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Cheap flights from Jacksonville to Chicago from $67

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 2/18. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
3:50 pm - 2:26 pm
JAX
-
MDW
23h 36m
2 stops
Multiple Airlines Logo
6:00 am - 6:39 pm
MDW
-
JAX
11h 39m
1 stop
$237Multiple Airlines
Thu, Feb 19 - Mon, Feb 23
Frontier Logo
8:56 pm - 12:05 pm
JAX
-
MDW
16h 09m
2 stops
Frontier Logo
6:20 am - 6:23 pm
MDW
-
JAX
11h 03m
1 stop
$238Frontier
Mon, Feb 2 - Fri, Feb 6
Frontier Logo
8:12 am - 11:42 pm
JAX
-
MDW
16h 30m
1 stop
Frontier Logo
12:33 pm - 7:12 am
MDW
-
JAX
17h 39m
1 stop
$241Frontier
Fri, Apr 10 - Sun, Apr 12
Multiple Airlines Logo
5:51 pm - 2:26 pm
JAX
-
MDW
21h 35m
2 stops
Multiple Airlines Logo
9:04 pm - 6:39 pm
MDW
-
JAX
20h 35m
1 stop
$248Multiple Airlines
Thu, Feb 19 - Sun, Feb 22
Southwest Logo
5:45 pm - 7:15 pm
JAX
-
MDW
2h 30mnonstop
Southwest Logo
8:10 am - 6:10 pm
MDW
-
JAX
9h 00m
1 stop
$249Southwest
Sat, Feb 21 - Tue, Feb 24
Frontier Logo
8:56 pm - 12:05 pm
JAX
-
MDW
16h 09m
2 stops
Frontier Logo
5:01 pm - 6:23 pm
MDW
-
JAX
24h 22m
1 stop
$252Frontier
Mon, Jan 26 - Thu, Jan 29
Frontier Logo
9:04 pm - 11:45 am
JAX
-
MDW
15h 41m
2 stops
Frontier Logo
6:20 am - 6:23 pm
MDW
-
JAX
11h 03m
1 stop
$254Frontier
Thu, Jan 29 - Mon, Feb 2
Southwest Logo
5:00 am - 11:45 am
JAX
-
MDW
7h 45m
1 stop
Southwest Logo
2:40 pm - 7:30 pm
MDW
-
JAX
3h 50m
1 stop
$259Southwest
Sat, Feb 7 - Sat, Feb 7
Frontier Logo
7:56 pm - 10:30 pm
JAX
-
MDW
27h 34m
1 stop
Frontier Logo
9:16 pm - 2:34 pm
MDW
-
JAX
16h 18m
2 stops
$260Frontier
Sat, Feb 28 - Sat, Mar 7
Southwest Logo
5:45 pm - 7:15 pm
JAX
-
MDW
2h 30mnonstop
Southwest Logo
1:35 pm - 4:50 pm
MDW
-
JAX
2h 15mnonstop
$269Southwest
Sat, Feb 21 - Tue, Feb 24

Frontier flights from Jacksonville to Chicago Midway Airport

Our best Frontier deals on Jacksonville to Chicago Midway Airport flight tickets
Frontier
Feb 2
JAX8:56 pmJacksonville
16h 09m
2 stops
MDW12:05 pmChicago Midway
Feb 6
MDW6:20 amChicago Midway
11h 03m
1 stop
JAX6:23 pmJacksonville
$238
Frontier
Apr 10
JAX8:12 amJacksonville
16h 30m
1 stop
MDW11:42 pmChicago Midway
Apr 12
MDW12:33 pmChicago Midway
17h 39m
1 stop
JAX7:12 amJacksonville
$241
Frontier
Jan 26
JAX8:56 pmJacksonville
16h 09m
2 stops
MDW12:05 pmChicago Midway
Jan 29
MDW5:01 pmChicago Midway
24h 22m
1 stop
JAX6:23 pmJacksonville
$252

Southwest flights from Jacksonville to Chicago Midway Airport

Our best Southwest deals on Jacksonville to Chicago Midway Airport flight tickets
Southwest
Feb 21
JAX5:45 pmJacksonville
2h 30m
MDW7:15 pmChicago Midway
Feb 24
MDW8:10 amChicago Midway
9h 00m
1 stop
JAX6:10 pmJacksonville
$249
Southwest
Feb 7
JAX5:00 amJacksonville
7h 45m
1 stop
MDW11:45 amChicago Midway
Feb 7
MDW2:40 pmChicago Midway
3h 50m
1 stop
JAX7:30 pmJacksonville
$259
Southwest
Feb 21
JAX5:45 pmJacksonville
2h 30m
MDW7:15 pmChicago Midway
Feb 24
MDW1:35 pmChicago Midway
2h 15m
JAX4:50 pmJacksonville
$269

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 January 14, 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

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 2/19

3:50 pm-2:26 pm

2 stops23h 36m

Chicago Midway

Mon 2/23

6:00 am-6:39 pm

1 stop11h 39m

$237

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Mon 2/2

8:56 pm-12:05 pm

2 stops16h 09m

Chicago Midway

Fri 2/6

6:20 am-6:23 pm

1 stop11h 03m

$238

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 4/10

8:12 am-11:42 pm

1 stop16h 30m

Chicago Midway

Sun 4/12

12:33 pm-7:12 am

1 stop17h 39m

$241

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 2/19

5:51 pm-2:26 pm

2 stops21h 35m

Chicago Midway

Sun 2/22

9:04 pm-6:39 pm

1 stop20h 35m

$248

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 2/21

5:45 pm-7:15 pm

Nonstop2h 30m

Chicago Midway

Tue 2/24

8:10 am-6:10 pm

1 stop9h 00m

$249

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Mon 1/26

8:56 pm-12:05 pm

2 stops16h 09m

Chicago Midway

Thu 1/29

5:01 pm-6:23 pm

1 stop24h 22m

$252

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 1/29

9:04 pm-11:45 am

2 stops15h 41m

Chicago Midway

Mon 2/2

6:20 am-6:23 pm

1 stop11h 03m

$254

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 2/7

5:00 am-11:45 am

1 stop7h 45m

Chicago Midway

Sat 2/7

2:40 pm-7:30 pm

1 stop3h 50m

$259

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 2/28

7:56 pm-10:30 pm

1 stop27h 34m

Chicago Midway

Sat 3/7

9:16 pm-2:34 pm

2 stops16h 18m

$260

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 2/21

5:45 pm-7:15 pm

Nonstop2h 30m

Chicago Midway

Tue 2/24

1:35 pm-4:50 pm

Nonstop2h 15m

$269

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 $337. 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 $434. 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?

As of January 2026, prices for Jacksonville to Chicago Midway Airport flights are approximately 51% cheaper 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

$258

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 $258. The best round-trip flight deal from Jacksonville to Chicago Midway Airport found on momondo in the last 72 hours is $323.
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

  • 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
FrontierPriceFrom $136Free CancellationRating
5.7
3,056 reviews
Search Frontier flights
SouthwestPriceFrom $203Free CancellationRating
8.0
4,258 reviews
Search Southwest flights
DeltaPriceFrom $216Free CancellationRating
7.9
8,042 reviews
Search Delta flights

  • Southwest Flights From Jacksonville to Chicago Midway Airport

    Southwest flight deals from Jacksonville to Chicago Midway Airport start from $203 round-trip. Over the 4 Southwest flights for this route in a normal week, average airfare is usually $379 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
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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