HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$105+ 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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
JAX — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 74 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 September 11, 2025.

Round-trip from

$187
(Frontier)

One-way from

$105
(Priceline)

Popular in

December

Cheapest in

September

Average price

$289

Good round-trip deal

$281 or less

Good one-way deal

$152 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 ($26 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 September 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 September 11, 2025.

This Frontier deal was found by Cheapflights users on 9/9. 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.
Sat 10/1811:46 amJAX - ORD
1 stop10h 02mFrontier
Mon 10/2011:51 amORD - JAX
1 stop7h 56mFrontier
Deal found 9/9$187
This Southwest deal was found by Cheapflights users on 9/9. 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 10/297:30 pmJAX - MDW
1 stop3h 55mSouthwest
Sat 11/15:45 pmMDW - JAX
Nonstop2h 15mSouthwest
Deal found 9/9$187
This Southwest deal was found by Cheapflights users on 9/10. 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 10/82:50 pmJAX - MDW
Nonstop2h 20mSouthwest
Wed 10/155:15 amMDW - JAX
1 stop7h 50mSouthwest
Deal found 9/10$189
This Southwest deal was found by Cheapflights users on 9/10. 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 10/26:05 amJAX - ORD
1 stop11h 20mSouthwest
Tue 10/73:10 pmORD - JAX
1 stop4h 15mSouthwest
Deal found 9/10$190
This Frontier deal was found by Cheapflights users on 9/10. 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 10/1011:37 amJAX - MDW
1 stop12h 43mFrontier
Sun 10/126:20 amMDW - JAX
1 stop9h 50mFrontier
Deal found 9/10$190
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/305:13 pmJAX - MDW
1 stop5h 50mFrontier
Sun 11/25:20 amMDW - JAX
1 stop8h 53mFrontier
Deal found 9/9$191
This United Airlines deal was found by Cheapflights users on 9/10. 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 9/301:25 pmJAX - ORD
1 stop7h 50mUnited Airlines
Thu 10/27:00 amORD - JAX
Nonstop2h 25mUnited Airlines
Deal found 9/10$192
This Frontier deal was found by Cheapflights users on 9/11. 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 11/65:13 pmJAX - ORD
2 stops15h 13mFrontier
Sun 11/95:11 amORD - JAX
1 stop8h 33mFrontier
Deal found 9/11$194
This Delta deal was found by Cheapflights users on 9/11. 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 10/16:37 pmJAX - ORD
1 stop4h 37mDelta
Thu 10/29:10 amORD - JAX
1 stop7h 08mDelta
Deal found 9/11$197
This Delta deal was found by Cheapflights users on 9/11. 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 10/227:10 pmJAX - MDW
1 stop4h 04mDelta
Sat 10/254:23 pmMDW - JAX
1 stop6h 36mDelta
Deal found 9/11$197
This Booking.com deal was found by Cheapflights users on 9/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/179:39 pmJAX - ORD
1 stop24h 09mFrontier
Mon 10/2011:51 amORD - JAX
1 stop7h 56mFrontier
Deal found 9/10$198
This Frontier deal was found by Cheapflights users on 9/10. 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 10/212:38 pmJAX - ORD
2 stops11h 42mFrontier
Sun 10/55:10 amORD - JAX
1 stop5h 33mFrontier
Deal found 9/10$199

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 September 11, 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

