Flights from Jacksonville (JAX) to Chicago (MDW)
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Jacksonville to Chicago Flight Information
Find the Cheapest Flights from Jacksonville (JAX) to Chicago (MDW)
Work hard, travel harder! Wotif brings you the cheapest Jacksonville to Chicago flights, making it possible to have a five star holiday without that five star price tag. Browse and compare our top JAX to MDW routes and airport options. So, go ahead and treat yourself, your sweetheart, or the kids to an unforgettable holiday this year.
to Information
Traveling From | Jacksonville Intl. |
|---|---|
Origin Airport | |
Origin Airport IATA Code | JAX |
Traveling To | Midway Intl. |
Destination Airport | |
Destination Airport IATA Code | MDW |
Number of Airlines Serving | |
Average Flight Time | hours mins |
Direct Flight Time | hours mins |
Flight Price |
Jacksonville to Chicago Flight Deals from
Considering a quick trip to Chicago, but not sure which is the best route for you? Well, you’re in luck! Wotif has done the hard work, so all you need to do is check out these flights from JAX to MDW. With heaps of cheap fares from Jacksonville, we guarantee you’ll be arriving to your holiday destination in style without emptying your bank account in the process.
It’s easy to book flights to Chicago from Jacksonville
For a huge choice of flights, simply enter your travel dates and hit search and we’ll hunt out fantastic deals on one-way, return and multi-city airfares to Chicago from Jacksonville from different airlines. If you click the ‘direct flights’ box, you see flights that’ll get you to Chicago in just hour(s) and mins, too.
Snap up great deals on flights to Chicago from Jacksonville
Choose from flights a day on average, with prices starting at and rising to depending on the cabin class, travel dates, and airline carrier. And if you’re up for a last-minute getaway, you can get great deals on flights from Jacksonville to Chicago today!
Find cheap airfares to Chicago from Jacksonville
Here are our insider tips for bagging a flight bargain:
- Look for midweek flights and late night, early morning arrival and departure times
- Check out other airports near Jacksonville and Chicago
- Avoid peak season (prices tend to be lower in )
- Be flexible with your travel dates and you can usually get cheaper options
Reasons to book your flights to Chicago from Jacksonville with Wotif
Wotif is a super-easy way to find the best flight for you to Chicago. Get more bang for your buck on flight and hotel or car rental combos and download the free Wotif app to tap into exclusive deals. Book now with Wotif and have a great flight!
Great places to stay after flight from Jacksonville to Chicago
Hotel Chicago West Loop, SureStay Collection by Best Western
"Nice place, great staff, and excellent service. Everyone was friendly and helpful. Highly recommend!"
Reviewed on 25 June 2026
Hyatt Regency McCormick Place Chicago
"What a lovely property. The room was fantastic. Abraham was so kind and helpful. This is my favorite hotel to stay at in Chicago. Highly recommend."
Reviewed on 24 June 2026
Holiday Inn & Suites Chicago - Downtown by IHG
"Overall stay was nice and convenient. Would stay here again. The only thing was cleanliness could be better in the bathroom"
Reviewed on 24 June 2026
Discover top hotels, vacation package, cheap car rental deals and more with Wotif!
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^Savings based on all package bookings made with Flight + Hotel on Wotif.com from , as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.