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$83+ 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 10/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JAX
Oct 19 — Oct 261
Sun 10/19
Sun 10/26
1 adult, Economy
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Cheap 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 September 19, 2025.

Round-trip from

$215
(Kiwi.com)

One-way from

$83
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$279

Good round-trip deal

$259 or less

Good one-way deal

$198 or less
From Chicago Midway to Jacksonville
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One-way flight from Chicago Midway to Jacksonville
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Highest demand for flights based on searches. 9% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 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 Chicago Midway to Jacksonville.
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Price to beat on a one-way flight from Chicago Midway to Jacksonville.
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Find 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 September 19, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/16. 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 9/256:20 amMDW - JAX
1 stop4h 23mMultiple Airlines
Sun 9/285:27 pmJAX - MDW
1 stop21h 59mMultiple Airlines
Deal found 9/16$206
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/175:28 pmMDW - JAX
2 stops16h 23mFrontier
Sun 10/196:05 pmJAX - MDW
1 stop6h 41mFrontier
Deal found 9/17$215
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Fri 10/316:20 amMDW - JAX
2 stops14h 33mFrontier
Thu 11/65:13 pmJAX - MDW
1 stop5h 50mFrontier
Deal found 9/16$222
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 11/81:37 pmMDW - JAX
2 stops24h 07mFrontier
Sun 11/165:18 pmJAX - MDW
1 stop5h 45mFrontier
Deal found 9/17$224
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 11/122:06 pmMDW - JAX
2 stops22h 39mMultiple Airlines
Fri 11/143:20 pmJAX - MDW
1 stop4h 19mMultiple Airlines
Deal found 9/18$226
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 10/56:20 amMDW - JAX
1 stop4h 23mFrontier
Fri 10/109:39 pmJAX - MDW
2 stops26h 08mFrontier
Deal found 9/18$227
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 11/136:30 amMDW - JAX
1 stop8h 43mFrontier
Fri 11/1410:38 pmJAX - MDW
2 stops21h 01mFrontier
Deal found 9/18$230
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/235:20 pmMDW - JAX
2 stops26h 24mFrontier
Mon 10/2711:37 amJAX - MDW
1 stop12h 43mFrontier
Deal found 9/16$231
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/316:29 pmMDW - JAX
2 stops26h 24mFrontier
Sun 11/25:08 pmJAX - MDW
1 stop5h 55mFrontier
Deal found 9/17$232
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 11/146:15 amMDW - JAX
1 stop7h 10mFrontier
Sun 11/165:18 pmJAX - MDW
2 stops16h 14mFrontier
Deal found 9/17$234

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 September 19, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Jacksonville that are best for you.

Fly from

Midway

Fly to

Jacksonville

Route

Depart

Return

Price

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 11/11

1:40 pm-4:55 pm

Nonstop2h 15m

Jacksonville

Mon 11/17

5:00 pm-6:25 pm

Nonstop2h 25m

$288

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 11/11

5:34 pm-12:06 am

1 stop5h 32m

Jacksonville

Wed 11/19

5:28 pm-11:32 pm

1 stop7h 04m

$297

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 10/14

5:45 am-11:10 am

1 stop4h 25m

Jacksonville

Tue 10/21

2:50 pm-4:10 pm

Nonstop2h 20m

$297

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Wed 10/29

3:05 pm-6:15 pm

Nonstop2h 10m

Jacksonville

Mon 11/3

5:00 pm-6:25 pm

Nonstop2h 25m

$301

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Wed 10/22

7:35 am-5:35 pm

2 stops9h 00m

Jacksonville

Tue 10/28

8:25 am-2:25 pm

1 stop7h 00m

$302

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Mon 11/24

6:00 am-12:02 pm

1 stop5h 02m

Jacksonville

Tue 12/2

5:10 am-9:54 am

1 stop5h 44m

$307

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Sat 11/15

6:00 am-1:42 pm

1 stop6h 42m

Jacksonville

Wed 11/19

11:49 am-4:39 pm

1 stop5h 50m

$307

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 11/11

9:32 am-5:27 pm

1 stop6h 55m

Jacksonville

Sat 11/15

6:38 pm-11:32 pm

1 stop5h 54m

$307

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 10/14

9:35 am-5:30 pm

1 stop6h 55m

Jacksonville

Sat 10/18

7:10 pm-10:14 pm

1 stop4h 04m

$307

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Mon 11/17

5:34 pm-11:04 pm

1 stop4h 30m

Jacksonville

Tue 11/18

1:07 pm-4:38 pm

1 stop4h 31m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 22 results
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The best insider tips for Chicago Midway Airport to Jacksonville 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 Chicago Midway Airport to Jacksonville trip
Airports
MDW

Order food via the airport’s mobile system directly to your gate to save time and ensure you don't miss boarding.

Read more about MDWby Ramsey Qubein
JAX

Rental car counters are inside baggage claim. Get your rental while waiting for bags to save time.

Read more about JAXby Matt Meltzer
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 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 $278). Flying from Chicago Midway Airport to Jacksonville in March is currently the most expensive (average of $365). 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 September 19, 2025.

It’s optimal to fly from Chicago Midway Airport to Jacksonville in the morning. By choosing this option you can save up to 32% on the cost of your flight, compared to a flight in the evening.

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 September 19, 2025.
See what other customers who have flown with Southwest and Delta 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
8.0
Very good
4,242 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Delta
8.0
Very good
7,964 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

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 are 0 flights from Chicago Midway to Jacksonville per day from 2 different airlines.

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

    A quick flight from Chicago Midway Airport to Jacksonville can take about 2h 15m. Southwest provides one of the quickest options available for as low as $288. There are 849 mi between Chicago Midway Airport and Jacksonville. This flight may include one or multiple stops.

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

    Our cheapest airline available from Chicago Midway Airport to Jacksonville is Delta. Our recent data shows that you can find tickets from as low as $131 on this airline. An additional option worth looking into is Southwest, starting at $203. These flights start at 63% 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 $306, our data shows the cheapest flight currently is $164. When looking at the most popular route, (Chicago Midway - Jacksonville), you can expect to pay $151 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 $278). Flying from Chicago Midway Airport to Jacksonville in March is currently the most expensive (average of $365). 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
Orange Park
Kingsland
Fernandina Beach
Waycross

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Alternative routes for Midway to Jacksonville

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$131Average$346FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$203Average$390FlexibilityNo cancel feeOn-time63%

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