Illinois

$129+ Cheap flights from Jacksonville (JAX) to Illinois

JAX — ORD
Dec 10 — Dec 171
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Cheap flight deals from Jacksonville to Illinois

Cheapest flights from Jacksonville to Illinois

Sat 11/215:59 pm -
1 stop6h 19m
Tue 11/2411:53 pm -
1 stop17h 26m
Deal found 11/5$280
Fri 12/45:55 pm -
1 stop18h 38m
Mon 12/75:02 pm -
2 stops15h 43m
Deal found 11/10$280
Wed 12/23:39 pm -
1 stop6h 56m
Fri 12/47:59 am -
2 stops29h 21m
Deal found 11/9$281
Fri 12/45:55 pm -
1 stop18h 38m
Sun 12/65:02 pm -
1 stop23h 00m
Deal found 11/10$281
Wed 12/23:39 pm -
1 stop6h 56m
Thu 12/33:55 pm -
2 stops24h 15m
Deal found 11/8$282
Wed 12/23:39 pm -
1 stop25h 28m
Sat 12/1212:28 pm -
2 stops19h 07m
Deal found 11/6$282
Thu 12/312:19 pm -
1 stop9h 10m
Mon 12/78:30 am -
1 stop7h 32m
Deal found 11/6$283
Sat 12/53:39 pm -
1 stop25h 27m
Mon 12/75:02 pm -
2 stops15h 43m
Deal found 11/9$283
Wed 12/23:39 pm -
1 stop6h 56m
Sat 12/124:00 pm -
2 stops15h 35m
Deal found 11/6$284
Fri 12/44:37 pm -
1 stop21h 53m
Mon 12/77:00 am -
1 stop12h 33m
Deal found 11/7$285
Fri 11/133:56 pm -
1 stop24h 41m
Mon 11/167:55 am -
1 stop24h 50m
Deal found 11/6$286
Fri 12/45:55 pm -
1 stop21h 35m
Mon 12/710:29 pm -
2 stops16h 57m
Deal found 11/9$287

Find flight deals from Jacksonville to Illinois

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$281
(Mytrip)

One-way from

$129
(Super.com)

Popular in

May

Cheapest in

September

Average price

$402

Good round-trip deal

$373 or less

Good one-way deal

$218 or less
Provider with most accurate pricing for Jacksonville-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Jacksonville-Chicago (CHI) flights.
From Jacksonville to Illinois
One-way flight from Jacksonville to Illinois
Highest demand for flights based on searches. 7% potential increase in price ($26 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Average for round-trip flights in November 2026
Price to beat on a round-trip flight from Jacksonville to Illinois.
Price to beat on a one-way flight from Jacksonville to Illinois.

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Jacksonville to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

