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Cheap flights from Jacksonville to Chicago from $71

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 10/19. 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

Frontier Logo
10:38 pm - 5:15 pmJAX-MDW
19h 37m2 stops
Frontier Logo
8:32 am - 9:53 pmMDW-JAX
12h 21m1 stop
$196Frontier
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Thu, Oct 30 - Sun, Nov 2
Multiple Airlines Logo
5:27 pm - 2:26 pmJAX-MDW
21h 59m1 stop
Multiple Airlines Logo
8:15 am - 2:38 pmMDW-JAX
5h 23m1 stop
$208Multiple Airlines
Find Deal
Sun, Sep 28 - Thu, Oct 2
Multiple Airlines Logo
5:27 pm - 2:26 pmJAX-MDW
21h 59m1 stop
Multiple Airlines Logo
6:20 am - 11:43 amMDW-JAX
4h 23m1 stop
$215Multiple Airlines
Find Deal
Sun, Sep 28 - Sun, Oct 5
Multiple Airlines Logo
6:03 pm - 11:46 pmJAX-MDW
6h 43m1 stop
Multiple Airlines Logo
8:05 am - 8:58 amMDW-JAX
23h 53m2 stops
$216Multiple Airlines
Find Deal
Thu, Oct 9 - Tue, Oct 14
Frontier Logo
6:03 pm - 11:46 pmJAX-MDW
6h 43m1 stop
Frontier Logo
12:03 pm - 10:51 amMDW-JAX
21h 48m2 stops
$219Frontier
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Thu, Oct 23 - Fri, Oct 24
Multiple Airlines Logo
11:37 am - 11:20 pmJAX-MDW
12h 43m1 stop
Multiple Airlines Logo
8:05 am - 8:58 amMDW-JAX
23h 53m2 stops
$222Multiple Airlines
Find Deal
Fri, Oct 10 - Tue, Oct 14
Southwest Logo
5:00 pm - 6:25 pmJAX-MDW
2h 25mnonstop
Southwest Logo
1:40 pm - 4:55 pmMDW-JAX
2h 15mnonstop
$277Southwest
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Tue, Dec 9 - Wed, Dec 10
Southwest Logo
3:55 pm - 5:20 pmJAX-MDW
2h 25mnonstop
Southwest Logo
3:05 pm - 6:15 pmMDW-JAX
2h 10mnonstop
$288Southwest
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Thu, Oct 23 - Tue, Oct 28
Delta Logo
5:32 pm - 10:14 pmJAX-MDW
5h 42m1 stop
Delta Logo
9:35 am - 5:30 pmMDW-JAX
6h 55m1 stop
$307Delta
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Sat, Oct 11 - Tue, Oct 14
Delta Logo
11:48 am - 5:20 pmJAX-MDW
6h 32m1 stop
Delta Logo
5:25 pm - 10:45 pmMDW-JAX
4h 20m1 stop
$308Delta
Find Deal
Mon, Dec 22 - Tue, Jan 6

Southwest flights from Jacksonville to Chicago Midway Airport

Our best Southwest deals on Jacksonville to Chicago Midway Airport flight tickets
Southwest
Dec 9
JAX5:00 pmJacksonville
2h 25m
MDW6:25 pmChicago Midway
Dec 10
MDW1:40 pmChicago Midway
2h 15m
JAX4:55 pmJacksonville
$277
Find similar
Southwest
Oct 23
JAX3:55 pmJacksonville
2h 25m
MDW5:20 pmChicago Midway
Oct 28
MDW3:05 pmChicago Midway
2h 10m
JAX6:15 pmJacksonville
$288
Find similar
Southwest
Oct 15
JAX2:50 pmJacksonville
2h 20m
MDW4:10 pmChicago Midway
Oct 22
MDW7:35 amChicago Midway
9h 00m
2 stops
JAX5:35 pmJacksonville
$292
Find similar

Delta flights from Jacksonville to Chicago Midway Airport

Our best Delta deals on Jacksonville to Chicago Midway Airport flight tickets
Delta
Oct 11
JAX5:32 pmJacksonville
5h 42m
1 stop
MDW10:14 pmChicago Midway
Oct 14
MDW9:35 amChicago Midway
6h 55m
1 stop
JAX5:30 pmJacksonville
$307
Find similar
Delta
Dec 22
JAX11:48 amJacksonville
6h 32m
1 stop
MDW5:20 pmChicago Midway
Jan 6
MDW5:25 pmChicago Midway
4h 20m
1 stop
JAX10:45 pmJacksonville
$308
Find similar
Delta
Sep 30
JAX6:37 pmJacksonville
3h 59m
1 stop
MDW9:36 pmChicago Midway
Oct 4
MDW11:00 amChicago Midway
4h 03m
1 stop
JAX4:03 pmJacksonville
$479
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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 September 17, 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

Thu 10/30

10:38 pm-5:15 pm

2 stops19h 37m

Chicago Midway

Sun 11/2

8:32 am-9:53 pm

1 stop12h 21m

$196

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sun 9/28

5:27 pm-2:26 pm

1 stop21h 59m

Chicago Midway

Thu 10/2

8:15 am-2:38 pm

1 stop5h 23m

$208

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sun 9/28

5:27 pm-2:26 pm

1 stop21h 59m

Chicago Midway

Sun 10/5

6:20 am-11:43 am

1 stop4h 23m

$215

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 10/9

6:03 pm-11:46 pm

1 stop6h 43m

Chicago Midway

Tue 10/14

8:05 am-8:58 am

2 stops23h 53m

$216

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 10/23

6:03 pm-11:46 pm

1 stop6h 43m

Chicago Midway

Fri 10/24

12:03 pm-10:51 am

2 stops21h 48m

$219

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 10/10

11:37 am-11:20 pm

1 stop12h 43m

Chicago Midway

Tue 10/14

8:05 am-8:58 am

2 stops23h 53m

$222

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Tue 12/9

5:00 pm-6:25 pm

Nonstop2h 25m

Chicago Midway

Wed 12/10

1:40 pm-4:55 pm

Nonstop2h 15m

$277

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 10/23

3:55 pm-5:20 pm

Nonstop2h 25m

Chicago Midway

Tue 10/28

3:05 pm-6:15 pm

Nonstop2h 10m

$288

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 10/11

5:32 pm-10:14 pm

1 stop5h 42m

Chicago Midway

Tue 10/14

9:35 am-5:30 pm

1 stop6h 55m

$307

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Mon 12/22

11:48 am-5:20 pm

1 stop6h 32m

Chicago Midway

Tue 1/6

5:25 pm-10:45 pm

1 stop4h 20m

$308

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 $322.

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 $354. 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 $314 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $458. 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

How far in advance should I book a flight to Chicago Midway Airport?

You are more likely to see cheaper flights to Chicago Midway Airport from Jacksonville when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $416 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Jacksonville for as low as $270 on momondo.

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

$176

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 $176. The best round-trip flight deal from Jacksonville to Chicago Midway Airport found on momondo in the last 72 hours is $282.
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 $158Free CancellationRating
5.8
3,173 reviews
Search Frontier flights
SouthwestPriceFrom $207Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
DeltaPriceFrom $216Free CancellationRating
7.9
7,961 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 5 Southwest flights for this route in a normal week, average airfare is usually $397 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
Lansing
Portage
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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