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$68+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find cheap flights from Jacksonville to Chicago with Cheapflights

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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

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 October 30, 2025.

This Priceline deal was found by Cheapflights users on 10/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/610:38 pmJAX - ORD
1 stop9h 48mFrontier
Sun 11/95:11 amORD - JAX
1 stop8h 33mFrontier
Deal found 10/30$221
This Priceline deal was found by Cheapflights users on 10/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/37:03 pmJAX - ORD
1 stop6h 56mFrontier
Fri 11/77:20 amORD - JAX
1 stop9h 49mFrontier
Deal found 10/29$222
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/279:48 amJAX - MDW
2 stops13h 55mMultiple Airlines
Thu 12/47:23 pmMDW - JAX
1 stop21h 17mMultiple Airlines
Deal found 10/30$222
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:36 pmJAX - MDW
1 stop4h 36mFrontier
Sun 12/76:37 pmMDW - JAX
2 stops18h 48mFrontier
Deal found 10/28$223
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/41:57 pmJAX - ORD
2 stops21h 19mFrontier
Sun 12/79:47 amORD - JAX
1 stop27h 38mFrontier
Deal found 10/28$225
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2610:59 amJAX - ORD
1 stop14h 09mFrontier
Wed 12/34:01 pmORD - JAX
2 stops19h 30mFrontier
Deal found 10/28$227
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/79:48 amJAX - MDW
2 stops13h 24mMultiple Airlines
Mon 12/86:15 amMDW - JAX
1 stop10h 21mMultiple Airlines
Deal found 10/30$227
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3010:38 pmJAX - ORD
1 stop9h 48mFrontier
Sun 11/25:11 amORD - JAX
1 stop10h 02mFrontier
Deal found 10/28$228
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/305:13 pmJAX - MDW
1 stop5h 50mFrontier
Fri 10/319:15 amMDW - JAX
1 stop11h 38mFrontier
Deal found 10/28$228
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/510:55 amJAX - MDW
2 stops12h 17mMultiple Airlines
Mon 12/86:15 amMDW - JAX
1 stop10h 21mMultiple Airlines
Deal found 10/30$229
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/41:57 pmJAX - ORD
1 stop26h 50mMultiple Airlines
Sun 12/74:47 pmORD - JAX
1 stop20h 38mMultiple Airlines
Deal found 10/29$230
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/275:48 pmJAX - ORD
1 stop22h 35mMultiple Airlines
Thu 12/44:47 pmORD - JAX
1 stop16h 49mMultiple Airlines
Deal found 10/28$232

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 October 30, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$221
(Priceline)

One-way from

$68
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$349

Good round-trip deal

$358 or less

Good one-way deal

$172 or less
Provider with most accurate pricing for Jacksonville-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Jacksonville-Chicago (CHI) flights.
Search Deals
From Jacksonville to Chicago (CHI)
Search Deals
One-way flight from Jacksonville to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Jacksonville to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Jacksonville to Chicago (CHI).
Search Deals

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 October 30, 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 - ORD

JAXORD

Jacksonville

Thu 11/6

10:38 pm-7:26 am

1 stop9h 48m

Chicago O'Hare Intl

Sun 11/9

5:11 am-2:44 pm

1 stop8h 33m

$221

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Sat 12/6

11:15 am-10:35 am

1 stop24h 20m

Chicago O'Hare Intl

Sat 12/13

11:25 am-10:07 am

1 stop21h 42m

$253

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Mon 11/17

11:30 am-1:15 pm

Nonstop2h 45m

Chicago O'Hare Intl

Mon 11/17

4:00 pm-11:04 am

2 stops18h 04m

$263

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Thu 12/4

5:16 pm-7:43 pm

1 stop27h 27m

Chicago O'Hare Intl

Mon 12/8

8:38 pm-10:07 am

1 stop12h 29m

$273

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 12/4

5:00 pm-6:25 pm

Nonstop2h 25m

Chicago Midway

Mon 12/8

1:45 pm-5:00 pm

Nonstop2h 15m

$277

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Wed 12/3

8:10 am-9:54 am

Nonstop2h 44m

Chicago O'Hare Intl

Mon 12/8

11:05 am-2:38 pm

Nonstop2h 33m

$277

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Sat 1/17

9:20 am-8:03 am

2 stops23h 43m

Chicago O'Hare Intl

Sun 1/18

11:12 am-2:46 pm

Nonstop2h 34m

$277

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Wed 1/21

11:00 am-5:44 pm

1 stop7h 44m

Chicago O'Hare Intl

Sat 1/24

8:45 am-7:15 pm

1 stop9h 30m

$281

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Tue 12/23

4:39 pm-6:25 pm

Nonstop2h 46m

Chicago O'Hare Intl

Wed 12/31

1:24 pm-8:10 pm

1 stop5h 46m

$281

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Thu 11/27

9:20 am-1:55 pm

1 stop5h 35m

Chicago O'Hare Intl

Thu 12/4

11:05 am-2:38 pm

Nonstop2h 33m

$281

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 39 results
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Compare providers for flights from Jacksonville to Chicago

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 Jacksonville to Chicago in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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 Jacksonville-Chicago flights, users find the pricing of Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on Jacksonville-Chicago flight deals on Cheapflights vs. Mytrip >95% of the time. Price accuracy is based on data collected from Jacksonville-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Jacksonville-Chicago flights, Cheapflights users trust Mytrip the most. Mytrip 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 Jacksonville-Chicago 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 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 October 24, 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, May is the cheapest month in which you can book a flight from Jacksonville to Chicago (average of $98). Flying from Jacksonville to Chicago in December is currently the most expensive (average of $242). 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 October 30, 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 afternoon tend to be the most expensive. A flight at noon could potentially save you up to 20% 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 October 26, 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.

How much does it cost to fly round-trip from Jacksonville to Chicago?

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

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 October 30, 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
4,243 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

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
7.9
Good
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

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
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

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
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

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
3,122 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

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 7 daily outbound flights to Chicago from 5 different airlines.

  • How long is the flight from Jacksonville to Chicago?

    Airlines like Frontier, JetBlue, and United Airlines fly from Jacksonville to Chicago in about 2h 45m. The time it takes to get you to your destination can typically vary by up to 21h 35m. 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 $108. 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 69% 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 ($123), Southwest ($123), and Delta ($133).

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

    Consider Republic Airways (100%), Envoy Air (96%) or ANA (86%) 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 $836, our data indicates the cheapest price to be $138. The most popular route (Jacksonville - Chicago O'Hare Intl), is priced around $193.

  • 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, May is the cheapest month in which you can book a flight from Jacksonville to Chicago (average of $98). Flying from Jacksonville to Chicago in December is currently the most expensive (average of $242). 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
Porter
Benton Harbor

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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$108Average$394FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$145Average$247FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$179Average$343FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$207Average$394FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$232Average$394FlexibilityNo cancel feeOn-time69%

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