Flights from Jacksonville to Chicago (JAX to ORD)

Discover more affordable routes and cheaper dates from Jacksonville to Chicago (JAX to ORD) within a date range.

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US$159

12:42pm - 7:09pm
Mon Jun 2nd 2025

7h 27m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Mon Jun 2nd 2025 Sun Country Airlines · SY 326 Depart at 12:42pm from Jacksonville (JAX) Fly for 3h 12m Arrive at 2:54pm in Minneapolis (MSP)

Layover in Minneapolis for 2h 36m

Mon Jun 2nd 2025 Sun Country Airlines · SY 261 Depart at 5:30pm from Minneapolis (MSP) Fly for 1h 39m Arrive at 7:09pm in Chicago (ORD)
US$186

8:00am - 9:45am
Sat May 31st 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

Sat May 31st 2025 United Airlines · UA 1746 Depart at 8:00am from Jacksonville (JAX) Fly for 2h 45m Arrive at 9:45am in Chicago (ORD)
US$223

4:40pm - 6:25pm
Sat May 31st 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

Sat May 31st 2025 United Airlines · UA 457 Depart at 4:40pm from Jacksonville (JAX) Fly for 2h 45m Arrive at 6:25pm in Chicago (ORD)
US$223

11:20am - 1:13pm
Sat May 31st 2025

2h 53m
Jacksonville (JAX) → Chicago (ORD)

Direct

Sat May 31st 2025 United Airlines · UA 3638 Depart at 11:20am from Jacksonville (JAX) Fly for 2h 53m Arrive at 1:13pm in Chicago (ORD)
US$236

10:27am - 8:12pm
Mon Jun 2nd 2025

10h 45m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Mon Jun 2nd 2025 United Airlines · UA 2328 Depart at 10:27am from Jacksonville (JAX) Fly for 2h 20m Arrive at 12:47pm in New York (EWR)

Layover in New York for 5h 43m

Mon Jun 2nd 2025 United Airlines · UA 254 Depart at 6:30pm from New York (EWR) Fly for 2h 42m Arrive at 8:12pm in Chicago (ORD)
US$240

6:30am - 2:55pm
Tue Jun 3rd 2025

9h 25m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Tue Jun 3rd 2025 United Airlines · UA 1321 Depart at 6:30am from Jacksonville (JAX) Fly for 2h 20m Arrive at 8:50am in New York (EWR)

Layover in New York for 4h 28m

Tue Jun 3rd 2025 United Airlines · UA 1832 Depart at 1:18pm from New York (EWR) Fly for 2h 37m Arrive at 2:55pm in Chicago (ORD)
US$240

10:27am - 8:12pm
Tue Jun 3rd 2025

10h 45m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Tue Jun 3rd 2025 United Airlines · UA 2328 Depart at 10:27am from Jacksonville (JAX) Fly for 2h 20m Arrive at 12:47pm in New York (EWR)

Layover in New York for 5h 43m

Tue Jun 3rd 2025 United Airlines · UA 254 Depart at 6:30pm from New York (EWR) Fly for 2h 42m Arrive at 8:12pm in Chicago (ORD)
US$240

6:30am - 4:46pm
Tue Jun 3rd 2025

11h 16m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Tue Jun 3rd 2025 United Airlines · UA 1321 Depart at 6:30am from Jacksonville (JAX) Fly for 2h 20m Arrive at 8:50am in New York (EWR)

Layover in New York for 6h 10m

Tue Jun 3rd 2025 United Airlines · UA 1144 Depart at 3:00pm from New York (EWR) Fly for 2h 46m Arrive at 4:46pm in Chicago (ORD)
US$240

10:27am - 10:12pm
Tue Jun 3rd 2025

12h 45m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Tue Jun 3rd 2025 United Airlines · UA 2328 Depart at 10:27am from Jacksonville (JAX) Fly for 2h 20m Arrive at 12:47pm in New York (EWR)

Layover in New York for 7h 43m

Tue Jun 3rd 2025 United Airlines · UA 546 Depart at 8:30pm from New York (EWR) Fly for 2h 42m Arrive at 10:12pm in Chicago (ORD)
US$242

