Cheap flights from Jacksonville to Chicago from $79
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 8/4. 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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Frontier flights from Jacksonville to Chicago Midway Airport
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Southwest flights from Jacksonville to Chicago Midway Airport
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How to get the cheapest flight ticket from Jacksonville to Chicago Midway Airport
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 cheapest month to fly to Chicago Midway Airport?
The month of April is, on average, the cheapest month to fly to Chicago Midway Airport from Jacksonville, with most prices found around $340. If you are unable to visit Chicago Midway Airport during the month of April, then departing from Jacksonville during the month February 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 Chicago Midway Airport?
According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Jacksonville. The lowest ticket price found for a Wednesday departure recently was $361. 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, Sunday is the most expensive day to depart from Jacksonville because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $506.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Jacksonville 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. Try not to purchase tickets in the morning because they tend to be around $433. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Jacksonville to Chicago Midway flight route?
Fly from Jacksonville to Chicago Midway for the best Jacksonville - Chicago Midway flight prices
How far in advance should I book a flight to Chicago Midway Airport?
You are more likely to see cheaper flights to Chicago Midway Airport from Jacksonville when booking 9 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $448 when searching 9 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Jacksonville for as low as $276 on momondo.
What cabin class options are available on Jacksonville to Chicago Midway flights?
There are 1 cabin classes available to choose from on Jacksonville to Chicago Midway 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 Midway Airport flights?
No. A direct flight is the cheapest option for a flight between Jacksonville to Chicago Midway Airport.
How have Jacksonville to Chicago Midway Airport flight prices changed over time?
How many flights depart from Jacksonville to Chicago Midway Airport on average per week?
5 flights are operational weekly from Jacksonville to Chicago Midway Airport as of June 2025. The most popular departure day for this route is Mon, with 20% of flights per week taking off on this day.
When to book flights from Jacksonville to Chicago Midway Airport
Cheap Jacksonville to Chicago Midway Airport (JAX to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Jacksonville to Chicago Midway Airport
How far is Jacksonville to Chicago Midway by plane?
A flight from Jacksonville to Chicago Midway will travel around 860.2 mi. A reasonable flight in good conditions will take 2h 25m.
When did momondo last update prices for flights from Jacksonville Airport to Chicago Midway Airport?
Prices for flights from Jacksonville Airport to Chicago Midway Airport were last updated today.
How many operators does momondo search for flights from Jacksonville Airport to Chicago Midway Airport?
There are 2 operators available for flights from Jacksonville Airport to Chicago Midway Airport as of June 2025.
How old do you have to be to fly from Jacksonville Airport to Chicago Midway Airport?
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 Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Jacksonville to Chicago Midway Airport?
momondo data reveals that the most frequently booked plane model on the route from Jacksonville to Chicago Midway Airport is Boeing 737-800, representing 18.16% of all bookings. The subsequent popular models are Airbus A319 at 16.49%, Embraer 175 (Enhanced Winglets) at 14.20%, and Boeing 737 MAX 8 at 11.27%.
What is the most popular airline from Jacksonville to Chicago Midway Airport?
momondo data reveals that the most frequently booked airline on the route from Jacksonville to Chicago Midway Airport is Southwest, representing 76% of all bookings. The subsequent popular airline is Delta at 24%.
Best airlines flying from Jacksonville to Chicago Midway Airport
Compare and see reviews for airlines that fly from Jacksonville to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $236 | Free Cancellation | Rating 8.0 7,946 reviews | |||
| PriceFrom $267 | Free Cancellation | Rating 8.0 4,287 reviews |
Southwest Flights From Jacksonville to Chicago Midway Airport
Southwest flight deals from Jacksonville to Chicago Midway Airport start from $267 round-trip. Over the 5 Southwest flights for this route in a normal week, average airfare is usually $399 round-trip - but some users have found much cheaper deals with momondo.
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?
Finding the right flight to Chicago from Jacksonville is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.
Can I find flights from Jacksonville to Chicago with flexible booking policies on momondo?
Flights from Jacksonville to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Jacksonville to Chicago?
Once all potential Jacksonville to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Jacksonville to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from Jacksonville are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.