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Cheap flights from Jacksonville to Chicago from $68

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 1/29. 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.
Southwest Logo
12:30 pm - 6:40 pm
JAX
-
MDW
7h 10m2 stops
Southwest Logo
12:15 pm - 8:15 pm
MDW
-
JAX
7h 00m1 stop
$243Southwest
Sat, Jan 17 - Tue, Jan 20
JetBlue Logo
12:00 pm - 5:43 pm
JAX
-
ORD
6h 43m1 stop
JetBlue Logo
9:15 am - 6:15 pm
ORD
-
JAX
8h 00m1 stop
$244JetBlue
Sat, Jan 10 - Mon, Jan 12
JetBlue Logo
10:15 am - 7:36 pm
JAX
-
ORD
10h 21m1 stop
JetBlue Logo
9:15 am - 6:15 pm
ORD
-
JAX
8h 00m1 stop
$245JetBlue
Sat, Jan 17 - Sun, Jan 18
Southwest Logo
5:30 pm - 6:55 pm
JAX
-
MDW
2h 25mnonstop
Southwest Logo
9:20 am - 6:10 pm
MDW
-
JAX
7h 50m1 stop
$245Southwest
Wed, Feb 11 - Sat, Feb 14
American Airlines Logo
7:03 am - 8:54 am
JAX
-
ORD
2h 51mnonstop
American Airlines Logo
5:30 pm - 8:58 pm
ORD
-
JAX
2h 28mnonstop
$247American Airlines
Sat, Jan 17 - Sun, Jan 18
United Airlines Logo
1:45 pm - 6:37 pm
JAX
-
ORD
5h 52m1 stop
United Airlines Logo
6:06 pm - 9:44 pm
ORD
-
JAX
2h 38mnonstop
$249United Airlines
Wed, Feb 4 - Sat, Feb 7
Frontier Logo
7:53 pm - 2:26 pm
JAX
-
MDW
19h 33m2 stops
Frontier Logo
6:00 am - 6:41 pm
MDW
-
JAX
11h 41m1 stop
$253Frontier
Wed, Feb 11 - Sat, Feb 14
United Airlines Logo
8:00 am - 9:46 am
JAX
-
ORD
2h 46mnonstop
United Airlines Logo
10:35 am - 2:09 pm
ORD
-
JAX
2h 34mnonstop
$255United Airlines
Sat, Jan 17 - Sun, Jan 18
Delta Logo
1:16 pm - 5:29 pm
JAX
-
MDW
5h 13m1 stop
Delta Logo
6:25 am - 12:41 pm
MDW
-
JAX
5h 16m1 stop
$259Delta
Tue, Feb 3 - Sat, Feb 7
Frontier Logo
10:51 pm - 1:53 pm
JAX
-
MDW
16h 02m2 stops
Frontier Logo
6:00 am - 6:44 pm
MDW
-
JAX
11h 44m1 stop
$267Frontier
Thu, Feb 26 - Mon, Mar 2

JetBlue flights from Jacksonville to Chicago

Our best JetBlue deals on Jacksonville to Chicago flight tickets
JetBlue
Jan 10
JAX12:00 pmJacksonville
6h 43m
1 stop
ORD5:43 pmChicago O'Hare Intl
Jan 12
ORD9:15 amChicago O'Hare Intl
8h 00m
1 stop
JAX6:15 pmJacksonville
$244
Find similar
JetBlue
Jan 17
JAX10:15 amJacksonville
10h 21m
1 stop
ORD7:36 pmChicago O'Hare Intl
Jan 18
ORD9:15 amChicago O'Hare Intl
8h 00m
1 stop
JAX6:15 pmJacksonville
$245
Find similar
JetBlue
Feb 6
JAX12:00 pmJacksonville
6h 43m
1 stop
ORD5:43 pmChicago O'Hare Intl
Feb 9
ORD9:40 amChicago O'Hare Intl
8h 35m
1 stop
JAX7:15 pmJacksonville
$251
Find similar