10:27am - 6:37pm
Mon Jun 2nd 2025

9h 10m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Mon Jun 2nd 2025 United Airlines · UA 2328 Depart at 10:27am from Jacksonville (JAX) Fly for 2h 20m Arrive at 12:47pm in New York (EWR)

Layover in New York for 4h 8m

Mon Jun 2nd 2025 United Airlines · UA 661 Depart at 4:55pm from New York (EWR) Fly for 2h 42m Arrive at 6:37pm in Chicago (ORD)
US$242

6:30am - 2:55pm
Mon Jun 2nd 2025

9h 25m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Mon Jun 2nd 2025 United Airlines · UA 1321 Depart at 6:30am from Jacksonville (JAX) Fly for 2h 20m Arrive at 8:50am in New York (EWR)

Layover in New York for 4h 28m

Mon Jun 2nd 2025 United Airlines · UA 1832 Depart at 1:18pm from New York (EWR) Fly for 2h 37m Arrive at 2:55pm in Chicago (ORD)
US$242

6:30am - 4:46pm
Mon Jun 2nd 2025

11h 16m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Mon Jun 2nd 2025 United Airlines · UA 1321 Depart at 6:30am from Jacksonville (JAX) Fly for 2h 20m Arrive at 8:50am in New York (EWR)

Layover in New York for 6h 10m

Mon Jun 2nd 2025 United Airlines · UA 1144 Depart at 3:00pm from New York (EWR) Fly for 2h 46m Arrive at 4:46pm in Chicago (ORD)
US$242

10:27am - 10:12pm
Mon Jun 2nd 2025

12h 45m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Mon Jun 2nd 2025 United Airlines · UA 2328 Depart at 10:27am from Jacksonville (JAX) Fly for 2h 20m Arrive at 12:47pm in New York (EWR)

Layover in New York for 7h 43m

Mon Jun 2nd 2025 United Airlines · UA 546 Depart at 8:30pm from New York (EWR) Fly for 2h 42m Arrive at 10:12pm in Chicago (ORD)
US$242

6:30am - 6:37pm
Mon Jun 2nd 2025

13h 7m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Mon Jun 2nd 2025 United Airlines · UA 1321 Depart at 6:30am from Jacksonville (JAX) Fly for 2h 20m Arrive at 8:50am in New York (EWR)

Layover in New York for 8h 5m

Mon Jun 2nd 2025 United Airlines · UA 661 Depart at 4:55pm from New York (EWR) Fly for 2h 42m Arrive at 6:37pm in Chicago (ORD)
US$270

9:20am - 2:33pm
Sat May 31st 2025

6h 13m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Sat May 31st 2025 United Airlines · UA 1786 Depart at 9:20am from Jacksonville (JAX) Fly for 1h 53m Arrive at 11:13am in Washington, D.C. (IAD)

Layover in Washington, D.C. for 2h 7m

Sat May 31st 2025 United Airlines · UA 2331 Depart at 1:20pm from Washington, D.C. (IAD) Fly for 2h 13m Arrive at 2:33pm in Chicago (ORD)
US$272

8:00am - 9:45am
Tue Jun 3rd 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

Tue Jun 3rd 2025 United Airlines · UA 1746 Depart at 8:00am from Jacksonville (JAX) Fly for 2h 45m Arrive at 9:45am in Chicago (ORD)
US$272

8:00am - 9:45am
Sun Jun 1st 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

Sun Jun 1st 2025 United Airlines · UA 1746 Depart at 8:00am from Jacksonville (JAX) Fly for 2h 45m Arrive at 9:45am in Chicago (ORD)
US$272

4:48pm - 6:33pm
Sun Jun 1st 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

Sun Jun 1st 2025 United Airlines · UA 457 Depart at 4:48pm from Jacksonville (JAX) Fly for 2h 45m Arrive at 6:33pm in Chicago (ORD)
US$272

4:40pm - 6:25pm
Mon Jun 2nd 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

Mon Jun 2nd 2025 United Airlines · UA 457 Depart at 4:40pm from Jacksonville (JAX) Fly for 2h 45m Arrive at 6:25pm in Chicago (ORD)
US$272

8:00am - 9:45am
Mon Jun 2nd 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

Mon Jun 2nd 2025 United Airlines · UA 1746 Depart at 8:00am from Jacksonville (JAX) Fly for 2h 45m Arrive at 9:45am in Chicago (ORD)
US$272

