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$173+ Cheap flights from Jacksonville, NC (OAJ) 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
OAJ — CHI
Jun 8 — Jun 151
Mon 6/8
Mon 6/15
1 adult, Economy
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Cheap 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 9, 2026.

This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:06 pm
OAJ
-
ORD
1 stop5h 58m
Delta
Tue 7/145:30 am
ORD
-
OAJ
1 stop4h 49m
Delta
Deal found 5/6$332
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:06 pm
OAJ
-
MDW
1 stop4h 34m
Delta
Tue 7/1411:05 am
MDW
-
OAJ
1 stop5h 59m
Delta
Deal found 5/6$332
This Delta deal was found by Cheapflights users on 5/7. 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 6/44:07 pm
OAJ
-
MDW
1 stop6h 02m
Delta
Mon 6/86:00 am
MDW
-
OAJ
1 stop4h 21m
Delta
Deal found 5/7$355
This Delta deal was found by Cheapflights users on 5/4. 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 6/1112:06 pm
OAJ
-
ORD
1 stop5h 58m
Delta
Tue 6/165:30 am
ORD
-
OAJ
1 stop4h 51m
Delta
Deal found 5/4$398
This Delta deal was found by Cheapflights users on 5/4. 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.
Sun 7/56:00 am
OAJ
-
MDW
1 stop7h 05m
Delta
Tue 7/216:00 am
MDW
-
OAJ
1 stop4h 19m
Delta
Deal found 5/4$398
This American Airlines deal was found by Cheapflights users on 5/4. 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.
Sun 7/51:14 pm
OAJ
-
ORD
1 stop4h 32m
American Airlines
Wed 7/86:30 am
ORD
-
OAJ
1 stop7h 02m
American Airlines
Deal found 5/4$407
This Delta deal was found by Cheapflights users on 5/4. 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.
Sun 7/512:06 pm
OAJ
-
MDW
1 stop5h 20m
Delta
Wed 7/86:00 am
MDW
-
OAJ
1 stop4h 19m
Delta
Deal found 5/4$407
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 7/206:44 pm
OAJ
-
ORD
1 stop6h 09m
Delta
Fri 7/245:30 am
ORD
-
OAJ
1 stop4h 49m
Delta
Deal found 5/5$417
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 7/206:44 pm
OAJ
-
MDW
1 stop4h 31m
Delta
Fri 7/246:00 am
MDW
-
OAJ
1 stop4h 19m
Delta
Deal found 5/5$417
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/241:14 pm
OAJ
-
ORD
1 stop4h 29m
American Airlines
Wed 7/15:10 am
ORD
-
OAJ
1 stop6h 39m
American Airlines
Deal found 5/6$427
This Delta deal was found by Cheapflights users on 5/8. 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.
Fri 7/174:35 pm
OAJ
-
MDW
1 stop6h 40m
Delta
Mon 7/2011:05 am
MDW
-
OAJ
1 stop5h 59m
Delta
Deal found 5/8$427
This Delta deal was found by Cheapflights users on 5/7. 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 5/266:47 pm
OAJ
-
ORD
1 stop4h 40m
Delta
Wed 6/1711:23 am
ORD
-
OAJ
1 stop5h 37m
Delta
Deal found 5/7$437

Find flight deals from Jacksonville to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Jacksonville (OAJ) 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 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$332
(Delta)

One-way from

$173
(American Airlines)
Provider with most accurate pricing for Jacksonville Albert J Ellis-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Jacksonville Albert J Ellis-Chicago (CHI) flights.
Search Deals
From Jacksonville Albert J Ellis to Chicago (CHI)
Search Deals
One-way flight from Jacksonville Albert J Ellis to Chicago (CHI)
Search Deals

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 9, 2026.
Use the filters below to find and compare flights from Jacksonville to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Thu 6/4

4:07 pm-9:09 pm

1 stop6h 02m

Chicago Midway

Mon 6/8

6:00 am-11:21 am

1 stop4h 21m

$355

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Thu 6/11

12:06 pm-5:04 pm

1 stop5h 58m

Chicago O'Hare Intl

Tue 6/16

5:30 am-11:21 am

1 stop4h 51m

$398

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Sat 7/18

4:35 pm-8:33 pm

1 stop4h 58m

Chicago O'Hare Intl

Mon 7/20

9:45 am-6:04 pm

1 stop7h 19m

$398

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Sun 7/5

1:14 pm-4:46 pm

1 stop4h 32m

Chicago O'Hare Intl

Wed 7/8

6:30 am-2:32 pm

1 stop7h 02m

$407

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sun 7/5

12:06 pm-4:26 pm

1 stop5h 20m

Chicago Midway

Wed 7/8

6:00 am-11:19 am

1 stop4h 19m

$407

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Mon 7/20

6:44 pm-11:53 pm

1 stop6h 09m

Chicago O'Hare Intl

Fri 7/24

8:03 am-3:54 pm

1 stop6h 51m

$417
Quickest round-trip

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Mon 7/20

6:44 pm-10:15 pm

1 stop4h 31m

Chicago Midway

Fri 7/24

6:00 am-11:19 am

1 stop4h 19m

$417

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Sat 7/18

4:35 pm-10:15 pm

1 stop6h 40m

Chicago Midway

Mon 7/20

12:41 pm-6:04 pm

1 stop4h 23m

$417

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

Fri 7/17

4:35 pm-10:08 pm

1 stop6h 33m

Chicago O'Hare Intl

Mon 7/20

5:30 am-11:19 am

1 stop4h 49m

$427

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

Fri 7/17

4:35 pm-10:15 pm

1 stop6h 40m

Chicago Midway

Mon 7/20

11:05 am-6:04 pm

1 stop5h 59m

$427

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/5

Showing 1-10 of 28 resultsSorted by cheapest first
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2
3

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*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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, North Carolina-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Jacksonville, North Carolina-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Jacksonville, North Carolina-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Jacksonville, North Carolina-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, North Carolina-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
No data available for this route at this time. Please check back soon.

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?

    Jacksonville Albert J Ellis (OAJ) is the airport you will fly out of if you book a flight from Jacksonville to Chicago. You should not have trouble finding flights to Chicago from Albert J Ellis; the airport handles an average of 0 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 1 airline has flights from the Jacksonville airport to Chicago. It is only a 11.3 mi journey to Albert J Ellis (OAJ) from Jacksonville’s city center.

  • How long is the flight from Jacksonville, North Carolina to Chicago?

    There are many flights that can get you from Jacksonville, North Carolina to Chicago in 4h 32m. Fly via Delta or American Airlines to get the fastest option. Airlines will cover a distance of 743 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Jacksonville, North Carolina to Chicago round-trip?

    According to our current data, American Airlines ($362), offers the cheapest pricing from Jacksonville, North Carolina to Chicago.

  • 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.

See more FAQs

Traveling to a place near Chicago?

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

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Top airline flying from Jacksonville to Chicago

Discover the top airline 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 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$362Average$509FlexibilityNo cancel feeOn-time71%

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