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Midway

$71+ 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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — MDW
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Jacksonville to Chicago Midway are usually found in August or September, booked 58 days in advance, depart on a Wednesday or Friday and return on a Thursday

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 September 15, 2025.

Round-trip from

$189
(Cheapflightsfares)

One-way from

$71
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$322

Good round-trip deal

$281 or less

Good one-way deal

$152 or less
From Jacksonville to Chicago Midway
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One-way flight from Jacksonville to Chicago Midway
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Highest demand for flights based on searches. 13% potential increase in price ($66 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($32 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Jacksonville to Chicago Midway.
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Price to beat on a one-way flight from Jacksonville to Chicago Midway.
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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 September 15, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2512:38 pmJAX - MDW
1 stop4h 20mFrontier
Sun 9/286:20 amMDW - JAX
1 stop4h 23mFrontier
Deal found 9/14$189
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 9/2512:38 pmJAX - MDW
1 stop4h 20mFrontier
Mon 9/298:15 amMDW - JAX
1 stop6h 06mFrontier
Deal found 9/15$190
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/239:42 pmJAX - MDW
2 stops19h 27mFrontier
Sun 10/268:25 amMDW - JAX
1 stop11h 39mFrontier
Deal found 9/14$193
This Frontier deal was found by Cheapflights users on 9/13. 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.
Thu 10/3010:38 pmJAX - MDW
2 stops19h 37mFrontier
Sun 11/28:32 amMDW - JAX
1 stop12h 21mFrontier
Deal found 9/13$196
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1811:46 amJAX - MDW
2 stops12h 01mFrontier
Sun 10/196:20 amMDW - JAX
1 stop9h 50mFrontier
Deal found 9/14$197
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 9/2512:38 pmJAX - MDW
1 stop11h 42mMultiple Airlines
Tue 10/78:05 amMDW - JAX
2 stops23h 53mMultiple Airlines
Deal found 9/13$206
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Sun 9/285:27 pmJAX - MDW
1 stop21h 59mMultiple Airlines
Thu 10/28:15 amMDW - JAX
1 stop5h 23mMultiple Airlines
Deal found 9/13$208
This Frontier deal was found by Cheapflights users on 9/13. 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.
Sat 10/1811:46 amJAX - MDW
2 stops12h 01mFrontier
Mon 10/2012:13 pmMDW - JAX
1 stop7h 34mFrontier
Deal found 9/13$212
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/96:03 pmJAX - MDW
1 stop6h 43mMultiple Airlines
Tue 10/148:05 amMDW - JAX
2 stops23h 53mMultiple Airlines
Deal found 9/13$216
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 9/2512:38 pmJAX - MDW
1 stop11h 42mMultiple Airlines
Wed 10/19:00 amMDW - JAX
2 stops24h 38mMultiple Airlines
Deal found 9/13$217
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/236:03 pmJAX - MDW
1 stop6h 43mFrontier
Fri 10/2412:03 pmMDW - JAX
2 stops21h 48mFrontier
Deal found 9/15$219

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 September 15, 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

Fri 11/14

3:50 pm-5:15 pm

Nonstop2h 25m

Chicago Midway

Sun 11/16

11:05 am-2:20 pm

Nonstop2h 15m

$254

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 12/24

11:34 am-2:38 pm

1 stop4h 04m

Chicago Midway

Tue 1/6

6:00 am-12:27 pm

1 stop5h 27m

$297

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 11/19

6:10 am-9:55 am

1 stop4h 45m

Chicago Midway

Sat 11/22

8:40 pm-11:55 pm

Nonstop2h 15m

$297

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 12/24

6:00 am-9:09 am

1 stop4h 09m

Chicago Midway

Wed 12/31

3:30 pm-9:20 pm

1 stop4h 50m

$297

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Mon 12/22

7:35 pm-9:05 pm

Nonstop2h 30m

Chicago Midway

Wed 12/31

12:55 pm-8:15 pm

1 stop6h 20m

$298

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 11/7

3:50 pm-5:15 pm

Nonstop2h 25m

Chicago Midway

Tue 11/11

1:40 pm-4:55 pm

Nonstop2h 15m

$301

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 12/25

11:34 am-2:38 pm

1 stop4h 04m

Chicago Midway

Wed 12/31

3:30 pm-9:20 pm

1 stop4h 50m

$307

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 12/25

11:34 am-2:38 pm

1 stop4h 04m

Chicago Midway

Tue 1/6

5:25 pm-10:45 pm

1 stop4h 20m

$307

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 10/22

7:10 pm-10:14 pm

1 stop4h 04m

Chicago Midway

Sat 10/25

4:23 pm-11:59 pm

1 stop6h 36m

$307

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 10/23

3:55 pm-5:20 pm

Nonstop2h 25m

Chicago Midway

Mon 10/27

11:25 am-7:30 pm

1 stop7h 05m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 22 results
1
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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

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

How far ahead should I book a flight from Jacksonville to Chicago Midway Airport?

Use this chart to determine the optimal time to book a round-trip flight from Jacksonville to Midway. Price data was last updated on September 12, 2025.

Booking 58 days in advance of your planned departure date is, on average, the best time to get cheap flights from Jacksonville to Chicago Midway Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, April is the cheapest month in which you can book a flight from Jacksonville to Chicago Midway Airport (average of $160). Flying from Jacksonville to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 September 15, 2025.

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.

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 September 15, 2025.
Peruse reviews from past customers who have flown with Southwest and Delta 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
4,242 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

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
8.0
Very good
7,954 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

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 25m. 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 Southwest. Our recent data shows that you can find tickets from as low as $207 on this airline. An additional option worth looking into is Delta, starting at $216. Southwest is 50% 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 $75. On average you can expect to pay $324. The most popular route, (Jacksonville - Chicago Midway), can usually be booked for $144.

  • 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, April is the cheapest month in which you can book a flight from Jacksonville to Chicago Midway Airport (average of $160). Flying from Jacksonville to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Jacksonville to Midway

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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$158Average$232FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$207Average$397FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$402FlexibilityNo cancel feeOn-timeN/A

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