11:20am - 1:13pm
Mon Jun 2nd 2025

2h 53m
Jacksonville (JAX) → Chicago (ORD)

Direct

Mon Jun 2nd 2025 United Airlines · UA 5614 Depart at 11:20am from Jacksonville (JAX) Fly for 2h 53m Arrive at 1:13pm in Chicago (ORD)
US$272

11:20am - 1:13pm
Tue Jun 3rd 2025

2h 53m
Jacksonville (JAX) → Chicago (ORD)

Direct

Tue Jun 3rd 2025 United Airlines · UA 5614 Depart at 11:20am from Jacksonville (JAX) Fly for 2h 53m Arrive at 1:13pm in Chicago (ORD)
US$274

4:40pm - 6:25pm
Tue Jun 3rd 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

Tue Jun 3rd 2025 United Airlines · UA 457 Depart at 4:40pm from Jacksonville (JAX) Fly for 2h 45m Arrive at 6:25pm in Chicago (ORD)
US$277

12:55pm - 4:48pm
Mon Jun 2nd 2025

4h 53m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Mon Jun 2nd 2025 United Airlines · UA 1938 Depart at 12:55pm from Jacksonville (JAX) Fly for 1h 53m Arrive at 2:48pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 0h 47m

Mon Jun 2nd 2025 United Airlines · UA 1057 Depart at 3:35pm from Washington, D.C. (IAD) Fly for 2h 13m Arrive at 4:48pm in Chicago (ORD)
US$277

6:54pm - 11:30pm
Mon Jun 2nd 2025

5h 36m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Mon Jun 2nd 2025 United Airlines · UA 6209 Depart at 6:54pm from Jacksonville (JAX) Fly for 1h 57m Arrive at 8:51pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 27m

Mon Jun 2nd 2025 United Airlines · UA 1738 Depart at 10:18pm from Washington, D.C. (IAD) Fly for 2h 12m Arrive at 11:30pm in Chicago (ORD)
US$282

12:55pm - 4:48pm
Tue Jun 3rd 2025

4h 53m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Tue Jun 3rd 2025 United Airlines · UA 1938 Depart at 12:55pm from Jacksonville (JAX) Fly for 1h 53m Arrive at 2:48pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 0h 47m

Tue Jun 3rd 2025 United Airlines · UA 1057 Depart at 3:35pm from Washington, D.C. (IAD) Fly for 2h 13m Arrive at 4:48pm in Chicago (ORD)
US$282

6:54pm - 11:30pm
Tue Jun 3rd 2025

5h 36m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Tue Jun 3rd 2025 United Airlines · UA 6209 Depart at 6:54pm from Jacksonville (JAX) Fly for 1h 57m Arrive at 8:51pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 27m

Tue Jun 3rd 2025 United Airlines · UA 1738 Depart at 10:18pm from Washington, D.C. (IAD) Fly for 2h 12m Arrive at 11:30pm in Chicago (ORD)
US$303

11:20am - 1:13pm
Sun Jun 1st 2025

2h 53m
Jacksonville (JAX) → Chicago (ORD)

Direct

Sun Jun 1st 2025 United Airlines · UA 5614 Depart at 11:20am from Jacksonville (JAX) Fly for 2h 53m Arrive at 1:13pm in Chicago (ORD)
US$303

6:00am - 11:48am
Sat May 31st 2025

6h 48m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Sat May 31st 2025 United Airlines · UA 1321 Depart at 6:00am from Jacksonville (JAX) Fly for 2h 20m Arrive at 8:20am in New York (EWR)

Layover in New York for 1h 49m

Sat May 31st 2025 United Airlines · UA 1525 Depart at 10:09am from New York (EWR) Fly for 2h 39m Arrive at 11:48am in Chicago (ORD)
US$304

12:49pm - 4:48pm
Sat May 31st 2025

4h 59m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Sat May 31st 2025 United Airlines · UA 3621 Depart at 12:49pm from Jacksonville (JAX) Fly for 1h 59m Arrive at 2:48pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 0h 47m

Sat May 31st 2025 United Airlines · UA 1057 Depart at 3:35pm from Washington, D.C. (IAD) Fly for 2h 13m Arrive at 4:48pm in Chicago (ORD)
US$304

