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$159+ 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 6/29. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — CHI
May 11 — May 181
Sun 5/11
Sun 5/18
1 adult, Economy
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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”

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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 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 May 6, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$301
(Southwest)

One-way from

$159
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$347

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)
Search Deals
One-way flight from Jacksonville to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 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 6, 2025.

This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/244:20 pmJAX - MDW
Nonstop2h 25mSouthwest
Thu 6/261:25 pmMDW - JAX
Nonstop2h 15mSouthwest
Deal found 5/6$301
This Mytrip deal was found by Cheapflights users on 5/6. 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.
Tue 6/2411:15 amJAX - ORD
2 stops20h 22mMultiple Airlines
Thu 6/267:56 amORD - JAX
2 stops29h 16mMultiple Airlines
Deal found 5/6$302
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/136:25 amJAX - ORD
2 stops9h 55mSouthwest
Sat 8/167:00 amORD - JAX
1 stop8h 40mSouthwest
Deal found 5/6$306
This American Airlines deal was found by Cheapflights users on 5/5. 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 5/267:00 amJAX - ORD
Nonstop2h 46mAmerican Airlines
Tue 5/277:00 amORD - JAX
1 stop5h 43mAmerican Airlines
Deal found 5/5$310
This United Airlines deal was found by Cheapflights users on 5/5. 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.
Wed 6/44:40 pmJAX - ORD
Nonstop2h 45mUnited Airlines
Fri 6/66:20 pmORD - JAX
Nonstop2h 34mUnited Airlines
Deal found 5/5$317
This Delta deal was found by Cheapflights users on 5/5. 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 5/265:10 amJAX - ORD
1 stop4h 19mDelta
Tue 5/277:05 amORD - JAX
1 stop5h 11mDelta
Deal found 5/5$320
This Delta deal was found by Cheapflights users on 5/5. 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.
Thu 6/53:57 pmJAX - MDW
1 stop6h 30mDelta
Sat 6/712:48 pmMDW - JAX
1 stop6h 25mDelta
Deal found 5/5$320
This Sun Country Air deal was found by Cheapflights users on 5/6. 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.
Fri 6/612:44 pmJAX - ORD
1 stop5h 31mSun Country Air
Sun 6/86:30 amORD - JAX
1 stop28h 08mSun Country Air
Deal found 5/6$325
This JetBlue deal was found by Cheapflights users on 5/6. 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.
Tue 5/2011:40 amJAX - ORD
1 stop7h 56mJetBlue
Sun 5/258:45 amORD - JAX
1 stop9h 42mJetBlue
Deal found 5/6$327
This FlightHub deal was found by Cheapflights users on 5/5. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/611:55 amJAX - ORD
1 stop7h 09mFrontier
Mon 6/96:20 amORD - JAX
1 stop10h 58mFrontier
Deal found 5/5$330
This Mytrip deal was found by Cheapflights users on 5/6. 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.
Tue 6/2411:15 amJAX - MDW
2 stops29h 22mAllegiant Air
Thu 6/2611:45 amMDW - JAX
2 stops25h 27mAllegiant Air
Deal found 5/6$339
This Frontier deal was found by Cheapflights users on 5/6. 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 6/157:49 pmJAX - MDW
1 stop4h 29mFrontier
Fri 6/276:00 amMDW - JAX
1 stop11h 07mFrontier
Deal found 5/6$352

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 6, 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

Tue 6/24

4:20 pm-5:45 pm

Nonstop2h 25m

Chicago Midway

Thu 6/26

1:25 pm-4:40 pm

Nonstop2h 15m

$301

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Tue 6/24

11:15 am-6:37 am

2 stops20h 22m

Chicago O'Hare Intl

Thu 6/26

7:56 am-2:12 pm

2 stops29h 16m

$302

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Mon 5/26

7:00 am-8:46 am

Nonstop2h 46m

Chicago O'Hare Intl

Tue 5/27

7:00 am-1:43 pm

1 stop5h 43m

$310

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Wed 5/28

6:05 am-3:00 pm

2 stops9h 55m

Chicago O'Hare Intl

Tue 6/17

7:30 am-2:10 pm

1 stop5h 40m

$313

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Wed 6/4

4:40 pm-6:25 pm

Nonstop2h 45m

Chicago O'Hare Intl

Fri 6/6

6:20 pm-9:54 pm

Nonstop2h 34m

$317

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Mon 5/26

5:10 am-8:29 am

1 stop4h 19m

Chicago O'Hare Intl

Tue 5/27

7:05 am-1:16 pm

1 stop5h 11m

$320

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 6/5

3:57 pm-9:27 pm

1 stop6h 30m

Chicago Midway

Sat 6/7

12:48 pm-8:13 pm

1 stop6h 25m

$320

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Fri 6/6

12:44 pm-5:15 pm

1 stop5h 31m

Chicago O'Hare Intl

Sun 6/8

6:30 am-11:38 am

1 stop28h 08m

$325

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Tue 5/20

11:40 am-6:36 pm

1 stop7h 56m

Chicago O'Hare Intl

Sun 5/25

8:45 am-7:27 pm

1 stop9h 42m

$327

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Fri 6/6

11:55 am-6:04 pm

1 stop7h 09m

Chicago O'Hare Intl

Mon 6/9

6:20 am-6:18 pm

1 stop10h 58m

$330

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/5

Showing 1-10 of 24 results
1
2
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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 May 2, 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 6, 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 in the evening 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 May 5, 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. Friday 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 6, 2025.

The most flights from JAX to CHI are scheduled on a Tuesday (21 on average). You will have fewer flight options on Saturday, 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 6, 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
4,292 reviews

Food

7.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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
4,292 reviews
Southwest
8.0
Very good
4,292 reviews

Food

7.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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
7,942 reviews
Southwest
8.0
Very good
4,292 reviews

Food

7.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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
8,708 reviews
Southwest
8.0
Very good
4,292 reviews

Food

7.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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
2,921 reviews
Southwest
8.0
Very good
4,292 reviews

Food

7.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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
4,292 reviews

Food

7.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

Boarding

8.2

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 15 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 $301. Additional round-trip tickets that might be worth considering are offered by American Airlines and United Airlines, with the lowest prices starting at $310 and $317, respectively. Southwest is priced at 18% 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 Allegiant Air ($159), Frontier ($160), and American Airlines ($162).

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

    Consider SkyWest Airlines (94%), Republic Airways (90%) or ANA (90%) 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 $737, our data indicates the cheapest price to be $144. The most popular route (Jacksonville - Chicago O'Hare Intl), is priced around $227.

  • 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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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 May 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$147Average$185FlexibilityNo cancel feeOn-time62%
DeltaCheapest$148Average$438FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$217Average$365FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$219Average$389FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$236Average$398FlexibilityNo cancel feeOn-time63%

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