HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$103+ 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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — CHI
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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

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 July 30, 2025.

Round-trip from

$181
(American Airlines)

One-way from

$103
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$361

Good round-trip deal

$236 or less

Good one-way deal

$181 or less
From Jacksonville to Chicago (CHI)
Search Deals
One-way flight from Jacksonville to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($25 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 July 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 July 30, 2025.

This American Airlines deal was found by Cheapflights users on 7/30. 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.
Tue 8/2612:34 pmJAX - ORD
Nonstop2h 39mAmerican Airlines
Tue 8/266:55 pmORD - JAX
Nonstop2h 32mAmerican Airlines
Deal found 7/30$181
This Southwest deal was found by Cheapflights users on 7/27. 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 8/232:05 pmJAX - MDW
Nonstop2h 25mSouthwest
Sat 8/235:30 pmMDW - JAX
Nonstop2h 15mSouthwest
Deal found 7/27$181
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/96:54 pmJAX - ORD
1 stop5h 21mUnited Airlines
Tue 9/166:26 pmORD - JAX
Nonstop2h 32mUnited Airlines
Deal found 7/29$191
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/205:20 amJAX - ORD
1 stop4h 17mDelta
Wed 8/2012:59 pmORD - JAX
1 stop8h 38mDelta
Deal found 7/28$201
This Delta deal was found by Cheapflights users on 7/27. 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.
Sat 9/205:08 pmJAX - MDW
1 stop5h 02mDelta
Tue 9/236:00 amMDW - JAX
1 stop4h 40mDelta
Deal found 7/27$201
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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.
Thu 9/1812:38 pmJAX - MDW
1 stop4h 20mFrontier
Sun 9/218:06 amMDW - JAX
1 stop5h 33mFrontier
Deal found 7/29$205
This Frontier deal was found by Cheapflights users on 7/28. 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 8/215:30 pmJAX - ORD
1 stop7h 24mFrontier
Thu 8/285:10 amORD - JAX
1 stop10h 35mFrontier
Deal found 7/28$218
This Southwest deal was found by Cheapflights users on 7/30. 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.
Tue 8/198:15 amJAX - ORD
2 stops14h 15mSouthwest
Mon 8/251:50 pmORD - JAX
1 stop6h 20mSouthwest
Deal found 7/30$234
This JetBlue deal was found by Cheapflights users on 7/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/86:35 amJAX - ORD
1 stop6h 35mJetBlue
Fri 9/121:36 pmORD - JAX
1 stop8h 45mJetBlue
Deal found 7/29$255
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1111:47 amJAX - ORD
2 stops10h 43mMultiple Airlines
Thu 8/1410:12 amORD - JAX
2 stops24h 05mMultiple Airlines
Deal found 7/28$266

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 July 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

Tue 8/26

12:34 pm-2:13 pm

Nonstop2h 39m

Chicago O'Hare Intl

Tue 8/26

6:55 pm-10:27 pm

Nonstop2h 32m

$181

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 8/23

2:05 pm-3:30 pm

Nonstop2h 25m

Chicago Midway

Sat 8/23

5:30 pm-8:45 pm

Nonstop2h 15m

$181

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Tue 9/9

9:15 am-2:29 pm

1 stop6h 14m

Chicago O'Hare Intl

Tue 9/16

11:17 am-2:46 pm

Nonstop2h 29m

$191

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Wed 8/20

5:20 am-8:37 am

1 stop4h 17m

Chicago O'Hare Intl

Wed 8/20

12:59 pm-10:37 pm

1 stop8h 38m

$201

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sat 9/20

5:08 pm-9:10 pm

1 stop5h 02m

Chicago Midway

Tue 9/23

6:00 am-11:40 am

1 stop4h 40m

$201

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Thu 9/18

12:38 pm-3:58 pm

1 stop4h 20m

Chicago Midway

Sun 9/21

8:06 am-2:39 pm

1 stop5h 33m

$205

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Thu 8/21

5:30 pm-11:54 pm

1 stop7h 24m

Chicago O'Hare Intl

Thu 8/28

5:10 am-4:45 pm

1 stop10h 35m

$218

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Tue 8/19

8:15 am-9:30 pm

2 stops14h 15m

Chicago O'Hare Intl

Mon 8/25

1:50 pm-9:10 pm

1 stop6h 20m

$234

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Mon 9/8

6:35 am-12:10 pm

1 stop6h 35m

Chicago O'Hare Intl

Fri 9/12

1:36 pm-11:21 pm

1 stop8h 45m

$255

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Mon 8/11

11:47 am-9:30 pm

2 stops10h 43m

Chicago O'Hare Intl

Thu 8/14

10:12 am-11:17 am

2 stops24h 05m

$266

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 21 results
1
2
3

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

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 July 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 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, 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 July 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 morning tend to be the most expensive. A flight at noon could potentially save you up to 18% 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 July 27, 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.

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 July 30, 2025.

The most flights from JAX to CHI are scheduled on a Wednesday (21 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

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

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 July 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
4,241 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

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
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

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
8,896 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

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
2,913 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

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
10,000 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

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 14 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 $181. Additional round-trip tickets that might be worth considering are offered by Southwest and United Airlines, with the lowest prices starting at $181 and $191, respectively. American Airlines is priced at 50% 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 ($103), Southwest ($106), and American Airlines ($113).

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

    Consider Republic Airways (100%), Envoy Air (95%) or American Airlines (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 $2,329, our data indicates the cheapest price to be $112. The most popular route (Jacksonville - Chicago O'Hare Intl), is priced around $181.

  • 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Jacksonville to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Fort Lauderdale to O'Hare Intl flights
Miami to O'Hare Intl flights
Orlando to O'Hare Intl flights
Tampa to O'Hare Intl flights
West Palm Beach to O'Hare Intl flights
Miami to Midway flights
Orlando to Midway flights
Tampa to Midway flights
Jacksonville to O'Hare Intl flights
Fort Myers to O'Hare Intl flights
Fort Lauderdale to Midway flights
Pensacola to O'Hare Intl flights
West Palm Beach to Midway flights
Sarasota to O'Hare Intl flights
Miami to St. Louis flights
Jacksonville to Midway flights
Fort Myers to St. Louis flights
Orlando to St. Louis flights
Tampa to St. Louis flights
Pensacola to Midway flights
Fort Myers to Midway flights
Panama City to O'Hare Intl flights
Jacksonville to St. Louis flights
Fort Lauderdale to St. Louis flights
West Palm Beach to St. Louis flights
St Petersburg to Rockford flights
Panama City to Moline flights
Sarasota to Midway flights
Sarasota to St. Louis flights
Tallahassee to O'Hare Intl flights
Valparaiso to O'Hare Intl flights
Pensacola to Moline flights
Orlando to Moline flights
Fort Lauderdale to Rockford flights
Key West to O'Hare Intl flights
Melbourne to O'Hare Intl flights
Tallahassee to Midway flights
Pensacola to St. Louis flights
Fort Myers to Peoria flights
Daytona Beach to O'Hare Intl flights
Jacksonville to Moline flights
Panama City to Midway flights
Tampa to Peoria flights
Orlando Sanford Intl to Rockford flights
Gainesville to O'Hare Intl flights
Daytona Beach to Midway flights
Key West to Midway flights
Panama City to St. Louis flights
Tampa to Moline flights
Jacksonville to Peoria flights

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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$140Average$275FlexibilityNo cancel feeOn-time62%
DeltaCheapest$148Average$401FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$179Average$358FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$207Average$397FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$217Average$398FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
Privacy Preferences©2025 Cheapflights