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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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Find the cheapest flights from Jacksonville to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
8:17 pm - 12:08 pm
JAX
-
ORD
16h 51m1 stop
Frontier Logo
5:40 am - 6:23 pm
ORD
-
JAX
11h 43m1 stop
$204Frontier
Fri, Jan 16 - Fri, Jan 23
Multiple Airlines Logo
9:04 pm - 7:38 pm
JAX
-
ORD
23h 34m2 stops
Multiple Airlines Logo
6:03 am - 4:23 pm
ORD
-
JAX
9h 20m1 stop
$205Multiple Airlines
Thu, Feb 5 - Sat, Feb 7
Multiple Airlines Logo
5:51 pm - 11:26 am
JAX
-
ORD
18h 35m2 stops
Multiple Airlines Logo
6:20 am - 7:22 pm
ORD
-
JAX
12h 02m1 stop
$209Multiple Airlines
Thu, Jan 15 - Mon, Jan 19
Multiple Airlines Logo
9:43 pm - 6:16 pm
JAX
-
ORD
21h 33m2 stops
Multiple Airlines Logo
5:50 am - 4:57 pm
ORD
-
JAX
10h 07m1 stop
$216Multiple Airlines
Thu, Jan 8 - Mon, Jan 12
Frontier Logo
7:23 pm - 11:45 am
JAX
-
MDW
17h 22m1 stop
Frontier Logo
5:01 pm - 8:01 pm
MDW
-
JAX
26h 00m2 stops
$219Frontier
Wed, Jan 21 - Sun, Jan 25
Frontier Logo
8:01 pm - 10:46 am
JAX
-
ORD
15h 45m1 stop
Frontier Logo
11:51 am - 7:01 pm
ORD
-
JAX
6h 10m1 stop
$220Frontier
Sat, Feb 14 - Wed, Feb 18
JetBlue Logo
6:10 am - 2:20 pm
JAX
-
ORD
9h 10m1 stop
JetBlue Logo
9:30 am - 8:18 pm
ORD
-
JAX
9h 48m1 stop
$226JetBlue
Tue, May 5 - Wed, May 13
Multiple Airlines Logo
6:27 pm - 10:39 pm
JAX
-
ORD
5h 12m1 stop
Multiple Airlines Logo
9:40 am - 6:15 pm
ORD
-
JAX
7h 35m1 stop
$229Multiple Airlines
Mon, Jan 12 - Wed, Jan 14
Southwest Logo
5:30 pm - 6:55 pm
JAX
-
MDW
2h 25mnonstop
Southwest Logo
3:15 pm - 11:50 pm
MDW
-
JAX
7h 35m1 stop
$245Southwest
Wed, Feb 25 - Sat, Feb 28
Southwest Logo
5:30 pm - 6:55 pm
JAX
-
MDW
2h 25mnonstop
Southwest Logo
8:10 am - 6:10 pm
MDW
-
JAX
9h 00m1 stop
$249Southwest
Tue, Jan 20 - Tue, Jan 27

Frontier flights from Jacksonville to Chicago

Our best Frontier deals on Jacksonville to Chicago flight tickets
Frontier
Jan 16
JAX8:17 pmJacksonville
16h 51m
1 stop
ORD12:08 pmChicago O'Hare Intl
Jan 23
ORD5:40 amChicago O'Hare Intl
11h 43m
1 stop
JAX6:23 pmJacksonville
$204
Find similar
Frontier
Jan 31
JAX5:28 pmJacksonville
19h 17m
1 stop
MDW11:45 amChicago Midway
Feb 7
MDW9:38 amChicago Midway
33h 23m
2 stops
JAX8:01 pmJacksonville
$219
Find similar
Frontier
Feb 14
JAX8:01 pmJacksonville
15h 45m
1 stop
ORD10:46 amChicago O'Hare Intl
Feb 18
ORD11:51 amChicago O'Hare Intl
6h 10m
1 stop
JAX7:01 pmJacksonville
$220
Find similar

