$211+ 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 7/17. Fares are subject to change and may not be available on all flights or dates of travel.
OAJ — CHI
Jul 8 — Jul 151
Round-trip
1 adult, Economy
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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
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Jacksonville to Chicago
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Best
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Cheapest flights from Jacksonville to ChicagoExplore 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 June 8, 2026.
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 June 8, 2026.
This American Airlines deal was found by Cheapflights users on 6/6. 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.
Sat 7/46:37 am
OAJ
- ORD
1 stop5h 23m
American Airlines
Sat 7/114:45 pm
ORD
- OAJ
1 stop4h 31m
American Airlines
Deal found 6/6![American Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 6/7. 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.
Fri 7/36:40 pm
OAJ
- ORD
1 stop6h 19m
Delta
Thu 7/98:03 am
ORD
- OAJ
1 stop6h 51m
Delta
Deal found 6/7![Delta logo]()
$386
This Delta deal was found by Cheapflights users on 6/4. 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.
Fri 7/36:40 pm
OAJ
- MDW
1 stop4h 37m
Delta
Thu 7/912:41 pm
MDW
- OAJ
1 stop4h 21m
Delta
Deal found 6/4![Delta logo]()
$396
This Delta deal was found by Cheapflights users on 6/7. 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.
Sun 8/96:00 am
OAJ
- ORD
1 stop7h 40m
Delta
Wed 8/193:25 pm
ORD
- OAJ
1 stop6h 04m
Delta
Deal found 6/7![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 6/7. 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.
Sun 8/96:00 am
OAJ
- MDW
1 stop6h 51m
Delta
Wed 8/196:05 am
MDW
- OAJ
1 stop6h 41m
Delta
Deal found 6/7![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 6/7. 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.
Mon 8/106:00 am
OAJ
- ORD
1 stop5h 13m
Delta
Thu 8/205:30 am
ORD
- OAJ
1 stop5h 00m
Delta
Deal found 6/7![Delta logo]()
$417
This Delta deal was found by Cheapflights users on 6/7. 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.
Mon 8/106:00 am
OAJ
- MDW
1 stop6h 51m
Delta
Thu 8/206:05 am
MDW
- OAJ
1 stop4h 25m
Delta
Deal found 6/7![Delta logo]()
$417
This American Airlines deal was found by Cheapflights users on 6/6. 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.
Fri 7/31:14 pm
OAJ
- ORD
1 stop7h 37m
American Airlines
Sun 7/56:30 am
ORD
- OAJ
1 stop7h 02m
American Airlines
Deal found 6/6![American Airlines logo]()
$428
Best flights from Jacksonville to ChicagoDiscover carefully curated flight deals from Jacksonville to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 8, 2026.
Discover carefully curated flight deals from Jacksonville to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 8, 2026.
This Delta deal was found by Cheapflights users on 6/8. 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 7/36:40 pm
OAJ
- ORD
1 stop6h 19m
Delta
Thu 7/98:03 am
ORD
- OAJ
1 stop6h 51m
Delta
Deal found 6/8![Delta logo]()
$386
This American Airlines deal was found by Cheapflights users on 6/4. 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.
Fri 9/251:52 pm
OAJ
- ORD
1 stop4h 46m
American Airlines
Sun 9/276:45 am
ORD
- OAJ
1 stop6h 39m
American Airlines
Deal found 6/4![American Airlines logo]()
$417
This Delta deal was found by Cheapflights users on 6/4. 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.
Fri 7/36:40 pm
OAJ
- MDW
1 stop4h 37m
Delta
Thu 7/912:41 pm
MDW
- OAJ
1 stop4h 21m
Delta
Deal found 6/4![Delta logo]()
$396
This Delta deal was found by Cheapflights users on 6/7. 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.
Sun 8/96:00 am
OAJ
- ORD
1 stop7h 40m
Delta
Wed 8/193:25 pm
ORD
- OAJ
1 stop6h 04m
Delta
Deal found 6/7![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 6/7. 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 8/112:27 pm
OAJ
- ORD
1 stop5h 22m
Delta
Fri 8/216:40 am
ORD
- OAJ
1 stop6h 06m
Delta
Deal found 6/7![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 6/7. 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.
Sun 8/96:00 am
OAJ
- MDW
1 stop6h 51m
Delta
Wed 8/196:05 am
MDW
- OAJ
1 stop6h 41m
Delta
Deal found 6/7![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 6/7. 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 8/116:00 am
OAJ
- MDW
1 stop4h 59m
Delta
Fri 8/2112:46 pm
MDW
- OAJ
1 stop4h 21m
Delta
Deal found 6/7![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 6/7. 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.
