Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

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 2/11. 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
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Jacksonville to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
5:58 pm - 10:19 pm
JAX
-
MDW
5h 21m
1 stop
Frontier Logo
6:05 am - 3:34 pm
MDW
-
JAX
8h 29m
1 stop
$221Frontier
lun., mar. 16 - jue., mar. 19
Frontier Logo
7:47 pm - 1:41 pm
JAX
-
MDW
18h 54m
2 stops
Frontier Logo
6:05 am - 3:33 pm
MDW
-
JAX
8h 28m
1 stop
$231Frontier
vie., mar. 6 - dom., mar. 8
Frontier Logo
7:47 pm - 1:41 pm
JAX
-
MDW
18h 54m
2 stops
Frontier Logo
6:05 am - 7:33 pm
MDW
-
JAX
12h 28m
1 stop
$236Frontier
vie., mar. 6 - lun., mar. 9
Southwest Logo
5:45 pm - 7:15 pm
JAX
-
MDW
2h 30mnonstop
Southwest Logo
1:35 pm - 4:50 pm
MDW
-
JAX
2h 15mnonstop
$237Southwest
sáb., feb. 21 - mar., feb. 24
Frontier Logo
8:18 pm - 10:19 pm
JAX
-
MDW
27h 01m
1 stop
Frontier Logo
6:00 am - 7:33 pm
MDW
-
JAX
12h 33m
1 stop
$241Frontier
mié., mar. 25 - lun., mar. 30
Southwest Logo
5:45 pm - 7:15 pm
JAX
-
MDW
2h 30mnonstop
Southwest Logo
9:50 am - 5:00 pm
MDW
-
JAX
6h 10m
1 stop
$247Southwest
sáb., feb. 21 - mar., feb. 24
Frontier Logo
6:58 pm - 7:07 pm
JAX
-
MDW
25h 09m
1 stop
Frontier Logo
6:48 pm - 9:12 pm
MDW
-
JAX
25h 24m
2 stops
$249Frontier
lun., feb. 9 - vie., feb. 13
Southwest Logo
5:45 pm - 7:15 pm
JAX
-
MDW
2h 30mnonstop
Southwest Logo
1:25 pm - 9:15 pm
MDW
-
JAX
6h 50m
2 stops
$252Southwest
sáb., feb. 21 - mar., feb. 24
Southwest Logo
6:40 am - 8:10 am
JAX
-
MDW
2h 30mnonstop
Southwest Logo
7:00 pm - 10:15 pm
MDW
-
JAX
2h 15mnonstop
$258Southwest
jue., mar. 5 - sáb., mar. 7
Southwest Logo
7:35 am - 1:55 pm
JAX
-
MDW
7h 20m
2 stops
Southwest Logo
2:35 pm - 9:15 pm
MDW
-
JAX
5h 40m
1 stop
$262Southwest
mar., feb. 24 - mar., mar. 3

Delta flights from Jacksonville to Chicago Midway Airport

Our best Delta deals on Jacksonville to Chicago Midway Airport flight tickets
Delta
Apr 23
JAX11:45 amJacksonville
7h 13m
1 stop
MDW5:58 pmChicago Midway
Apr 27
MDW12:53 pmChicago Midway
6h 19m
1 stop
JAX8:12 pmJacksonville
$303
Delta
May 30
JAX5:30 amJacksonville
5h 21m
1 stop
MDW9:51 amChicago Midway
Jun 3
MDW1:05 pmChicago Midway
6h 36m
1 stop
JAX8:41 pmJacksonville
$317
Delta
Apr 24
JAX6:30 amJacksonville
4h 26m
1 stop
MDW9:56 amChicago Midway
Apr 27
MDW12:53 pmChicago Midway
6h 19m
1 stop
JAX8:12 pmJacksonville
$321

Frontier flights from Jacksonville to Chicago Midway Airport

Our best Frontier deals on Jacksonville to Chicago Midway Airport flight tickets
Frontier
Mar 16
JAX5:58 pmJacksonville
5h 21m
1 stop
MDW10:19 pmChicago Midway
Mar 19
MDW6:05 amChicago Midway
8h 29m
1 stop
JAX3:34 pmJacksonville
$221
Frontier
Mar 6
JAX7:47 pmJacksonville
18h 54m
2 stops
MDW1:41 pmChicago Midway
Mar 8
MDW6:05 amChicago Midway
8h 28m
1 stop
JAX3:33 pmJacksonville
$231
Frontier
Mar 6
JAX7:47 pmJacksonville
18h 54m
2 stops
MDW1:41 pmChicago Midway
Mar 9
MDW6:05 amChicago Midway
12h 28m
1 stop
JAX7:33 pmJacksonville
$236

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 enero 27, 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

lun. 3/16

5:58 pm-10:19 pm

1 stop5h 21m

Chicago Midway

jue. 3/19

6:05 am-3:34 pm

1 stop8h 29m

$221

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

vie. 3/6

7:47 pm-1:41 pm

2 stops18h 54m

Chicago Midway

dom. 3/8

6:05 am-3:33 pm

1 stop8h 28m

$231

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

vie. 3/6

7:47 pm-1:41 pm

2 stops18h 54m

Chicago Midway

lun. 3/9

6:05 am-7:33 pm

1 stop12h 28m

$236

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

sáb. 2/21

5:45 pm-7:15 pm

Nonstop2h 30m

Chicago Midway

mar. 2/24

1:35 pm-4:50 pm

Nonstop2h 15m

$237

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

mié. 3/25

8:18 pm-10:19 pm

1 stop27h 01m

Chicago Midway

lun. 3/30

6:00 am-7:33 pm

1 stop12h 33m

$241

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

sáb. 2/21

5:45 pm-7:15 pm

Nonstop2h 30m

Chicago Midway

mar. 2/24

9:50 am-5:00 pm

1 stop6h 10m

$247

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

lun. 2/9

6:58 pm-7:07 pm

1 stop25h 09m

Chicago Midway

vie. 2/13

6:48 pm-9:12 pm

2 stops25h 24m

$249

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

sáb. 2/21

5:45 pm-7:15 pm

Nonstop2h 30m

Chicago Midway

mar. 2/24

1:25 pm-9:15 pm

2 stops6h 50m

$252

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

jue. 3/5

6:40 am-8:10 am

Nonstop2h 30m

Chicago Midway

sáb. 3/7

7:00 pm-10:15 pm

Nonstop2h 15m

$258

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

mar. 2/24

7:35 am-1:55 pm

2 stops7h 20m

Chicago Midway

mar. 3/3

2:35 pm-9:15 pm

1 stop5h 40m

$262

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $340. 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 $440. 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

$218

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 $218. The best round-trip flight deal from Jacksonville to Chicago Midway Airport found on momondo in the last 72 hours is $332.
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
DeltaPriceFrom $129Free CancellationRating
7.9
8,121 reviews
Search Delta flights
FrontierPriceFrom $136Free CancellationRating
5.7
3,056 reviews
Search Frontier flights
SouthwestPriceFrom $203Free CancellationRating
8.0
4,268 reviews
Search Southwest 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 5 Southwest flights for this route in a normal week, average airfare is usually $372 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

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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
jue. 2/26
jue. 3/5
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago