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$71+ Cheap flights from Jacksonville (JAX) to Chicago (CHI)

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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — CHI
Oct 22 — Oct 291
Wed 10/22
Wed 10/29
1 adult, Economy
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Cheapflights Tip: The best prices from Jacksonville to Chicago are usually found in September or August, booked 74 days in advance, depart on a Thursday or Friday and return on a Wednesday

Cheap flight deals from Jacksonville to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Jacksonville (JAX) to Chicago (CHI). 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 September 22, 2025.

Round-trip from

$184
(Frontier)

One-way from

$71
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$289

Good round-trip deal

$282 or less

Good one-way deal

$176 or less
From Jacksonville to Chicago (CHI)
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One-way flight from Jacksonville to Chicago (CHI)
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Highest demand for flights based on searches. 7% potential increase in price ($28 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 September 2025
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Price to beat on a round-trip flight from Jacksonville to Chicago (CHI).
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Price to beat on a one-way flight from Jacksonville to Chicago (CHI).
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Find flight deals from Jacksonville to Chicago

Cheapest flights from Jacksonville to Chicago
Explore the most affordable flight options available from Jacksonville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 22, 2025.

This Frontier deal was found by Cheapflights users on 9/20. 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 10/1811:46 amJAX - ORD
2 stops12h 43mFrontier
Sun 10/265:05 amORD - JAX
1 stop11h 05mFrontier
Deal found 9/20$184
This Frontier deal was found by Cheapflights users on 9/19. 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 10/1811:46 amJAX - MDW
2 stops12h 01mFrontier
Sun 10/196:20 amMDW - JAX
1 stop9h 50mFrontier
Deal found 9/19$184
This Frontier deal was found by Cheapflights users on 9/19. 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 10/96:03 pmJAX - ORD
1 stop6h 36mFrontier
Sun 10/125:05 amORD - JAX
1 stop11h 05mFrontier
Deal found 9/19$188
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 10/1011:37 amJAX - MDW
1 stop12h 43mFrontier
Sun 10/126:20 amMDW - JAX
1 stop9h 50mFrontier
Deal found 9/22$188
This Booking.com deal was found by Cheapflights users on 9/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/512:38 pmJAX - ORD
1 stop22h 53mFrontier
Wed 10/83:12 pmORD - JAX
1 stop24h 56mFrontier
Deal found 9/20$191
This Frontier deal was found by Cheapflights users on 9/20. 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 10/236:03 pmJAX - ORD
2 stops14h 31mFrontier
Sun 10/265:05 amORD - JAX
1 stop11h 05mFrontier
Deal found 9/20$192
This Frontier deal was found by Cheapflights users on 9/22. 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 10/212:38 pmJAX - MDW
1 stop4h 20mFrontier
Mon 10/68:15 amMDW - JAX
1 stop6h 06mFrontier
Deal found 9/22$192
This Frontier deal was found by Cheapflights users on 9/19. 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 10/305:13 pmJAX - ORD
2 stops15h 13mFrontier
Sun 11/25:11 amORD - JAX
1 stop10h 02mFrontier
Deal found 9/19$194
This Frontier deal was found by Cheapflights users on 9/19. 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 10/305:13 pmJAX - MDW
2 stops16h 19mFrontier
Sun 11/25:20 amMDW - JAX
1 stop8h 53mFrontier
Deal found 9/19$198
This Frontier deal was found by Cheapflights users on 9/20. 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 10/249:39 pmJAX - ORD
2 stops14h 56mFrontier
Mon 10/2711:51 amORD - JAX
1 stop7h 56mFrontier
Deal found 9/20$199
This Expedia deal was found by Cheapflights users on 9/19. 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.
Sat 11/110:38 pmJAX - MDW
1 stop10h 52mFrontier
Sun 11/28:32 amMDW - JAX
1 stop12h 21mFrontier
Deal found 9/19$202
This Frontier deal was found by Cheapflights users on 9/20. 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 10/126:05 pmJAX - ORD
1 stop6h 34mFrontier
Sun 10/195:05 amORD - JAX
1 stop11h 05mFrontier
Deal found 9/20$204

Cheapflights Fare Finder

 
Customize your flight search to find flights from Jacksonville to Chicago 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 September 22, 2025.
Use the filters below to find and compare flights from Jacksonville to Chicago that are best for you.

