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$73+ 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — MDW
Jun 12 — Jun 191
Thu 6/12
Thu 6/19
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 June 7, 2025.

Round-trip from

$255
(Booking.com)

One-way from

$73
(Southwest)

Popular in

March

Cheapest in

April

Average price

$397

Good round-trip deal

$357 or less

Good one-way deal

$198 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. 7% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 7, 2025.

This Booking.com deal was found by Cheapflights users on 6/5. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/304:26 pmJAX - MDW
1 stop8h 25mFrontier
Thu 7/36:20 amMDW - JAX
1 stop11h 32mFrontier
Deal found 6/5$255
This Southwest deal was found by Cheapflights users on 6/6. 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 8/66:25 amJAX - MDW
1 stop5h 20mSouthwest
Sun 8/1012:45 pmMDW - JAX
Nonstop2h 15mSouthwest
Deal found 6/6$261
This Delta deal was found by Cheapflights users on 6/4. 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 8/210:42 amJAX - MDW
1 stop5h 55mDelta
Wed 8/66:00 amMDW - JAX
1 stop4h 47mDelta
Deal found 6/4$287
This Mytrip deal was found by Cheapflights users on 6/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/104:18 pmJAX - MDW
2 stops22h 46mAllegiant Air
Sun 7/1311:37 amMDW - JAX
2 stops25h 52mAllegiant Air
Deal found 6/4$324

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 June 7, 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

Mon 6/30

4:26 pm-11:51 pm

1 stop8h 25m

Chicago Midway

Thu 7/3

6:20 am-6:52 pm

1 stop11h 32m

$255

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 8/6

6:25 am-10:45 am

1 stop5h 20m

Chicago Midway

Sun 8/10

12:45 pm-4:00 pm

Nonstop2h 15m

$261

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 8/2

10:42 am-3:37 pm

1 stop5h 55m

Chicago Midway

Wed 8/6

6:00 am-11:47 am

1 stop4h 47m

$287

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 7/10

4:18 pm-2:04 pm

2 stops22h 46m

Chicago Midway

Sun 7/13

11:37 am-2:29 pm

2 stops25h 52m

$324

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 8/13

1:20 pm-2:45 pm

Nonstop2h 25m

$73

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 9/4

5:27 pm-7:00 pm

1 stop26h 33m

$91

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 8/30

5:20 am-9:16 am

1 stop4h 56m

$99

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 10/17

12:02 pm-5:20 pm

1 stop6h 18m

$100

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 9/11

11:18 am-4:43 pm

3 stops30h 25m

$364

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/4

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 May 23, 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 June 7, 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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 7, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Allegiant Air from Jacksonville to Chicago 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
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Crew

8.6

Entertainment

7.6

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Crew

8.6

Entertainment

7.6

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
7,956 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Crew

8.6

Entertainment

7.6

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.
Allegiant Air
7.3
Good
728 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Crew

8.6

Entertainment

7.6

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.
Frontier
6.0
Okay
3,291 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Crew

8.6

Entertainment

7.6

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 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 Frontier. Our recent data shows that you can find tickets from as low as $255 on this airline. Additional options worth looking into are Southwest and Delta, starting at $261 and $287 round-trip. Frontier is 42% 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?

    $73 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Allegiant Air and Delta, with prices starting from $91 and $99, respectively.

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

    The cheapest flight price from Jacksonville to Chicago Midway Airport is $158. On average you can expect to pay $329. The most popular route, (Jacksonville - Chicago Midway), can usually be booked for $175.

  • 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
Hammond
Benton Harbor
Porter
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 June 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$236Average$477FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$267Average$399FlexibilityNo cancel feeOn-time63%

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