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$83+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JAX
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find cheap flights from Chicago to Jacksonville with Cheapflights

1. Tell us where you want to go

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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 Thursday 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 October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/28. 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 11/247:00 amORD - JAX
Nonstop2h 28mAmerican Airlines
Tue 12/26:00 amJAX - ORD
1 stop7h 28mAmerican Airlines
Deal found 10/28$281
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/117:23 pmMDW - JAX
1 stop21h 17mMultiple Airlines
Sun 1/49:48 amJAX - MDW
2 stops28h 33mMultiple Airlines
Deal found 10/28$282
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 12/126:11 amORD - JAX
1 stop10h 29mMultiple Airlines
Sun 12/145:48 pmJAX - ORD
2 stops21h 15mMultiple Airlines
Deal found 10/27$283
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/248:55 amORD - JAX
1 stop7h 32mDelta
Thu 11/272:00 pmJAX - ORD
1 stop5h 52mDelta
Deal found 10/29$285
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/246:00 amMDW - JAX
1 stop5h 02mDelta
Mon 11/246:38 pmJAX - MDW
1 stop6h 02mDelta
Deal found 10/28$285
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 12/61:53 pmORD - JAX
Nonstop2h 30mAmerican Airlines
Mon 12/86:49 amJAX - ORD
Nonstop2h 52mAmerican Airlines
Deal found 10/28$286
This Southwest deal was found by Cheapflights users on 10/29. 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.
Thu 12/111:45 pmMDW - JAX
Nonstop2h 15mSouthwest
Sat 12/135:35 amJAX - MDW
Nonstop2h 25mSouthwest
Deal found 10/29$286
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Tue 12/211:05 amORD - JAX
Nonstop2h 33mUnited Airlines
Thu 12/48:10 amJAX - ORD
Nonstop2h 44mUnited Airlines
Deal found 10/28$287
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/235:30 amMDW - JAX
1 stop14h 18mFrontier
Mon 11/2410:59 amJAX - MDW
1 stop12h 44mFrontier
Deal found 10/28$289
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 12/258:25 amORD - JAX
1 stop6h 39mAmerican Airlines
Thu 1/19:33 amJAX - ORD
1 stop7h 32mAmerican Airlines
Deal found 10/28$290
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/248:55 amORD - JAX
1 stop7h 32mDelta
Tue 12/25:05 amJAX - ORD
1 stop4h 34mDelta
Deal found 10/28$291
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/246:00 amMDW - JAX
1 stop5h 02mDelta
Tue 12/25:05 amJAX - MDW
1 stop5h 49mDelta
Deal found 10/28$291

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$281
(Delta)

One-way from

$83
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$349

Good round-trip deal

$303 or less

Good one-way deal

$162 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. 10% potential increase in price ($45 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 October 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 October 30, 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

MDW - JAX

MDWJAX

Chicago Midway

Tue 12/30

5:05 pm-10:43 pm

1 stop4h 38m

Jacksonville

Thu 1/1

6:00 am-9:05 am

1 stop4h 05m

$291

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Mon 11/24

6:00 am-12:02 pm

1 stop5h 02m

Jacksonville

Tue 12/2

5:05 am-9:54 am

1 stop5h 49m

$291

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Wed 12/24

6:12 am-4:34 pm

1 stop9h 22m

Jacksonville

Tue 12/30

10:15 pm-2:37 pm

2 stops17h 22m

$293

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Thu 12/11

8:50 am-3:20 pm

1 stop5h 30m

Jacksonville

Sat 12/13

5:35 am-7:00 am

Nonstop2h 25m

$296

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Tue 12/16

8:45 am-2:58 pm

1 stop5h 13m

Jacksonville

Wed 1/7

1:45 pm-8:25 pm

1 stop7h 40m

$297

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Wed 1/28

1:45 pm-9:15 pm

1 stop6h 30m

Jacksonville

Tue 2/3

6:50 am-12:15 pm

1 stop6h 25m

$297

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 12/30

5:05 pm-10:43 pm

1 stop4h 38m

Jacksonville

Wed 1/7

6:30 am-10:34 am

1 stop5h 04m

$297

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 12/16

12:50 pm-5:35 pm

1 stop3h 45m

Jacksonville

Wed 1/7

5:30 am-10:34 am

1 stop6h 04m

$297

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Wed 12/10

10:49 am-4:30 pm

1 stop4h 41m

Jacksonville

Wed 12/17

11:47 am-4:34 pm

1 stop5h 47m

$297

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Tue 12/16

5:30 am-10:41 am

1 stop4h 11m

Jacksonville

Mon 1/5

1:16 pm-4:43 pm

1 stop4h 27m

$297

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 38 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 October.
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 24, 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 October 30, 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 October 26, 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.

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 October 30, 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
4,243 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

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
7.9
Good
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

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
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

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
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

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
3,122 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

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 7 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, Southwest, and United Airlines can get you from Chicago to Jacksonville in just under 4h 38m. Your travel time can differ by up to 52m. The distance from Chicago to Jacksonville is about 849 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 Delta and Southwest, with prices starting from $133 and $133, respectively.

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

    Consider Republic Airways (100%), Air Canada (80%) or Air New Zealand (80%) 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 $117. On average you can expect to pay $478. The most popular route, (Chicago O'Hare Intl - Jacksonville), can usually be booked for $209.

  • 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$112Average$218FlexibilityNo cancel feeOn-time62%
DeltaCheapest$144Average$376FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$176Average$357FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$198Average$390FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$255Average$413FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$265Average$356FlexibilityNo cancel feeOn-time62%

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