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$66+ 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 6/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JAX
Jun 6 — Jun 131
Sat 6/6
Sat 6/13
1 adult, Economy
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Find cheap flights from Chicago to Jacksonville with Cheapflights

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Cheapflights Tip: The best prices from Chicago to Jacksonville are usually found in August or September, booked 51 days in advance, depart on a Saturday or Wednesday and return on a Thursday

Cheap 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 May 7, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/6. 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.
Tue 6/305:29 pm
ORD
-
JAX
2 stops23h 04m
Multiple Airlines
Tue 7/78:44 pm
JAX
-
ORD
1 stop16h 41m
Multiple Airlines
Deal found 5/6$239
This Expedia deal was found by Cheapflights users on 5/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/226:55 am
ORD
-
JAX
1 stop9h 40m
Frontier
Sun 5/2411:28 am
JAX
-
ORD
1 stop12h 18m
Frontier
Deal found 5/2$240
This Frontier deal was found by Cheapflights users on 5/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/256:00 am
MDW
-
JAX
1 stop10h 35m
Frontier
Mon 6/16:30 pm
JAX
-
MDW
1 stop4h 32m
Frontier
Deal found 5/5$240
This Kiwi.com deal was found by Cheapflights users on 5/4. 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 7/157:05 am
ORD
-
JAX
1 stop9h 28m
Multiple Airlines
Wed 7/159:38 pm
JAX
-
ORD
1 stop15h 47m
Multiple Airlines
Deal found 5/4$241
This Frontier deal was found by Cheapflights users on 5/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:00 am
MDW
-
JAX
1 stop10h 35m
Frontier
Thu 5/216:30 pm
JAX
-
MDW
1 stop4h 32m
Frontier
Deal found 5/3$241
This American Airlines deal was found by Cheapflights users on 5/2. 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.
Tue 5/267:25 pm
ORD
-
JAX
Nonstop2h 33m
American Airlines
Sat 5/305:59 pm
JAX
-
ORD
Nonstop2h 55m
American Airlines
Deal found 5/2$242
This Southwest deal was found by Cheapflights users on 5/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1511:50 am
MDW
-
JAX
2 stops8h 00m
Southwest
Tue 7/2111:05 am
JAX
-
MDW
1 stop7h 50m
Southwest
Deal found 5/4$242
This Trip.com deal was found by Cheapflights users on 5/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 am
MDW
-
JAX
1 stop10h 35m
Frontier
Wed 5/136:30 pm
JAX
-
MDW
1 stop4h 32m
Frontier
Deal found 5/4$243
This Frontier deal was found by Cheapflights users on 5/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/187:05 am
ORD
-
JAX
1 stop9h 28m
Frontier
Fri 7/241:17 pm
JAX
-
ORD
1 stop6h 43m
Frontier
Deal found 5/5$244
This Kiwi.com deal was found by Cheapflights users on 5/4. 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.
Mon 6/16:00 am
MDW
-
JAX
1 stop10h 35m
Frontier
Mon 6/86:30 pm
JAX
-
MDW
1 stop17h 42m
Frontier
Deal found 5/4$244
This Kiwi.com deal was found by Cheapflights users on 5/4. 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.
Mon 6/16:55 am
ORD
-
JAX
1 stop9h 40m
Multiple Airlines
Mon 6/84:09 pm
JAX
-
ORD
2 stops45h 15m
Multiple Airlines
Deal found 5/4$245
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 6/126:00 am
MDW
-
JAX
1 stop10h 33m
Frontier
Sun 6/146:28 pm
JAX
-
MDW
1 stop17h 41m
Frontier
Deal found 5/5$245

Find 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 May 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$239
(Kiwi.com)

One-way from

$66
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$358

Good round-trip deal

$252 or less

Good one-way deal

$195 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. 6% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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 May 7, 2026.
Use the filters below to find and compare flights from Chicago to Jacksonville that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Sat 6/6

