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$137+ Cheap flights from Jacksonville (JAX) to Midway (MDW)

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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — MDW
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Find flight deals from Jacksonville to Midway

Cheapest flights from Jacksonville to Midway
Explore the most affordable flight options available from Jacksonville to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 13, 2025.

This Frontier deal was found by Cheapflights users on 11/11. 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.
Sat 11/1510:38 pmJAX - MDW
1 stop9h 52mFrontier
Mon 11/179:15 amMDW - JAX
1 stop11h 38mFrontier
Deal found 11/11$250
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 11/2610:59 amJAX - MDW
2 stops12h 18mFrontier
Mon 12/15:30 amMDW - JAX
1 stop14h 19mFrontier
Deal found 11/12$254
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Sun 11/239:34 pmJAX - MDW
1 stop27h 39mFrontier
Sun 11/305:30 amMDW - JAX
1 stop14h 18mFrontier
Deal found 11/12$260
This Kiwi.com deal was found by Cheapflights users on 11/13. 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.
Mon 12/156:36 pmJAX - MDW
2 stops19h 25mFrontier
Fri 12/198:15 amMDW - JAX
1 stop7h 12mFrontier
Deal found 11/13$267
This Frontier deal was found by Cheapflights users on 11/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/135:13 pmJAX - MDW
1 stop5h 50mFrontier
Mon 11/179:15 amMDW - JAX
1 stop11h 38mFrontier
Deal found 11/12$270
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Fri 11/219:38 pmJAX - MDW
1 stop22h 51mFrontier
Sun 11/305:30 amMDW - JAX
1 stop14h 18mFrontier
Deal found 11/12$274
This Kiwi.com deal was found by Cheapflights users on 11/13. 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.
Sat 11/2210:59 amJAX - MDW
1 stop4h 41mFrontier
Sun 11/236:15 pmMDW - JAX
1 stop25h 34mFrontier
Deal found 11/13$283
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 11/209:07 pmJAX - MDW
1 stop17h 14mMultiple Airlines
Mon 11/245:47 pmMDW - JAX
2 stops24h 00mMultiple Airlines
Deal found 11/12$287
This Kiwi.com deal was found by Cheapflights users on 11/13. 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.
Sat 12/68:37 pmJAX - MDW
2 stops22h 35mMultiple Airlines
Mon 12/86:15 amMDW - JAX
1 stop10h 21mMultiple Airlines
Deal found 11/13$288
This Kiwi.com deal was found by Cheapflights users on 11/13. 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.
Mon 12/19:34 pmJAX - MDW
2 stops36h 12mMultiple Airlines
Fri 12/56:15 amMDW - JAX
1 stop10h 25mMultiple Airlines
Deal found 11/13$296
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Tue 11/259:38 pmJAX - MDW
2 stops19h 52mMultiple Airlines
Mon 12/15:30 amMDW - JAX
1 stop14h 19mMultiple Airlines
Deal found 11/12$297

Cheap flight deals from Jacksonville to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Jacksonville (JAX) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$254
(Kiwi.com)

One-way from

$137
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$501

Good round-trip deal

$403 or less

Good one-way deal

$148 or less
Provider with most accurate pricing for Jacksonville-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Jacksonville-Chicago Midway flights.
Search Deals
From Jacksonville to Chicago Midway
Search Deals
One-way flight from Jacksonville to Chicago Midway
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($87 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($34 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Jacksonville to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Jacksonville to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Jacksonville to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 13, 2025.
Use the filters below to find and compare flights from Jacksonville to Chicago Midway Airport that are best for you.

