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$149+ 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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — MDW
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
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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 December 18, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$282
(Southwest)

One-way from

$149
(Southwest)

Popular in

November

Cheapest in

February

Average price

$524
Provider with most accurate pricing for Jacksonville-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Jacksonville-Chicago Midway flights.
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From Jacksonville to Chicago Midway
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One-way flight from Jacksonville to Chicago Midway
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High demand for flights, 21% potential price rise
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Best time to find cheap flights, 2% potential price drop
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Average for round-trip flights in December 2024
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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 December 18, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 12/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/304:33 pmJAX - MDW
1 stop5h 31mFrontier
Thu 1/27:34 amMDW - JAX
1 stop6h 09mFrontier
Deal found 12/17$333
This Southwest deal was found by Cheapflights users on 12/16. 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.
Tue 12/314:35 pmJAX - MDW
Nonstop2h 30mSouthwest
Wed 1/112:35 pmMDW - JAX
Nonstop2h 15mSouthwest
Deal found 12/16$450
This Delta deal was found by Cheapflights users on 12/17. 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 12/2511:23 amJAX - MDW
1 stop5h 47mDelta
Tue 12/313:32 pmMDW - JAX
1 stop4h 47mDelta
Deal found 12/17$527

Find flights from Jacksonville to Midway within your budget

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 December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 2/28

9:05 pm-12:15 am

1 stop4h 10m

Chicago Midway

Sun 3/2

1:15 pm-4:30 pm

Nonstop2h 15m

$282

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 1/9

12:24 pm-6:14 pm

1 stop6h 50m

Chicago Midway

Sun 1/12

6:00 am-12:54 pm

1 stop5h 54m

$307

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Mon 12/30

4:33 pm-9:04 pm

1 stop5h 31m

Chicago Midway

Thu 1/2

7:34 am-2:43 pm

1 stop6h 09m

$333

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 1/22

4:35 pm-6:15 pm

Nonstop2h 40m

$149

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Mon 12/23

4:33 pm-9:04 pm

1 stop5h 31m

$153

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sun 1/19

12:24 pm-4:17 pm

1 stop4h 53m

$178

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 3/6

10:28 am-7:50 am

2 stops22h 22m

$181

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Compare providers for flights from Jacksonville to Midway

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 Jacksonville to Midway in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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 Jacksonville-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Jacksonville-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Jacksonville-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Jacksonville-Chicago Midway Airport 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 Jacksonville-Chicago Midway Airport 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 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.

Travel insights for flights from Jacksonville to Midway

Get recent, data-driven insights about flights from Jacksonville to Midway including ideal travel times, pricing trends, and more.

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 October is currently the most expensive (average of $232). 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 December 18, 2024.

It’s optimal to fly from Jacksonville to Chicago Midway Airport in the evening. By choosing this option you can save up to 24% on the cost of your flight, compared to a flight in the afternoon.

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 December 18, 2024.
Peruse reviews from past customers who have flown with Delta, Frontier and Southwest 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
8.1
Very good
4,848 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Delta
8.0
Very good
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Frontier
6.1
Okay
3,479 reviews
Southwest
8.1
Very good
4,848 reviews

Food

7.2

Entertainment

7.7

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

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 3 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 $282 on this airline. Additional options worth looking into are Delta and Frontier, starting at $307 and $333 round-trip. Southwest is 31% 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?

    $149 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Frontier and Delta, with prices starting from $153 and $178, respectively.

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

    The cheapest flight price from Jacksonville to Chicago Midway Airport is $151. On average you can expect to pay $318. The most popular route, (Jacksonville - Chicago Midway), can usually be booked for $236.

  • 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 October is currently the most expensive (average of $232). 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.

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Alternative routes for Jacksonville to Midway

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Top 3 airlines flying from Jacksonville to Midway

Discover the top 3 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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$143Average$218FlexibilityNo cancel feeOn-time62%
DeltaCheapest$266Average$449FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$268Average$434FlexibilityNo cancel feeOn-time63%
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