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Cheap flights from Jacksonville to Chicago from $104

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Jacksonville to Chicago departing on 9/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Jacksonville to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
3:05 pm - 11:20 pm
JAX
-
MDW
9h 15m
1 stop
Southwest Logo
7:45 am - 2:25 pm
MDW
-
JAX
5h 40m
1 stop
$217Southwest
Wed, Oct 7 - Tue, Oct 13
Frontier Logo
6:46 pm - 10:58 am
JAX
-
MDW
17h 12m
1 stop
Frontier Logo
7:25 am - 5:51 pm
MDW
-
JAX
9h 26m
1 stop
$218Frontier
Fri, Sep 18 - Mon, Sep 21
Southwest Logo
4:45 pm - 9:40 pm
JAX
-
MDW
5h 55m
1 stop
Southwest Logo
7:50 am - 4:55 pm
MDW
-
JAX
8h 05m
2 stops
$222Southwest
Tue, Jul 7 - Tue, Jul 14
Frontier Logo
6:46 pm - 10:58 am
JAX
-
MDW
17h 12m
1 stop
Frontier Logo
7:25 am - 5:51 pm
MDW
-
JAX
9h 26m
1 stop
$224Frontier
Fri, Sep 11 - Sun, Sep 13
Frontier Logo
6:29 pm - 10:03 pm
JAX
-
MDW
4h 34m
1 stop
Frontier Logo
11:06 am - 5:34 pm
MDW
-
JAX
5h 28m
1 stop
$225Frontier
Wed, Aug 5 - Mon, Aug 10
Frontier Logo
6:29 pm - 10:03 pm
JAX
-
MDW
4h 34m
1 stop
Frontier Logo
11:06 am - 5:34 pm
MDW
-
JAX
5h 28m
1 stop
$226Frontier
Fri, Aug 7 - Tue, Aug 11
Southwest Logo
7:55 am - 2:05 pm
JAX
-
MDW
7h 10m
2 stops
Southwest Logo
7:50 am - 4:55 pm
MDW
-
JAX
8h 05m
2 stops
$227Southwest
Wed, Jul 15 - Wed, Jul 22
Frontier Logo
6:29 pm - 11:07 am
JAX
-
MDW
17h 38m
1 stop
Frontier Logo
6:05 am - 5:34 pm
MDW
-
JAX
10h 29m
1 stop
$229Frontier
Fri, Jul 17 - Sun, Jul 19
Frontier Logo
6:29 pm - 11:07 am
JAX
-
MDW
17h 38m
1 stop
Frontier Logo
6:05 am - 5:34 pm
MDW
-
JAX
10h 29m
1 stop
$231Frontier
Mon, Jul 13 - Fri, Jul 17
Frontier Logo
6:29 pm - 10:03 pm
JAX
-
MDW
28h 34m
1 stop
Frontier Logo
6:05 am - 5:34 pm
MDW
-
JAX
10h 29m
1 stop
$232Frontier
Thu, Jul 16 - Sun, Jul 19

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Frontier flights from Jacksonville to Chicago Midway Airport

Our best Frontier deals on Jacksonville to Chicago Midway Airport flight tickets
Frontier
Sep 18
JAX6:46 pmJacksonville
17h 12m
1 stop
MDW10:58 amChicago Midway
Sep 21
MDW7:25 amChicago Midway
9h 26m
1 stop
JAX5:51 pmJacksonville
$218
Frontier
Sep 11
JAX6:46 pmJacksonville
17h 12m
1 stop
MDW10:58 amChicago Midway
Sep 13
MDW7:25 amChicago Midway
9h 26m
1 stop
JAX5:51 pmJacksonville
$224
Frontier
Aug 5
JAX6:29 pmJacksonville
4h 34m
1 stop
MDW10:03 pmChicago Midway
Aug 10
MDW11:06 amChicago Midway
5h 28m
1 stop
JAX5:34 pmJacksonville
$225

Southwest flights from Jacksonville to Chicago Midway Airport

Our best Southwest deals on Jacksonville to Chicago Midway Airport flight tickets
Southwest
Oct 7
JAX3:05 pmJacksonville
9h 15m
1 stop
MDW11:20 pmChicago Midway
Oct 13
MDW7:45 amChicago Midway
5h 40m
1 stop
JAX2:25 pmJacksonville
$217
Southwest
Jul 7
JAX4:45 pmJacksonville
5h 55m
1 stop
MDW9:40 pmChicago Midway
Jul 14
MDW7:50 amChicago Midway
8h 05m
2 stops
JAX4:55 pmJacksonville
$222
Southwest
Jul 15
JAX7:55 amJacksonville
7h 10m
2 stops
MDW2:05 pmChicago Midway
Jul 22
MDW7:50 amChicago Midway
8h 05m
2 stops
JAX4:55 pmJacksonville
$227

momondo Fare Finder

 
Customize your flight search to find flights from Jacksonville to Chicago Midway Airport 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 June 19, 2026.
Use the filters below to find and compare flights from Jacksonville to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 10/7

