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$73+ 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 8/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JAX
juin 10 — juin 171
mar. 6/10
mar. 6/17
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Jacksonville are usually found in September or August, booked 56 days in advance, depart on a Wednesday or Tuesday and return on a Friday

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 juin 5, 2025.

Round-trip from

$226
(Frontier)

One-way from

$73
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$372

Good round-trip deal

$286 or less

Good one-way deal

$138 or less
From Chicago (CHI) to Jacksonville
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One-way flight from Chicago (CHI) to Jacksonville
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Highest demand for flights based on searches. 4% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in June 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 juin 5, 2025.

This Frontier deal was found by Cheapflights users on 6/5. 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.
ven. 8/86:00 amMDW - JAX
1 stop11h 03mFrontier
jeu. 8/147:49 pmJAX - MDW
1 stop4h 28mFrontier
Deal found 6/5$226
This American Airlines deal was found by Cheapflights users on 6/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 8/66:55 pmORD - JAX
Nonstop2h 32mAmerican Airlines
lun. 8/115:37 pmJAX - ORD
Nonstop2h 42mAmerican Airlines
Deal found 6/5$231
This United Airlines deal was found by Cheapflights users on 6/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 8/911:59 amORD - JAX
Nonstop2h 34mUnited Airlines
jeu. 8/144:30 pmJAX - ORD
Nonstop2h 45mUnited Airlines
Deal found 6/3$235
This Southwest deal was found by Cheapflights users on 6/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 8/238:00 amMDW - JAX
2 stops9h 10mSouthwest
mer. 8/277:05 pmJAX - MDW
1 stop4h 20mSouthwest
Deal found 6/2$235
This FlightHub deal was found by Cheapflights users on 6/5. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 7/25:38 pmORD - JAX
1 stop24h 14mFrontier
dim. 7/67:49 pmJAX - ORD
1 stop5h 33mFrontier
Deal found 6/5$236
This Delta deal was found by Cheapflights users on 6/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 9/1710:35 amORD - JAX
1 stop6h 01mDelta
mar. 9/239:57 amJAX - ORD
1 stop5h 16mDelta
Deal found 6/3$239
This Southwest deal was found by Cheapflights users on 6/4. 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.
jeu. 8/216:00 amORD - JAX
2 stops10h 40mSouthwest
mar. 8/268:15 amJAX - ORD
2 stops14h 15mSouthwest
Deal found 6/4$252
This Delta deal was found by Cheapflights users on 6/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/59:25 amMDW - JAX
1 stop6h 40mDelta
mar. 8/123:05 pmJAX - MDW
2 stops22h 23mDelta
Deal found 6/5$252
This Mytrip deal was found by Cheapflights users on 6/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 7/314:37 pmORD - JAX
1 stop27h 18mMultiple Airlines
dim. 8/312:57 pmJAX - ORD
2 stops33h 33mMultiple Airlines
Deal found 6/4$258
This JetBlue deal was found by Cheapflights users on 6/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 10/241:36 pmORD - JAX
1 stop8h 29mJetBlue
dim. 10/2610:12 amJAX - ORD
1 stop5h 56mJetBlue
Deal found 6/3$319
This Mytrip deal was found by Cheapflights users on 6/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 7/118:03 amMDW - JAX
2 stops34h 06mAllegiant Air
mar. 7/1511:16 amJAX - MDW
2 stops29h 21mAllegiant Air
Deal found 6/3$329

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 juin 5, 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

ven. 8/8

6:00 am-6:03 pm

1 stop11h 03m

Jacksonville

jeu. 8/14

7:49 pm-11:17 pm

1 stop4h 28m

$226

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

mer. 8/6

6:55 pm-10:27 pm

Nonstop2h 32m

Jacksonville

lun. 8/11

5:37 pm-7:19 pm

Nonstop2h 42m

$231

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

sam. 8/9

7:00 am-10:39 am

Nonstop2h 39m

Jacksonville

dim. 8/10

8:00 am-9:45 am

Nonstop2h 45m

$235

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

sam. 8/23

8:00 am-6:10 pm

2 stops9h 10m

Jacksonville

mer. 8/27

7:05 pm-10:25 pm

1 stop4h 20m

$235

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

mer. 7/2

5:38 pm-6:52 pm

1 stop24h 14m

Jacksonville

dim. 7/6

7:49 pm-12:22 am

1 stop5h 33m

$236

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

sam. 8/2

9:50 am-2:44 pm

1 stop3h 54m

Jacksonville

mer. 8/6

7:10 am-10:10 am

1 stop4h 00m

$247

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

jeu. 8/21

6:00 am-5:40 pm

2 stops10h 40m

Jacksonville

mar. 8/26

8:15 am-9:30 pm

2 stops14h 15m

$252

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

mar. 8/5

9:25 am-5:05 pm

1 stop6h 40m

Jacksonville

mar. 8/12

3:05 pm-12:28 pm

2 stops22h 23m

$252

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

jeu. 7/31

4:37 pm-8:55 pm

1 stop27h 18m

Jacksonville

dim. 8/3

12:57 pm-9:30 pm

2 stops33h 33m

$258

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

jeu. 7/31

11:37 am-2:29 pm

2 stops25h 52m

Jacksonville

dim. 8/3

4:18 pm-1:56 pm

2 stops22h 38m

$305

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/3

Showing 1-10 of 25 results
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The best insider tips for Chicago to Jacksonville flights

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

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

Read more about ORDby Ramsey Qubein
JAX

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

Read more about JAXby Matt Meltzer
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

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

Read more
Matt Meltzer

Matt Meltzer

Expert on JAX

Matt Meltzer

Matt Meltzer

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

Read more

Best time to book a flight from Chicago to Jacksonville

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

Cheapflights Insights

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

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Jacksonville. Price data was last updated on May 23, 2025.

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

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

Currently, August is the cheapest month in which you can book a flight from Chicago to Jacksonville (average of $278). Flying from Chicago to Jacksonville in March is currently the most expensive (average of $365). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to JAX?

Find hourly flight availability from Chicago to Jacksonville. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated juin 5, 2025.

It’s typically best to fly out from Chicago to Jacksonville in the evening. Doing so could potentially save you 5% 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 June 1, 2025.

Travelers seeking maximum savings on their Chicago to Jacksonville flight should consider departing on Tuesday evenings 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 juin 5, 2025.

The most flights from CHI to JAX are scheduled on a Monday (20 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 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 juin 5, 2025.
Read through reviews of airlines operating flights from Chicago to Jacksonville, such as Southwest, Delta and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

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
7,956 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

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
8,774 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

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
2,928 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

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.
Allegiant Air
7.3
Good
729 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Comfort

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

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 15 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 $226, 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 American Airlines and United Airlines - these airlines can fly you to your destination from $231 and $235, respectively. You may be able to fly from Chicago to Jacksonville for 41% less than the average price by searching for these airlines.

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

    $73 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Southwest and Delta, with prices starting from $73 and $99, respectively.

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

    Consider Republic Airways (100%), SkyWest Airlines (93%) or United Airlines (91%) 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 $87. On average you can expect to pay $274. The most popular route, (Chicago O'Hare Intl - Jacksonville), can usually be booked for $145.

  • 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
Orange Park
Kingsland
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 juin 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$112Average$250FlexibilityNo cancel feeOn-time62%
DeltaCheapest$131Average$291FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$198Average$378FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$198Average$468FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$218Average$412FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$233Average$351FlexibilityNo cancel feeOn-time62%

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