JacksonvilleChicago

JAX Jacksonville - MDW Chicago Midway

JAXMDW

Jacksonville

Fri 1/15

2:51 pm-4:18 pm

2 stops26h 27m

Chicago Midway

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$154

JacksonvilleChicago

JAX Jacksonville - ORD Chicago O'Hare Intl

JAXORD

Jacksonville

Fri 12/25

7:10 am-1:30 pm

1 stop7h 20m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$161

JacksonvilleChicago

JAX Jacksonville - ORD Chicago O'Hare Intl

JAXORD

Jacksonville

Tue 12/22

11:35 am-1:31 pm

Nonstop2h 56m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$179

JacksonvilleChicago

JAX Jacksonville - ORD Chicago O'Hare Intl

JAXORD

Jacksonville

Wed 12/9

12:00 pm-1:56 pm

Nonstop2h 56m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$190

JacksonvilleChicago

JAX Jacksonville - MDW Chicago Midway

JAXMDW

Jacksonville

Wed 12/9

12:00 pm-6:01 pm

1 stop7h 01m

Chicago Midway

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$200
Quickest round-trip

JacksonvilleChicago

JAX Jacksonville - MDW Chicago Midway

JAXMDW

Jacksonville

Mon 12/14

1:30 pm-2:55 pm

Nonstop2h 25m

Chicago Midway

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$205

JacksonvilleChicago

JAX Jacksonville - ORD Chicago O'Hare Intl

JAXORD

Jacksonville

Mon 12/14

9:40 am-11:34 am

Nonstop2h 54m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$205

JacksonvilleChicago

JAX Jacksonville - ORD Chicago O'Hare Intl

JAXORD

Jacksonville

Mon 1/11

7:30 am-9:18 am

Nonstop2h 48m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$205

JacksonvilleChicago

JAX Jacksonville - ORD Chicago O'Hare Intl

JAXORD

Jacksonville

Mon 12/28

7:10 am-1:30 pm

1 stop7h 20m

Chicago O'Hare Intl

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$211

JacksonvilleChicago

JAX Jacksonville - MDW Chicago Midway

JAXMDW

Jacksonville

Fri 1/15

7:00 pm-8:30 pm

Nonstop2h 30m

Chicago Midway

Wed 12/31

12:00 am-1:00 am

Nonstop0h 00m

$211

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

Showing 1-10 of 59 resultsSorted by cheapest first
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Best time to book a flight from Jacksonville to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Jacksonville with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Jacksonville to Illinois

What is the cheapest month to book a flight from Jacksonville to Illinois?

Currently, January is the cheapest month in which you can book a flight from Jacksonville to Illinois (average of $327). Flying from Jacksonville to Illinois in November is currently the most expensive (average of $433). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from JAX to IL?

When flying from Jacksonville to Illinois, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 23% versus a flight at noon.

Weekly flight availability from Jacksonville to Illinois

The most flights from JAX to USIL are scheduled on a Monday (27 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (8 on average).

How much does it cost to fly round-trip from Jacksonville to Illinois?

Airfare is below average for this route at the moment.
Jacksonville to Illinois flights typically cost between $381 and $551 in December.
The cheapest round-trip price found within the last 5 days was $281 on Frontier (Dec 2-Dec 4).

How far ahead should I book a flight from Jacksonville to Illinois?

The price you pay for your flight from Jacksonville to Illinois may vary depending on when you book. For the best chance of a lower fare, look to book 80 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest day to fly from Jacksonville to Illinois?

Travelers seeking maximum savings on their Jacksonville to Illinois flight should consider departing on Thursday mornings when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Illinois

See what other customers who have flown with Southwest,Delta, andUnited Airlines from Jacksonville to Illinois have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Comfort

8.0

Entertainment

7.4

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Comfort

8.0

Entertainment

7.4

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Comfort

8.0

Entertainment

7.4

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Comfort

8.0

Entertainment

7.4

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Comfort

8.0

Entertainment

7.4

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Comfort

8.0

Entertainment

7.4

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

  • What airport do you fly from for flights from Jacksonville to Illinois?

    Most people fly from Jacksonville (JAX) if they book a flight from Jacksonville to Illinois. Jacksonville is conveniently located just 11.2 mi from Jacksonville’s city center.

  • How long is the flight from Jacksonville to Illinois?

    Airlines like JetBlue, Delta, and United Airlines fly from Jacksonville to Illinois in about 5h 18m. The time it takes to get you to your destination can typically vary by up to 3h 20m. The distance from Jacksonville to Illinois is about 902 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Jacksonville to Illinois one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $80. Delta flights start at $83 while deals on Southwest start at $98 one-way.

  • What are the most popular routes from Jacksonville to Illinois?

  • What are the most reliable airlines from Jacksonville to Illinois?

    Before booking your flight to Illinois from Jacksonville, check out the most reliable airlines to get you to your destination on time: Porter Airlines (92%), Qatar Airways (91%), SWISS( 89%).

  • What are the cheapest flights from Jacksonville to Illinois?

    Looking for the cheapest flight from Jacksonville to Illinois? While on average our users pay $905, our data indicates the cheapest price to be $143. The most popular route (Jacksonville - Chicago O'Hare Intl), is priced around $181.

  • Can I find deals for flights from Jacksonville to Illinois that include hotel bookings?

    Yes. In addition to deals on Jacksonville to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Jacksonville to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Jacksonville to Illinois.

  • Can I find deals for business class flights from Jacksonville to Illinois?

    Yes. Cheapflights offers flight deals from Jacksonville to Illinois by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Jacksonville to Illinois?

    Currently, January is the cheapest month in which you can book a flight from Jacksonville to Illinois (average of $327). Flying from Jacksonville to Illinois in November is currently the most expensive (average of $433). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Jacksonville to Illinois

Top 6 airlines flying from Jacksonville to Illinois

AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$122Average$264FlexibilityNo cancel feeOn-time62%
DeltaCheapest$128Average$349FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$197Average$363FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$206Average$303FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$217Average$402FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$224Average$371FlexibilityNo cancel feeOn-time69%

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