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$90+ 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JAX
Apr 16 — Apr 231
Thu 4/16
Thu 4/23
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 March 17, 2026.

This Delta deal was found by Cheapflights users on 3/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:00 am
MDW
-
JAX
1 stop5h 09m
Delta
Sat 4/1811:27 am
JAX
-
MDW
1 stop5h 59m
Delta
Deal found 3/17$275
This Expedia deal was found by Cheapflights users on 3/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:04 pm
MDW
-
JAX
1 stop4h 31m
Frontier
Fri 5/296:30 pm
JAX
-
MDW
1 stop4h 32m
Frontier
Deal found 3/13$276
This Southwest deal was found by Cheapflights users on 3/14. 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.
Sat 4/253:45 pm
MDW
-
JAX
Nonstop2h 15m
Southwest
Sat 5/23:05 pm
JAX
-
MDW
Nonstop2h 30m
Southwest
Deal found 3/14$277
This Southwest deal was found by Cheapflights users on 3/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:50 pm
MDW
-
JAX
Nonstop2h 15m
Southwest
Sat 5/93:05 pm
JAX
-
MDW
Nonstop2h 30m
Southwest
Deal found 3/12$278
This Southwest deal was found by Cheapflights users on 3/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1611:40 am
MDW
-
JAX
1 stop4h 15m
Southwest
Tue 4/218:20 am
JAX
-
MDW
1 stop4h 15m
Southwest
Deal found 3/16$280
This Southwest deal was found by Cheapflights users on 3/14. 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.
Mon 4/206:50 pm
MDW
-
JAX
Nonstop2h 15m
Southwest
Sat 4/253:05 pm
JAX
-
MDW
Nonstop2h 30m
Southwest
Deal found 3/14$282
This Southwest deal was found by Cheapflights users on 3/15. 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 4/144:50 pm
MDW
-
JAX
1 stop3h 40m
Southwest
Tue 4/217:20 am
JAX
-
MDW
Nonstop2h 30m
Southwest
Deal found 3/15$283
This Southwest deal was found by Cheapflights users on 3/14. 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.
Tue 4/74:50 pm
MDW
-
JAX
1 stop3h 40m
Southwest
Tue 4/147:20 am
JAX
-
MDW
Nonstop2h 30m
Southwest
Deal found 3/14$288
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 5/76:00 am
MDW
-
JAX
1 stop10h 35m
Frontier
Fri 5/86:30 pm
JAX
-
MDW
1 stop17h 34m
Frontier
Deal found 3/12$289
This Delta deal was found by Cheapflights users on 3/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/79:35 am
MDW
-
JAX
1 stop6h 31m
Delta
Thu 4/95:30 am
JAX
-
MDW
1 stop5h 26m
Delta
Deal found 3/12$290

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 March 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$276
(Expedia)

One-way from

$90
(Priceline)

Popular in

May

Cheapest in

September

Average price

$379

Good round-trip deal

$317 or less

Good one-way deal

$452 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. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 17, 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 4/14

4:50 pm-9:30 pm

1 stop3h 40m

Jacksonville

Tue 4/21

7:20 am-8:50 am

Nonstop2h 30m

$283

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 4/7

10:45 am-4:28 pm

1 stop4h 43m

Jacksonville

Sat 4/11

5:30 am-9:56 am

1 stop5h 26m

$290

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Sat 4/18

3:45 pm-7:00 pm

Nonstop2h 15m

Jacksonville

Mon 4/20

8:15 pm-11:30 pm

1 stop4h 15m

$292

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Sat 4/11

12:05 pm-6:20 pm

1 stop5h 15m

Jacksonville

Mon 4/20

6:55 am-2:55 pm

2 stops9h 00m

$292

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Mon 4/20

6:50 pm-10:05 pm

Nonstop2h 15m

Jacksonville

Sat 4/25

7:35 am-2:40 pm

2 stops8h 05m

$297

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 5/19

12:50 pm-8:45 pm

2 stops6h 55m

Jacksonville

Sat 5/23

3:05 pm-4:35 pm

Nonstop2h 30m

$302

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Mon 5/4

9:27 am-5:06 pm

1 stop6h 39m

Jacksonville

Thu 5/7

6:05 am-10:00 am

1 stop4h 55m

$327

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Sun 5/24

7:50 pm-11:05 pm

Nonstop2h 15m

Jacksonville

Tue 5/26

8:20 am-2:55 pm

1 stop7h 35m

$331
Quickest round-trip

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 4/16

6:50 pm-10:05 pm

Nonstop2h 15m

Jacksonville

Sat 4/18

3:05 pm-4:35 pm

Nonstop2h 30m

$332

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Sun 5/3

6:50 pm-10:05 pm

Nonstop2h 15m

Jacksonville

Mon 5/11

6:05 am-12:10 pm

1 stop7h 05m

$352

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/12

Showing 1-10 of 22 resultsSorted by cheapest first
1
2
3

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust 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 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Jacksonville (average of $165). Flying from Chicago Midway Airport to Jacksonville in May is currently the most expensive (average of $371). 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 March 17, 2026.

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

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 March 17, 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
8.0
Very good
4,320 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

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
8.0
Very good
4,320 reviews
Southwest
8.0
Very good
4,320 reviews

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

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 are 0 flights 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 3h 40m. Southwest provides one of the quickest options available for as low as $283. 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 41% 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 $392, our data shows the cheapest flight currently is $151. When looking at the most popular route, (Chicago Midway - Jacksonville), you can expect to pay $180 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Jacksonville (average of $165). Flying from Chicago Midway Airport to Jacksonville in May is currently the most expensive (average of $371). 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
Fernandina Beach
Kingsland
Waycross
Yulee

Browse thousands of different options on Cheapflights for your next trip

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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 March 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$203Average$351FlexibilityNo cancel feeOn-time63%

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