HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Jacksonville

$149+ 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 6/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — JAX
May 4 — May 111
Sun 5/4
Sun 5/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Jacksonville with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 April 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$310
(Southwest)

One-way from

$149
(Delta)

Popular in

August

Cheapest in

September

Average price

$311

Good round-trip deal

$337 or less

Good one-way deal

$161 or less
Provider with most accurate pricing for Chicago Midway-Jacksonville flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Jacksonville flights.
Search Deals
From Chicago Midway to Jacksonville
Search Deals
One-way flight from Chicago Midway to Jacksonville
Search Deals
High demand for flights, 2% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Jacksonville.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Jacksonville.
Search Deals

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 April 29, 2025.

This Southwest deal was found by Cheapflights users on 4/27. 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 5/276:20 pmMDW - JAX
Nonstop2h 15mSouthwest
Tue 6/35:50 pmJAX - MDW
1 stop5h 00mSouthwest
Deal found 4/27$310
This Delta deal was found by Cheapflights users on 4/26. 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 5/276:00 amMDW - JAX
1 stop4h 51mDelta
Mon 6/212:56 pmJAX - MDW
1 stop5h 40mDelta
Deal found 4/26$320
This Frontier deal was found by Cheapflights users on 4/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/237:45 amMDW - JAX
1 stop9h 21mFrontier
Mon 5/2611:58 amJAX - MDW
1 stop8h 57mFrontier
Deal found 4/27$350
This Mytrip deal was found by Cheapflights users on 4/27. 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 6/511:45 amMDW - JAX
2 stops25h 27mAllegiant Air
Sun 6/154:23 pmJAX - MDW
2 stops22h 40mAllegiant Air
Deal found 4/27$381
This Mytrip deal was found by Cheapflights users on 4/28. 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.
Fri 6/68:05 amMDW - JAX
3 stops23h 41mMultiple Airlines
Sun 6/84:23 pmJAX - MDW
2 stops22h 40mMultiple Airlines
Deal found 4/28$546

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 April 29, 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

Tue 5/27

6:20 pm-9:35 pm

Nonstop2h 15m

Jacksonville

Tue 6/3

5:50 pm-9:50 pm

1 stop5h 00m

$310

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 5/27

6:00 am-11:51 am

1 stop4h 51m

Jacksonville

Mon 6/2

12:56 pm-5:36 pm

1 stop5h 40m

$320

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Fri 5/23

7:45 am-6:06 pm

1 stop9h 21m

Jacksonville

Mon 5/26

11:58 am-7:55 pm

1 stop8h 57m

$350

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 6/5

11:45 am-2:12 pm

2 stops25h 27m

Jacksonville

Sun 6/15

4:23 pm-2:03 pm

2 stops22h 40m

$381

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Fri 6/6

8:05 am-8:46 am

3 stops23h 41m

Jacksonville

Sun 6/8

4:23 pm-2:03 pm

2 stops22h 40m

$546

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Sat 6/14

6:00 am-1:32 pm

1 stop6h 32m

$149

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 7/15

11:00 am-8:55 pm

2 stops8h 55m

$154

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 6/12

6:20 am-6:52 pm

1 stop11h 32m

$155

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 6/12

11:45 am-2:12 pm

2 stops25h 27m

$167

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Sun 5/4

2:19 pm-11:43 am

2 stops20h 24m

$325

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 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 eDreams the most. eDreams 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.

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 April 29, 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.

Weekly flight availability from Chicago Midway Airport to Jacksonville

Explore weekly flight availability from Midway to Jacksonville. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 29, 2025.

The most flights from MDW to JAX are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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 April 29, 2025.
Read reviews from past customers who have flown Southwest, Delta and Allegiant Air 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
8.0
Very good
4,292 reviews

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

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
4,292 reviews
Southwest
8.0
Very good
4,292 reviews

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

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
7,929 reviews
Southwest
8.0
Very good
4,292 reviews

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

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.
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,292 reviews

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

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
6.0
Okay
3,285 reviews
Southwest
8.0
Very good
4,292 reviews

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

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 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 $310 on this airline. Additional options worth looking into are Delta and Frontier, starting at $320 and $350 round-trip. These flights start at 18% 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 $149. Users have also found prices from $154 and $155 on Southwest 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 $298, our data shows the cheapest flight currently is $143. When looking at the most popular route, (Chicago Midway - Jacksonville), you can expect to pay $297 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
Orange Park
Waycross
Fernandina Beach

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Jacksonville

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Miami flights
O'Hare Intl to Orlando flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Tampa flights
O'Hare Intl to Fort Myers flights
Midway to Orlando flights
Midway to Miami flights
O'Hare Intl to Jacksonville flights
O'Hare Intl to Sarasota flights
O'Hare Intl to West Palm Beach flights
O'Hare Intl to Pensacola flights
O'Hare Intl to Panama City flights
Midway to Tampa flights
Midway to Fort Lauderdale flights
O'Hare Intl to Key West flights
Midway to Fort Myers flights
O'Hare Intl to Valparaiso flights
Midway to West Palm Beach flights
Midway to Pensacola flights
Midway to Panama City flights
Midway to Sarasota flights
Midway to Key West flights
Rockford to Orlando Sanford Intl flights
O'Hare Intl to Daytona Beach flights
Rockford to St Petersburg flights
O'Hare Intl to Gainesville flights
O'Hare Intl to St Petersburg flights
Midway to Daytona Beach flights
Midway to Valparaiso flights
O'Hare Intl to Tallahassee flights
Midway to Gainesville flights
O'Hare Intl to Melbourne flights
Midway to Tallahassee flights
Rockford to Punta Gorda flights
O'Hare Intl to Punta Gorda flights
Midway to Melbourne flights
Midway to Valdosta flights
O'Hare Intl to Valdosta flights
Midway to Orlando Sanford Intl flights
Midway to Punta Gorda flights
O'Hare Intl to Orlando Sanford Intl flights
O'Hare Intl to Destin flights

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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$140Average$200FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$198Average$401FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$375FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.