Fly from

Jacksonville

Fly to

Chicago

Route

Depart

Return

Price

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 10/16

6:03 pm-11:46 pm

1 stop6h 43m

Chicago Midway

Mon 10/20

12:13 pm-8:47 pm

1 stop7h 34m

$192

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 10/23

6:03 pm-11:46 pm

1 stop6h 43m

Chicago Midway

Mon 10/27

9:45 am-8:58 am

2 stops46h 13m

$257

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Wed 10/22

8:00 am-9:44 am

Nonstop2h 44m

Chicago O'Hare Intl

Sat 10/25

11:10 am-2:39 pm

Nonstop2h 29m

$287

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Tue 10/21

5:10 am-8:32 am

1 stop4h 22m

Chicago O'Hare Intl

Tue 10/21

2:35 pm-10:59 pm

1 stop7h 24m

$297

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Wed 10/15

3:39 pm-10:26 pm

1 stop7h 47m

Chicago O'Hare Intl

Tue 10/21

6:00 am-2:35 pm

1 stop7h 35m

$297

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Tue 10/21

6:10 am-9:40 am

1 stop4h 30m

Chicago Midway

Tue 10/21

5:04 pm-11:59 pm

1 stop5h 55m

$297

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 10/15

6:10 am-11:53 am

1 stop6h 43m

Chicago Midway

Tue 10/21

5:04 pm-11:59 pm

1 stop5h 55m

$297

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 10/16

3:55 pm-5:20 pm

Nonstop2h 25m

Chicago Midway

Sat 10/18

5:45 pm-9:00 pm

Nonstop2h 15m

$300

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Fri 10/31

11:30 am-1:15 pm

Nonstop2h 45m

Chicago O'Hare Intl

Mon 11/3

7:05 am-10:33 am

Nonstop2h 28m

$300

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 12/25

11:10 am-4:35 pm

2 stops6h 25m

Chicago Midway

Tue 1/6

1:35 pm-4:50 pm

Nonstop2h 15m

$302

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/21

Showing 1-10 of 43 results
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The best insider tips for Jacksonville to Chicago 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 Jacksonville to Chicago trip
Airports
JAX

JAX offers quick screening times at TSA and easy check-in, making it one of the most convenient airports in Florida.

Read more about JAXby Matt Meltzer
ORD

For a quick city connection, take the 'L' train from ORD to downtown Chicago, avoiding traffic delays.

Read more about ORDby Ramsey Qubein
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 Jacksonville to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Jacksonville 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 Jacksonville to Chicago

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

Use this chart to determine the optimal time to book a round-trip flight from Jacksonville to Chicago. Price data was last updated on September 19, 2025.

The price you pay for your flight from Jacksonville to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 74 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 Jacksonville to Chicago?

Currently, August is the cheapest month in which you can book a flight from Jacksonville to Chicago (average of $245). Flying from Jacksonville to Chicago in March is currently the most expensive (average of $321). 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 JAX to CHI?

Find hourly flight availability from Jacksonville to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 22, 2025.

One of the essential ways to save on airfare from Jacksonville to Chicago is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 27% on airfare.

What is the cheapest day to fly from Jacksonville to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Jacksonville to Chicago. Price data was last updated on September 14, 2025.

Travelers seeking maximum savings on their Jacksonville to Chicago flight should consider departing on Thursday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Jacksonville to Chicago

Explore weekly flight availability from Jacksonville to Chicago. 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 September 22, 2025.

The most flights from JAX to CHI are scheduled on a Monday (24 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (16 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 22, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Jacksonville to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Delta
8.0
Very good
7,971 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
United Airlines
7.4
Good
8,922 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Frontier
5.8
Fair
3,166 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Jacksonville to Chicago. 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 from for flights from Jacksonville to Chicago?

    Located just 11.2 mi from the city center, Jacksonville is the airport most travelers will use when flying to Chicago from Jacksonville. Booking flights from Jacksonville (JAX) to Chicago should be relatively easy as there are 19 daily outbound flights to Chicago from 5 different airlines.

  • How long is the flight from Jacksonville to Chicago?

    Airlines like Frontier, United Airlines, and Delta fly from Jacksonville to Chicago in about 2h 44m. The time it takes to get you to your destination can typically vary by up to 3h 59m. Jacksonville and Chicago are separated by a distance of 865 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 Jacksonville to Chicago round-trip?

    Flying on Delta is currently your cheapest option to Chicago, with prices starting at $128. Additional round-trip tickets that might be worth considering are offered by Frontier and American Airlines, with the lowest prices starting at $145 and $179, respectively. Delta is priced at 64% lower than the current average price of a flight leaving 3 months from now.

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

    The cheapest airlines for a one-way flight from Jacksonville to Chicago are United Airlines ($139), Southwest ($139), and Delta ($149).

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

    Consider Envoy Air (100%), Republic Airways (100%) or ANA (83%) when booking your flight. These represent the most reliable airlines when flying from Jacksonville to Chicago.

  • What are the cheapest flights from Jacksonville to Chicago?

    Looking for the cheapest flight from Jacksonville to Chicago? While on average our users pay $896, our data indicates the cheapest price to be $101. The most popular route (Jacksonville - Chicago O'Hare Intl), is priced around $191.

  • Can I find deals for flights from Jacksonville to Chicago that include hotel bookings?

    Yes. In addition to deals on Jacksonville to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Jacksonville to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Jacksonville to Chicago.

  • Can I find deals for business class flights from Jacksonville to Chicago?

    Yes. Cheapflights offers flight deals from Jacksonville to Chicago 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 Jacksonville to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Jacksonville to Chicago (average of $245). Flying from Jacksonville to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Jacksonville to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Jacksonville to Chicago

Discover the top 5 airlines that operate flights from Jacksonville to Chicago. 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 September 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$128Average$389FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$145Average$252FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$179Average$339FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$207Average$397FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$236Average$404FlexibilityNo cancel feeOn-time69%

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