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
Address:
5700 South Cicero
Chicago IL, 60638
United States
IATA code:
MDW
Longitude:
-87.740871
Latitude:
41.788136
Time zone:
America/Chicago
Address:
2400 Yankee Clipper Drive
Jacksonville FL, 32218
United States
IATA code:
JAX
Longitude:
-81.683053
Latitude:
30.491254
Time zone:
America/New_York

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

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is AU$248 per night from 13 Feb to 14 Feb
AU$248
13 Feb - 14 Feb
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8/10 Very Good! (9,849 reviews)
Friendly staff. Clean room.

Reviewed on 5 Feb 2026

Congress Plaza Hotel
Hyatt House Chicago West Loop

Hyatt House Chicago West Loop

3.5 out of 5
105 N MAY STREET Chicago IL
The price is AU$241 per night from 15 Feb to 16 Feb
AU$241
15 Feb - 16 Feb
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free Wi-Fi and a 24-hour fitness centre. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,179 reviews)
The front desk staff (during check-in and out) were great! Definitely staying in this property the next time we’re in Chicago.

Reviewed on 6 Feb 2026

Hyatt House Chicago West Loop
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street Chicago IL
The price is AU$172 per night from 16 Feb to 17 Feb
AU$172
16 Feb - 17 Feb
includes taxes & fees
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, breakfast (surcharge) and a fitness centre. Our guests praise the helpful staff in their reviews. ...
8.8/10 Excellent! (1,952 reviews)
Super helpful, knowledgeable with great communication through text as well. Everything was clean. Wish parking wasn’t so much money :(. The hotel staff went above and beyond for us. Even had a kind man offer to make me a sandwich after the restaurants were closed following a night out. Took the time ...

Reviewed on 6 Feb 2026

Crowne Plaza Chicago West Loop by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

More Destinations

^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.