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Cheap flights from Jacksonville to Chicago from $64

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 1/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

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Multiple Airlines Logo
8:39 pm - 10:19 pm
JAX
-
MDW
26h 40m2 stops
Multiple Airlines Logo
9:38 am - 4:23 pm
MDW
-
JAX
5h 45m1 stop
$242Multiple Airlines
Wed, Jan 28 - Sat, Jan 31
Southwest Logo
5:30 pm - 6:55 pm
JAX
-
MDW
2h 25mnonstop
Southwest Logo
8:00 am - 11:20 am
MDW
-
JAX
2h 20mnonstop
$243Southwest
Wed, Feb 18 - Sat, Feb 21
Multiple Airlines Logo
10:51 pm - 7:11 pm
JAX
-
ORD
21h 20m2 stops
Multiple Airlines Logo
5:05 am - 6:27 pm
ORD
-
JAX
12h 22m1 stop
$244Multiple Airlines
Thu, Feb 26 - Sat, Feb 28
JetBlue Logo
12:00 pm - 5:43 pm
JAX
-
ORD
6h 43m1 stop
JetBlue Logo
9:40 am - 6:15 pm
ORD
-
JAX
7h 35m1 stop
$245JetBlue
Fri, Jan 23 - Tue, Jan 27
Multiple Airlines Logo
7:18 pm - 8:43 am
JAX
-
MDW
14h 25m1 stop
Multiple Airlines Logo
1:20 pm - 10:41 am
MDW
-
JAX
20h 21m2 stops
$245Multiple Airlines
Fri, Jan 30 - Wed, Feb 4
United Airlines Logo
11:33 am - 1:24 pm
JAX
-
ORD
2h 51mnonstop
United Airlines Logo
7:58 pm - 11:30 pm
ORD
-
JAX
2h 32mnonstop
$247United Airlines
Mon, Mar 2 - Thu, Mar 5
American Airlines Logo
12:05 pm - 2:02 pm
JAX
-
ORD
2h 57mnonstop
American Airlines Logo
7:34 pm - 10:58 pm
ORD
-
JAX
2h 24mnonstop
$249American Airlines
Fri, Mar 20 - Mon, Mar 23
United Airlines Logo
11:33 am - 1:24 pm
JAX
-
ORD
2h 51mnonstop
United Airlines Logo
1:06 pm - 9:21 pm
ORD
-
JAX
7h 15m1 stop
$253United Airlines
Mon, Mar 2 - Thu, Mar 5
Frontier Logo
5:58 pm - 10:52 am
JAX
-
ORD
17h 54m1 stop
Frontier Logo
5:01 am - 5:13 pm
ORD
-
JAX
11h 12m1 stop
$255Frontier
Mon, Mar 16 - Fri, Mar 20
Delta Logo
5:30 am - 9:56 am
JAX
-
MDW
5h 26m1 stop
Delta Logo
5:31 pm - 10:55 pm
MDW
-
JAX
4h 24m1 stop
$258Delta
Thu, Apr 9 - Tue, Apr 14

Sun Country Air flights from Jacksonville to Chicago

Our best Sun Country Air deals on Jacksonville to Chicago flight tickets
Sun Country Air
Apr 2
JAX11:44 amJacksonville
6h 42m
1 stop
ORD5:26 pmChicago O'Hare Intl
Apr 5
ORD8:14 pmChicago O'Hare Intl
13h 45m
1 stop
JAX10:59 amJacksonville
$305
Sun Country Air
Apr 10
JAX11:59 amJacksonville
7h 04m
1 stop
ORD6:03 pmChicago O'Hare Intl
Apr 12
ORD9:13 pmChicago O'Hare Intl
13h 24m
1 stop
JAX11:37 amJacksonville
$306

JetBlue flights from Jacksonville to Chicago

Our best JetBlue deals on Jacksonville to Chicago flight tickets
JetBlue
Jan 23
JAX12:00 pmJacksonville
6h 43m
1 stop
ORD5:43 pmChicago O'Hare Intl
Jan 26
ORD9:40 amChicago O'Hare Intl
7h 35m
1 stop
JAX6:15 pmJacksonville
$245
JetBlue
Mar 3
JAX8:38 pmJacksonville
13h 32m
1 stop
ORD9:10 amChicago O'Hare Intl
Mar 8
ORD12:41 pmChicago O'Hare Intl
6h 45m
1 stop
JAX8:26 pmJacksonville
$248
JetBlue
Feb 4
JAX12:00 pmJacksonville
6h 43m
1 stop
ORD5:43 pmChicago O'Hare Intl
Feb 8
ORD9:15 amChicago O'Hare Intl
7h 55m
1 stop
JAX6:10 pmJacksonville
$251

momondo Fare Finder

 
Customize your flight search to find flights from Jacksonville to Chicago 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 8, 2026.
Use the filters below to find and compare flights from Jacksonville to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 1/28

