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$91+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JAX
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$181
(Southwest)

One-way from

$91
(Southwest)

Popular in

March

Cheapest in

September

Average price

$412

Good round-trip deal

$165 or less

Good one-way deal

$133 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. 6% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 31, 2025.

This Southwest deal was found by Cheapflights users on 7/30. 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 9/135:30 pmMDW - JAX
Nonstop2h 15mSouthwest
Sat 9/202:05 pmJAX - MDW
Nonstop2h 25mSouthwest
Deal found 7/30$181
This Cheapflightsfares deal was found by Cheapflights users on 7/31. 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 9/46:20 amMDW - JAX
1 stop4h 23mFrontier
Sun 9/712:38 pmJAX - MDW
1 stop4h 20mFrontier
Deal found 7/31$216
This Delta deal was found by Cheapflights users on 7/29. 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.
Fri 8/229:31 amMDW - JAX
1 stop6h 16mDelta
Tue 8/266:44 pmJAX - MDW
1 stop4h 00mDelta
Deal found 7/29$223

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 July 31, 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

Sat 9/13

5:30 pm-8:45 pm

Nonstop2h 15m

Jacksonville

Sat 9/20

2:05 pm-3:30 pm

Nonstop2h 25m

$181

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 9/4

6:20 am-11:43 am

1 stop4h 23m

Jacksonville

Sun 9/7

12:38 pm-3:58 pm

1 stop4h 20m

$216

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Fri 8/22

9:31 am-4:47 pm

1 stop6h 16m

Jacksonville

Tue 8/26

6:44 pm-9:44 pm

1 stop4h 00m

$223

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Sat 8/30

5:30 pm-8:45 pm

Nonstop2h 15m

$91

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Wed 10/29

6:00 am-1:34 pm

1 stop6h 34m

$101

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Sun 8/24

11:03 am-4:45 pm

1 stop4h 42m

$110

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

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 July 31, 2025.

It’s optimal to fly from Chicago Midway Airport to Jacksonville in the morning. By choosing this option you can save up to 11% on the cost of your flight, compared to a flight in the afternoon.

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 July 31, 2025.
See what other customers who have flown with Southwest, Delta, and Frontier 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
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

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
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

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.
Frontier
5.9
Fair
3,239 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

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.

  • 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 Southwest. Our recent data shows that you can find tickets from as low as $181 on this airline. Additional options worth looking into are Frontier and Delta, starting at $218 and $223 round-trip. These flights start at 51% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Jacksonville one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $91. Users have also found prices from $101 and $109 on Delta and Frontier, respectively.

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

    While on average a flight from Chicago Midway Airport to Jacksonville is generally $201, our data shows the cheapest flight currently is $53. When looking at the most popular route, (Chicago Midway - Jacksonville), you can expect to pay $181 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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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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$131Average$346FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$190Average$397FlexibilityNo cancel feeOn-time63%

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