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$82+ 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JAX
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 Thursday or Wednesday and return on a Friday

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 November 6, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Thu 12/46:15 amMDW - JAX
2 stops13h 50mFrontier
Fri 12/56:36 pmJAX - MDW
1 stop4h 36mFrontier
Deal found 11/6$279
This United Airlines deal was found by Cheapflights users on 11/6. 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.
Wed 12/108:45 amORD - JAX
1 stop5h 13mUnited Airlines
Sat 12/134:37 pmJAX - ORD
Nonstop2h 53mUnited Airlines
Deal found 11/6$281
This Southwest deal was found by Cheapflights users on 11/6. 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.
Wed 12/101:45 pmMDW - JAX
Nonstop2h 15mSouthwest
Sat 12/137:50 amJAX - MDW
1 stop5h 35mSouthwest
Deal found 11/6$281
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Sat 11/226:35 pmORD - JAX
1 stop14h 29mFrontier
Thu 12/410:00 pmJAX - ORD
1 stop15h 40mFrontier
Deal found 11/5$285
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Sun 11/238:59 amORD - JAX
1 stop10h 49mMultiple Airlines
Sun 12/75:48 pmJAX - ORD
2 stops17h 08mMultiple Airlines
Deal found 11/5$286
This American Airlines deal was found by Cheapflights users on 11/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/244:40 pmORD - JAX
1 stop6h 34mAmerican Airlines
Thu 11/276:54 amJAX - ORD
Nonstop2h 55mAmerican Airlines
Deal found 11/4$287
This Trip.com deal was found by Cheapflights users on 11/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/146:15 amMDW - JAX
1 stop7h 10mFrontier
Sun 11/165:18 pmJAX - MDW
1 stop5h 45mFrontier
Deal found 11/6$287
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Sun 11/238:59 amORD - JAX
1 stop10h 49mFrontier
Fri 12/197:06 pmJAX - ORD
1 stop17h 25mFrontier
Deal found 11/5$288
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/56:15 amMDW - JAX
1 stop10h 25mMultiple Airlines
Sun 12/75:48 pmJAX - MDW
2 stops18h 32mMultiple Airlines
Deal found 11/5$288
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 11/145:11 amORD - JAX
1 stop8h 14mMultiple Airlines
Mon 11/177:56 pmJAX - ORD
1 stop17h 57mMultiple Airlines
Deal found 11/3$289
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Mon 11/179:15 amMDW - JAX
1 stop11h 38mFrontier
Fri 12/195:23 pmJAX - MDW
1 stop5h 49mFrontier
Deal found 11/5$289
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Wed 11/1910:00 amORD - JAX
1 stop26h 45mMultiple Airlines
Wed 12/310:33 amJAX - ORD
2 stops36h 18mMultiple Airlines
Deal found 11/4$290

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 November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$278
(Kiwi.com)

One-way from

$82
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$382

Good round-trip deal

$312 or less

Good one-way deal

$157 or less
Provider with most accurate pricing for Chicago (CHI)-Jacksonville flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Jacksonville flights.
Search Deals
From Chicago (CHI) to Jacksonville
Search Deals
One-way flight from Chicago (CHI) to Jacksonville
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Jacksonville.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Jacksonville.
Search Deals

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 November 6, 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

Wed 12/31

5:31 pm-11:56 pm

1 stop5h 25m

Jacksonville

Thu 1/1

7:00 am-12:12 pm

1 stop6h 12m

$297

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Mon 11/24

5:34 pm-12:10 am

1 stop5h 36m

Jacksonville

Tue 12/2

6:05 am-11:55 am

1 stop6h 50m

$307

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Thu 11/27

11:19 am-7:03 pm

1 stop6h 44m

Jacksonville

Tue 12/2

1:14 pm-6:43 pm

1 stop6h 29m

$307

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Mon 11/24

6:00 am-12:53 pm

1 stop5h 53m

Jacksonville

Tue 12/2

6:05 am-12:10 pm

1 stop7h 05m

$307

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Sat 12/13

11:05 am-2:38 pm

Nonstop2h 33m

Jacksonville

Mon 12/15

8:10 am-9:54 am

Nonstop2h 44m

$311

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Wed 11/19

7:00 am-6:05 pm

1 stop10h 05m

Jacksonville

Wed 12/3

6:00 am-4:39 pm

1 stop11h 39m

$323

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Mon 12/29

6:04 pm-9:42 pm

Nonstop2h 38m

Jacksonville

Wed 12/31

7:40 am-9:26 am

Nonstop2h 46m

$327

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Mon 11/17

7:00 am-10:26 pm

1 stop14h 26m

Jacksonville

Wed 12/3

6:00 am-7:20 pm

1 stop14h 20m

$329

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 12/16

6:00 am-1:42 pm

1 stop6h 42m

Jacksonville

Sat 12/20

6:00 am-9:05 am

1 stop4h 05m

$331

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Fri 12/19

6:00 am-1:45 pm

1 stop6h 45m

Jacksonville

Sun 12/21

6:41 pm-10:22 pm

1 stop4h 41m

$331

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

Showing 1-10 of 42 results
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Compare providers for flights from Chicago to Jacksonville

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Jacksonville in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Jacksonville flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Jacksonville flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Jacksonville flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Jacksonville flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Jacksonville flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 October 31, 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, June is the cheapest month in which you can book a flight from Chicago to Jacksonville (average of $117). Flying from Chicago to Jacksonville in November is currently the most expensive (average of $235). 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 November 6, 2025.

It’s typically best to fly out from Chicago to Jacksonville at noon. Doing so could potentially save you 31% 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 November 2, 2025.

Travelers seeking maximum savings on their Chicago to Jacksonville flight should consider departing on Sunday evenings when fares are most often at their lowest. Friday 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 November 6, 2025.

The most flights from CHI to JAX are scheduled on a Monday (22 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).

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

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

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 November 6, 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
4,241 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

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
7.9
Good
8,001 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

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
9,007 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

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
11,040 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

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
3,115 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

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 19 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?

    Delta and Southwest can get you from Chicago to Jacksonville in just under 5h 25m. Your travel time can differ by up to 2h 35m. 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 $144 and $176, 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?

    $123 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Southwest and Delta, with prices starting from $123 and $133, respectively.

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

    Consider Envoy Air (88%), United Airlines (82%) or Air Canada (81%) 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 $116. On average you can expect to pay $441. The most popular route, (Chicago O'Hare Intl - Jacksonville), can usually be booked for $154.

  • 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, June is the cheapest month in which you can book a flight from Chicago to Jacksonville (average of $117). Flying from Chicago to Jacksonville in November is currently the most expensive (average of $235). 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
Fernandina Beach
Kingsland
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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$112Average$236FlexibilityNo cancel feeOn-time62%
DeltaCheapest$144Average$376FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$176Average$358FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$198Average$390FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$255Average$414FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$265Average$356FlexibilityNo cancel feeOn-time62%

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