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$91+ 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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JAX
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Jacksonville are usually found in August or September, booked 56 days in advance, depart on a 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 July 30, 2025.

Round-trip from

$181
(American Airlines)

One-way from

$91
(United Airlines)

Popular in

December

Cheapest in

August

Average price

$387

Good round-trip deal

$165 or less

Good one-way deal

$133 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. 5% potential increase in price ($21 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 July 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 July 30, 2025.

This Southwest deal was found by Cheapflights users on 7/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1610:30 amMDW - JAX
Nonstop2h 15mSouthwest
Sat 9/202:05 pmJAX - MDW
Nonstop2h 25mSouthwest
Deal found 7/27$181
This American Airlines deal was found by Cheapflights users on 7/30. 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 9/176:36 pmORD - JAX
Nonstop2h 23mAmerican Airlines
Tue 9/237:22 amJAX - ORD
Nonstop2h 41mAmerican Airlines
Deal found 7/30$181
This United Airlines deal was found by Cheapflights users on 7/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/168:50 amORD - JAX
1 stop5h 06mUnited Airlines
Sat 9/204:36 pmJAX - ORD
Nonstop2h 44mUnited Airlines
Deal found 7/27$191
This Delta deal was found by Cheapflights users on 7/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/166:00 amMDW - JAX
1 stop4h 40mDelta
Sat 9/205:08 pmJAX - MDW
1 stop5h 02mDelta
Deal found 7/27$201
This Delta deal was found by Cheapflights users on 7/28. 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.
Tue 10/1410:30 amORD - JAX
1 stop6h 00mDelta
Sat 10/181:12 pmJAX - ORD
1 stop6h 37mDelta
Deal found 7/28$201
This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/271:50 pmORD - JAX
1 stop5h 50mSouthwest
Wed 9/36:15 amJAX - ORD
2 stops10h 05mSouthwest
Deal found 7/28$206
This Cheapflightsfares deal was found by Cheapflights users on 7/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/268:15 amMDW - JAX
1 stop6h 06mFrontier
Sun 9/2812:38 pmJAX - MDW
1 stop4h 20mFrontier
Deal found 7/27$215
This Frontier deal was found by Cheapflights users on 7/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/95:10 amORD - JAX
1 stop9h 48mFrontier
Mon 10/1312:02 pmJAX - ORD
1 stop12h 24mFrontier
Deal found 7/29$218
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1410:12 amORD - JAX
2 stops24h 05mMultiple Airlines
Mon 8/1812:02 pmJAX - ORD
3 stops32h 05mMultiple Airlines
Deal found 7/29$269

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 July 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

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Wed 9/17

6:36 pm-9:59 pm

Nonstop2h 23m

Jacksonville

Tue 9/23

7:22 am-9:03 am

Nonstop2h 41m

$181

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 9/16

10:30 am-1:45 pm

Nonstop2h 15m

Jacksonville

Sat 9/20

2:05 pm-3:30 pm

Nonstop2h 25m

$181

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Tue 9/16

8:50 am-2:56 pm

1 stop5h 06m

Jacksonville

Sat 9/20

4:36 pm-6:20 pm

Nonstop2h 44m

$191

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Tue 10/14

10:30 am-5:30 pm

1 stop6h 00m

Jacksonville

Sat 10/18

1:12 pm-6:49 pm

1 stop6h 37m

$201

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Tue 9/16

6:00 am-11:40 am

1 stop4h 40m

Jacksonville

Sat 9/20

5:08 pm-9:10 pm

1 stop5h 02m

$201

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Wed 8/27

1:50 pm-8:40 pm

1 stop5h 50m

Jacksonville

Wed 9/3

6:15 am-3:20 pm

2 stops10h 05m

$206

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Fri 9/26

8:15 am-3:21 pm

1 stop6h 06m

Jacksonville

Sun 9/28

12:38 pm-3:58 pm

1 stop4h 20m

$215

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Thu 10/9

5:10 am-3:58 pm

1 stop9h 48m

Jacksonville

Mon 10/13

12:02 pm-11:26 pm

1 stop12h 24m

$218

ChicagoJacksonville

ORD - JAX

ORDJAX

Chicago O'Hare Intl

Thu 8/14

10:12 am-11:17 am

2 stops24h 05m

Jacksonville

Mon 8/18

12:02 pm-7:07 pm

3 stops32h 05m

$269

ChicagoJacksonville

MDW - JAX

MDWJAX

Chicago Midway

Sat 10/25

5:45 pm-9:00 pm

Nonstop2h 15m

$91

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 20 results
1
2

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 July 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 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 July 30, 2025.

It’s typically best to fly out from Chicago to Jacksonville at noon. Doing so could potentially save you 11% on the flight price compared to flying in the morning, 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 July 27, 2025.

Travelers seeking maximum savings on their Chicago to Jacksonville flight should consider departing on Saturday at noon 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 July 30, 2025.

The most flights from CHI to JAX are scheduled on a Monday (19 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

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 July 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
4,241 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

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
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

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
8,896 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

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
10,000 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

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.
Sun Country Air
6.9
Okay
334 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

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 12 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 $181, 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 United Airlines - these airlines can fly you to your destination from $181 and $191, respectively. You may be able to fly from Chicago to Jacksonville for 52% less than the average price by searching for these airlines.

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

    $91 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Southwest and Delta, with prices starting from $91 and $101, respectively.

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

    Consider Envoy Air (85%), SkyWest Airlines (83%) or Air Canada (77%) 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 $89. On average you can expect to pay $281. The most popular route, (Chicago O'Hare Intl - Jacksonville), can usually be booked for $181.

  • 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 Jacksonville?

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

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Alternative routes for Chicago to Jacksonville

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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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$112Average$318FlexibilityNo cancel feeOn-time62%
DeltaCheapest$131Average$338FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$178Average$369FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$190Average$468FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$233Average$351FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$236Average$420FlexibilityNo cancel feeOn-time69%

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