu 7/16
Thu 7/23
1 adult, Economy
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Cheap flight deals from Midway to Jacksonville

Cheapest flights from Midway to Jacksonville
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 June 16, 2026.

This Southwest deal was found by Cheapflights users on 6/15. 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 7/147:50 am
MDW
-
JAX
2 stops8h 05m
Southwest
Tue 7/212:55 pm
JAX
-
MDW
2 stops8h 05m
Southwest
Deal found 6/15$227
This Southwest deal was found by Cheapflights users on 6/11. 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.
Tue 8/185:55 pm
MDW
-
JAX
Nonstop2h 20m
Southwest
Mon 8/247:00 am
JAX
-
MDW
Nonstop2h 25m
Southwest
Deal found 6/11$230
This Kiwi.com deal was found by Cheapflights users on 6/12. 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.
Thu 7/92:48 pm
MDW
-
JAX
1 stop22h 12m
Multiple Airlines
Sun 7/126:29 pm
JAX
-
MDW
1 stop28h 34m
Multiple Airlines
Deal found 6/12$232
This Travelocity deal was found by Cheapflights users on 6/15. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:00 am
MDW
-
JAX
1 stop10h 37m
Frontier
Mon 8/246:28 pm
JAX
-
MDW
1 stop4h 43m
Frontier
Deal found 6/15$234
This Kiwi.com deal was found by Cheapflights users on 6/11. 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 9/2412:03 pm
MDW
-
JAX
1 stop4h 48m
Frontier
Sun 9/276:46 pm
JAX
-
MDW
1 stop17h 12m
Frontier
Deal found 6/11$238
This Orbitz deal was found by Cheapflights users on 6/13. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:05 am
MDW
-
JAX
1 stop10h 29m
Frontier
Tue 8/116:29 pm
JAX
-
MDW
1 stop4h 34m
Frontier
Deal found 6/13$239
This Southwest deal was found by Cheapflights users on 6/11. 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 8/812:45 pm
MDW
-
JAX
Nonstop2h 15m
Southwest
Tue 8/115:25 pm
JAX
-
MDW
Nonstop2h 25m
Southwest
Deal found 6/11$241
This deal was found by Cheapflights users on 6/11. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/711:06 am
MDW
-
JAX
1 stop5h 28m
Frontier
Mon 8/106:29 pm
JAX
-
MDW
1 stop4h 34m
Frontier
Deal found 6/11$242
This Booking.com deal was found by Cheapflights users on 6/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/66:05 am
MDW
-
JAX
1 stop10h 29m
Frontier
Mon 8/106:29 pm
JAX
-
MDW
1 stop4h 34m
Frontier
Deal found 6/11$243
This Southwest deal was found by Cheapflights users on 6/13. 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 8/66:45 pm
MDW
-
JAX
Nonstop2h 15m
Southwest
Tue 8/115:25 pm
JAX
-
MDW
Nonstop2h 25m
Southwest
Deal found 6/13$246
This Southwest deal was found by Cheapflights users on 6/11. 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.
Tue 9/228:15 am
MDW
-
JAX
2 stops7h 30m
Southwest
Wed 9/238:55 am
JAX
-
MDW
2 stops8h 05m
Southwest
Deal found 6/11$247

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 June 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$227
(Southwest)

One-way from

$88
(Kiwi.com)

Popular in

November

Cheapest in

August

Average price

$415

Good round-trip deal

$290 or less

Good one-way deal

$148 or less
Provider with most accurate pricing for Chicago Midway-Jacksonville flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Jacksonville flights.
Search Deals
From Chicago Midway to Jacksonville
Search Deals
One-way flight from Chicago Midway to Jacksonville
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Jacksonville.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Jacksonville.
Search Deals

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 June 16, 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