3:05 pm-11:20 pm

1 stop9h 15m

Chicago Midway

Tue 10/13

7:45 am-2:25 pm

1 stop5h 40m

$217

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 9/18

6:46 pm-10:58 am

1 stop17h 12m

Chicago Midway

Mon 9/21

7:25 am-5:51 pm

1 stop9h 26m

$218

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Tue 7/7

4:45 pm-9:40 pm

1 stop5h 55m

Chicago Midway

Tue 7/14

7:50 am-4:55 pm

2 stops8h 05m

$222

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 9/11

6:46 pm-10:58 am

1 stop17h 12m

Chicago Midway

Sun 9/13

7:25 am-5:51 pm

1 stop9h 26m

$224
Quickest round-trip

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 8/5

6:29 pm-10:03 pm

1 stop4h 34m

Chicago Midway

Mon 8/10

11:06 am-5:34 pm

1 stop5h 28m

$225

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 8/7

6:29 pm-10:03 pm

1 stop4h 34m

Chicago Midway

Tue 8/11

11:06 am-5:34 pm

1 stop5h 28m

$226

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 7/15

7:55 am-2:05 pm

2 stops7h 10m

Chicago Midway

Wed 7/22

7:50 am-4:55 pm

2 stops8h 05m

$227

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 7/17

6:29 pm-11:07 am

1 stop17h 38m

Chicago Midway

Sun 7/19

6:05 am-5:34 pm

1 stop10h 29m

$229

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Mon 7/13

6:29 pm-11:07 am

1 stop17h 38m

Chicago Midway

Fri 7/17

6:05 am-5:34 pm

1 stop10h 29m

$231

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 7/16

6:29 pm-10:03 pm

1 stop28h 34m

Chicago Midway

Sun 7/19

6:05 am-5:34 pm

1 stop10h 29m

$232

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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

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 typical price of a round-trip flight between Jacksonville and Chicago Midway Airport?

What is the cheapest month to fly to Chicago Midway Airport?

The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from Jacksonville, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Jacksonville during the month August is also very affordable. Most momondo users find prices during this month for around $218.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Jacksonville. The lowest ticket price found for a Friday departure recently was $403. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Jacksonville because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $545.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Jacksonville at noon is the least expensive time of day to depart. momondo users have found prices as low as $311 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $459. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Jacksonville to Chicago Midway flight route?

Fly from Jacksonville to Chicago Midway for the best Jacksonville - Chicago Midway flight prices

What cabin class options are available on Jacksonville to Chicago Midway Airport flights?

There is only 1 cabin class available to choose from on Jacksonville to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Jacksonville to Chicago Midway Airport flights?

You could potentially save up to 4% on your flight if you consider stops on a Jacksonville to Chicago Midway Airport flight.

How have Jacksonville to Chicago Midway Airport flight prices changed over time?

As of June 2026, prices for Jacksonville to Chicago Midway Airport flights are approximately 11% more expensive when compared to flights at the same time last year.

When to book flights from Jacksonville to Chicago Midway Airport

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

Cheap Jacksonville to Chicago Midway Airport (JAX to MDW) flight deals and tips

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

Best Price Found

$219

Fastest flight time

2h 20m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Jacksonville in the past 72 hours is $219. The best round-trip flight deal from Jacksonville to Chicago Midway Airport found on momondo in the last 72 hours is $325.
The fastest flight from Jacksonville to Chicago Midway Airport takes 2h 20m
Direct flights go from Jacksonville to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Jacksonville to Chicago Midway Airport

  • How far is Jacksonville to Chicago Midway by plane?

    A flight from Jacksonville to Chicago Midway will travel around 860.2 mi. A reasonable flight in good conditions will take 2h 20m.

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

    Prices for flights from Jacksonville Airport to Chicago Midway Airport were last updated today.

  • How many operators does momondo search for flights from Jacksonville Airport to Chicago Midway Airport?

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Jacksonville Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway 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 Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Jacksonville to Chicago Midway Airport?

  • What is the most popular airline from Jacksonville to Chicago Midway Airport?

Best airlines flying from Jacksonville to Chicago Midway Airport

Compare and see reviews for airlines that fly from Jacksonville to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $129Free CancellationRating
7.8
8,419 reviews
Search Delta flights
FrontierPriceFrom $134Free CancellationRating
5.6
2,878 reviews
Search Frontier flights
SouthwestPriceFrom $197Free CancellationRating
7.9
4,241 reviews
Search Southwest flights

  • Southwest Flights From Jacksonville to Chicago Midway Airport

    Southwest flight deals from Jacksonville to Chicago Midway Airport start from $197 round-trip. Over the 10 Southwest flights for this route in a normal week, average airfare is usually $340 round-trip - but some users have found much cheaper deals with momondo.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Portage
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

Finding the right flight to Chicago from Jacksonville is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

Flights from Jacksonville to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once all potential Jacksonville to Chicago 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 Jacksonville to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Jacksonville are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago Midway Airport trip

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