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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 2/25. 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
7:53 pm - 10:30 am
JAX
-
ORD
15h 37m
1 stop
Multiple Airlines Logo
6:51 pm - 7:17 pm
ORD
-
JAX
23h 26m
2 stops
$225Multiple Airlines
Mon, Feb 16 - Thu, Feb 19
Frontier Logo
8:01 pm - 10:46 am
JAX
-
ORD
15h 45m
1 stop
Frontier Logo
5:05 am - 7:01 pm
ORD
-
JAX
12h 56m
1 stop
$226Frontier
Sat, Feb 14 - Mon, Feb 16
JetBlue Logo
6:15 am - 11:25 am
JAX
-
ORD
6h 10m
1 stop
JetBlue Logo
12:20 pm - 12:43 am
ORD
-
JAX
11h 23m
1 stop
$229JetBlue
Sat, Mar 14 - Wed, Mar 18
Frontier Logo
7:29 pm - 7:07 pm
JAX
-
MDW
24h 38m
1 stop
Frontier Logo
7:30 am - 9:56 pm
MDW
-
JAX
13h 26m
2 stops
$230Frontier
Mon, Mar 2 - Thu, Mar 5
Multiple Airlines Logo
7:53 pm - 9:39 am
JAX
-
ORD
14h 46m
2 stops
Multiple Airlines Logo
5:05 am - 7:17 pm
ORD
-
JAX
13h 12m
1 stop
$231Multiple Airlines
Wed, Feb 18 - Fri, Feb 20
Multiple Airlines Logo
7:53 pm - 9:39 am
JAX
-
ORD
14h 46m
2 stops
Multiple Airlines Logo
5:05 am - 7:17 pm
ORD
-
JAX
13h 12m
1 stop
$232Multiple Airlines
Wed, Feb 18 - Fri, Feb 20
Frontier Logo
5:58 pm - 10:52 am
JAX
-
ORD
17h 54m
1 stop
Frontier Logo
5:01 am - 7:33 pm
ORD
-
JAX
13h 32m
1 stop
$236Frontier
Mon, Mar 23 - Wed, Mar 25
United Airlines Logo
7:45 am - 9:35 am
JAX
-
ORD
2h 50mnonstop
United Airlines Logo
7:10 am - 10:49 am
ORD
-
JAX
2h 39mnonstop
$237United Airlines
Sat, Feb 14 - Tue, Feb 17
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
Sat, Feb 14 - Tue, Feb 17
Southwest Logo
5:30 pm - 6:55 pm
JAX
-
MDW
2h 25mnonstop
Southwest Logo
8:05 am - 3:20 pm
MDW
-
JAX
6h 15m
1 stop
$245Southwest
Wed, Feb 18 - Sat, Feb 21

Frontier flights from Jacksonville to Chicago

Our best Frontier deals on Jacksonville to Chicago flight tickets
Frontier
Feb 14
JAX8:01 pmJacksonville
15h 45m
1 stop
ORD10:46 amChicago O'Hare Intl
Feb 16
ORD5:05 amChicago O'Hare Intl
12h 56m
1 stop
JAX7:01 pmJacksonville
$226
Frontier
Feb 21
JAX8:01 pmJacksonville
15h 45m
1 stop
ORD10:46 amChicago O'Hare Intl
Feb 28
ORD12:06 pmChicago O'Hare Intl
33h 00m
2 stops
JAX10:06 pmJacksonville
$230
Frontier
Feb 11
JAX7:53 pmJacksonville
15h 58m
1 stop
ORD10:51 amChicago O'Hare Intl
Feb 14
ORD5:05 amChicago O'Hare Intl
12h 36m
1 stop
JAX6:41 pmJacksonville
$232

