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Cheap flights from Jacksonville to Chicago from $114

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 11/16. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
3:20 pm - 10:08 pmJAX-MDW
7h 48m1 stop
Frontier Logo
9:15 am - 9:53 pmMDW-JAX
11h 38m1 stop
$221Frontier
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Fri, Nov 14 - Mon, Nov 17
Frontier Logo
6:36 pm - 10:12 pmJAX-MDW
4h 36m1 stop
Frontier Logo
6:37 pm - 2:25 pmMDW-JAX
18h 48m2 stops
$223Frontier
Find Deal
Fri, Dec 12 - Sun, Dec 14
Multiple Airlines Logo
5:48 pm - 7:42 pmJAX-MDW
26h 54m2 stops
Multiple Airlines Logo
7:23 pm - 5:40 pmMDW-JAX
21h 17m1 stop
$228Multiple Airlines
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Thu, Dec 4 - Thu, Dec 11
Frontier Logo
10:38 pm - 7:30 amJAX-MDW
9h 52m1 stop
Frontier Logo
8:32 am - 9:53 pmMDW-JAX
12h 21m1 stop
$231Frontier
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Sat, Nov 15 - Sun, Nov 16
Southwest Logo
5:35 am - 7:00 amJAX-MDW
2h 25mnonstop
Southwest Logo
1:45 pm - 5:00 pmMDW-JAX
2h 15mnonstop
$245Southwest
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Sat, Dec 6 - Mon, Dec 8
Multiple Airlines Logo
10:38 pm - 9:22 pmJAX-MDW
23h 44m2 stops
Multiple Airlines Logo
3:40 pm - 10:04 amMDW-JAX
17h 24m1 stop
$246Multiple Airlines
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Fri, Nov 14 - Fri, Nov 21
Southwest Logo
5:00 pm - 6:25 pmJAX-MDW
2h 25mnonstop
Southwest Logo
5:55 am - 3:05 pmMDW-JAX
8h 10m1 stop
$255Southwest
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Fri, Dec 5 - Sun, Dec 7
Delta Logo
8:20 am - 11:55 amJAX-MDW
4h 35m1 stop
Delta Logo
10:49 am - 5:35 pmMDW-JAX
5h 46m1 stop
$265Delta
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Wed, Dec 3 - Wed, Dec 10
Allegiant Air Logo
9:07 pm - 1:21 pmJAX-MDW
17h 14m1 stop
Allegiant Air Logo
2:11 pm - 1:06 pmMDW-JAX
21h 55m1 stop
$267Allegiant Air
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Thu, Nov 20 - Mon, Nov 24
Delta Logo
1:48 pm - 6:18 pmJAX-MDW
5h 30m1 stop
Delta Logo
6:00 am - 12:52 pmMDW-JAX
5h 52m1 stop
$297Delta
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Mon, Nov 24 - Thu, Nov 27

Frontier flights from Jacksonville to Chicago Midway Airport

Our best Frontier deals on Jacksonville to Chicago Midway Airport flight tickets
Frontier
Nov 14
JAX3:20 pmJacksonville
7h 48m
1 stop
MDW10:08 pmChicago Midway
Nov 17
MDW9:15 amChicago Midway
11h 38m
1 stop
JAX9:53 pmJacksonville
$221
Find similar
Frontier
Dec 12
JAX6:36 pmJacksonville
4h 36m
1 stop
MDW10:12 pmChicago Midway
Dec 14
MDW6:37 pmChicago Midway
18h 48m
2 stops
JAX2:25 pmJacksonville
$223
Find similar
Frontier
Nov 15
JAX10:38 pmJacksonville
9h 52m
1 stop
MDW7:30 amChicago Midway
Nov 16
MDW8:32 amChicago Midway
12h 21m
1 stop
JAX9:53 pmJacksonville
$231
Find similar

