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.

Jacksonville to Chicago Information

Traveling From
Jacksonville Intl.
Origin Airport
Jacksonville
Origin Airport IATA Code
JAX
Traveling To
Midway Intl.
Destination Airport
Chicago
Destination Airport IATA Code
MDW
Number of Airlines Serving
1
Average Flight Time
2 hours 25 mins
Direct Flight Time
2 hours 25 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 2 hour(s) and 25 mins, too.   

Snap up great deals on flights to Chicago from Jacksonville 

Choose from 1 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

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$304 per night from 13 July to 14 July
AU$304
13 July - 14 July
includes taxes & fees
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,226 reviews)
"Super convenient location. Friendly staff. Room sparkling clean and nicely appointed. Would stay again"

Reviewed on 5 Jul. 2025

Crowne Plaza Chicago West Loop by IHG
Holiday Inn & Suites Chicago - Downtown by IHG
Holiday Inn & Suites Chicago - Downtown by IHG
3 out of 5
506 West Harrison Street, Chicago, IL
The price is AU$312 per night from 9 July to 10 July
AU$312
9 July - 10 July
includes taxes & fees
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.2/10 Very Good! (1,006 reviews)
"I love the pool and the atmosphere of the whole hotel. Very clean and quiet."

Reviewed on 4 Jul. 2025

Holiday Inn & Suites Chicago - Downtown by IHG
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$446 per night from 27 July to 28 July
AU$446
27 July - 28 July
includes taxes & fees
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...
8.8/10 Excellent! (1,001 reviews)
Nice neighborhood, clean, friendly
"Very clean hotel with friendly staff in a nice neighborhood! Great rooftop terrace with incredible views and comfy seating area. It was hard to get a comfortable temperature in the room at night, but I think that’s most hotels. My only complaint is that and the noise of the air conditioner kicking ..."

Reviewed on 3 Jul. 2025

Hyatt House Chicago West Loop
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.

^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.