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$134+ 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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — CHI
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
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The best prices from Jacksonville to Chicago are usually found in February or May, 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 December 18, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$277
(American Airlines)

One-way from

$134
(United Airlines)

Popular in

March

Cheapest in

February

Average price

$399
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, 4% 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 December 2024
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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 December 18, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 12/17. 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.
Mon 12/304:33 pmJAX - MDW
1 stop5h 31mFrontier
Thu 1/27:34 amMDW - JAX
1 stop6h 09mFrontier
Deal found 12/17$333
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Wed 12/256:04 amJAX - ORD
Nonstop2h 47mAmerican Airlines
Wed 1/16:40 pmORD - JAX
Nonstop2h 46mAmerican Airlines
Deal found 12/17$337
This Southwest deal was found by Cheapflights users on 12/17. 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 12/251:35 pmJAX - ORD
1 stop8h 55mSouthwest
Wed 1/15:45 amORD - JAX
2 stops13h 35mSouthwest
Deal found 12/17$403
This Delta deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/317:05 amJAX - ORD
1 stop6h 39mDelta
Mon 1/67:40 pmORD - JAX
1 stop14h 54mDelta
Deal found 12/17$443
This Southwest deal was found by Cheapflights users on 12/16. 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 12/314:35 pmJAX - MDW
Nonstop2h 30mSouthwest
Wed 1/112:35 pmMDW - JAX
Nonstop2h 15mSouthwest
Deal found 12/16$450
This Mytrip deal was found by Cheapflights users on 12/17. 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.
Sun 12/2910:05 pmJAX - ORD
2 stops19h 01mMultiple Airlines
Sat 1/41:24 pmORD - JAX
3 stops31h 01mMultiple Airlines
Deal found 12/17$475
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Tue 12/316:00 amJAX - ORD
Nonstop2h 46mUnited Airlines
Fri 1/37:25 amORD - JAX
1 stop8h 12mUnited Airlines
Deal found 12/17$479
This Delta deal was found by Cheapflights users on 12/17. 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.
Wed 12/2511:23 amJAX - MDW
1 stop5h 47mDelta
Tue 12/313:32 pmMDW - JAX
1 stop4h 47mDelta
Deal found 12/17$527

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 December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Wed 2/12

9:40 am-11:22 am

Nonstop2h 42m

Chicago O'Hare Intl

Sat 2/15

8:16 am-1:20 pm

1 stop4h 04m

$277

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 2/28

9:05 pm-12:15 am

1 stop4h 10m

Chicago Midway

Sun 3/2

1:15 pm-4:30 pm

Nonstop2h 15m

$282

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Thu 1/16

12:20 pm-2:13 pm

Nonstop2h 53m

Chicago O'Hare Intl

Tue 1/21

6:10 pm-9:42 pm

Nonstop2h 32m

$287

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Thu 1/16

6:55 am-3:44 pm

1 stop9h 49m

Chicago O'Hare Intl

Thu 1/23

7:00 am-2:00 pm

1 stop6h 00m

$298

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Fri 5/2

12:30 pm-7:09 pm

1 stop7h 39m

Chicago O'Hare Intl

Sun 5/4

8:05 pm-11:43 am

1 stop14h 38m

$299

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 1/9

12:24 pm-6:14 pm

1 stop6h 50m

Chicago Midway

Sun 1/12

6:00 am-12:54 pm

1 stop5h 54m

$307

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Tue 2/4

2:59 pm-8:46 pm

1 stop6h 47m

Chicago O'Hare Intl

Sat 2/8

8:00 am-1:54 pm

1 stop4h 54m

$316

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Wed 1/8

9:31 am-10:57 pm

1 stop14h 26m

Chicago O'Hare Intl

Wed 1/15

5:11 am-10:40 am

3 stops28h 29m

$333

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Mon 12/30

4:33 pm-9:04 pm

1 stop5h 31m

Chicago Midway

Thu 1/2

7:34 am-2:43 pm

1 stop6h 09m

$333

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Fri 2/28

7:25 am-2:00 pm

1 stop7h 35m

Chicago O'Hare Intl

Sun 3/2

11:25 am-9:40 pm

2 stops9h 15m

$347

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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 December 13, 2024.

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, September is the cheapest month in which you can book a flight from Jacksonville to Chicago (average of $232). Flying from Jacksonville to Chicago in June is currently the most expensive (average of $308). 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 December 18, 2024.

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 evening tend to be the most expensive. A flight at noon could potentially save you up to 30% 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 December 16, 2024.

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.

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 December 18, 2024.
To help decide which airline to fly from Jacksonville to Chicago, see what other customers have to say about American Airlines, United Airlines and Delta. 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
4,848 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Delta
8.0
Very good
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

JetBlue
7.4
Good
3,279 reviews
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

United Airlines
7.4
Good
9,055 reviews
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

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 6 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 $277. Additional round-trip tickets that might be worth considering are offered by Southwest and United Airlines, with the lowest prices starting at $282 and $287, respectively. American Airlines is priced at 20% 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 ($134), Sun Country Air ($140), and Southwest ($149).

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

    Consider ANA (93%), Qatar Airways (89%) or Gulf Air (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 $1,219, our data indicates the cheapest price to be $138. The most popular route (Jacksonville - Chicago O'Hare Intl), is priced around $202.

  • 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, September is the cheapest month in which you can book a flight from Jacksonville to Chicago (average of $232). Flying from Jacksonville to Chicago in June is currently the most expensive (average of $308). 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.

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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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$143Average$218FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$183Average$316FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$408FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$198Average$376FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$268Average$434FlexibilityNo cancel feeOn-time63%
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