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$90+ Cheap flights from Chicago (CHI) to Jacksonville (JAX)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JAX
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Jacksonville are usually found in August or September, booked 56 days in advance, depart on a Wednesday or Tuesday and return on a Thursday

Cheap flight deals from Chicago to Jacksonville

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Jacksonville (JAX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 11, 2025.

Round-trip from

$203
(United Airlines)

One-way from

$90
(Frontier)

Popular in

March

Cheapest in

August

Average price

$313

Good round-trip deal

$257 or less

Good one-way deal

$148 or less
From Chicago (CHI) to Jacksonville
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One-way flight from Chicago (CHI) to Jacksonville
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Highest demand for flights based on searches. 9% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Jacksonville.
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Price to beat on a one-way flight from Chicago (CHI) to Jacksonville.
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Find flight deals from Chicago to Jacksonville

Cheapest flights from Chicago to Jacksonville
Explore the most affordable flight options available from Chicago to Jacksonville. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Gotogate deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/166:50 pmORD - JAX
1 stop24h 54mFrontier
Sun 10/196:05 pmJAX - ORD
1 stop17h 36mFrontier
Deal found 9/8$195
This Booking.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1711:50 amORD - JAX
1 stop7h 54mFrontier
Sun 10/196:05 pmJAX - ORD
1 stop17h 36mFrontier
Deal found 9/8$196
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/111:45 pmORD - JAX
1 stop6h 30mSouthwest
Sat 11/156:35 amJAX - ORD
1 stop6h 40mSouthwest
Deal found 9/9$197
This Frontier deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/138:26 amORD - JAX
1 stop12h 27mFrontier
Sun 11/165:18 pmJAX - ORD
2 stops15h 08mFrontier
Deal found 9/8$199
This CheapOair deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1312:22 pmORD - JAX
1 stop22h 21mFrontier
Sun 9/2812:38 pmJAX - ORD
1 stop22h 53mFrontier
Deal found 9/9$201
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/411:10 amORD - JAX
Nonstop2h 29mUnited Airlines
Wed 10/84:26 pmJAX - ORD
Nonstop2h 44mUnited Airlines
Deal found 9/11$203
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/287:30 amORD - JAX
2 stops11h 55mSouthwest
Tue 11/46:10 amJAX - ORD
1 stop7h 05mSouthwest
Deal found 9/11$204
This Kiwi.com deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/268:15 amMDW - JAX
1 stop6h 06mMultiple Airlines
Sun 9/285:27 pmJAX - MDW
1 stop21h 59mMultiple Airlines
Deal found 9/11$204
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/47:00 amORD - JAX
Nonstop2h 25mUnited Airlines
Tue 10/76:51 pmJAX - ORD
1 stop5h 24mUnited Airlines
Deal found 9/10$205
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/71:50 pmORD - JAX
1 stop6h 00mSouthwest
Tue 10/216:25 amJAX - ORD
2 stops9h 55mSouthwest
Deal found 9/9$206
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2812:35 pmMDW - JAX
2 stops8h 30mSouthwest
Tue 11/411:50 amJAX - MDW
2 stops6h 45mSouthwest
Deal found 9/9$207
This CheapOair deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/36:10 amORD - JAX
1 stop8h 11mFrontier
Sun 10/512:38 pmJAX - ORD
1 stop22h 53mFrontier
Deal found 9/11$208

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Jacksonville 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, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
Use the filters below to find and compare flights from Chicago to Jacksonville that are best for you.

Fly from

Chicago

Fly to

Jacksonville

Route

Depart

Return

Price

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Tue 11/11

1:45 pm-9:15 pm

1 stop6h 30m

Jacksonville

Sat 11/15

6:35 am-12:15 pm

1 stop6h 40m

$197

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Wed 10/22

8:50 am-2:56 pm

1 stop5h 06m

Jacksonville

Sun 10/26

8:00 am-9:44 am

Nonstop2h 44m

$208

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Wed 11/5

11:05 am-2:38 pm

Nonstop2h 33m

Jacksonville

Sun 11/9

4:32 pm-6:25 pm

Nonstop2h 53m

$219

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Fri 10/3

8:15 am-3:21 pm

1 stop6h 06m

Jacksonville

Sun 10/5

12:38 pm-11:41 pm

1 stop12h 03m

$220

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Thu 10/30

7:05 am-10:33 am

Nonstop2h 28m

Jacksonville

Sun 11/2

8:00 am-9:44 am

Nonstop2h 44m

$222

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Tue 10/7

7:30 am-8:25 pm

2 stops11h 55m

Jacksonville

Tue 10/21

6:25 am-3:20 pm

2 stops9h 55m

$229

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 10/30

7:50 am-4:15 pm

1 stop7h 25m

Jacksonville

Thu 11/6

3:50 pm-5:15 pm

Nonstop2h 25m

$229

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Mon 11/10

11:05 am-2:20 pm

Nonstop2h 15m

Jacksonville

Wed 11/12

6:10 am-2:55 pm

2 stops9h 45m

$234

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Fri 11/14

9:35 am-4:20 pm

1 stop5h 45m

Jacksonville

Tue 11/18

3:55 pm-9:05 pm

1 stop6h 10m

$250

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Fri 10/17

5:20 pm-10:51 am

2 stops16h 31m

Jacksonville

Mon 10/20

11:37 am-11:20 pm

1 stop12h 43m

$252

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 42 results
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The best insider tips for Chicago to Jacksonville flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Jacksonville trip
Airports
ORD

For a quick departure, use the 'L' train to avoid Chicago traffic when heading to ORD.