United Airlines flights from Jacksonville to Chicago

Our best United Airlines deals on Jacksonville to Chicago flight tickets
United Airlines
Jan 20
JAX4:23 pmJacksonville
2h 47m
ORD6:10 pmChicago O'Hare Intl
Jan 21
ORD6:06 pmChicago O'Hare Intl
2h 38m
JAX9:44 pmJacksonville
$239
Find similar
United Airlines
Jan 1
JAX7:40 amJacksonville
2h 46m
ORD9:26 amChicago O'Hare Intl
Jan 31
ORD6:06 pmChicago O'Hare Intl
2h 38m
JAX9:44 pmJacksonville
$247
Find similar
United Airlines
Jan 20
JAX2:40 pmJacksonville
2h 46m
ORD4:26 pmChicago O'Hare Intl
Jan 21
ORD1:00 pmChicago O'Hare Intl
6h 10m
1 stop
JAX8:10 pmJacksonville
$249
Find similar

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 December 23, 2025.
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

Fri 1/16

8:17 pm-12:08 pm

1 stop16h 51m

Chicago O'Hare Intl

Fri 1/23

5:40 am-6:23 pm

1 stop11h 43m

$204

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Thu 2/5

9:04 pm-7:38 pm

2 stops23h 34m

Chicago O'Hare Intl

Sat 2/7

6:03 am-4:23 pm

1 stop9h 20m

$205

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Thu 1/15

5:51 pm-11:26 am

2 stops18h 35m

Chicago O'Hare Intl

Mon 1/19

6:20 am-7:22 pm

1 stop12h 02m

$209

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Thu 1/8

9:43 pm-6:16 pm

2 stops21h 33m

Chicago O'Hare Intl

Mon 1/12

5:50 am-4:57 pm

1 stop10h 07m

$216

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 1/21

7:23 pm-11:45 am

1 stop17h 22m

Chicago Midway

Sun 1/25

5:01 pm-8:01 pm

2 stops26h 00m

$219

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Sat 2/14

8:01 pm-10:46 am

1 stop15h 45m

Chicago O'Hare Intl

Wed 2/18

11:51 am-7:01 pm

1 stop6h 10m

$220

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Tue 5/5

6:10 am-2:20 pm

1 stop9h 10m

Chicago O'Hare Intl

Wed 5/13

9:30 am-8:18 pm

1 stop9h 48m

$226

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Mon 1/12

6:27 pm-10:39 pm

1 stop5h 12m

Chicago O'Hare Intl

Wed 1/14

9:40 am-6:15 pm

1 stop7h 35m

$229

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 2/25

5:30 pm-6:55 pm

Nonstop2h 25m

Chicago Midway

Sat 2/28

3:15 pm-11:50 pm

1 stop7h 35m

$245

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Tue 1/20

5:30 pm-6:55 pm

Nonstop2h 25m

Chicago Midway

Tue 1/27

8:10 am-6:10 pm

1 stop9h 00m

$249

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 $289. 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 $691.

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 morning when prices are around $467.

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 $364 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 December 2025, prices for Jacksonville to Chicago flights are approximately 18% more expensive 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

$175

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 $175. The best round-trip flight deal from Jacksonville to Chicago found on momondo in the last 72 hours is $337.
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 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 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
8,014 reviews
Search Delta flights
FrontierPriceFrom $136Free CancellationRating
5.8
3,075 reviews
Search Frontier flights
American AirlinesPriceFrom $179Free CancellationRating
7.2
11,054 reviews
Search American Airlines flights
SouthwestPriceFrom $203Free CancellationRating
8.0
4,253 reviews
Search Southwest flights
United AirlinesPriceFrom $223Free CancellationRating
7.4
9,105 reviews
Search United Airlines flights

  • Southwest Flights From Jacksonville to Chicago

    Southwest flies from Jacksonville to Chicago around 4 times per week, with 4,253 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, 9,105 ratings). United Airlines flies from Jacksonville to Chicago around 18 times per week, with deals starting from $223 round-trip and rising to an average price of around $387.

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
Valparaiso
Schererville
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