Fly from

Jacksonville

Fly to

Midway

Route

Depart

Return

Price

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 1/17

12:30 pm-4:55 pm

1 stop5h 25m

Chicago Midway

Sun 1/18

1:35 pm-4:50 pm

Nonstop2h 15m

$287

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Tue 4/7

7:20 am-8:50 am

Nonstop2h 30m

Chicago Midway

Wed 4/8

5:55 pm-9:10 pm

Nonstop2h 15m

$297

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 12/31

5:05 pm-6:30 pm

Nonstop2h 25m

Chicago Midway

Sat 1/3

8:40 pm-11:55 pm

Nonstop2h 15m

$308

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 1/17

12:30 pm-4:55 pm

1 stop5h 25m

Chicago Midway

Mon 1/19

2:40 pm-10:15 pm

1 stop6h 35m

$308

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 12/6

5:35 am-7:00 am

Nonstop2h 25m

Chicago Midway

Mon 12/8

1:45 pm-5:00 pm

Nonstop2h 15m

$310

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 1/8

5:30 pm-6:55 pm

Nonstop2h 25m

Chicago Midway

Mon 1/12

10:00 am-8:15 pm

2 stops9h 15m

$314

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Tue 12/9

6:05 am-9:54 am

1 stop4h 49m

Chicago Midway

Tue 12/16

12:50 pm-5:35 pm

1 stop3h 45m

$317

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 12/13

11:42 am-3:44 pm

1 stop5h 02m

Chicago Midway

Mon 12/15

10:49 am-5:35 pm

1 stop5h 46m

$318

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Tue 12/30

6:00 am-9:05 am

1 stop4h 05m

Chicago Midway

Sat 1/3

6:00 am-12:38 pm

1 stop5h 38m

$319

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sun 12/14

10:00 pm-10:18 pm

2 stops25h 18m

$141

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/13

Showing 1-10 of 19 results
1
2

Compare providers for flights from Jacksonville to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Jacksonville to Midway in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*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 Jacksonville-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Jacksonville-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Jacksonville-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Jacksonville-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Jacksonville-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Jacksonville to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Jacksonville with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Jacksonville to Chicago Midway Airport

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

Currently, October is the cheapest month in which you can book a flight from Jacksonville to Chicago Midway Airport (average of $163). Flying from Jacksonville to Chicago Midway Airport in July is currently the most expensive (average of $357). 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 JAX to MDW?

Find hourly flight availability from Jacksonville to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 13, 2025.

It’s optimal to fly from Jacksonville to Chicago Midway Airport at noon. By choosing this option you can save up to 31% on the cost of your flight, compared to a flight in the morning.

The best insider tips for Jacksonville to Chicago Midway Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Jacksonville to Chicago Midway Airport trip
Airports
JAX

JAX offers quick screening times at TSA, making it one of the most convenient major airports in Florida for departures.

Read more about JAXby Matt Meltzer
MDW

The Orange Line train is a cheap and efficient way to reach downtown Chicago from MDW, taking less than 30 minutes.

Read more about MDWby Ramsey Qubein
Our travel experts
Matt Meltzer

Matt Meltzer

Expert on JAX

Matt Meltzer

Matt Meltzer

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

Ramsey Qubein

Ramsey Qubein

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 Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated November 13, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Frontier from Jacksonville to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,238 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
7.9
Good
4,238 reviews
Southwest
7.9
Good
4,238 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Delta
7.9
Good
8,008 reviews
Southwest
7.9
Good
4,238 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Frontier
5.8
Fair
3,111 reviews
Southwest
7.9
Good
4,238 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Jacksonville to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    Jacksonville (JAX) is the airport you will fly out of if you book a flight from Jacksonville to Chicago Midway. You should not have trouble finding flights to Chicago Midway from Jacksonville; the airport handles an average of 1 outbound flight to Chicago Midway per day. You should also have plenty of airline options to choose from since 3 airlines have flights from the Jacksonville airport to Chicago Midway. It is only a 11.2 mi journey to Jacksonville (JAX) from Jacksonville’s city center.

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

    Departing from Jacksonville to Chicago Midway Airport will take you 5h 25m. The distance between Jacksonville and Chicago Midway Airport is about 849 mi.

  • What are the cheapest airlines flying from Jacksonville to Chicago Midway Airport round-trip?

    Our cheapest airline available from Jacksonville to Chicago Midway Airport is Frontier. Our recent data shows that you can find tickets from as low as $158 on this airline. Additional options worth looking into are Southwest and Delta, starting at $207 and $216 round-trip. Frontier is 60% cheaper than the average price of flights available within the next 90 days to this destination.

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

    The cheapest flight price from Jacksonville to Chicago Midway Airport is $135. On average you can expect to pay $318. The most popular route, (Jacksonville - Chicago Midway), can usually be booked for $297.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Jacksonville to Midway 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 Jacksonville to Chicago Midway Airport?

    Currently, October is the cheapest month in which you can book a flight from Jacksonville to Chicago Midway Airport (average of $163). Flying from Jacksonville to Chicago Midway Airport in July is currently the most expensive (average of $357). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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Top 3 airlines flying from Jacksonville to Midway

Discover the top 3 airlines that operate flights from Jacksonville to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$158Average$232FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$207Average$393FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$402FlexibilityNo cancel feeOn-timeN/A

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