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OAJ - MDW

Find cheap flights from Jacksonville to Chicago Midway Airport from $289

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Jacksonville to Midway departing on 7/18. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Thu 5/23
Thu 5/30

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Jacksonville to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Jacksonville to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 44,632,927 times on KAYAK, and here is why:

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Filter your dealsChoose cabin class, free Wi-Fi and more.

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Cheap flight deals from Jacksonville to Midway (OAJ-MDW)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Jacksonville to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
5:44 am - 9:51 amOAJ-MDW
5h 07m1 stop
1:24 pm - 10:54 pmMDW-OAJ
8h 30m2 stops
$408Delta
Find Deal
Thu, Jun 13 - Mon, Jun 17
5:44 am - 12:43 pmOAJ-MDW
7h 59m2 stops
1:24 pm - 10:54 pmMDW-OAJ
8h 30m2 stops
$413Delta
Find Deal
Thu, Jun 13 - Mon, Jun 17
5:44 am - 9:51 amOAJ-MDW
5h 07m1 stop
3:45 pm - 10:54 pmMDW-OAJ
6h 09m1 stop
$478Delta
Find Deal
Thu, Jun 13 - Mon, Jun 17
5:55 am - 12:40 pmOAJ-MDW
7h 45m2 stops
1:21 pm - 11:32 pmMDW-OAJ
9h 11m2 stops
$503Delta
Find Deal
Wed, May 8 - Fri, May 10
5:55 am - 12:40 pmOAJ-MDW
7h 45m2 stops
3:45 pm - 11:32 pmMDW-OAJ
6h 47m1 stop
$558Delta
Find Deal
Wed, May 8 - Fri, May 10
5:55 am - 11:52 amOAJ-MDW
6h 57m1 stop
6:00 am - 12:27 pmMDW-OAJ
5h 27m1 stop
$628Delta
Find Deal
Wed, May 8 - Fri, May 10

Good to know

Cheapest flight

$289
Flight from Jacksonville to Chicago Midway Airport

When to book flights from Jacksonville to Midway

Are your dates flexible? Find out the best times to travel from Jacksonville to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Jacksonville to Chicago Midway Airport flights

  • What is the cheapest flight from Jacksonville, North Carolina to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Jacksonville, North Carolina to Chicago Midway Airport was $289 for a one-way ticket and $408 for a round-trip.

  • Do I need a passport to fly between Jacksonville and Chicago Midway Airport?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which aircraft models fly most regularly from Jacksonville to Chicago Midway Airport?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Jacksonville to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Jacksonville and Chicago Midway Airport.

  • How does KAYAK find such low prices on flights from Jacksonville to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Jacksonville to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Jacksonville to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Jacksonville is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Jacksonville to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Jacksonville with another airline. Booking your flights between Jacksonville and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Jacksonville to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Jacksonville up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airline flying from Jacksonville to Midway

 
See real verified KAYAK customer reviews for airlines flying from Jacksonville to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Jacksonville to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 11028 reviews
7.5food
7.9comfort
8.6crew
8.2boarding
8.0entertainment
Airline reviews

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

2.0 MediocreMarisol, Apr 2024DFW - ATL
Read more about Delta reviews

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

They did a fine job. Can't wait to use Delta in the future.

There was a loud squeaky sound the whole time we were flying.

Had a broken tray in business class. Crew just shrugged it off.

Seat back monitors and outlets were dead and not working.

Everything was great except for the seat. The backrest would not stay in the upright position.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

Flight delayed about 2 hrs so it made it a VERY late night

Flight was late. Club was full. Experience is exactly what I expected.

Book cheap flights from Jacksonville to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Jacksonville to Chicago found on KAYAK in the last 72 hours.
7/18Thu
1 stopDelta
5h 45mOAJ-MDW
$289
7/18Thu
2 stopsDelta
8h 00mOAJ-MDW
$564

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Last minute flights from Jacksonville to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Jacksonville to Chicago that are departing in the next 10 days.
4/24Wed
multi-stopDelta
4h 10mOAJ-MDW
4/26Fri
multi-stopDelta
5h 36mMDW-OAJ
$703
4/24Wed
multi-stopDelta
7h 00mOAJ-MDW
4/26Fri
multi-stopDelta
8h 58mMDW-OAJ
$708
4/24Wed
multi-stopDelta
7h 50mOAJ-MDW
4/26Fri
multi-stopDelta
8h 58mMDW-OAJ
$790

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Jacksonville - Chicago Midway Airport Flights

Departure:

Jacksonville (OAJ)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Jacksonville

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