
Keep the following information in mind while searching for Jacksonville to Illinois flight deals. Data was last updated November 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $281 (Mytrip) |
One-way from | $129 (Super.com) |
Popular in | May |
Cheapest in | September |
Average price | $402 |
Good round-trip deal | $373 or less |
Good one-way deal | $218 or less |
Fly from
Fly to
Route
Depart
Return
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Fri 1/15
2:51 pm-4:18 pm
2 stops26h 27m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
JacksonvilleChicago
JAX Jacksonville - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Fri 12/25
7:10 am-1:30 pm
1 stop7h 20m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
JacksonvilleChicago
JAX Jacksonville - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Tue 12/22
11:35 am-1:31 pm
Nonstop2h 56m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
JacksonvilleChicago
JAX Jacksonville - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Wed 12/9
12:00 pm-1:56 pm
Nonstop2h 56m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Wed 12/9
12:00 pm-6:01 pm
1 stop7h 01m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Mon 12/14
1:30 pm-2:55 pm
Nonstop2h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
JacksonvilleChicago
JAX Jacksonville - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Mon 12/14
9:40 am-11:34 am
Nonstop2h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
JacksonvilleChicago
JAX Jacksonville - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Mon 1/11
7:30 am-9:18 am
Nonstop2h 48m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
JacksonvilleChicago
JAX Jacksonville - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Mon 12/28
7:10 am-1:30 pm
1 stop7h 20m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Fri 1/15
7:00 pm-8:30 pm
Nonstop2h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
Everything you need to know about your flight from Jacksonville to Illinois
Comfort
Entertainment
Food
Overall
Crew
Boarding
Reviews
Reza,Jun 2026
TPA - MDW
Comfort
Entertainment
Food
Overall
Crew
Boarding
Reviews
Reza,Jun 2026
TPA - MDW
Comfort
Entertainment
Food
Overall
Crew
Boarding
Reviews
Reza,Jun 2026
TPA - MDW
Comfort
Entertainment
Food
Overall
Crew
Boarding
Reviews
Reza,Jun 2026
TPA - MDW
Comfort
Entertainment
Food
Overall
Crew
Boarding
Reviews
Reza,Jun 2026
TPA - MDW
Comfort
Entertainment
Food
Overall
Crew
Boarding
Reviews
Reza,Jun 2026
TPA - MDW
Find useful and relevant information for your journey from Jacksonville to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$122 | Average$264 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$128 | Average$349 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$197 | Average$363 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$206 | Average$303 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$217 | Average$402 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$224 | Average$371 | FlexibilityNo cancel fee | On-time69% |