6:54pm - 11:30pm
Sat May 31st 2025

5h 36m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Sat May 31st 2025 United Airlines · UA 6209 Depart at 6:54pm from Jacksonville (JAX) Fly for 2h 2m Arrive at 8:56pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 22m

Sat May 31st 2025 United Airlines · UA 1738 Depart at 10:18pm from Washington, D.C. (IAD) Fly for 2h 12m Arrive at 11:30pm in Chicago (ORD)
US$311

7:00am - 12:26pm
Sun Jun 1st 2025

6h 26m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Sun Jun 1st 2025 United Airlines · UA 2453 Depart at 7:00am from Jacksonville (JAX) Fly for 2h 23m Arrive at 8:23am in Houston (IAH)

Layover in Houston for 1h 7m

Sun Jun 1st 2025 United Airlines · UA 2124 Depart at 9:30am from Houston (IAH) Fly for 2h 56m Arrive at 12:26pm in Chicago (ORD)
US$311

6:17am - 12:05pm
Sun Jun 1st 2025

6h 48m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Sun Jun 1st 2025 United Airlines · UA 1321 Depart at 6:17am from Jacksonville (JAX) Fly for 2h 20m Arrive at 8:37am in New York (EWR)

Layover in New York for 1h 49m

Sun Jun 1st 2025 United Airlines · UA 1525 Depart at 10:26am from New York (EWR) Fly for 2h 39m Arrive at 12:05pm in Chicago (ORD)
US$312

7:00am - 12:26pm
Mon Jun 2nd 2025

6h 26m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Mon Jun 2nd 2025 United Airlines · UA 2453 Depart at 7:00am from Jacksonville (JAX) Fly for 2h 23m Arrive at 8:23am in Houston (IAH)

Layover in Houston for 1h 7m

Mon Jun 2nd 2025 United Airlines · UA 2124 Depart at 9:30am from Houston (IAH) Fly for 2h 56m Arrive at 12:26pm in Chicago (ORD)
US$312

6:30am - 12:05pm
Mon Jun 2nd 2025

6h 35m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Mon Jun 2nd 2025 United Airlines · UA 1321 Depart at 6:30am from Jacksonville (JAX) Fly for 2h 20m Arrive at 8:50am in New York (EWR)

Layover in New York for 1h 36m

Mon Jun 2nd 2025 United Airlines · UA 1525 Depart at 10:26am from New York (EWR) Fly for 2h 39m Arrive at 12:05pm in Chicago (ORD)
US$312

12:55pm - 6:45pm
Mon Jun 2nd 2025

6h 50m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Mon Jun 2nd 2025 United Airlines · UA 1938 Depart at 12:55pm from Jacksonville (JAX) Fly for 1h 53m Arrive at 2:48pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 2h 30m

Mon Jun 2nd 2025 United Airlines · UA 2497 Depart at 5:18pm from Washington, D.C. (IAD) Fly for 2h 27m Arrive at 6:45pm in Chicago (ORD)
US$314

6:30am - 12:05pm
Tue Jun 3rd 2025

6h 35m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Tue Jun 3rd 2025 United Airlines · UA 1321 Depart at 6:30am from Jacksonville (JAX) Fly for 2h 20m Arrive at 8:50am in New York (EWR)

Layover in New York for 1h 36m

Tue Jun 3rd 2025 United Airlines · UA 1525 Depart at 10:26am from New York (EWR) Fly for 2h 39m Arrive at 12:05pm in Chicago (ORD)
US$324

9:20am - 2:33pm
Tue Jun 3rd 2025

6h 13m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Tue Jun 3rd 2025 United Airlines · UA 1786 Depart at 9:20am from Jacksonville (JAX) Fly for 1h 53m Arrive at 11:13am in Washington, D.C. (IAD)

Layover in Washington, D.C. for 2h 7m

Tue Jun 3rd 2025 United Airlines · UA 2331 Depart at 1:20pm from Washington, D.C. (IAD) Fly for 2h 13m Arrive at 2:33pm in Chicago (ORD)
US$355

7:00am - 12:26pm
Tue Jun 3rd 2025

6h 26m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Tue Jun 3rd 2025 United Airlines · UA 2453 Depart at 7:00am from Jacksonville (JAX) Fly for 2h 23m Arrive at 8:23am in Houston (IAH)

