Cheap flights from Chicago to Jacksonville from $139
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Jacksonville departing on 12/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Fly from
Fly to
Route
Depart
Return
ChicagoJacksonville
ORD Chicago O'Hare Intl - JAX Jacksonville
ORDJAX
Chicago O'Hare Intl
Thu 11/5
10:19 am-6:11 pm
1 stop6h 52m
Jacksonville
Sun 11/8
7:03 pm-9:14 am
1 stop15h 11m
ChicagoJacksonville
ORD Chicago O'Hare Intl - JAX Jacksonville
ORDJAX
Chicago O'Hare Intl
Wed 11/25
7:00 am-3:08 pm
1 stop7h 08m
Jacksonville
Sat 12/12
7:09 am-1:30 pm
1 stop7h 21m
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Sat 11/21
8:28 am-5:07 pm
1 stop7h 39m
Jacksonville
Wed 11/25
5:59 pm-8:14 am
1 stop15h 15m
ChicagoJacksonville
ORD Chicago O'Hare Intl - JAX Jacksonville
ORDJAX
Chicago O'Hare Intl
Sat 1/23
8:00 am-11:49 am
Nonstop2h 49m
Jacksonville
Tue 1/26
12:19 pm-2:14 pm
Nonstop2h 55m
ChicagoJacksonville
ORD Chicago O'Hare Intl - JAX Jacksonville
ORDJAX
Chicago O'Hare Intl
Sat 1/23
7:29 pm-10:56 pm
Nonstop2h 27m
Jacksonville
Tue 1/26
12:19 pm-2:14 pm
Nonstop2h 55m
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Thu 2/4
1:30 pm-4:45 pm
Nonstop2h 15m
Jacksonville
Mon 2/8
1:25 pm-2:55 pm
Nonstop2h 30m
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Wed 11/4
6:40 pm-10:10 pm
Nonstop2h 30m
Jacksonville
Wed 11/11
1:30 pm-2:55 pm
Nonstop2h 25m
ChicagoJacksonville
ORD Chicago O'Hare Intl - JAX Jacksonville
ORDJAX
Chicago O'Hare Intl
Sat 1/16
6:00 am-8:35 am
2 stops25h 35m
Jacksonville
Fri 1/22
7:54 pm-11:50 am
1 stop16h 56m
ChicagoJacksonville
MDW Chicago Midway - JAX Jacksonville
MDWJAX
Chicago Midway
Thu 11/12
6:08 am-6:11 pm
1 stop11h 03m
Jacksonville
Sun 11/22
9:08 pm-8:14 am
2 stops36h 06m
ChicagoJacksonville
ORD Chicago O'Hare Intl - JAX Jacksonville
ORDJAX
Chicago O'Hare Intl
Thu 11/19
11:00 am-7:30 pm
1 stop7h 30m
Jacksonville
Tue 12/1
4:37 pm-11:33 pm
1 stop7h 56m
See travel insights to Jacksonville from
How to get the cheapest flight ticket from Chicago to Jacksonville
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Chicago and Jacksonville?
Prices are currently low for flights on this route.
Typical prices usually range from $274 to $409.The lowest price recently found on this route was $246.
What is the cheapest month to fly to Jacksonville?
If you are unable to visit Jacksonville during the month of January, then departing from Chicago during the month April is also very affordable. Most momondo users find prices during this month for around $344.
What is the cheapest day to depart on your flight to Jacksonville?
According to our data, Saturday is the cheapest day to fly to Jacksonville from Chicago. The lowest ticket price found for a Saturday departure recently was $336. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $435.
What is the cheapest time of day to depart on your flight to Jacksonville?
Flying to Jacksonville from Chicago at noon is the least expensive time of day to depart. momondo users have found prices as low as $354 when looking at flights departing at noon. Flights to Jacksonville are more costly in the morning, with an average ticket price of $382. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.
What is the cheapest Chicago to Jacksonville flight route?
Fly from Chicago Midway to Jacksonville for the best Chicago - Jacksonville flight prices
How far in advance should I book a flight from Chicago to Jacksonville?
You are more likely to see cheaper flights to Jacksonville from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Jacksonville for around $372 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Jacksonville from Chicago for as low as $313 on momondo.
What cabin class options are available on Chicago to Jacksonville flights?
