Cheap flights from Jacksonville to Chicago from $112
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Jacksonville to Chicago departing on 12/6. 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
JacksonvilleChicago
JAX Jacksonville - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Thu 11/5
7:03 pm-3:37 pm
2 stops21h 34m
Chicago O'Hare Intl
Sun 11/8
10:19 am-6:11 pm
1 stop6h 52m
JacksonvilleChicago
JAX Jacksonville - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Tue 10/20
7:46 pm-3:30 pm
2 stops20h 44m
Chicago O'Hare Intl
Tue 10/27
2:11 pm-6:08 pm
2 stops26h 57m
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Thu 10/22
6:20 pm-11:43 pm
1 stop6h 23m
Chicago Midway
Mon 10/26
6:15 am-4:26 pm
2 stops33h 11m
JacksonvilleChicago
JAX Jacksonville - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Thu 10/29
3:00 pm-11:36 pm
1 stop9h 36m
Chicago O'Hare Intl
Mon 11/2
10:19 am-6:08 pm
1 stop6h 49m
JacksonvilleChicago
JAX Jacksonville - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Mon 11/2
7:30 am-9:19 am
Nonstop2h 49m
Chicago O'Hare Intl
Wed 11/4
2:21 pm-9:10 pm
1 stop5h 49m
JacksonvilleChicago
JAX Jacksonville - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Mon 11/2
4:45 pm-6:34 pm
Nonstop2h 49m
Chicago O'Hare Intl
Wed 11/4
1:30 pm-9:10 pm
1 stop6h 40m
JacksonvilleChicago
JAX Jacksonville - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Wed 11/18
5:50 pm-7:52 pm
Nonstop3h 02m
Chicago O'Hare Intl
Sat 11/21
4:58 pm-11:55 pm
1 stop5h 57m
JacksonvilleChicago
JAX Jacksonville - ORD Chicago O'Hare Intl
JAXORD
Jacksonville
Sat 11/7
7:31 am-11:00 am
1 stop4h 29m
Chicago O'Hare Intl
Mon 11/9
8:13 am-11:42 am
Nonstop2h 29m
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Thu 12/3
7:05 pm-10:45 pm
1 stop4h 40m
Chicago Midway
Tue 12/8
6:40 pm-10:05 pm
Nonstop2h 25m
JacksonvilleChicago
JAX Jacksonville - MDW Chicago Midway
JAXMDW
Jacksonville
Thu 12/10
1:30 pm-2:55 pm
Nonstop2h 25m
Chicago Midway
Wed 12/16
6:00 am-1:15 pm
1 stop6h 15m
See travel insights to Chicago from
How to get the cheapest flight ticket from Jacksonville to Chicago
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 Jacksonville and Chicago?
Prices are currently typical for flights on this route.
Typical prices usually range from $248 to $421.The lowest price recently found on this route was $253.
What is the cheapest month to fly to Chicago?
The month of January is, on average, the cheapest month to fly to Chicago from Jacksonville, with most prices found around $309. If you’re not able to fly to Chicago in January, then October is your next best option. Flight prices from Jacksonville to Chicago during October average around $327.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $425. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Jacksonville to Chicago for around $678.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Jacksonville to Chicago during this time can be as low as $394. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $580.
What is the cheapest Jacksonville to Chicago flight route?
Fly from Jacksonville to Chicago Midway for the best Jacksonville - Chicago flight prices
How far in advance should I book a flight from Jacksonville to Chicago?
You are more likely to see cheaper flights to Chicago from Jacksonville when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $365 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Jacksonville for as low as $284 on momondo.
What cabin class options are available on Jacksonville to Chicago flights?
There are 4 cabin classes available to choose from on Jacksonville to Chicago 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 Jacksonville to Chicago flights?
No. A direct flight is the cheapest option for a flight between Jacksonville to Chicago.
How have Jacksonville to Chicago flight prices changed over time?
As of October 2026, prices for Jacksonville to Chicago flights are approximately 37% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from Jacksonville to Chicago?
United Airlines, JetBlue, and Southwest are the most popular carriers operating from Jacksonville to Chicago
What airlines fly to Chicago?
American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Chicago from Jacksonville according to our data. American Airlines is the first choice among our users, with 49% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Jacksonville to Chicago on average per day?
As of October 2026, there are 22 flights per day flying from Jacksonville to Chicago. The most common time of day flights depart is 12:00PM, with 48% of flights taking off in the afternoon.
How many flights depart from Jacksonville to Chicago on average per week?
As of October 2026, 156 flights take off from Jacksonville and land in Chicago each week. The most common flight departure day for this route is Thu, with 18% of weekly flights taking off on this day.
When to book flights from Jacksonville to Chicago
Cheap Jacksonville to Chicago (JAX to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Jacksonville to Chicago
Frequently asked questions about flying from Jacksonville to Chicago
How far is Jacksonville to Chicago by plane?
The straight-line distance from Jacksonville to Chicago is 863.3 mi. In terms of flight time, this usually takes a little over 2h 20m.
When did momondo last update prices for flights from Jacksonville Airport to Chicago?
Prices for flights from Jacksonville Airport to Chicago refresh daily.
How many operators does momondo search for flights from Jacksonville Airport to Chicago?
As of October 2026, there are 6 operators available to choose from for flights from Jacksonville Airport to Chicago.
How old do you have to be to fly from Jacksonville Airport to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Jacksonville Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Jacksonville to Chicago?
Based on momondo bookings for flights between Jacksonville and Chicago, the leading plane model is Embraer 175 (Enhanced Winglets), making up 17.61% of the total bookings. Other popular models include Embraer 175 with 16.27%, Airbus A319 with 14.97%, and Boeing 737-800 with 13.78%.
What is the most popular airline from Jacksonville to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Jacksonville to Chicago is United Airlines (43% of total bookings). The next most popular airlines are American Airlines (33%), Southwest (16%), and Frontier (7%).
Best airlines flying from Jacksonville to Chicago
Compare and see reviews for airlines that fly from Jacksonville to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $121 | Free Cancellation | Rating 7.8 8,646 reviews | |||
| PriceFrom $134 | Free Cancellation | Rating 5.6 2,551 reviews | |||
| PriceFrom $197 | Free Cancellation | Rating 7.9 4,224 reviews | |||
| PriceFrom $206 | Free Cancellation | Rating 7.1 3,048 reviews | |||
| PriceFrom $216 | Free Cancellation | Rating 7.4 10,319 reviews | |||
| PriceFrom $217 | Free Cancellation | Rating 7.0 12,146 reviews |
Southwest Flights From Jacksonville to Chicago
Southwest flies from Jacksonville to Chicago around 8 times per week, with 4,224 momondo users rating the airline 7.9/10. The cheapest Southwest deal from Jacksonville to Chicago in the last 72 hours was $197 (round-trip), much lower than the average airfare cost of $389 for Southwest flights on this route.
United Airlines Flights From Jacksonville to Chicago
Another popular option for Jacksonville to Chicago flights is United Airlines (7.4/10, 10,319 ratings). United Airlines flies from Jacksonville to Chicago around 24 times per week, with deals starting from $216 round-trip and rising to an average price of around $380.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Jacksonville to Chicago?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Jacksonville to Chicago. momondo saves you time and could save you money on your trip.
Can I find flights from Jacksonville to Chicago with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to Chicago from Jacksonville with this policy.
How can momondo help me find flights from Jacksonville to Chicago?
Once you have performed a search for Jacksonville to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.
I’m not ready to book a flight from Jacksonville to Chicago right now. Can momondo alert me if prices change?
If you are not ready to book a flight from Jacksonville to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.