Layover in Houston for 1h 7m

Tue Jun 3rd 2025 United Airlines · UA 2124 Depart at 9:30am from Houston (IAH) Fly for 2h 56m Arrive at 12:26pm in Chicago (ORD)
US$360

9:20am - 2:33pm
Mon Jun 2nd 2025

6h 13m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Mon Jun 2nd 2025 United Airlines · UA 1786 Depart at 9:20am from Jacksonville (JAX) Fly for 1h 53m Arrive at 11:13am in Washington, D.C. (IAD)

Layover in Washington, D.C. for 2h 7m

Mon Jun 2nd 2025 United Airlines · UA 2331 Depart at 1:20pm from Washington, D.C. (IAD) Fly for 2h 13m Arrive at 2:33pm in Chicago (ORD)
US$361

6:54pm - 11:30pm
Sun Jun 1st 2025

5h 36m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Sun Jun 1st 2025 United Airlines · UA 6209 Depart at 6:54pm from Jacksonville (JAX) Fly for 1h 57m Arrive at 8:51pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 27m

Sun Jun 1st 2025 United Airlines · UA 1738 Depart at 10:18pm from Washington, D.C. (IAD) Fly for 2h 12m Arrive at 11:30pm in Chicago (ORD)
US$687

12:51pm - 4:48pm
Sun Jun 1st 2025

4h 57m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Sun Jun 1st 2025 United Airlines · UA 6143 Depart at 12:51pm from Jacksonville (JAX) Fly for 1h 59m Arrive at 2:50pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 0h 45m

Sun Jun 1st 2025 United Airlines · UA 1057 Depart at 3:35pm from Washington, D.C. (IAD) Fly for 2h 13m Arrive at 4:48pm in Chicago (ORD)
US$705

11:41am - 5:10pm
Mon Jun 2nd 2025

6h 29m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Mon Jun 2nd 2025 United Airlines · UA 6228 Depart at 11:41am from Jacksonville (JAX) Fly for 2h 33m Arrive at 1:14pm in Houston (IAH)

Layover in Houston for 1h 0m

Mon Jun 2nd 2025 United Airlines · UA 2135 Depart at 2:14pm from Houston (IAH) Fly for 2h 56m Arrive at 5:10pm in Chicago (ORD)
US$806

9:25am - 2:51pm
Sun Jun 1st 2025

6h 26m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

Sun Jun 1st 2025 United Airlines · UA 5211 Depart at 9:25am from Jacksonville (JAX) Fly for 2h 33m Arrive at 10:58am in Houston (IAH)

Layover in Houston for 0h 57m

Sun Jun 1st 2025 United Airlines · UA 2417 Depart at 11:55am from Houston (IAH) Fly for 2h 56m Arrive at 2:51pm in Chicago (ORD)

Sarah Belizaire

@sarahbb1

Have flexible travel plans or looking for alternative routes given the chaos? Check out all the connection possibilities via a super helpful site created by @ismaelyws flightlist.io thanks to @andy_travels for the recommendation #travel #flights

John Ford

@eyupitsjohn

There seem to be lots of sites launching at the moment that promise to find you cheap flights but not many have the professional finish of Flightlist by @ismaelyws #travel #flights

Roaming Sonaa

@roamingsonaa

For people wanting to maximize their trips, Flightlist is my newest travel hack for uncovering the coolest routes at irresistible prices. No stress, no annoying ads — just seamless flight booking with amazing functionality.

Andy Travels

@andy_travels

@ismaelyws Just tried out Flightlist for the first time. Really nice idea, well made, and just what I need at the moment 👍

Travel With Bender

@travelwitbender

Did you spot my recent article about how to score cheap one way flights? ✈️ FlightList is my new secret tool for discovering cheap routes, within a departure date range. Plus you can also search by country/region for departures & destinations. Powerful! 💪

Wesley Mergard

@travel.with.wes

One useful tool I've found for evaluating different departure and return dates is called FlightList.io. You can quickly scan different travel date ranges, carriers and one way flight options to easily determine the cheapest flight combinations for your trip.

Flights from Jacksonville to Chicago (JAX to ORD)

Sarah Belizaire

John Ford

Roaming Sonaa

Andy Travels

Travel With Bender

Wesley Mergard

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