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$79+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — CHI
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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The best prices from Jacksonville to Chicago are usually found in May or September, booked 73 days in advance, depart on a Wednesday 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 January 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$271
(United Airlines)

One-way from

$79
(Trip.com)

Popular in

March

Cheapest in

May

Average price

$393
Provider with most accurate pricing for Jacksonville-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Jacksonville-Chicago (CHI) flights.
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From Jacksonville to Chicago (CHI)
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One-way flight from Jacksonville to Chicago (CHI)
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High demand for flights, 2% potential price rise
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Best time to find cheap flights, 1% potential price drop
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Average for round-trip flights in January 2025
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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 January 21, 2025.

This Delta deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/137:36 amJAX - ORD
1 stop11h 11mDelta
Wed 2/2610:00 amORD - JAX
1 stop9h 41mDelta
Deal found 1/19$273
This JetBlue deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/76:55 amJAX - ORD
1 stop9h 48mJetBlue
Thu 2/2012:45 pmORD - JAX
1 stop6h 19mJetBlue
Deal found 1/19$280
This Frontier deal was found by Cheapflights users on 1/21. 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 5/168:59 amJAX - MDW
1 stop9h 29mFrontier
Mon 5/1912:15 pmMDW - JAX
1 stop8h 21mFrontier
Deal found 1/21$280
This Mytrip deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/148:34 pmJAX - ORD
1 stop16h 16mMultiple Airlines
Mon 2/177:10 amORD - JAX
2 stops11h 44mMultiple Airlines
Deal found 1/20$286
This Delta deal was found by Cheapflights users on 1/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2012:15 pmJAX - MDW
1 stop6h 56mDelta
Mon 2/245:05 pmMDW - JAX
1 stop5h 52mDelta
Deal found 1/21$287
This Frontier deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/110:26 pmJAX - ORD
1 stop9h 16mFrontier
Sun 5/49:45 amORD - JAX
1 stop10h 51mFrontier
Deal found 1/20$290
This Sun Country Air deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1112:40 pmJAX - ORD
1 stop7h 31mSun Country Air
Sun 7/138:10 pmORD - JAX
1 stop14h 28mSun Country Air
Deal found 1/20$295
This American Airlines deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/185:42 amJAX - ORD
Nonstop2h 40mAmerican Airlines
Tue 3/256:38 pmORD - JAX
Nonstop2h 31mAmerican Airlines
Deal found 1/20$297
This Southwest deal was found by Cheapflights users on 1/21. 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.
Thu 2/204:20 pmJAX - MDW
Nonstop2h 40mSouthwest
Mon 2/249:00 amMDW - JAX
Nonstop2h 15mSouthwest
Deal found 1/21$297
This United Airlines deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/159:25 amJAX - ORD
1 stop5h 31mUnited Airlines
Sun 2/1611:20 amORD - JAX
Nonstop2h 28mUnited Airlines
Deal found 1/19$332
This Southwest deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/157:25 amJAX - ORD
1 stop6h 20mSouthwest
Sun 2/1611:25 amORD - JAX
1 stop9h 55mSouthwest
Deal found 1/19$341

Find flights from Jacksonville to Chicago within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Thu 2/13

7:36 am-5:47 pm

1 stop11h 11m

Chicago O'Hare Intl

Wed 2/26

10:00 am-8:41 pm

1 stop9h 41m

$273

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Fri 2/7

6:55 am-3:43 pm

1 stop9h 48m

Chicago O'Hare Intl

Thu 2/20

12:45 pm-8:04 pm

1 stop6h 19m

$280

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Fri 2/14

8:34 pm-11:50 am

1 stop16h 16m

Chicago O'Hare Intl

Mon 2/17

7:10 am-7:54 pm

2 stops11h 44m

$286

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Thu 5/1

10:26 pm-6:42 am

1 stop9h 16m

Chicago O'Hare Intl

Sun 5/4

9:45 am-9:36 pm

1 stop10h 51m

$290

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Fri 7/11

12:40 pm-7:11 pm

1 stop7h 31m

Chicago O'Hare Intl

Sun 7/13

8:10 pm-11:38 am

1 stop14h 28m

$295

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Tue 3/18

5:42 am-7:22 am

Nonstop2h 40m

Chicago O'Hare Intl

Tue 3/25

6:38 pm-10:09 pm

Nonstop2h 31m

$297

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Mon 5/5

8:59 am-5:28 pm

1 stop9h 29m

Chicago Midway

Fri 5/9

12:15 pm-9:36 pm

1 stop8h 21m

$308

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 2/28

5:20 pm-6:50 pm

Nonstop2h 30m

Chicago Midway

Tue 3/4

6:25 am-3:15 pm

1 stop7h 50m

$327

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Sat 2/15

9:25 am-1:56 pm

1 stop5h 31m

Chicago O'Hare Intl

Sun 2/16

11:20 am-2:48 pm

Nonstop2h 28m

$332

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Sat 2/15

7:25 am-12:45 pm

1 stop6h 20m

Chicago O'Hare Intl

Sun 2/16

11:25 am-10:20 pm

1 stop9h 55m

$341

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 24 results
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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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Jacksonville-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.

Travel insights for flights from Jacksonville to Chicago

Get recent, data-driven insights about flights from Jacksonville to Chicago including ideal travel times, pricing trends, and more.

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 January 17, 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 73 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 $320). 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 January 21, 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 in the evening could potentially save you up to 22% 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 January 21, 2025.

Travelers seeking maximum savings on their Jacksonville to Chicago flight should consider departing on Wednesday at noon when fares are most often at their lowest. Saturday evenings 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 January 21, 2025.

The most flights from JAX to CHI are scheduled on a Monday (16 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 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 January 21, 2025.
To help decide which airline to fly from Jacksonville to Chicago, see what other customers have to say about Delta, JetBlue and Southwest. 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
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

JetBlue
7.4
Good
3,201 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

United Airlines
7.4
Good
8,984 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Allegiant Air
7.4
Good
801 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

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 12 daily outbound flights to Chicago from 5 different airlines.

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

    Flying on United Airlines is currently your cheapest option to Chicago, with prices starting at $271. Additional round-trip tickets that might be worth considering are offered by Delta and JetBlue, with the lowest prices starting at $273 and $280, respectively. United Airlines is priced at 23% 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 Frontier ($79), United Airlines ($99), and Southwest ($99).

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

    Consider Gulf Air (92%), ANA (91%) or Alaska Airlines (91%) 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 $1,202, our data indicates the cheapest price to be $133. The most popular route (Jacksonville - Chicago O'Hare Intl), is priced around $249.

  • 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 $320). 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
New Buffalo
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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$143Average$218FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$183Average$320FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$414FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$198Average$378FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$267Average$436FlexibilityNo cancel feeOn-time63%
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