American Airlines flights from Jacksonville to Chicago

Our best American Airlines deals on Jacksonville to Chicago flight tickets
American Airlines
Jan 17
JAX7:03 amJacksonville
2h 51m
ORD8:54 amChicago O'Hare Intl
Jan 18
ORD5:30 pmChicago O'Hare Intl
2h 28m
JAX8:58 pmJacksonville
$247
Find similar
American Airlines
Feb 4
JAX7:25 amJacksonville
5h 57m
1 stop
ORD12:22 pmChicago O'Hare Intl
Feb 4
ORD4:49 pmChicago O'Hare Intl
6h 10m
1 stop
JAX11:59 pmJacksonville
$259
Find similar
American Airlines
Jan 17
JAX11:53 amJacksonville
4h 47m
1 stop
ORD3:40 pmChicago O'Hare Intl
Jan 18
ORD5:30 pmChicago O'Hare Intl
2h 28m
JAX8:58 pmJacksonville
$266
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 30, 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 - MDW

JAXMDW

Jacksonville

Sat 1/17

12:30 pm-6:40 pm

2 stops7h 10m

Chicago Midway

Tue 1/20

12:15 pm-8:15 pm

1 stop7h 00m

$243

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Sat 1/10

12:00 pm-5:43 pm

1 stop6h 43m

Chicago O'Hare Intl

Mon 1/12

9:15 am-6:15 pm

1 stop8h 00m

$244

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Sat 1/17

10:15 am-7:36 pm

1 stop10h 21m

Chicago O'Hare Intl

Sun 1/18

9:15 am-6:15 pm

1 stop8h 00m

$245

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 2/11

5:30 pm-6:55 pm

Nonstop2h 25m

Chicago Midway

Sat 2/14

9:20 am-6:10 pm

1 stop7h 50m

$245

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Sat 1/17

7:03 am-8:54 am

Nonstop2h 51m

Chicago O'Hare Intl

Sun 1/18

5:30 pm-8:58 pm

Nonstop2h 28m

$247

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Wed 2/4

1:45 pm-6:37 pm

1 stop5h 52m

Chicago O'Hare Intl

Sat 2/7

6:06 pm-9:44 pm

Nonstop2h 38m

$249

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 2/11

7:53 pm-2:26 pm

2 stops19h 33m

Chicago Midway

Sat 2/14

6:00 am-6:41 pm

1 stop11h 41m

$253

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Sat 1/17

8:00 am-9:46 am

Nonstop2h 46m

Chicago O'Hare Intl

Sun 1/18

10:35 am-2:09 pm

Nonstop2h 34m

$255

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Tue 2/3

1:16 pm-5:29 pm

1 stop5h 13m

Chicago Midway

Sat 2/7

6:25 am-12:41 pm

1 stop5h 16m

$259

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 2/26

10:51 pm-1:53 pm

2 stops16h 02m

Chicago Midway

Mon 3/2

6:00 am-6:44 pm

1 stop11h 44m

$267

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 $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 $684.

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 $466.

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 19% 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 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 $175. The best round-trip flight deal from Jacksonville to Chicago found on momondo in the last 72 hours is $330.
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
8,014 reviews
Search Delta flights
FrontierPriceFrom $136Free CancellationRating
5.7
3,065 reviews
Search Frontier flights
American AirlinesPriceFrom $179Free CancellationRating
7.2
11,072 reviews
Search American Airlines flights
SouthwestPriceFrom $203Free CancellationRating
8.0
4,251 reviews
Search Southwest flights
United AirlinesPriceFrom $221Free CancellationRating
7.4
9,121 reviews
Search United Airlines flights

  • Southwest Flights From Jacksonville to Chicago

    Southwest flies from Jacksonville to Chicago around 5 times per week, with 4,251 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, 9,121 ratings). United Airlines flies from Jacksonville to Chicago around 18 times per week, with deals starting from $221 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
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.

An easier way to manage your Chicago trip

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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