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Cheap flights from Jacksonville to Chicago from $70

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 8/31. 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.
Frontier Logo
7:46 pm - 11:44 pmJAX  Jacksonville-MDW Chicago Midway
4h 58m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:25 am - 7:01 pmMDW  Chicago Midway-JAX Jacksonville
11h 36m1 stop Atlanta Hartsfield-Jackson
$197Frontier
Thu, Sep 17 - Fri, Sep 18
Southwest Logo
1:30 pm - 2:50 pmJAX  Jacksonville-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
12:50 pm - 4:05 pmMDW  Chicago Midway-JAX Jacksonville
2h 15mnonstop
$197Southwest
Thu, Oct 29 - Mon, Nov 2
Southwest Logo
7:20 am - 8:50 amJAX  Jacksonville-MDW Chicago Midway
2h 30mnonstop
Southwest Logo
7:00 pm - 10:15 pmMDW  Chicago Midway-JAX Jacksonville
2h 15mnonstop
$197Southwest
Thu, Nov 5 - Mon, Nov 9
Southwest Logo
7:00 am - 8:25 amJAX  Jacksonville-MDW Chicago Midway
2h 25mnonstop
Southwest Logo
5:55 pm - 9:20 pmMDW  Chicago Midway-JAX Jacksonville
2h 25mnonstop
$197Southwest
Mon, Sep 28 - Wed, Sep 30
Frontier Logo
7:46 pm - 11:44 pmJAX  Jacksonville-MDW Chicago Midway
4h 58m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:25 am - 7:01 pmMDW  Chicago Midway-JAX Jacksonville
11h 36m1 stop Atlanta Hartsfield-Jackson
$198Frontier
Fri, Sep 18 - Mon, Sep 21
Frontier Logo
7:46 pm - 11:44 pmJAX  Jacksonville-MDW Chicago Midway
4h 58m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:25 am - 7:01 pmMDW  Chicago Midway-JAX Jacksonville
11h 36m1 stop Atlanta Hartsfield-Jackson
$199Frontier
Mon, Sep 28 - Thu, Oct 1
Multiple Airlines Logo
8:45 pm - 3:41 pmJAX  Jacksonville-MDW Chicago Midway
19h 56m1 stop Knoxville McGhee Tyson
Multiple Airlines Logo
7:25 am - 5:51 pmMDW  Chicago Midway-JAX Jacksonville
9h 26m1 stop Atlanta Hartsfield-Jackson
$210Multiple Airlines
Sun, Nov 8 - Thu, Nov 12
Delta Logo
5:10 am - 10:03 amJAX  Jacksonville-MDW Chicago Midway
5h 53m1 stop Atlanta Hartsfield-Jackson
Delta Logo
11:39 am - 4:43 pmMDW  Chicago Midway-JAX Jacksonville
4h 04m1 stop Atlanta Hartsfield-Jackson
$217Delta
Thu, Oct 29 - Tue, Nov 3
Delta Logo
5:30 pm - 10:56 pmJAX  Jacksonville-MDW Chicago Midway
6h 26m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:09 pm - 10:52 pmMDW  Chicago Midway-JAX Jacksonville
4h 43m1 stop Atlanta Hartsfield-Jackson
$217Delta
Sat, Dec 5 - Mon, Dec 7
Multiple Airlines Logo
7:46 pm - 11:44 pmJAX  Jacksonville-MDW Chicago Midway
4h 58m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
6:25 am - 4:26 pmMDW  Chicago Midway-JAX Jacksonville
9h 01m2 stops Atlanta Hartsfield-Jackson Raleigh-Durham
$228Multiple Airlines
Mon, Sep 21 - Tue, Sep 22

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Southwest flights from Jacksonville to Chicago Midway Airport

Our best Southwest deals on Jacksonville to Chicago Midway Airport flight tickets
Southwest
Sep 28
JAX7:00 amJacksonville
2h 25m
MDW8:25 amChicago Midway
Oct 1
MDW3:00 pmChicago Midway
2h 15m
JAX6:15 pmJacksonville
$197
Southwest
Sep 28
JAX2:00 pmJacksonville
6h 20m
1 stop
MDW7:20 pmChicago Midway
Oct 1
MDW3:00 pmChicago Midway
2h 15m
JAX6:15 pmJacksonville
$207
Southwest
Sep 1
JAX6:45 amJacksonville
9h 35m
2 stops
MDW3:20 pmChicago Midway
Sep 5
MDW12:45 pmChicago Midway
2h 15m
JAX4:00 pmJacksonville
$208

