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$96+ 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 6/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JAX
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Jacksonville are usually found in September or August, booked 5 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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$310
(American Airlines)

One-way from

$96
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$371

Good round-trip deal

$337 or less

Good one-way deal

$161 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
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One-way flight from Chicago (CHI) to Jacksonville
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
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 May 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 May 1, 2025.

This FlightHub deal was found by Cheapflights users on 4/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/268:38 pmORD - JAX
1 stop14h 06mMultiple Airlines
Sun 6/297:49 pmJAX - ORD
1 stop5h 25mMultiple Airlines
Deal found 4/29$309
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Wed 5/286:55 pmORD - JAX
Nonstop2h 40mAmerican Airlines
Mon 6/22:11 pmJAX - ORD
1 stop4h 48mAmerican Airlines
Deal found 4/30$310
This Southwest deal was found by Cheapflights users on 4/30. 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 5/282:40 pmMDW - JAX
1 stop6h 25mSouthwest
Mon 6/25:45 pmJAX - MDW
Nonstop2h 35mSouthwest
Deal found 4/30$310
This JetBlue deal was found by Cheapflights users on 4/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/198:40 amORD - JAX
1 stop9h 13mJetBlue
Tue 9/236:15 amJAX - ORD
1 stop7h 25mJetBlue
Deal found 4/29$319
This Delta deal was found by Cheapflights users on 4/29. 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.
Wed 8/67:05 amORD - JAX
1 stop6h 15mDelta
Mon 8/115:05 pmJAX - ORD
1 stop5h 16mDelta
Deal found 4/29$320
This Delta deal was found by Cheapflights users on 4/30. 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.
Tue 5/206:00 amMDW - JAX
1 stop6h 16mDelta
Mon 5/266:10 amJAX - MDW
1 stop4h 30mDelta
Deal found 4/30$320
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/27:00 amORD - JAX
Nonstop2h 39mUnited Airlines
Mon 6/911:20 amJAX - ORD
Nonstop2h 53mUnited Airlines
Deal found 4/29$323
This Southwest deal was found by Cheapflights users on 4/30. 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 5/287:30 amORD - JAX
2 stops8h 30mSouthwest
Mon 6/26:30 amJAX - ORD
1 stop6h 20mSouthwest
Deal found 4/30$325
This Sun Country Air deal was found by Cheapflights users on 4/29. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/116:11 pmORD - JAX
1 stop16h 32mSun Country Air
Fri 5/1612:30 pmJAX - ORD
1 stop7h 39mSun Country Air
Deal found 4/29$338
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/303:16 pmMDW - JAX
2 stops27h 06mMultiple Airlines
Sun 6/18:19 pmJAX - MDW
2 stops22h 51mMultiple Airlines
Deal found 4/30$346
This Frontier deal was found by Cheapflights users on 4/30. 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 6/298:24 amORD - JAX
1 stop6h 07mFrontier
Thu 7/107:49 pmJAX - ORD
1 stop5h 33mFrontier
Deal found 4/30$352
This Frontier deal was found by Cheapflights users on 4/30. 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.
Fri 6/276:00 amMDW - JAX
1 stop11h 07mFrontier
Fri 7/114:33 pmJAX - MDW
1 stop8h 18mFrontier
Deal found 4/30$352

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 1, 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

Thu 6/26

8:38 pm-11:44 am

1 stop14h 06m

Jacksonville

Sun 6/29

7:49 pm-12:14 am

1 stop5h 25m

$309

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Wed 5/28

6:55 pm-10:35 pm

Nonstop2h 40m

Jacksonville

Mon 6/2

2:11 pm-5:59 pm

1 stop4h 48m

$310

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Wed 5/28

2:40 pm-10:05 pm

1 stop6h 25m

Jacksonville

Mon 6/2

5:45 pm-7:20 pm

Nonstop2h 35m

$310

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 5/20

6:00 am-1:16 pm

1 stop6h 16m

Jacksonville

Mon 5/26

6:10 am-9:40 am

1 stop4h 30m

$320

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Mon 6/2

7:00 am-10:39 am

Nonstop2h 39m

Jacksonville

Mon 6/9

11:20 am-1:13 pm

Nonstop2h 53m

$323

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Wed 5/28

7:30 am-5:00 pm

2 stops8h 30m

Jacksonville

Mon 6/2

6:30 am-11:50 am

1 stop6h 20m

$325

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Sun 5/11

6:11 pm-11:43 am

1 stop16h 32m

Jacksonville

Fri 5/16

12:30 pm-7:09 pm

1 stop7h 39m

$338

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Sat 6/28

5:35 am-1:28 pm

1 stop6h 53m

Jacksonville

Mon 7/14

8:25 pm-8:32 am

1 stop13h 07m

$341

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Fri 5/30

3:16 pm-7:22 pm

2 stops27h 06m

Jacksonville

Sun 6/1

8:19 pm-6:10 pm

2 stops22h 51m

$346

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Wed 5/14

4:03 pm-11:38 pm

1 stop6h 35m

Jacksonville

Mon 5/19

6:15 am-3:04 pm

1 stop9h 49m

$351

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 27 results
1
2
3

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*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 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 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 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 April 25, 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 5 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 May 1, 2025.

It’s typically best to fly out from Chicago to Jacksonville in the afternoon. Doing so could potentially save you 13% on the flight price compared to flying at noon, 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 March 30, 2025.

Travelers seeking maximum savings on their Chicago to Jacksonville flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Wednesday at noon 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 1, 2025.

The most flights from CHI to JAX are scheduled on a Wednesday (20 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 on average).

Rainfall in Jacksonville by month

Plan your trip to Jacksonville by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Jacksonville ranges from 2.1 - 8.2 inches per month. September is typically the wettest month, when rainfall can reach 8.2 in. November is typically the driest time to visit Jacksonville when rainfall is around 2.1 in.

Temperature in Jacksonville by month

Plan your trip to Jacksonville by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Jacksonville, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 53.6 F).

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 1, 2025.
Read through reviews of airlines operating flights from Chicago to Jacksonville, such as Southwest, Delta and Avelo Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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.
Avelo Airlines
7.5
Good
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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
8,696 reviews
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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.
JetBlue
7.3
Good
2,924 reviews
Southwest
8.0
Very good
4,294 reviews

Crew

8.6

Food

7.1

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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 11 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.

  • What are the cheapest airlines flying from Chicago to Jacksonville round-trip?

    Currently priced at $310, American Airlines will fly you from Chicago to Jacksonville and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Southwest and JetBlue - these airlines can fly you to your destination from $310 and $319, respectively. You may be able to fly from Chicago to Jacksonville for 18% less than the average price by searching for these airlines.

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

    $96 is the cheapest one-way deal found within the past few days, from Avelo Airlines. You may also be able to find cheap deals on Frontier and Sun Country Air, with prices starting from $105 and $120, respectively.

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

    Consider SkyWest Airlines (97%), United Airlines (82%) or Air Canada (79%) 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 $143. On average you can expect to pay $343. The most popular route, (Chicago O'Hare Intl - Jacksonville), can usually be booked for $223.

  • 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 Chicago?

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

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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 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$140Average$259FlexibilityNo cancel feeOn-time62%
DeltaCheapest$144Average$306FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$198Average$470FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$217Average$376FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$219Average$414FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$233Average$356FlexibilityNo cancel feeOn-time62%

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