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Midway

$68+ 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 3/21. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — MDW
Mar 18 — Mar 251
Wed 3/18
Wed 3/25
1 adult, Economy
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Cheap 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 February 16, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/12. 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 4/18:18 pm
JAX
-
MDW
1 stop27h 03m
Frontier
Mon 4/66:00 am
MDW
-
JAX
1 stop12h 33m
Frontier
Deal found 2/12$255
This Kiwi.com deal was found by Cheapflights users on 2/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/146:08 pm
JAX
-
MDW
2 stops14h 56m
Frontier
Mon 5/186:00 am
MDW
-
JAX
1 stop12h 22m
Frontier
Deal found 2/15$256
This Delta deal was found by Cheapflights users on 2/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/175:30 am
JAX
-
MDW
1 stop5h 26m
Delta
Tue 3/2412:47 pm
MDW
-
JAX
1 stop5h 15m
Delta
Deal found 2/15$257
This Southwest deal was found by Cheapflights users on 2/13. 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 3/266:40 am
JAX
-
MDW
Nonstop2h 30m
Southwest
Tue 3/316:00 pm
MDW
-
JAX
Nonstop2h 15m
Southwest
Deal found 2/13$260
This Kiwi.com deal was found by Cheapflights users on 2/16. 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 4/95:28 pm
JAX
-
MDW
2 stops21h 33m
Frontier
Mon 4/136:00 am
MDW
-
JAX
1 stop12h 33m
Frontier
Deal found 2/16$261
This Priceline deal was found by Cheapflights users on 2/16. 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.
Thu 3/124:29 pm
JAX
-
MDW
1 stop6h 50m
Frontier
Sun 3/156:05 am
MDW
-
JAX
1 stop8h 29m
Frontier
Deal found 2/16$264
This Southwest deal was found by Cheapflights users on 2/14. 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 5/104:30 pm
JAX
-
MDW
1 stop7h 45m
Southwest
Sat 5/163:45 pm
MDW
-
JAX
Nonstop2h 15m
Southwest
Deal found 2/14$265
This Kiwi.com deal was found by Cheapflights users on 2/13. 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.
Thu 3/264:29 pm
JAX
-
MDW
1 stop6h 50m
Multiple Airlines
Tue 3/319:30 am
MDW
-
JAX
2 stops33h 03m
Multiple Airlines
Deal found 2/13$266
This Southwest deal was found by Cheapflights users on 2/14. 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 3/196:40 am
JAX
-
MDW
Nonstop2h 30m
Southwest
Tue 3/246:00 pm
MDW
-
JAX
Nonstop2h 15m
Southwest
Deal found 2/14$267
This Kiwi.com deal was found by Cheapflights users on 2/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/278:17 pm
JAX
-
MDW
2 stops17h 43m
Multiple Airlines
Thu 4/306:00 am
MDW
-
JAX
1 stop10h 13m
Multiple Airlines
Deal found 2/15$274

Find 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 February 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$255
(Kiwi.com)

One-way from

$68
(Southwest)

Popular in

March

Cheapest in

August

Average price

$521

Good round-trip deal

$341 or less

Good one-way deal

$208 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. 29% potential increase in price ($158 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease ($35 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 16, 2026.
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 5/30

5:41 pm-9:09 pm

1 stop4h 28m

Chicago Midway

Wed 6/3

6:30 am-1:35 pm

1 stop6h 05m

$257

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Tue 3/17

5:30 am-9:56 am

1 stop5h 26m

Chicago Midway

Tue 3/24

12:47 pm-7:02 pm

1 stop5h 15m

$257

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 4/2

6:40 am-8:10 am

Nonstop2h 30m

Chicago Midway

Tue 4/7

6:00 pm-9:15 pm

Nonstop2h 15m

$260

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 3/19

6:40 am-8:10 am

Nonstop2h 30m

Chicago Midway

Tue 3/24

6:00 pm-9:15 pm

Nonstop2h 15m

$267

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 3/26

6:40 am-8:10 am

Nonstop2h 30m

Chicago Midway

Tue 3/31

9:20 am-6:05 pm

1 stop7h 45m

$270

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 4/22

7:10 pm-10:15 pm

1 stop4h 05m

Chicago Midway

Fri 4/24

6:50 pm-10:05 pm

Nonstop2h 15m

$270

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Mon 3/30

6:40 am-8:10 am

Nonstop2h 30m

Chicago Midway

Wed 4/1

6:00 am-3:00 pm

1 stop8h 00m

$270

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Tue 4/21

7:20 am-8:50 am

Nonstop2h 30m

Chicago Midway

Thu 4/23

12:10 pm-10:45 pm

1 stop9h 35m

$276

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Tue 4/7

7:20 am-8:50 am

Nonstop2h 30m

Chicago Midway

Thu 4/9

6:50 pm-10:05 pm

Nonstop2h 15m

$283

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 6/11

7:15 pm-8:45 pm

Nonstop2h 30m

Chicago Midway

Tue 6/16

6:20 pm-9:40 pm

Nonstop2h 20m

$297

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/15

Showing 1-10 of 21 results
1
2
3

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 February.
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 Jacksonville-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Jacksonville-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 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 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, December is the cheapest month in which you can book a flight from Jacksonville to Chicago Midway Airport (average of $126). Flying from Jacksonville to Chicago Midway Airport in July is currently the most expensive (average of $335). 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 February 16, 2026.

It’s optimal to fly from Jacksonville to Chicago Midway Airport at noon. By choosing this option you can save up to 30% on the cost of your flight, compared to a flight in the morning.

The best insider tips for Jacksonville to Chicago Midway Airport 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 Jacksonville to Chicago Midway Airport 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 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 February 16, 2026.
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
8.0
Very good
4,285 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

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
8.0
Very good
4,285 reviews
Southwest
8.0
Very good
4,285 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

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
8,204 reviews
Southwest
8.0
Very good
4,285 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

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
5.7
Fair
3,047 reviews
Southwest
8.0
Very good
4,285 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

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 0 outbound flights 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 2h 30m. The distance between Jacksonville and Chicago Midway Airport is about 849 mi. This flight may include one or multiple stops.

  • 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 Delta. Our recent data shows that you can find tickets from as low as $129 on this airline. Additional options worth looking into are Frontier and Southwest, starting at $136 and $217 round-trip. Delta is 65% 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 $166. On average you can expect to pay $353. The most popular route, (Jacksonville - Chicago Midway), can usually be booked for $179.

  • 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, December is the cheapest month in which you can book a flight from Jacksonville to Chicago Midway Airport (average of $126). Flying from Jacksonville to Chicago Midway Airport in July is currently the most expensive (average of $335). 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
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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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 February 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$129Average$324FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$136Average$232FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$217Average$370FlexibilityNo cancel feeOn-time63%

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