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Cheap flights from Chicago Midway Airport to Jacksonville from $277

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Jacksonville departing on 10/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to Jacksonville

Cheap round-trip flights

Delta Logo
6:00 am - 11:13 amMDW-OAJ
4h 13m1 stop
Delta Logo
4:30 pm - 10:14 pmOAJ-MDW
6h 44m1 stop
$277Delta
Find Deal
Wed, Oct 29 - Wed, Oct 29
Delta Logo
6:00 am - 11:08 amMDW-OAJ
4h 08m1 stop
Delta Logo
5:05 pm - 9:10 pmOAJ-MDW
5h 05m1 stop
$287Delta
Find Deal
Wed, Sep 24 - Sat, Sep 27
Delta Logo
6:00 am - 11:08 amMDW-OAJ
4h 08m1 stop
Delta Logo
5:05 pm - 9:10 pmOAJ-MDW
5h 05m1 stop
$297Delta
Find Deal
Thu, Sep 25 - Sat, Sep 27
Delta Logo
6:00 am - 11:08 amMDW-OAJ
4h 08m1 stop
Delta Logo
11:51 am - 5:35 pmOAJ-MDW
6h 44m1 stop
$358Delta
Find Deal
Tue, Sep 23 - Thu, Sep 25
Delta Logo
4:25 pm - 9:59 pmMDW-OAJ
4h 34m1 stop
Delta Logo
11:51 am - 3:26 pmOAJ-MDW
4h 35m1 stop
$395Delta
Find Deal
Tue, Sep 9 - Sat, Sep 13
Delta Logo
6:00 am - 11:08 amMDW-OAJ
4h 08m1 stop
Delta Logo
5:52 am - 11:48 amOAJ-MDW
6h 56m1 stop
$558Delta
Find Deal
Thu, Sep 11 - Mon, Sep 15
Delta Logo
6:00 am - 11:08 amMDW-OAJ
4h 08m1 stop
Delta Logo
5:52 am - 9:40 amOAJ-MDW
4h 48m1 stop
$629Delta
Find Deal
Fri, Sep 26 - Sun, Sep 28
Delta Logo
6:00 am - 11:08 amMDW-OAJ
4h 08m1 stop
Delta Logo
5:52 am - 12:28 pmOAJ-MDW
7h 36m2 stops
$750Delta
Find Deal
Tue, Sep 23 - Thu, Sep 25
Delta Logo
6:00 am - 11:08 amMDW-OAJ
4h 08m1 stop
Delta Logo
11:51 am - 6:35 pmOAJ-MDW
7h 44m2 stops
$760Delta
Find Deal
Thu, Sep 25 - Sat, Sep 27
Delta Logo
1:08 pm - 9:59 pmMDW-OAJ
7h 51m2 stops
Delta Logo
5:05 pm - 9:10 pmOAJ-MDW
5h 05m1 stop
$820Delta
Find Deal
Tue, Sep 9 - Sat, Sep 13

Delta flights from Chicago Midway Airport to Jacksonville, North Carolina

Our best Delta deals on Chicago Midway Airport to Jacksonville, North Carolina flight tickets
Delta
Oct 29
MDW6:00 amChicago Midway
4h 13m
1 stop
OAJ11:13 amJacksonville Albert J Ellis
Oct 29
OAJ4:30 pmJacksonville Albert J Ellis
6h 44m
1 stop
MDW10:14 pmChicago Midway
$277
Find similar
Delta
Sep 24
MDW6:00 amChicago Midway
4h 08m
1 stop
OAJ11:08 amJacksonville Albert J Ellis
Sep 27
OAJ5:05 pmJacksonville Albert J Ellis
5h 05m
1 stop
MDW9:10 pmChicago Midway
$287
Find similar
Delta
Sep 25
MDW6:00 amChicago Midway
4h 08m
1 stop
OAJ11:08 amJacksonville Albert J Ellis
Sep 27
OAJ5:05 pmJacksonville Albert J Ellis
5h 05m
1 stop
MDW9:10 pmChicago Midway
$297
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Jacksonville, North Carolina 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, momondo users made 832,500 searches. Data last updated August 27, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Jacksonville, North Carolina that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Wed 10/29