8:39 pm-10:19 pm

2 stops26h 40m

Chicago Midway

Sat 1/31

9:38 am-4:23 pm

1 stop5h 45m

$242

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 2/18

5:30 pm-6:55 pm

Nonstop2h 25m

Chicago Midway

Sat 2/21

8:00 am-11:20 am

Nonstop2h 20m

$243

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Thu 2/26

10:51 pm-7:11 pm

2 stops21h 20m

Chicago O'Hare Intl

Sat 2/28

5:05 am-6:27 pm

1 stop12h 22m

$244

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Fri 1/23

12:00 pm-5:43 pm

1 stop6h 43m

Chicago O'Hare Intl

Tue 1/27

9:40 am-6:15 pm

1 stop7h 35m

$245

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 1/30

7:18 pm-8:43 am

1 stop14h 25m

Chicago Midway

Wed 2/4

1:20 pm-10:41 am

2 stops20h 21m

$245

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Mon 3/2

11:33 am-1:24 pm

Nonstop2h 51m

Chicago O'Hare Intl

Thu 3/5

7:58 pm-11:30 pm

Nonstop2h 32m

$247

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Fri 3/20

12:05 pm-2:02 pm

Nonstop2h 57m

Chicago O'Hare Intl

Mon 3/23

7:34 pm-10:58 pm

Nonstop2h 24m

$249

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Mon 3/2

11:33 am-1:24 pm

Nonstop2h 51m

Chicago O'Hare Intl

Thu 3/5

1:06 pm-9:21 pm

1 stop7h 15m

$253

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Mon 3/16

5:58 pm-10:52 am

1 stop17h 54m

Chicago O'Hare Intl

Fri 3/20

5:01 am-5:13 pm

1 stop11h 12m

$255

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 4/9

5:30 am-9:56 am

1 stop5h 26m

Chicago Midway

Tue 4/14

5:31 pm-10:55 pm

1 stop4h 24m

$258

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

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?

The month of September is, on average, the cheapest month to fly to Chicago from Jacksonville, with most prices found around $287. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Jacksonville to Chicago during August average around $291.

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

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $409. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Jacksonville to Chicago for around $680.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Jacksonville to Chicago during this time can be as low as $406. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $465.

What is the cheapest Jacksonville to Chicago flight route?

Fly from Jacksonville to Chicago O'Hare Intl for the best Jacksonville - Chicago flight prices

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

You are more likely to see cheaper flights to Chicago from Jacksonville when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $361 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Jacksonville for as low as $281 on momondo.

What cabin class options are available on Jacksonville to Chicago flights?

There are 4 cabin classes available to choose from on Jacksonville to Chicago 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 flights?

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

How have Jacksonville to Chicago flight prices changed over time?

As of January 2026, prices for Jacksonville to Chicago flights are approximately 42% cheaper when compared to flights at the same time last year.

When to book flights from Jacksonville to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Jacksonville to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Jacksonville to Chicago (JAX to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Jacksonville to Chicago

Best Price Found

$192

Fastest flight time

2h 20m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Jacksonville in the past 72 hours is $192. The best round-trip flight deal from Jacksonville to Chicago found on momondo in the last 72 hours is $329.
The fastest flight from Jacksonville to Chicago takes 2h 20m
Direct flights go from Jacksonville to Chicago every day.
There are 3 airports in Chicago. From Jacksonville there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

  • How far is Jacksonville to Chicago by plane?

    The straight-line distance from Jacksonville to Chicago is 863.3 mi. In terms of flight time, this usually takes a little over 2h 20m.

  • When did momondo last update prices for flights from Jacksonville Airport to Chicago?

    Prices for flights from Jacksonville Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Jacksonville Airport to Chicago?

  • How old do you have to be to fly from Jacksonville Airport to Chicago?

    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.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Jacksonville to Chicago?

  • What is the most popular airline from Jacksonville to Chicago?

Best airlines flying from Jacksonville to Chicago

Compare and see reviews for airlines that fly from Jacksonville to Chicago with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $108Free CancellationRating
7.9
8,025 reviews
Search Delta flights
FrontierPriceFrom $136Free CancellationRating
5.7
3,062 reviews
Search Frontier flights
American AirlinesPriceFrom $179Free CancellationRating
7.2
11,095 reviews
Search American Airlines flights
SouthwestPriceFrom $203Free CancellationRating
8.0
4,250 reviews
Search Southwest flights
United AirlinesPriceFrom $222Free CancellationRating
7.4
9,139 reviews
Search United Airlines flights

  • Southwest Flights From Jacksonville to Chicago

    Southwest flies from Jacksonville to Chicago around 5 times per week, with 4,250 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Jacksonville to Chicago in the last 72 hours was $203 (round-trip), much lower than the average airfare cost of $383 for Southwest flights on this route.

  • United Airlines Flights From Jacksonville to Chicago

    Another popular option for Jacksonville to Chicago flights is United Airlines (7.4/10, 9,139 ratings). United Airlines flies from Jacksonville to Chicago around 4 times per week, with deals starting from $222 round-trip and rising to an average price of around $385.

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?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Jacksonville to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Jacksonville to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Jacksonville with this policy.

How can momondo help me find flights from Jacksonville to Chicago?

Once you have performed a search for Jacksonville to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Jacksonville to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Jacksonville to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport