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$139+ 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 7/25. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — CHI
Jun 28 — Jul 51
Sat 6/28
Sat 7/5
1 adult, Economy
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Cheapflights Tip: The best prices from Jacksonville to Chicago are usually found in September or August, booked 64 days in advance, depart on a Friday or Thursday 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 June 23, 2025.

Round-trip from

$220
(Southwest)

One-way from

$139
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$397

Good round-trip deal

$370 or less

Good one-way deal

$185 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. 5% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($4 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 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 June 23, 2025.

This Southwest deal was found by Cheapflights users on 6/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/207:05 amJAX - MDW
2 stops10h 30mSouthwest
Mon 9/227:15 amMDW - JAX
1 stop10h 25mSouthwest
Deal found 6/22$220
This United Airlines deal was found by Cheapflights users on 6/21. 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.
Fri 9/261:25 pmJAX - ORD
1 stop7h 33mUnited Airlines
Mon 9/297:00 amORD - JAX
Nonstop2h 25mUnited Airlines
Deal found 6/21$221
This Delta deal was found by Cheapflights users on 6/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/227:51 pmJAX - ORD
1 stop5h 05mDelta
Wed 8/277:10 amORD - JAX
1 stop6h 12mDelta
Deal found 6/22$223
This Delta deal was found by Cheapflights users on 6/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/55:35 pmJAX - MDW
1 stop5h 07mDelta
Thu 8/149:31 amMDW - JAX
1 stop6h 16mDelta
Deal found 6/22$223
This American Airlines deal was found by Cheapflights users on 6/21. 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.
Thu 9/186:34 pmJAX - ORD
1 stop6h 05mAmerican Airlines
Sat 9/209:46 amORD - JAX
Nonstop2h 25mAmerican Airlines
Deal found 6/21$224
This Mytrip deal was found by Cheapflights users on 6/21. 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 7/319:44 amJAX - ORD
2 stops15h 09mMultiple Airlines
Sat 8/165:15 pmORD - JAX
2 stops20h 45mMultiple Airlines
Deal found 6/21$242
This Frontier deal was found by Cheapflights users on 6/21. 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 7/137:49 pmJAX - ORD
1 stop5h 33mFrontier
Mon 7/145:20 amORD - JAX
1 stop11h 43mFrontier
Deal found 6/21$248
This Frontier deal was found by Cheapflights users on 6/21. 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 7/184:33 pmJAX - MDW
1 stop8h 18mFrontier
Mon 7/216:00 amMDW - JAX
1 stop11h 03mFrontier
Deal found 6/21$268
This Southwest deal was found by Cheapflights users on 6/21. 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.
Fri 9/267:20 amJAX - ORD
2 stops10h 05mSouthwest
Sat 9/277:00 amORD - JAX
1 stop8h 40mSouthwest
Deal found 6/21$273
This Sun Country Air deal was found by Cheapflights users on 6/22. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/211:02 pmJAX - ORD
1 stop22h 43mSun Country Air
Thu 7/316:23 pmORD - JAX
1 stop16h 37mSun Country Air
Deal found 6/22$285

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 June 23, 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

Sat 9/20

7:05 am-4:35 pm

2 stops10h 30m

Chicago Midway

Mon 9/22

7:15 am-6:40 pm

1 stop10h 25m

$220

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Fri 9/26

1:25 pm-7:58 pm

1 stop7h 33m

Chicago O'Hare Intl

Mon 9/29

7:00 am-10:25 am

Nonstop2h 25m

$221

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Fri 8/22

6:44 pm-11:56 pm

1 stop6h 12m

Chicago O'Hare Intl

Wed 8/27

5:45 am-1:29 pm

1 stop6h 44m

$223

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Tue 8/5

5:35 pm-9:42 pm

1 stop5h 07m

Chicago Midway

Thu 8/14

9:31 am-4:47 pm

1 stop6h 16m

$223

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Thu 9/18

6:34 pm-11:39 pm

1 stop6h 05m

Chicago O'Hare Intl

Sat 9/20

9:46 am-1:11 pm

Nonstop2h 25m

$224

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Thu 7/31

9:44 am-11:53 pm

2 stops15h 09m

Chicago O'Hare Intl

Sat 8/16

5:15 pm-3:00 pm

2 stops20h 45m

$242

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Sun 7/13

7:49 pm-12:22 am

1 stop5h 33m

Chicago O'Hare Intl

Mon 7/14

5:20 am-6:03 pm

1 stop11h 43m

$248

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 7/18

4:33 pm-11:51 pm

1 stop8h 18m

Chicago Midway

Mon 7/21

6:00 am-6:03 pm

1 stop11h 03m

$268

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Fri 9/26

7:20 am-4:25 pm

2 stops10h 05m

Chicago O'Hare Intl

Sat 9/27

7:00 am-4:40 pm

1 stop8h 40m

$273

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Mon 7/21

1:02 pm-10:45 am

1 stop22h 43m

Chicago O'Hare Intl

Thu 7/31

6:23 pm-12:00 pm

1 stop16h 37m

$285

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/22

Showing 1-10 of 23 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 June 20, 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 64 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 June 23, 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 12% 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 June 22, 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 June 23, 2025.

The most flights from JAX to CHI are scheduled on a Monday (21 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (7 on average).

Rainfall in Chicago by month

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

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

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

If weather is an important factor for your trip to Chicago, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 23, 2025.
To help decide which airline to fly from Jacksonville to Chicago, see what other customers have to say about Southwest, Delta and United Airlines. 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
4,278 reviews

Food

7.0

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

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
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Food

7.0

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

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
7,965 reviews
Southwest
8.0
Very good
4,278 reviews

Food

7.0

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

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
8,830 reviews
Southwest
8.0
Very good
4,278 reviews

Food

7.0

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

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.
JetBlue
7.3
Good
2,922 reviews
Southwest
8.0
Very good
4,278 reviews

Food

7.0

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

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
4,278 reviews

Food

7.0

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

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 17 daily outbound flights to Chicago from 5 different airlines.

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

    Flying on Southwest is currently your cheapest option to Chicago, with prices starting at $220. Additional round-trip tickets that might be worth considering are offered by United Airlines and Delta, with the lowest prices starting at $221 and $223, respectively. Southwest is priced at 40% 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 American Airlines ($139), Southwest ($139), and Frontier ($144).

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

    Consider Republic Airways (100%), Alaska Airlines (94%) or Envoy Air (94%) 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 $1,197, our data indicates the cheapest price to be $138. The most popular route (Jacksonville - Chicago O'Hare Intl), is priced around $181.

  • 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 Jacksonville?

Book flights to Jacksonville if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
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 June 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$140Average$275FlexibilityNo cancel feeOn-time62%
DeltaCheapest$155Average$447FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$213Average$390FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$217Average$364FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$267Average$399FlexibilityNo cancel feeOn-time63%

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