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$124+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JAX
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
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 January 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$316
(Southwest)

One-way from

$144
(Delta)

Popular in

August

Cheapest in

September

Average price

$398

Good round-trip deal

$318 or less
Provider with most accurate pricing for Chicago Midway-Jacksonville flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Jacksonville flights.
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From Chicago Midway to Jacksonville
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One-way flight from Chicago Midway to Jacksonville
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High demand for flights, 3% potential price rise
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in January 2025
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Price to beat on a round-trip 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 January 21, 2025.

This Southwest deal was found by Cheapflights users on 1/21. 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 3/266:00 amMDW - JAX
1 stop10h 30mSouthwest
Mon 3/317:30 pmJAX - MDW
1 stop4h 45mSouthwest
Deal found 1/21$316
This Delta deal was found by Cheapflights users on 1/21. 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 3/259:54 amMDW - JAX
1 stop4h 10mDelta
Tue 4/14:10 pmJAX - MDW
1 stop7h 13mDelta
Deal found 1/21$338
This Mytrip deal was found by Cheapflights users on 1/21. 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 3/66:26 pmMDW - JAX
2 stops24h 57mMultiple Airlines
Sun 3/99:58 amJAX - MDW
2 stops22h 52mMultiple Airlines
Deal found 1/21$487

Find flights from Midway to Jacksonville within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Wed 4/16

5:30 am-2:50 pm

1 stop8h 20m

Jacksonville

Sun 4/20

8:00 am-11:25 am

1 stop4h 25m

$316

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 3/27

9:54 am-3:04 pm

1 stop4h 10m

Jacksonville

Tue 4/1

4:10 pm-10:23 pm

1 stop7h 13m

$338

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 3/6

6:26 pm-8:23 pm

2 stops24h 57m

Jacksonville

Thu 3/13

9:58 am-7:50 am

2 stops22h 52m

$498

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Mon 5/19

12:15 pm-9:36 pm

1 stop8h 21m

$124

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Mon 2/24

9:00 am-12:15 pm

Nonstop2h 15m

$134

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 2/20

10:57 am-6:54 pm

1 stop6h 57m

$144

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Sun 3/9

6:26 pm-6:17 pm

3 stops22h 51m

$182

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Sun 4/6

6:10 pm-8:43 pm

2 stops25h 33m

$196

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice 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.

Travel insights for flights from Midway to Jacksonville

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

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 January 21, 2025.

It’s optimal to fly from Chicago Midway Airport to Jacksonville in the evening. By choosing this option you can save up to 63% on the cost of your flight, compared to a flight at noon.

Rainfall in Jacksonville by month

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

In terms of precipitation, rainfall in Jacksonville ranges from 2.1 - 8.2 inches per month. September is typically the wettest month, when rainfall can reach 8.2 in. November is typically the driest time to visit Jacksonville when rainfall is around 2.1 in.

Temperature in Jacksonville by month

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

If weather is an important factor for your trip to Jacksonville, 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 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 53.6 F).

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 January 21, 2025.
Read reviews from past customers who have flown Delta and Southwest from Chicago to Jacksonville. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

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
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

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
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

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.

Allegiant Air
7.4
Good
801 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

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 is 1 flight from Chicago Midway to Jacksonville per day from 3 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 $316 on this airline. An additional option worth looking into is Delta, starting at $338. These flights start at 17% 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 Delta. According to our data, you can fly for as low as $144. Users have also found prices from $164 and $196 on Southwest and Allegiant Air, 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 $397, our data shows the cheapest flight currently is $315. When looking at the most popular route, (Chicago Midway - Jacksonville), you can expect to pay $309 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Jacksonville Beach
Kingsland
Waycross
Orange Park
Fernandina Beach

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Alternative routes for Midway to Jacksonville

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Midway to Jacksonville

Discover the top 3 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$140Average$182FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$198Average$398FlexibilityNo cancel feeOn-time63%
DeltaCheapest$289Average$365FlexibilityNo cancel feeOn-timeN/A
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