Mon 8/106:48 pm
OAJ
- MDW
1 stop4h 48m
Delta
Wed 8/196:05 am
MDW
- OAJ
1 stop4h 25m
Delta
Deal found 6/7![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 6/7. 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.
Mon 8/106:00 am
OAJ
- ORD
1 stop5h 13m
Delta
Thu 8/205:30 am
ORD
- OAJ
1 stop5h 00m
Delta
Deal found 6/7![Delta logo]()
$417
This Delta deal was found by Cheapflights users on 6/7. 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.
Mon 8/1012:10 pm
OAJ
- MDW
1 stop5h 05m
Delta
Thu 8/2012:46 pm
MDW
- OAJ
1 stop4h 21m
Delta
Deal found 6/7![Delta logo]()
$417
Last-minute flights from Jacksonville to ChicagoDiscover last-minute flight deals from Jacksonville to Chicago. Data last updated June 8, 2026 and is based on user searches.
Discover last-minute flight deals from Jacksonville to Chicago. Data last updated June 8, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/171:14 pm
OAJ
- ORD
1 stop5h 28m
American Airlines
Sat 6/206:29 am
ORD
- OAJ
1 stop5h 20m
American Airlines
Deal found 6/7![American Airlines logo]()
$475
This American Airlines deal was found by Cheapflights users on 6/4. 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.
Wed 6/178:53 am
OAJ
- ORD
1 stop6h 30m
American Airlines
Mon 6/225:10 am
ORD
- OAJ
1 stop6h 39m
American Airlines
Deal found 6/4![American Airlines logo]()
$501
This Delta deal was found by Cheapflights users on 6/4. 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.
Wed 6/176:00 am
OAJ
- MDW
2 stops7h 46m
Delta
Mon 6/2211:05 am
MDW
- OAJ
1 stop5h 55m
Delta
Deal found 6/4![Delta logo]()
$721
This Delta deal was found by Cheapflights users on 6/6. 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.
Sat 6/2012:31 pm
OAJ
- ORD
1 stop7h 11m
Delta
Tue 6/305:30 am
ORD
- OAJ
1 stop4h 51m
Delta
Deal found 6/6![Delta logo]()
$467
This Delta deal was found by Cheapflights users on 6/6. 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.
Sat 6/204:45 pm
OAJ
- MDW
1 stop6h 32m
Delta
Tue 6/306:00 am
MDW
- OAJ
1 stop4h 21m
Delta
Deal found 6/6![Delta logo]()
$502
This Delta deal was found by Cheapflights users on 6/6. 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.
Mon 6/226:40 pm
OAJ
- MDW
1 stop4h 37m
Delta
Tue 6/306:00 am
MDW
- OAJ
1 stop4h 21m
Delta
Deal found 6/6![Delta logo]()
$642
This Delta deal was found by Cheapflights users on 6/7. 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.
Fri 7/36:40 pm
OAJ
- ORD
1 stop6h 19m
Delta
Thu 7/98:03 am
ORD
- OAJ
1 stop6h 51m
Delta
Deal found 6/7![Delta logo]()
$386
This Delta deal was found by Cheapflights users on 6/4. 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.
Fri 7/36:40 pm
OAJ
- MDW
1 stop4h 37m
Delta
Thu 7/912:41 pm
MDW
- OAJ
1 stop4h 21m
Delta
Deal found 6/4![Delta logo]()
$396
This American Airlines deal was found by Cheapflights users on 6/6. 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.
Fri 7/31:14 pm
OAJ
- ORD
1 stop7h 37m
American Airlines
Sun 7/56:30 am
ORD
- OAJ
1 stop7h 02m
American Airlines
Deal found 6/6![American Airlines logo]()
$428
This Delta deal was found by Cheapflights users on 6/6. 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 7/36:40 pm
OAJ
- MDW
1 stop4h 37m
Delta
Sun 7/56:00 am
MDW
- OAJ
1 stop4h 21m
Delta
Deal found 6/6![Delta logo]()
$506
This American Airlines deal was found by Cheapflights users on 6/6. 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.
Sat 7/46:37 am
OAJ
- ORD
1 stop5h 23m
American Airlines
Sat 7/114:45 pm
ORD
- OAJ
1 stop4h 31m
American Airlines
Deal found 6/6![American Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 6/7. 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.
Sat 7/412:31 pm
OAJ
- ORD
1 stop5h 46m
Delta
Sat 7/115:30 am
ORD
- OAJ
1 stop4h 48m
Delta
Deal found 6/7![Delta logo]()
$427
One-way flights from Jacksonville to ChicagoSearch for one-way flight options from Jacksonville to Chicago. Find affordable one-way fares based on user searches. Data last updated June 8, 2026.
