
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $239 (Kiwi.com) |
One-way from | $121 (Kiwi.com) |
Popular in | April |
Cheapest in | September |
Average price | $376 |
Good round-trip deal | $367 or less |
Good one-way deal | $195 or less |
Fly from
Fly to
Route
Depart
Return
JacksonvilleChicago
JAX - ORD
JAXORD
Jacksonville
Tue 6/2
6:42 pm-8:38 pm
Nonstop2h 56m
Chicago O'Hare Intl
Thu 6/4
6:19 pm-9:59 pm
Nonstop2h 40m
JacksonvilleChicago
JAX - MDW
JAXMDW
Jacksonville
Thu 6/4
7:15 pm-8:45 pm
Nonstop2h 30m
Chicago Midway
Mon 6/8
7:20 pm-10:35 pm
Nonstop2h 15m
JacksonvilleChicago
JAX - ORD
JAXORD
Jacksonville
Sat 5/23
7:20 am-9:12 am
Nonstop2h 52m
Chicago O'Hare Intl
Wed 5/27
7:00 am-10:40 am
Nonstop2h 40m
JacksonvilleChicago
JAX - MDW
JAXMDW
Jacksonville
Sat 5/23
3:05 pm-4:35 pm
Nonstop2h 30m
Chicago Midway
Wed 5/27
6:00 pm-9:15 pm
Nonstop2h 15m
JacksonvilleChicago
JAX - ORD
JAXORD
Jacksonville
Tue 6/16
11:40 am-6:29 pm
1 stop7h 49m
Chicago O'Hare Intl
Fri 8/21
7:10 am-1:38 pm
1 stop5h 28m
JacksonvilleChicago
JAX - ORD
JAXORD
Jacksonville
Thu 8/6
4:10 pm-8:46 pm
1 stop5h 36m
Chicago O'Hare Intl
Tue 8/11
8:28 am-4:52 pm
1 stop7h 24m
JacksonvilleChicago
JAX - MDW
JAXMDW
Jacksonville
Thu 8/6
5:34 pm-10:36 pm
1 stop6h 02m
Chicago Midway
Tue 8/11
9:59 am-4:52 pm
1 stop5h 53m
JacksonvilleChicago
JAX - MDW
JAXMDW
Jacksonville
Fri 9/25
6:30 am-9:50 am
1 stop4h 20m
Chicago Midway
Tue 9/29
10:35 am-4:22 pm
1 stop4h 47m
JacksonvilleChicago
JAX - ORD
JAXORD
Jacksonville
Thu 5/28
3:48 pm-9:53 pm
1 stop7h 05m
Chicago O'Hare Intl
Mon 6/1
9:49 am-5:59 pm
1 stop7h 10m
JacksonvilleChicago
JAX - MDW
JAXMDW
Jacksonville
Wed 9/23
5:25 pm-6:50 pm
Nonstop2h 25m
Chicago Midway
Sun 9/27
5:00 am-12:25 pm
1 stop6h 25m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
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 70 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Currently, September is the cheapest month in which you can book a flight from Jacksonville to Chicago (average of $78). Flying from Jacksonville to Chicago in February is currently the most expensive (average of $177). 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.
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 afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 17% on airfare.
Travelers seeking maximum savings on their Jacksonville to Chicago flight should consider departing on Wednesday at noon when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from JAX to CHI are scheduled on a Monday (25 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (13 on average).
Boarding
Overall
Comfort
Crew
Entertainment
Food
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Overall
Comfort
Crew
Entertainment
Food
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Overall
Comfort
Crew
Entertainment
Food
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Overall
Comfort
Crew
Entertainment
Food
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Overall
Comfort
Crew
Entertainment
Food
Reviews
Dominic,Mar 2026
MCO - SMF
Boarding
Overall
Comfort
Crew
Entertainment
Food
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$121 | Average$246 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$136 | Average$231 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$179 | Average$333 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$202 | Average$347 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$229 | Average$370 | FlexibilityNo cancel fee | On-time69% |