Price

Cheapest round-trip

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 8/18

12:45 pm-7:45 pm

2 stops6h 00m

Jacksonville

Tue 8/25

8:00 am-1:05 pm

2 stops6h 05m

$227

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Sat 7/25

7:50 am-11:15 am

Nonstop2h 25m

Jacksonville

Tue 7/28

6:50 pm-8:15 pm

Nonstop2h 25m

$269
Quickest round-trip

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Fri 9/4

6:45 pm-10:00 pm

Nonstop2h 15m

Jacksonville

Mon 9/7

7:00 am-8:25 am

Nonstop2h 25m

$287

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 7/16

2:40 pm-11:00 pm

2 stops7h 20m

Jacksonville

Tue 7/21

4:45 pm-11:15 pm

2 stops7h 30m

$299

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Sat 9/5

6:05 am-1:36 pm

1 stop6h 31m

Jacksonville

Sat 9/12

6:59 pm-10:45 pm

1 stop4h 46m

$315

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 7/14

6:20 pm-9:45 pm

Nonstop2h 25m

Jacksonville

Sun 7/19

3:30 pm-10:00 pm

1 stop7h 30m

$317

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 8/13

6:45 pm-10:00 pm

Nonstop2h 15m

Jacksonville

Sun 8/16

5:35 pm-7:00 pm

Nonstop2h 25m

$341

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 7/23

8:40 am-12:00 pm

Nonstop2h 20m

Jacksonville

Sat 7/25

10:55 am-12:20 pm

Nonstop2h 25m

$341

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 7/9

7:50 am-4:15 pm

2 stops7h 25m

Jacksonville

Tue 7/14

8:25 am-2:30 pm

2 stops7h 05m

$357

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 7/23

6:00 am-1:45 pm

1 stop6h 45m

Jacksonville

Sat 7/25

5:40 pm-10:15 pm

1 stop5h 35m

$361

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/15

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 June.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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.
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, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Jacksonville (average of $218). Flying from Chicago Midway Airport to Jacksonville in November is currently the most expensive (average of $418). 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 June 16, 2026.

It’s optimal to fly from Chicago Midway Airport to Jacksonville at noon. By choosing this option you can save up to 14% on the cost of your flight, compared to a flight in the afternoon.

How much does it cost to fly round-trip from Chicago Midway Airport to Jacksonville?

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
Matt Meltzer

Matt Meltzer

Expert on JAX

Matt Meltzer has been a travel writer for over a decade, covering U.S. domestic locations and hotels for Thrillist, Fifty Grande, Matador Network, Conde Nast Traveler, and other top publications. He's won multiple travel journalism awards from the Society of American Travel Writers and North American Travel Journalists Association, and currently resides in South Florida.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on MDW

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

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 June 16, 2026.
See what other customers who have flown with Southwest 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.
Southwest
7.9
Good
4,237 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Southwest
7.9
Good
4,237 reviews
Southwest
7.9
Good
4,237 reviews

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

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.

  • What airport do you fly into for flights to Jacksonville from Chicago Midway?

    If you book a flight to Jacksonville from Chicago Midway, you will be flying to Jacksonville, which is the city’s only airport. Jacksonville (JAX) is located 11.2 mi from the center of Jacksonville. There is 1 flight from Chicago Midway to Jacksonville per day from 1 airline.

  • How long is the flight from Chicago Midway Airport to Jacksonville?

    A quick flight from Chicago Midway Airport to Jacksonville can take about 6h. Southwest provides one of the quickest options available for as low as $227. There are 849 mi between Chicago Midway Airport and Jacksonville. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Chicago Midway Airport to Jacksonville round-trip?

    Our cheapest airline available from Chicago Midway Airport to Jacksonville is Southwest. Our recent data shows that you can find tickets from as low as $203 on this airline. This flight start at 39% lower than the current average price 3 months from now.

  • What are the cheapest flights from Chicago Midway Airport to Jacksonville?

    While on average a flight from Chicago Midway Airport to Jacksonville is generally $279, our data shows the cheapest flight currently is $108. When looking at the most popular route, (Chicago Midway - Jacksonville), you can expect to pay $197 for that flight.

  • Can I find deals for flights from Midway to Jacksonville that include hotel bookings?

    Yes. In addition to deals on Midway to Jacksonville flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Jacksonville?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Jacksonville.

  • Can I find deals for business class flights from Midway to Jacksonville?

    Yes. Cheapflights offers flight deals from Midway to Jacksonville by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Jacksonville?

    Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Jacksonville (average of $218). Flying from Chicago Midway Airport to Jacksonville in November is currently the most expensive (average of $418). 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.

See more FAQs

Traveling to a place near Jacksonville?

Book flights to Jacksonville if you plan to visit one of these locations
Jacksonville 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.

Top airline flying from Midway to Jacksonville

Discover the top airline 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 June 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$203Average$360FlexibilityNo cancel feeOn-time63%

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