6:00 am-11:13 am

1 stop4h 13m

Jacksonville Albert J Ellis

Wed 10/29

4:30 pm-10:14 pm

1 stop6h 44m

$277

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Wed 9/24

6:00 am-11:08 am

1 stop4h 08m

Jacksonville Albert J Ellis

Sat 9/27

5:05 pm-9:10 pm

1 stop5h 05m

$287

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Thu 9/25

6:00 am-11:08 am

1 stop4h 08m

Jacksonville Albert J Ellis

Sat 9/27

5:05 pm-9:10 pm

1 stop5h 05m

$297

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Tue 9/23

6:00 am-11:08 am

1 stop4h 08m

Jacksonville Albert J Ellis

Thu 9/25

11:51 am-5:35 pm

1 stop6h 44m

$358

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Tue 9/9

4:25 pm-9:59 pm

1 stop4h 34m

Jacksonville Albert J Ellis

Sat 9/13

11:51 am-3:26 pm

1 stop4h 35m

$395

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Thu 9/11

6:00 am-11:08 am

1 stop4h 08m

Jacksonville Albert J Ellis

Mon 9/15

5:52 am-11:48 am

1 stop6h 56m

$558

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Fri 9/26

6:00 am-11:08 am

1 stop4h 08m

Jacksonville Albert J Ellis

Sun 9/28

5:52 am-9:40 am

1 stop4h 48m

$629

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Tue 9/23

6:00 am-11:08 am

1 stop4h 08m

Jacksonville Albert J Ellis

Thu 9/25

5:52 am-12:28 pm

2 stops7h 36m

$750

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Thu 9/25

6:00 am-11:08 am

1 stop4h 08m

Jacksonville Albert J Ellis

Sat 9/27

11:51 am-6:35 pm

2 stops7h 44m

$760

ChicagoJacksonville

MDW - OAJ

MDWOAJ

Chicago Midway

Tue 9/9

1:08 pm-9:59 pm

2 stops7h 51m

Jacksonville Albert J Ellis

Sat 9/13

5:05 pm-9:10 pm

1 stop5h 05m

$820

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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How to get the cheapest flight ticket from Chicago Midway Airport to Jacksonville, North Carolina

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Jacksonville, North Carolina?

The cheapest day to depart from Chicago Midway Airport to Jacksonville, North Carolina is on a Tuesday. Travelers who choose to depart for Jacksonville, North Carolina on a Tuesday will often find tickets for as low as $294. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Jacksonville, North Carolina on Sunday is $587.

What is the cheapest time of day to depart on your flight to Jacksonville, North Carolina?

In the afternoon is the cheapest time of day to fly from Chicago Midway Airport to Jacksonville, North Carolina when you can find flight prices for as low as $380. Flying to Jacksonville, North Carolina in the afternoon is an ideal time because this is during off-peak travel hours. In contrast, the most expensive time of day to depart to Jacksonville, North Carolina is at noon when prices are around $686.

When to book flights from Chicago Midway Airport to Jacksonville, North Carolina

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Jacksonville, North Carolina according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Jacksonville, North Carolina (MDW to OAJ) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Jacksonville, North Carolina

Direct flights

None
There are no direct flights from Chicago Midway Airport to Jacksonville, North Carolina. There are no popular flight routes from Chicago Midway Airport to Jacksonville, North Carolina.
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  • How far is Chicago Midway to Jacksonville Albert J Ellis by plane?

    There are 739.6 mi between Chicago Midway and Jacksonville Albert J Ellis. Flights usually cover this in 4h 08m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago Midway Airport to Jacksonville Albert J Ellis Airport?

    Prices for flights from Chicago Midway Airport to Jacksonville Albert J Ellis Airport refresh daily.

  • How old do you have to be to fly from Chicago Midway Airport to Jacksonville Albert J Ellis Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Jacksonville Albert J Ellis Airport.

  • What documentation or ID do you need to fly to Jacksonville Albert J Ellis Airport?

    The travel and health documents required for your trip to Jacksonville Albert J Ellis Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Jacksonville Albert J Ellis Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Jacksonville?

Book flights to Jacksonville if you plan to visit one of these locations
North Topsail Beach

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Jacksonville?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Jacksonville. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Jacksonville with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Jacksonville from Chicago with this policy.

How can momondo help me find flights from Chicago to Jacksonville?

Once all potential Chicago to Jacksonville flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Jacksonville right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Jacksonville, momondo offers a useful price alert feature which will track prices for flights to Jacksonville from Chicago and alert you when they change.

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