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$163+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Find cheap flights from Jacksonville to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

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Cheapflights Tip: The best prices from Jacksonville to Chicago are usually found in September or August, booked 86 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 May 1, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$310
(American Airlines)

One-way from

$163
(United Airlines)

Popular in

December

Cheapest in

September

Average price

$349

Good round-trip deal

$337 or less

Good one-way deal

$178 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)
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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. 0% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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

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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2012:44 pmJAX - ORD
1 stop5h 31mSun Country Air
Sun 6/298:17 pmORD - JAX
1 stop14h 37mSun Country Air
Deal found 4/29$309
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Mon 6/911:05 amJAX - ORD
1 stop7h 30mAmerican Airlines
Tue 6/107:59 pmORD - JAX
Nonstop2h 36mAmerican Airlines
Deal found 4/30$310
This Southwest deal was found by Cheapflights users on 4/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/287:25 amJAX - MDW
Nonstop2h 30mSouthwest
Wed 6/46:25 amMDW - JAX
1 stop4h 15mSouthwest
Deal found 4/30$310
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/510:29 amJAX - ORD
1 stop9h 00mMultiple Airlines
Thu 5/88:05 pmORD - JAX
1 stop14h 26mMultiple Airlines
Deal found 4/30$312
This JetBlue deal was found by Cheapflights users on 4/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/86:15 amJAX - ORD
1 stop7h 25mJetBlue
Sat 9/131:35 pmORD - JAX
1 stop8h 07mJetBlue
Deal found 4/30$319
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/96:10 amJAX - ORD
1 stop4h 59mDelta
Sat 6/1411:20 amORD - JAX
1 stop5h 29mDelta
Deal found 4/29$320
This Southwest deal was found by Cheapflights users on 4/28. 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.
Thu 5/296:30 amJAX - ORD
1 stop6h 20mSouthwest
Tue 6/37:30 amORD - JAX
2 stops8h 30mSouthwest
Deal found 4/28$325
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/63:57 pmJAX - MDW
1 stop6h 30mDelta
Wed 6/119:24 amMDW - JAX
1 stop6h 42mDelta
Deal found 4/29$347
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/37:49 pmJAX - ORD
1 stop5h 25mFrontier
Mon 7/75:20 amORD - JAX
1 stop11h 43mFrontier
Deal found 4/30$352
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/249:20 amJAX - ORD
1 stop6h 13mUnited Airlines
Sun 5/257:00 amORD - JAX
Nonstop2h 39mUnited Airlines
Deal found 4/30$358
This Mytrip deal was found by Cheapflights users on 4/29. 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 5/293:02 pmJAX - MDW
2 stops28h 08mAllegiant Air
Thu 6/511:45 amMDW - JAX
2 stops25h 27mAllegiant Air
Deal found 4/29$373

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 May 1, 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

Mon 6/9

7:05 am-8:51 am

Nonstop2h 46m

Chicago O'Hare Intl

Wed 6/11

8:05 am-1:42 pm

1 stop4h 37m

$310

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 5/28

7:25 am-8:55 am

Nonstop2h 30m

Chicago Midway

Wed 6/4

6:25 am-11:40 am

1 stop4h 15m

$310

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Fri 5/16

12:30 pm-7:09 pm

1 stop7h 39m

Chicago O'Hare Intl

Sun 5/18

9:15 am-11:43 am

1 stop25h 28m

$315

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Mon 9/8

6:15 am-12:40 pm

1 stop7h 25m

Chicago O'Hare Intl

Fri 9/12

1:35 pm-10:42 pm

1 stop8h 07m

$319

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Mon 6/9

5:40 pm-11:58 pm

1 stop7h 18m

Chicago O'Hare Intl

Tue 6/10

7:10 am-1:30 pm

1 stop5h 20m

$320

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Sun 6/1

9:43 am-11:50 am

2 stops27h 07m

Chicago O'Hare Intl

Tue 6/3

5:51 am-9:53 am

2 stops27h 02m

$321

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 6/6

3:57 pm-9:27 pm

1 stop6h 30m

Chicago Midway

Wed 6/11

9:24 am-5:06 pm

1 stop6h 42m

$347

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Wed 5/28

6:05 am-3:00 pm

2 stops9h 55m

Chicago O'Hare Intl

Wed 6/4

7:30 am-9:25 pm

2 stops12h 55m

$348

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Thu 7/3

7:49 pm-12:14 am

1 stop5h 25m

Chicago O'Hare Intl

Sun 7/6

8:24 am-9:10 pm

1 stop11h 46m

$354

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Sat 5/31

9:20 am-2:33 pm

1 stop6h 13m

Chicago O'Hare Intl

Wed 6/11

11:58 am-3:32 pm

Nonstop2h 34m

$357

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 22 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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust 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 April 25, 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 86 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 May 1, 2025.

One of the essential ways to save on airfare from Jacksonville to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 15% 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 March 30, 2025.

Travelers seeking maximum savings on their Jacksonville to Chicago flight should consider departing on Monday 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 May 1, 2025.

The most flights from JAX to CHI are scheduled on a Thursday (21 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (9 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 May 1, 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
4,294 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

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
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

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
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

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
8,696 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

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.
JetBlue
7.3
Good
2,922 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

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.
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.2

Overall

8.0

Entertainment

7.6

Crew

8.6

Comfort

8.0

Food

7.1

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 11 daily outbound flights to Chicago from 5 different airlines.

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

    Flying on American Airlines is currently your cheapest option to Chicago, with prices starting at $310. Additional round-trip tickets that might be worth considering are offered by Southwest and Sun Country Air, with the lowest prices starting at $310 and $315, respectively. American Airlines is priced at 15% 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 ($163), Allegiant Air ($164), and Frontier ($166).

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

    Consider SkyWest Airlines (97%), Emirates (90%) or ANA (88%) 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 $716, our data indicates the cheapest price to be $148. The most popular route (Jacksonville - Chicago O'Hare Intl), is priced around $255.

  • 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$147Average$185FlexibilityNo cancel feeOn-time62%
DeltaCheapest$196Average$434FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$217Average$362FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$218Average$389FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$236Average$398FlexibilityNo cancel feeOn-time63%

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