Search for one-way flight options from Jacksonville to Chicago. Find affordable one-way fares based on user searches. Data last updated June 8, 2026.
This Trip.com deal was found by Cheapflights users on 6/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1712:05 pm
OAJ
- ORD
1 stop6h 07m
Delta
Deal found 6/5![Delta logo]()
$211
This American Airlines deal was found by Cheapflights users on 6/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:11 pm
OAJ
- ORD
1 stop6h 50m
American Airlines
Deal found 6/5![American Airlines logo]()
$285
This Delta deal was found by Cheapflights users on 6/5. 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.
Wed 7/296:00 am
OAJ
- ORD
2 stops8h 03m
Delta
Deal found 6/5![Delta logo]()
$315
This Trip.com deal was found by Cheapflights users on 6/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/174:43 pm
OAJ
- MDW
1 stop6h 32m
Delta
Deal found 6/5![Delta logo]()
$398
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 June 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $379 (American Airlines) |
One-way from | $211 (Trip.com) |
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 June 8, 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
Cheapest round-trip
JacksonvilleChicago
OAJ - ORD
OAJORD
Jacksonville Albert J Ellis
Fri 7/3
6:40 pm-11:59 pm
1 stop6h 19m
Chicago O'Hare Intl
Thu 7/9
8:03 am-3:54 pm
1 stop6h 51m
$386
Quickest round-trip
JacksonvilleChicago
OAJ - MDW
OAJMDW
Jacksonville Albert J Ellis
Fri 7/3
6:40 pm-10:17 pm
1 stop4h 37m
Chicago Midway
Thu 7/9
12:41 pm-6:02 pm
1 stop4h 21m
$396
JacksonvilleChicago
OAJ - ORD
OAJORD
Jacksonville Albert J Ellis
Sun 8/9
6:00 am-12:40 pm
1 stop7h 40m
Chicago O'Hare Intl
Wed 8/19
3:25 pm-10:29 pm
1 stop6h 04m
$398
JacksonvilleChicago
OAJ - ORD
OAJORD
Jacksonville Albert J Ellis
Tue 8/11
2:27 pm-6:49 pm
1 stop5h 22m
Chicago O'Hare Intl
Fri 8/21
6:40 am-1:46 pm
1 stop6h 06m
$398
JacksonvilleChicago
OAJ - MDW
OAJMDW
Jacksonville Albert J Ellis
Sun 8/9
6:00 am-11:51 am
1 stop6h 51m
Chicago Midway
Wed 8/19
6:05 am-1:46 pm
1 stop6h 41m
$398
JacksonvilleChicago
OAJ - MDW
OAJMDW
Jacksonville Albert J Ellis
Tue 8/11
6:00 am-9:59 am
1 stop4h 59m
Chicago Midway
Fri 8/21
12:46 pm-6:07 pm
1 stop4h 21m
$398
JacksonvilleChicago
OAJ - MDW
OAJMDW
Jacksonville Albert J Ellis
Mon 8/10
6:48 pm-10:36 pm
1 stop4h 48m
Chicago Midway
Wed 8/19
6:05 am-11:30 am
1 stop4h 25m
$398
JacksonvilleChicago
OAJ - ORD
OAJORD
Jacksonville Albert J Ellis
Fri 9/25
1:52 pm-5:38 pm
1 stop4h 46m
Chicago O'Hare Intl
Sun 9/27
6:45 am-2:24 pm
1 stop6h 39m
$417
JacksonvilleChicago
OAJ - ORD
OAJORD
Jacksonville Albert J Ellis
Mon 8/10
6:00 am-10:13 am
1 stop5h 13m
Chicago O'Hare Intl
Thu 8/20
5:30 am-11:30 am
1 stop5h 00m
$417
JacksonvilleChicago
OAJ - MDW
OAJMDW
Jacksonville Albert J Ellis
Mon 8/10
12:10 pm-4:15 pm
1 stop5h 05m
Chicago Midway
Thu 8/20
12:46 pm-6:07 pm
1 stop4h 21m
$417
Showing 1-10 of 13 resultsSorted by cheapest first
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 June.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- 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.
OAJ-CHI
OAJ-ORD
OAJ-MDW
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
OAJ-CHI
OAJ-ORD
OAJ-MDW
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 8, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
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Jacksonville and Chicago flights
Browse other Jacksonville and Chicago flight options. Last updated on June 8, 2026.
Other flights from Jacksonville
Browse through other flights departing from Jacksonville. Flights are based on user searches made on Cheapflights and were last updated on June 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Jacksonville to Chicago flights
Consider these flights traveling from Jacksonville to Chicago.
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 June 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$362 | Average$509 | FlexibilityNo cancel fee | On-time71% |