Delta flights from Jacksonville to Chicago Midway Airport

Our best Delta deals on Jacksonville to Chicago Midway Airport flight tickets
Delta
Dec 3
JAX8:20 amJacksonville
4h 35m
1 stop
MDW11:55 amChicago Midway
Dec 10
MDW10:49 amChicago Midway
5h 46m
1 stop
JAX5:35 pmJacksonville
$265
Find similar
Delta
Nov 24
JAX1:48 pmJacksonville
5h 30m
1 stop
MDW6:18 pmChicago Midway
Nov 27
MDW6:00 amChicago Midway
5h 52m
1 stop
JAX12:52 pmJacksonville
$297
Find similar
Delta
Nov 24
JAX1:48 pmJacksonville
5h 30m
1 stop
MDW6:18 pmChicago Midway
Dec 2
MDW6:00 amChicago Midway
5h 09m
1 stop
JAX12:09 pmJacksonville
$306
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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 November 4, 2025.
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

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 11/14

3:20 pm-10:08 pm

1 stop7h 48m

Chicago Midway

Mon 11/17

9:15 am-9:53 pm

1 stop11h 38m

$221

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 12/12

6:36 pm-10:12 pm

1 stop4h 36m

Chicago Midway

Sun 12/14

6:37 pm-2:25 pm

2 stops18h 48m

$223

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 12/4

5:48 pm-7:42 pm

2 stops26h 54m

Chicago Midway

Thu 12/11

7:23 pm-5:40 pm

1 stop21h 17m

$228

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 11/15

10:38 pm-7:30 am

1 stop9h 52m

Chicago Midway

Sun 11/16

8:32 am-9:53 pm

1 stop12h 21m

$231

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 12/6

5:35 am-7:00 am

Nonstop2h 25m

Chicago Midway

Mon 12/8

1:45 pm-5:00 pm

Nonstop2h 15m

$245

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 11/14

10:38 pm-9:22 pm

2 stops23h 44m

Chicago Midway

Fri 11/21

3:40 pm-10:04 am

1 stop17h 24m

$246

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 12/5

5:00 pm-6:25 pm

Nonstop2h 25m

Chicago Midway

Sun 12/7

5:55 am-3:05 pm

1 stop8h 10m

$255

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 12/3

8:20 am-11:55 am

1 stop4h 35m

Chicago Midway

Wed 12/10

10:49 am-5:35 pm

1 stop5h 46m

$265

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 11/20

9:07 pm-1:21 pm

1 stop17h 14m

Chicago Midway

Mon 11/24

2:11 pm-1:06 pm

1 stop21h 55m

$267

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Mon 11/24

1:48 pm-6:18 pm

1 stop5h 30m

Chicago Midway

Thu 11/27

6:00 am-12:52 pm

1 stop5h 52m

$297

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 cheapest month to fly to Chicago Midway Airport?

The month of August is, on average, the cheapest month to fly to Chicago Midway Airport from Jacksonville, with most prices found around $218. If you are unable to visit Chicago Midway Airport during the month of August, then departing from Jacksonville during the month September is also very affordable. Most momondo users find prices during this month for around $254.

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

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Jacksonville. The lowest ticket price found for a Wednesday departure recently was $357. 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, Sunday 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 $497.

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 $456. 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 flights?

There is only 1 cabin class available to choose from on Jacksonville to Chicago Midway 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?

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

$148

Fastest flight time

2h 25m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Jacksonville in the past 72 hours is $148. The best round-trip flight deal from Jacksonville to Chicago Midway Airport found on momondo in the last 72 hours is $403.
The fastest flight from Jacksonville to Chicago Midway Airport takes 2h 25m
Direct flights go from Jacksonville to Chicago Midway Airport every day.
Search flight deals

  • 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 25m.

  • 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
FrontierPriceFrom $158Free CancellationRating
5.8
3,116 reviews
Search Frontier flights
SouthwestPriceFrom $207Free CancellationRating
8.0
4,237 reviews
Search Southwest flights
DeltaPriceFrom $216Free CancellationRating
7.9
8,002 reviews
Search Delta flights

  • Southwest Flights From Jacksonville to Chicago Midway Airport

    Southwest flight deals from Jacksonville to Chicago Midway Airport start from $207 round-trip. Over the 6 Southwest flights for this route in a normal week, average airfare is usually $393 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
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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