Cheap flights from Jacksonville to Chicago from $99
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 8/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Jacksonville to Chicago
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
JetBlue flights from Jacksonville to Chicago
Our best JetBlue deals on Jacksonville to Chicago flight tickets
American Airlines flights from Jacksonville to Chicago
Our best American Airlines deals on Jacksonville to Chicago flight tickets
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?
What is the cheapest month to fly to Chicago?
The month of September is, on average, the cheapest month to fly to Chicago from Jacksonville, with most prices found around $305. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Jacksonville to Chicago during August average around $315.
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 Friday when prices can be found for as low as $433. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Jacksonville to Chicago for around $705.
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 $437. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $493.
What is the cheapest Jacksonville to Chicago flight route?
Fly from Jacksonville to Chicago O'Hare Intl for the best Jacksonville - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Jacksonville when booking 18 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $378 when searching 18 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 $253 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.
What is the cheapest airline that flies from Jacksonville to Chicago?
Frontier, Sun Country Air, and JetBlue are the most popular carriers operating from Jacksonville to Chicago
What airlines fly to Chicago?
United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago from Jacksonville according to our data. United Airlines is the first choice among our users, with 45% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 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 May 2025, there are 20 flights per day flying from Jacksonville to Chicago. The most common time of day flights depart is 11:00AM, with 55% of flights taking off at noon.
How many flights depart from Jacksonville to Chicago on average per week?
As of May 2025, 145 flights take off from Jacksonville and land in Chicago each week. The most common flight departure day for this route is Mon, with 14% 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
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 25m.
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 May 2025, there are 5 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 Boeing 737-800, making up 18.97% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 17.57%, Airbus A319 with 15.55%, and Boeing 737-700 with 13.73%.
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 (18%), and Frontier (3%).
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 $147 | Free Cancellation | Rating 6.0 3,287 reviews | |||
| PriceFrom $148 | Free Cancellation | Rating 8.0 7,950 reviews | |||
| PriceFrom $217 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $219 | Free Cancellation | Rating 7.4 8,723 reviews | |||
| PriceFrom $236 | Free Cancellation | Rating 8.0 4,288 reviews |
Southwest Flights From Jacksonville to Chicago
Southwest flies from Jacksonville to Chicago around 5 times per week, with 4,288 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Jacksonville to Chicago in the last 72 hours was $236 (round-trip), much lower than the average airfare cost of $398 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, 8,723 ratings). United Airlines flies from Jacksonville to Chicago around 21 times per week, with deals starting from $219 round-trip and rising to an average price of around $389.
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.