7:00 am-10:40 am

Nonstop2h 40m

Jacksonville

Tue 6/9

7:20 am-9:12 am

Nonstop2h 52m

$252

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Mon 6/1

9:25 am-5:19 pm

1 stop6h 54m

Jacksonville

Tue 6/30

2:48 pm-6:42 pm

1 stop4h 54m

$262

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Tue 6/30

5:30 am-1:43 pm

1 stop7h 13m

Jacksonville

Tue 7/7

5:30 am-10:10 am

1 stop5h 40m

$289

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Sat 6/13

6:00 am-12:00 pm

1 stop5h 00m

Jacksonville

Wed 6/17

5:38 pm-10:17 pm

1 stop5h 39m

$296

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Wed 7/15

6:19 pm-9:59 pm

Nonstop2h 40m

Jacksonville

Wed 8/12

7:30 am-9:16 am

Nonstop2h 46m

$297

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Tue 6/2

7:00 am-10:40 am

Nonstop2h 40m

Jacksonville

Wed 6/3

6:42 pm-8:38 pm

Nonstop2h 56m

$297

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Wed 5/20

9:49 am-4:33 pm

1 stop5h 44m

Jacksonville

Wed 5/27

2:40 pm-6:41 pm

1 stop5h 01m

$315
Quickest round-trip

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 8/11

5:55 pm-9:15 pm

Nonstop2h 20m

Jacksonville

Fri 8/28

7:00 am-8:25 am

Nonstop2h 25m

$320

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Wed 6/17

5:30 am-10:45 am

1 stop4h 15m

Jacksonville

Sun 6/21

11:40 am-6:29 pm

1 stop7h 49m

$321

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Fri 5/29

6:50 pm-10:05 pm

Nonstop2h 15m

Jacksonville

Mon 6/8

7:15 pm-8:45 pm

Nonstop2h 30m

$331

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/2

Showing 1-10 of 43 resultsSorted by cheapest first
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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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
WAYAPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
Trip.comPrice Accuracy1 starTrust 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Jacksonville flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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?

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 37 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 $78). Flying from Chicago to Jacksonville in March is currently the most expensive (average of $216). 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 May 7, 2026.

It’s typically best to fly out from Chicago to Jacksonville in the morning. Doing so could potentially save you 5% 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 May 2, 2026.

Travelers seeking maximum savings on their Chicago to Jacksonville flight should consider departing on Saturday afternoons when fares are most often at their lowest. Tuesday 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 May 7, 2026.

The most flights from CHI to JAX are scheduled on a Thursday (26 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (20 on average).

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

The best insider tips for Chicago to Jacksonville flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Jacksonville trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

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 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 May 7, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican 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
7.9
Good
4,301 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Entertainment

7.5

Food

7.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Southwest
7.9
Good
4,301 reviews
Southwest
7.9
Good
4,301 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Entertainment

7.5

Food

7.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
United Airlines
7.4
Good
9,692 reviews
Southwest
7.9
Good
4,301 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Entertainment

7.5

Food

7.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
American Airlines
7.1
Good
11,670 reviews
Southwest
7.9
Good
4,301 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Entertainment

7.5

Food

7.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
JetBlue
7.1
Good
2,980 reviews
Southwest
7.9
Good
4,301 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Entertainment

7.5

Food

7.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Frontier
5.6
Fair
2,964 reviews
Southwest
7.9
Good
4,301 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Entertainment

7.5

Food

7.0

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

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 23 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?

    United Airlines, Delta, and Southwest can get you from Chicago to Jacksonville in just under 2h 20m. Your travel time can differ by up to 4h 34m. 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 $83, Delta will fly you from Chicago to Jacksonville and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Frontier and American Airlines - these airlines can fly you to your destination from $112 and $180, respectively. You may be able to fly from Chicago to Jacksonville for 75% less than the average price by searching for these airlines.

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

    $70 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on American Airlines and Southwest, with prices starting from $87 and $89, respectively.

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

    Consider Envoy Air (95%), SkyWest Airlines (83%) or American Airlines (83%) 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 $98. On average you can expect to pay $346. The most popular route, (Chicago O'Hare Intl - Jacksonville), can usually be booked for $151.

  • 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 $78). Flying from Chicago to Jacksonville in March is currently the most expensive (average of $216). 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
Atlantic Beach
Yulee

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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 May 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$83Average$274FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$112Average$222FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$180Average$340FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$203Average$351FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$236Average$337FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$247Average$374FlexibilityNo cancel feeOn-time69%

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