There are 4 cabin classes available to choose from on Chicago to Jacksonville flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Chicago to Jacksonville flights?
No. A direct flight is the cheapest option for a flight between Chicago to Jacksonville.
How have Chicago to Jacksonville flight prices changed over time?
As of October 2026, prices for Chicago to Jacksonville flights are approximately 21% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from Chicago to Jacksonville?
Southwest, Delta, and Frontier are the most popular carriers operating from Chicago to Jacksonville
What airlines fly to Jacksonville?
United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Jacksonville from Chicago according to our data. United Airlines is the first choice among our users, with 47% of people opting to fly with this airline when traveling to Jacksonville. Keep in mind that there are 6 different airlines that fly to Jacksonville on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to Jacksonville on average per day?
17 flights are operational daily from Chicago to Jacksonville as of October 2026. The most popular departure time for this route is 10:00AM, with 47% of flights per day taking off at noon.
How many flights depart from Chicago to Jacksonville on average per week?
As of October 2026, there are 124 flights per week flying from Chicago to Jacksonville. The most common day of the week flights depart is Wed, with 19% of flights taking off on this day.
When to book flights from Chicago to Jacksonville
Cheap Chicago to Jacksonville (CHI to JAX) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Jacksonville
Frequently asked questions about flying from Chicago to Jacksonville
How far is Chicago to Jacksonville by plane?
The straight-line distance from Chicago to Jacksonville is 863.3 mi. By plane, this route typically takes 2h 10m.
When did momondo last update prices for flights from Chicago to Jacksonville Airport?
Prices for flights from Chicago to Jacksonville Airport are updated daily.
How many operators does momondo search for flights from Chicago to Jacksonville Airport?
As of October 2026, there are 6 operators available to choose from for flights from Chicago to Jacksonville Airport.
How old do you have to be to fly from Chicago to Jacksonville Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Jacksonville Airport.
What documentation or ID do you need to fly to Jacksonville Airport?
The travel and health documents you'll need for your trip to Jacksonville Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Jacksonville Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to Jacksonville?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Jacksonville is Airbus A319 (19.25% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (17.28%), Embraer 175 (16.06%), and Boeing 737-800 (14.30%).
What is the most popular airline from Chicago to Jacksonville?
momondo data reveals that the most frequently booked airline on the route from Chicago to Jacksonville is United Airlines, representing 46% of all bookings. The subsequent popular airlines are American Airlines at 35%, Southwest at 11%, and Frontier at 5%.
Best airlines flying from Chicago to Jacksonville
Compare and see reviews for airlines that fly from Chicago to Jacksonville with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $83 | Free Cancellation | Rating 7.8 8,635 reviews | |||
| PriceFrom $86 | Free Cancellation | Rating 5.6 2,551 reviews | |||
| PriceFrom $186 | Free Cancellation | Rating 7.0 12,136 reviews | |||
| PriceFrom $225 | Free Cancellation | Rating 7.9 4,220 reviews | |||
| PriceFrom $236 | Free Cancellation | Rating 7.1 3,046 reviews | |||
| PriceFrom $245 | Free Cancellation | Rating 7.4 10,315 reviews |
Southwest Flights From Chicago to Jacksonville
Southwest flies from Chicago to Jacksonville around 2 times per week, with 4,220 momondo users rating the airline 7.9/10. The cheapest Southwest deal from Chicago to Jacksonville in the last 72 hours was $225 (round-trip), much lower than the average airfare cost of $389 for Southwest flights on this route.
United Airlines Flights From Chicago to Jacksonville
The best United Airlines deal for Chicago to Jacksonville flight tickets found on momondo in the last 72 hours was $245, round-trip. It should be noted that an average United Airlines flight deal for this route in this time was higher, at $384 round-trip. United Airlines operates 22 flights out of Chicago into Jacksonville in an average week, so prices vary by time and availability. 10,315 United Airlines reviews by users on momondo have scored the airline at 7.4/10.
Traveling to a place near Jacksonville?
Book flights to Jacksonville if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to Jacksonville?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Jacksonville. momondo saves you time and could save you money on your trip.
Can I find flights from Chicago to Jacksonville with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Jacksonville from Chicago with this policy.
How can momondo help me find flights from Chicago to Jacksonville?
momondo helps you find the best flight between Chicago and Jacksonville by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from Chicago to Jacksonville right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Jacksonville from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.