JetBlue flights from Jacksonville to Chicago

Our best JetBlue deals on Jacksonville to Chicago flight tickets
JetBlue
Mar 14
JAX6:15 amJacksonville
6h 10m
1 stop
ORD11:25 amChicago O'Hare Intl
Mar 18
ORD12:20 pmChicago O'Hare Intl
11h 23m
1 stop
JAX12:43 amJacksonville
$229
JetBlue
Feb 5
JAX12:00 pmJacksonville
6h 43m
1 stop
ORD5:43 pmChicago O'Hare Intl
Feb 7
ORD9:40 amChicago O'Hare Intl
7h 30m
1 stop
JAX6:10 pmJacksonville
$245
JetBlue
Jan 30
JAX12:00 pmJacksonville
6h 43m
1 stop
ORD5:43 pmChicago O'Hare Intl
Feb 2
ORD7:44 amChicago O'Hare Intl
9h 31m
1 stop
JAX6:15 pmJacksonville
$270

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 20, 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 - ORD

JAXORD

Jacksonville

Mon 2/16

7:53 pm-10:30 am

1 stop15h 37m

Chicago O'Hare Intl

Thu 2/19

6:51 pm-7:17 pm

2 stops23h 26m

$225

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Sat 2/14

8:01 pm-10:46 am

1 stop15h 45m

Chicago O'Hare Intl

Mon 2/16

5:05 am-7:01 pm

1 stop12h 56m

$226

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Sat 3/14

6:15 am-11:25 am

1 stop6h 10m

Chicago O'Hare Intl

Wed 3/18

12:20 pm-12:43 am

1 stop11h 23m

$229

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Mon 3/2

7:29 pm-7:07 pm

1 stop24h 38m

Chicago Midway

Thu 3/5

7:30 am-9:56 pm

2 stops13h 26m

$230

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Wed 2/18

7:53 pm-9:39 am

2 stops14h 46m

Chicago O'Hare Intl

Fri 2/20

5:05 am-7:17 pm

1 stop13h 12m

$231

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Wed 2/18

7:53 pm-9:39 am

2 stops14h 46m

Chicago O'Hare Intl

Fri 2/20

5:05 am-7:17 pm

1 stop13h 12m

$232

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Mon 3/23

5:58 pm-10:52 am

1 stop17h 54m

Chicago O'Hare Intl

Wed 3/25

5:01 am-7:33 pm

1 stop13h 32m

$236

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Sat 2/14

7:45 am-9:35 am

Nonstop2h 50m

Chicago O'Hare Intl

Tue 2/17

7:10 am-10:49 am

Nonstop2h 39m

$237

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 2/14

5:45 pm-7:15 pm

Nonstop2h 30m

Chicago Midway

Tue 2/17

1:35 pm-4:50 pm

Nonstop2h 15m

$237

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 2/18

5:30 pm-6:55 pm

Nonstop2h 25m

Chicago Midway

Sat 2/21

8:05 am-3:20 pm

1 stop6h 15m

$245

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 typical price of a round-trip flight between Jacksonville and Chicago?

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 $293.

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 Thursday when prices can be found for as low as $410. 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 $678.

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 $467.

What is the cheapest Jacksonville to Chicago flight route?

Fly from Jacksonville to Chicago Midway 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 $359 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 25m

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 $323.
The fastest flight from Jacksonville to Chicago takes 2h 25m
Direct flights go from Jacksonville to Chicago every day.
There are 3 airports in Chicago. From Jacksonville there are direct flights to 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 25m.

  • 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
8,076 reviews
Search Delta flights
FrontierPriceFrom $136Free CancellationRating
5.7
3,056 reviews
Search Frontier flights
American AirlinesPriceFrom $179Free CancellationRating
7.2
11,164 reviews
Search American Airlines flights
SouthwestPriceFrom $203Free CancellationRating
8.0
4,267 reviews
Search Southwest flights
United AirlinesPriceFrom $219Free CancellationRating
7.4
9,180 reviews
Search United Airlines flights

  • Southwest Flights From Jacksonville to Chicago

    Southwest flies from Jacksonville to Chicago around 7 times per week, with 4,267 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 $375 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, 9,180 ratings). United Airlines flies from Jacksonville to Chicago around 13 times per week, with deals starting from $219 round-trip and rising to an average price of around $384.

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