Wed 10/1

5:20 am-8:40 am

1 stop4h 20m

Chicago O'Hare Intl

Sat 10/4

7:00 am-3:15 pm

1 stop7h 15m

$197

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Wed 10/22

6:25 am-12:45 pm

1 stop7h 20m

Chicago O'Hare Intl

Sat 10/25

1:30 pm-7:45 pm

1 stop5h 15m

$197

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Thu 10/23

12:14 pm-5:22 pm

1 stop6h 08m

Chicago O'Hare Intl

Sat 10/25

7:00 am-4:40 pm

1 stop8h 40m

$197

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Thu 12/11

8:08 pm-12:01 am

1 stop4h 53m

Chicago O'Hare Intl

Sat 12/13

5:32 am-1:42 pm

1 stop7h 10m

$197

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Fri 10/24

3:39 pm-8:37 pm

1 stop5h 58m

Chicago O'Hare Intl

Sat 10/25

6:10 pm-11:59 pm

1 stop4h 49m

$197

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Fri 10/3

1:49 pm-9:21 pm

1 stop8h 32m

Chicago O'Hare Intl

Sun 10/5

5:30 am-10:12 am

1 stop3h 42m

$197

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Wed 10/8

11:39 am-4:11 pm

1 stop5h 32m

Chicago O'Hare Intl

Wed 10/15

6:00 am-2:35 pm

1 stop7h 35m

$197

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 10/1

6:37 pm-9:36 pm

1 stop3h 59m

Chicago Midway

Tue 10/7

12:48 pm-6:05 pm

1 stop4h 17m

$197

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 10/1

6:20 am-9:40 am

1 stop4h 20m

Chicago Midway

Mon 10/6

5:04 pm-9:57 pm

1 stop3h 53m

$197

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Fri 10/3

6:37 pm-9:36 pm

1 stop3h 59m

Chicago Midway

Mon 10/6

5:04 pm-9:57 pm

1 stop3h 53m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 45 results
1
2
3
...
5

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 August 29, 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 74 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 September 11, 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 28% 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 September 7, 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 September 11, 2025.

The most flights from JAX to CHI are scheduled on a Monday (24 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).

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 September 11, 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
4,248 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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
4,248 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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.
Frontier
5.8
Fair
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

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 18 daily outbound flights to Chicago from 5 different airlines.

  • How long is the flight from Jacksonville to Chicago?

    Airlines like Delta and Southwest fly from Jacksonville to Chicago in about 4h 20m. The time it takes to get you to your destination can typically vary by up to 3h. Jacksonville and Chicago are separated by a distance of 865 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Flying on Delta is currently your cheapest option to Chicago, with prices starting at $128. Additional round-trip tickets that might be worth considering are offered by Frontier and American Airlines, with the lowest prices starting at $145 and $179, respectively. Delta is priced at 65% 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 Southwest ($105), JetBlue ($114), and United Airlines ($118).

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

    Consider Republic Airways (100%), ANA (81%) or Alaska Airlines (78%) 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 $940, our data indicates the cheapest price to be $128. The most popular route (Jacksonville - Chicago O'Hare Intl), is priced around $133.

  • 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
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.
Orlando to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Tampa to O'Hare Intl flights
Miami to O'Hare Intl flights
Orlando to Midway flights
Tampa to Midway flights
Miami to Midway flights
Jacksonville to O'Hare Intl flights
West Palm Beach to O'Hare Intl flights
Fort Myers to O'Hare Intl flights
Pensacola to O'Hare Intl flights
Orlando to St. Louis flights
Fort Lauderdale to Midway flights
Sarasota to O'Hare Intl flights
West Palm Beach to Midway flights
Tampa to St. Louis flights
Jacksonville to Midway flights
Miami to St. Louis flights
Fort Lauderdale to St. Louis flights
Pensacola to Midway flights
Fort Myers to St. Louis flights
Fort Myers to Midway flights
Sarasota to Midway flights
West Palm Beach to St. Louis flights
Tallahassee to O'Hare Intl flights
Jacksonville to St. Louis flights
Valparaiso to O'Hare Intl flights
Sarasota to St. Louis flights
Panama City to St. Louis flights
Panama City to O'Hare Intl flights
Tallahassee to Midway flights
Jacksonville to Peoria flights
Melbourne to O'Hare Intl flights
Daytona Beach to O'Hare Intl flights
Orlando to Moline flights
Pensacola to St. Louis flights
Key West to O'Hare Intl flights
Orlando to Peoria flights
Panama City to Midway flights
Tampa to Moline flights
Gainesville to O'Hare Intl flights
St Petersburg to Rockford flights
Jacksonville to Moline flights
Melbourne to Midway flights
Orlando Sanford Intl to Rockford flights
Valdosta to O'Hare Intl flights
Gainesville to Midway flights
Fort Lauderdale to Evansville flights
Gainesville to St. Louis 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$128Average$389FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$145Average$272FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$179Average$344FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$207Average$397FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$237Average$409FlexibilityNo 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.