Flight Routes from Chicago to Jacksonville, Florida

Compare cheap outbound and return flights from Chicago (CHI) to Jacksonville, Florida (JAX) and find the best offer from numerous airlines and travel agencies.

Trip type
Fastest flight
non-stop flights
57x / week
Flight distance
1,375 km
Time difference
Airports in Chicago
  1. O'Hare International Airport, IL
  2. Midway International Airport, IL
  3. Rockford, IL

Flight schedule from Chicago (CHI) to Jacksonville, Florida (JAX)

Select a travel date in the flight schedule for the route from Chicago (CHI) to Jacksonville, Florida (JAX) and compare affordable flight deals.

offers
Active filtersnone
Matching outbound flightsCHI–JAX · 16 of 16
fromto
dep.arr.
durationstopovers
  1. September 20 – 26, 2026
  2. Sep 27 – Oct 3, 2026
  3. October 4 – 10, 2026
    1. ORDJAX
      nonstop
      1. American Airlines
    2. ORDJAX
      nonstop
      1. United Airlines
    3. ORDJAX
      nonstop
      1. United Airlines
    4. MDWJAX
      nonstop
      1. Southwest Airlines
    5. ORDJAX
      nonstop
      1. American Airlines
    6. ORDJAX
      nonstop
      1. United Airlines
    7. ORDJAX
      nonstop
      1. United Airlines
    8. MDWJAX
      nonstop
      1. Southwest Airlines
    9. MDWJAX
      nonstop
      1. Southwest Airlines
    10. ORDJAX
      nonstop
      1. American Airlines
    11. ORDJAX
      nonstop
      1. United Airlines
    12. MDWJAX
      nonstop
      1. Southwest Airlines
    13. ORDJAX
      nonstop
      1. United Airlines
    14. ORDJAX
      nonstop
      1. American Airlines
    15. MDWJAX
      nonstop
      1. Southwest Airlines

      Tips and tricks to help you find cheap flights from Chicago to Jacksonville, Florida

      Favorite airline: United Airlines
      United Airlines is the most popular airline for flights from Chicago to Jacksonville, Florida.
      United Airlines
      44 %
      JetBlue Airways
      20 %
      American Airlines
      18 %
      Direct flights are more expensive
      On this route, direct flights are $ 6.00 more expensive than flights with a stopover.
      non stop flight
      1 stop
      2 stops
      02h 34min
      05h 44min
      14h 14min
      270 $
      264 $
      321 $
      The favorite connection is non-stop
      55 % of travelers decide to book a direct flight on this route.
      Route
      bookings
      Direct flights
      02h 34min, from 270 $
      55 %
      1 stopover New York - John F. Kennedy International Airport, NY
      06h 09min, from 1.927 $
      14 %
      1 stopover Minneapolis - St. Paul International Airport, MN
      14h 23min, from 308 $
      12 %

      Important flight information

      Discover more flights around Chicago and Jacksonville, Florida

      Departure airport Airport Chicago-IL, all airports (CHI)
      Arrival airport Airport Jacksonville, Florida (JAX)
      Destination country Flights to United States
      Departure airport - Destination country Chicago-IL, all airports - United States
      Alternative flights to Jacksonville, Florida
      Flight destinations with a similar price