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$123+ 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 8/3. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — MDW
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheapflights Tip: The best prices from Jacksonville to Chicago Midway are usually found in April or February, booked 60 days in advance, depart on a Wednesday or Friday and return on a Monday

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 July 3, 2025.

Round-trip from

$196
(Southwest)

One-way from

$123
(Delta)

Popular in

March

Cheapest in

April

Average price

$483

Good round-trip deal

$297 or less

Good one-way deal

$179 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. 8% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($29 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 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 July 3, 2025.

This Southwest deal was found by Cheapflights users on 7/2. 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.
Wed 7/304:20 pmJAX - MDW
Nonstop2h 25mSouthwest
Tue 8/51:00 pmMDW - JAX
2 stops6h 40mSouthwest
Deal found 7/2$196
This Delta deal was found by Cheapflights users on 7/3. 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.
Sat 8/25:36 pmJAX - MDW
1 stop5h 06mDelta
Wed 8/66:00 amMDW - JAX
1 stop6h 29mDelta
Deal found 7/3$201
This Priceline deal was found by Cheapflights users on 7/2. 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.
Fri 10/1712:02 pmJAX - MDW
1 stop6h 18mFrontier
Sun 10/196:15 amMDW - JAX
1 stop8h 43mFrontier
Deal found 7/2$216

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 July 3, 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

Wed 7/30

4:20 pm-5:45 pm

Nonstop2h 25m

Chicago Midway

Tue 8/5

1:00 pm-8:40 pm

2 stops6h 40m

$196

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 8/2

5:36 pm-9:42 pm

1 stop5h 06m

Chicago Midway

Wed 8/6

6:00 am-1:29 pm

1 stop6h 29m

$201

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 8/15

7:05 pm-1:50 pm

1 stop19h 45m

Chicago Midway

Sun 8/17

6:20 am-6:54 pm

1 stop11h 34m

$236

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sun 8/3

5:10 am-9:45 am

1 stop5h 35m

$123

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 9/24

1:20 pm-2:45 pm

Nonstop2h 25m

$124

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Mon 7/7

4:33 pm-11:51 pm

1 stop8h 18m

$134

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 7/17

4:18 pm-8:22 am

2 stops17h 04m

$192

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

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 June 27, 2025.

Booking 60 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 July 3, 2025.

It’s optimal to fly from Jacksonville to Chicago Midway Airport at noon. By choosing this option you can save up to 18% 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 July 3, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Allegiant Air 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
4,266 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

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
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

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
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

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.
Allegiant Air
7.3
Good
708 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

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
5.9
Fair
3,286 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

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 2 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.

  • 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 $196 on this airline. Additional options worth looking into are Delta and Frontier, starting at $201 and $236 round-trip. Southwest is 55% cheaper than the average price of flights available within the next 90 days to this destination.

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

    $123 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on Southwest and Frontier, with prices starting from $124 and $134, respectively.

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

    The cheapest flight price from Jacksonville to Chicago Midway Airport is $169. On average you can expect to pay $344. The most popular route, (Jacksonville - Chicago Midway), can usually be booked for $181.

  • 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 Jacksonville?

Book flights to Jacksonville if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Top 2 airlines flying from Jacksonville to Midway

Discover the top 2 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$517FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$267Average$399FlexibilityNo cancel feeOn-time63%

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