Read more about ORDby Ramsey Qubein
JAX

At JAX, rental cars are conveniently located inside baggage claim, perfect for quick access after landing.

Read more about JAXby Matt Meltzer
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Matt Meltzer

Matt Meltzer

Expert on JAX

Matt Meltzer

Matt Meltzer

Matt Meltzer has been a travel writer for over a decade, covering U.S. domestic locations and hotels for Thrillist, Fifty Grande, Matador Network, Conde Nast Traveler, and other top publications. He's won multiple travel journalism awards from the Society of American Travel Writers and North American Travel Journalists Association, and currently resides in South Florida.

Read more

Best time to book a flight from Chicago to Jacksonville

Have a flexible travel schedule? Discover the best time to fly to Jacksonville from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Jacksonville. Price data was last updated on August 29, 2025.

The price you pay for your flight from Chicago to Jacksonville may vary depending on when you book. For the best chance of a lower fare, look to book 56 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, August is the cheapest month in which you can book a flight from Chicago to Jacksonville (average of $278). Flying from Chicago to Jacksonville in March is currently the most expensive (average of $365). 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 CHI to JAX?

Find hourly flight availability from Chicago to Jacksonville. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

It’s typically best to fly out from Chicago to Jacksonville at noon. Doing so could potentially save you 20% on the flight price compared to flying in the evening, which is usually more expensive.

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

Use this chart to determine the cheapest time to fly round-trip from Chicago to Jacksonville. Price data was last updated on September 7, 2025.

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

Weekly flight availability from Chicago to Jacksonville

Explore weekly flight availability from Chicago to Jacksonville. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 11, 2025.

The most flights from CHI to JAX are scheduled on a Thursday (22 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (12 on average).

Reviews of airlines servicing Jacksonville

Get insights into the airlines that provide service to Jacksonville. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Jacksonville. Reviews last updated September 11, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Chicago to Jacksonville. 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.
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Delta
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Frontier
5.8
Fair
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Jacksonville. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    Jacksonville (JAX) is the airport you will fly into if you book a flight from Chicago to Jacksonville. You should not have trouble finding flights to Jacksonville from Chicago; the airport handles an average of 16 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 6 airlines have flights to the Jacksonville airport from Chicago. It is only a 11.2 mi journey from Jacksonville (JAX) to Jacksonville’s city center.

  • How long is the flight from Chicago to Jacksonville?

    Southwest, United Airlines, and Frontier can get you from Chicago to Jacksonville in just under 5h 06m. Your travel time can differ by up to 1h 24m. The distance from Chicago to Jacksonville is about 865 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 flying from Chicago to Jacksonville round-trip?

    Currently priced at $112, Frontier will fly you from Chicago to Jacksonville and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Delta and American Airlines - these airlines can fly you to your destination from $131 and $173, respectively. You may be able to fly from Chicago to Jacksonville for 69% less than the average price by searching for these airlines.

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

    $90 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Southwest and United Airlines, with prices starting from $92 and $93, respectively.

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

    Consider Republic Airways (100%), SkyWest Airlines (76%) or Air Canada (66%) when booking your flight. These represent the most reliable airlines when flying from Chicago to Jacksonville.

  • What are the cheapest flights from Chicago to Jacksonville?

    The cheapest flight price from Chicago to Jacksonville is $121. On average you can expect to pay $513. The most popular route, (Chicago O'Hare Intl - Jacksonville), can usually be booked for $133.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Jacksonville 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 Chicago to Jacksonville?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Jacksonville (average of $278). Flying from Chicago to Jacksonville in March is currently the most expensive (average of $365). 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

Traveling to a place near Jacksonville?

Book flights to Jacksonville if you plan to visit one of these locations
Jacksonville Beach
Orange Park
Kingsland
Fernandina Beach
Waycross

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Alternative routes for Chicago to Jacksonville

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Chicago to Jacksonville

Discover the top 6 airlines that operate flights from Chicago to Jacksonville. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$112Average$216FlexibilityNo cancel feeOn-time62%
DeltaCheapest$131Average$338FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$173Average$354FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$203Average$508FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$233Average$351FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$247Average$423FlexibilityNo cancel feeOn-time69%

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