Delta flights from Jacksonville to Chicago Midway Airport

Our best Delta deals on Jacksonville to Chicago Midway Airport flight tickets
Delta
Oct 28
JAX6:53 pmJacksonville
4h 40m
1 stop
MDW10:33 pmChicago Midway
Nov 2
MDW4:19 pmChicago Midway
4h 28m
1 stop
JAX9:47 pmJacksonville
$217
Delta
Dec 3
JAX7:15 amJacksonville
5h 50m
1 stop
MDW12:05 pmChicago Midway
Dec 8
MDW11:28 amChicago Midway
3h 57m
1 stop
JAX4:25 pmJacksonville
$241
Delta
Jan 26
JAX6:46 pmJacksonville
4h 24m
1 stop
MDW10:10 pmChicago Midway
Feb 1
MDW9:30 amChicago Midway
7h 08m
1 stop
JAX5:38 pmJacksonville
$248

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 August 17, 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 Jacksonville - MDW Chicago Midway

JAXMDW

Jacksonville

Thu 9/17

7:46 pm-11:44 pm

1 stop4h 58m

Chicago Midway

Fri 9/18

6:25 am-7:01 pm

1 stop11h 36m

$197
Quickest round-trip

JacksonvilleChicago

JAX Jacksonville - MDW Chicago Midway

JAXMDW

Jacksonville

Thu 10/29

1:30 pm-2:50 pm

Nonstop2h 20m

Chicago Midway

Mon 11/2

12:50 pm-4:05 pm

Nonstop2h 15m

$197

JacksonvilleChicago

JAX Jacksonville - MDW Chicago Midway

JAXMDW

Jacksonville

Thu 11/5

7:20 am-8:50 am

Nonstop2h 30m

Chicago Midway

Mon 11/9

7:00 pm-10:15 pm

Nonstop2h 15m

$197

JacksonvilleChicago

JAX Jacksonville - MDW Chicago Midway

JAXMDW

Jacksonville

Mon 9/28

7:00 am-8:25 am

Nonstop2h 25m

Chicago Midway

Wed 9/30

5:55 pm-9:20 pm

Nonstop2h 25m

$197

JacksonvilleChicago

JAX Jacksonville - MDW Chicago Midway

JAXMDW

Jacksonville

Fri 9/18

7:46 pm-11:44 pm

1 stop4h 58m

Chicago Midway

Mon 9/21

6:25 am-7:01 pm

1 stop11h 36m

$198

JacksonvilleChicago

JAX Jacksonville - MDW Chicago Midway

JAXMDW

Jacksonville

Mon 9/28

7:46 pm-11:44 pm

1 stop4h 58m

Chicago Midway

Thu 10/1

6:25 am-7:01 pm

1 stop11h 36m

$199

JacksonvilleChicago

JAX Jacksonville - MDW Chicago Midway

JAXMDW

Jacksonville

Sun 11/8

8:45 pm-3:41 pm

1 stop19h 56m

Chicago Midway

Thu 11/12

7:25 am-5:51 pm

1 stop9h 26m

$210

JacksonvilleChicago

JAX Jacksonville - MDW Chicago Midway

JAXMDW

Jacksonville

Thu 10/29

5:10 am-10:03 am

1 stop5h 53m

Chicago Midway

Tue 11/3

11:39 am-4:43 pm

1 stop4h 04m

$217

JacksonvilleChicago

JAX Jacksonville - MDW Chicago Midway

JAXMDW

Jacksonville

Sat 12/5

5:30 pm-10:56 pm

1 stop6h 26m

Chicago Midway

Mon 12/7

5:09 pm-10:52 pm

1 stop4h 43m

$217

JacksonvilleChicago

JAX Jacksonville - MDW Chicago Midway

JAXMDW

Jacksonville

Mon 9/21

7:46 pm-11:44 pm

1 stop4h 58m

Chicago Midway

Tue 9/22

6:25 am-4:26 pm

2 stops9h 01m

$228

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?

Prices are currently low for flights on this route.

Typical prices usually range from $259 to $361.
The lowest price recently found on this route was $197.

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 January is also very affordable. Most momondo users find prices during this month for around $251.

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

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Jacksonville. The lowest ticket price found for a Saturday departure recently was $378. 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 $526.

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

Flying to Chicago Midway Airport from Jacksonville in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $382 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $453. 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?

No. A direct flight is the cheapest option for a flight between Jacksonville to Chicago Midway Airport.

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

As of August 2026, prices for Jacksonville to Chicago Midway Airport flights are approximately 9% 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

$161

Fastest flight time

2h 20m

Direct flights

Mon, Tue, Thu, Fri, Sat and Sun
The best one-way flight to Chicago Midway Airport from Jacksonville in the past 72 hours is $161. The best round-trip flight deal from Jacksonville to Chicago Midway Airport found on momondo in the last 72 hours is $286.
The fastest flight from Jacksonville to Chicago Midway Airport takes 2h 20m
Direct flights go from Jacksonville to Chicago Midway Airport on Monday, Tuesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
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
8,503 reviews
Search Delta flights
FrontierPriceFrom $134Free CancellationRating
5.6
2,674 reviews
Search Frontier flights
SouthwestPriceFrom $197Free CancellationRating
8.0
4,218 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 4 Southwest flights for this route in a normal week, average airfare is usually $362 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
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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