Flights from Jacksonville to Chicago from $158

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Airfare Deals Jacksonville to Chicago

On HolidayPrice.com you will find 5 direct and 5 connecting flights from Jacksonville to Chicago at a price of from $158. You can compare airfare deals from airlines and multiple travel sites, book and save on cheap plane tickets and last minute offers. Also check out JAX - CHI flight schedule to find best flight time, convenient departure and arrival airports.

Sun

The cost of airline tickets from Jacksonville to Chicago (United States) and back without transfers can be found with the help of the calendar. Specify the search parameters: one way or round-trip, payment currency, click on the month/day you need and we will search for flights to Chicago.

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Cheap flights from Jacksonville
Cheap flights to Chicago
Airline tickets to United States

One way flight from Jacksonville to Chicago

Below are the prices of tickets for direct one-way flights from Jacksonville to Chicago. The cheapest flight from Jacksonville to Chicago starts from $158 – the departure date for this flight is 22 May 2025.

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03.06.2025 Tuesday

from $171 Mytrip.com

Economy Found yesterday

2 Stopovers 31 hours 38 min

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*Prices include: baggage, hand luggage, airline fees and charges.

Round trip from Jacksonville to Chicago

You can buy a round-trip ticket from Jacksonville to Chicago (United States) and back using the table below. The best offer starts from $225, the flight dates are: there on 22 May 2025 year and back on 29 May 2025 year.

*Prices include: baggage, hand luggage, airline fees and charges.

Not found promotions and sales.

Flight Schedule Jacksonville to Chicago 2025

The current flight schedule for the route from Jacksonville to Chicago for today, tomorrow and the next few days. This schedule will help you decide on the time of departure and arrival, the airline, the flight number and the day of the week.

More than 3 flights every day, from 2hours 30min. Local departure and arrival times are indicated.

06:00 → 07:35

Southwest Airlines WN3668

JAX → MDW

- - - - - Sa -

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07:40 → 09:10

Southwest Airlines WN2713

JAX → MDW

- Tu We - - - -

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07:45 → 09:32

United Airlines UA2414

JAX → ORD

- - - - - Sa -

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08:05 → 09:52

United Airlines UA2414

JAX → ORD

Mo Tu We Th Fr - Su

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11:27 → 13:15

United Airlines UA1239

JAX → ORD

Mo - - Th Fr - -

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11:35 → 13:10

Southwest Airlines WN2713

JAX → MDW

Mo - - Th Fr - -

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12:55 → 14:30

Southwest Airlines WN2713

JAX → MDW

- - - - - - Su

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15:05 → 16:54

United Airlines UA457

JAX → ORD

Mo - We Th Fr Sa Su

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15:07 → 16:56

United Airlines UA457

JAX → ORD

- Tu - - - - -

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19:35 → 21:05

Southwest Airlines WN2713

JAX → MDW

- - - - - Sa -

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*Schedule is indicated only for direct scheduled flights and low-cost airlines.

Flight Information

Flying to Chicago from Jacksonville takes 02:22 minutes (excluding transfers). The distance between Jacksonville and Chicago is 862 miles (1388 kilometers). Planes depart from Jacksonville between 00:00 and 23:58. The fastest flight from the company United Airlines with flight number UA 3559. Flies for just 02:12 minutes with departure from Jacksonville and arrival in O'Hare.

Airlines

Direct flight

There are 5 airlines that fly directly from Jacksonville to Chicago. The most popular company carrying out non-stop flights is Southwest Airlines.

Southwest Airlines: WN 4460, WN 857, WN 1029
United Airlines: UA 3484, UA 5622, UA 302
American Airlines: AA 1093, AA 4128, AA 2936
Spirit Airlines: NK 206, NK 1202
Frontier Airlines: F9 413

*Flight number

Flights with Transfers

Flights with transfers from Jacksonville to Chicago can be bought from 5 airlines:

Southwest Airlines: Raleigh/Durham, Baltimore, Nashville
JetBlue Airways: New York
United Airlines: New York
Frontier Airlines: Philadelphia
Delta Air Lines: Atlanta

*Transit cities

Airports

Airports serving the air communication between Jacksonville and Chicago. You can fly to Chicago from 1 Jacksonville airports. Planes arrive at 2 airport in Chicago.

Jacksonville airports:

Jacksonville ~ 18 km* from $ 50

Chicago airports:

Chicago Midway ~ 14 km* from $ 90O'Hare ~ 25 km* from $ 54

*Distance from the airport to the city center

Aircraft

You can fly from Jacksonville to Chicago on board of 5 airlines that utilize 8 aircraft models.

Airbus A319
Airbus A320
Boeing 737-700

Boeing 737-800
Canadair reg jet 700
Embraer 170

Embraer 175
Embraer EMB 175

Connecting cities

The list of cities on transfer flights to Chicago from Jacksonville. The best options are to fly through: Raleigh/Durham, New York, Philadelphia, Atlanta, Baltimore, Nashville.

Raleigh/Durham
New York
Philadelphia

Atlanta
Baltimore
Nashville

Cheap airline tickets from Jacksonville to United States

Here is a list of flights from Jacksonville to United States purchased on HolidayPrice.com in the past 48 hours. If you find an interesting offer for cheap tickets, do not delay your purchase, prices change every 15 minutes.

Jacksonville - New York DL 5266 Delta Air Lines Canadair Regional Jet 900

18:09 Jacksonville

in a way 1 hours 51 min Direct

20:00 LaGuardia

Flights
from $246 21 May 2025

Jacksonville - Los Angeles WN 391 Southwest Airlines Boeing 737-700

23:05 Jacksonville

in a way 6 hours 25 min Direct

05:30 Los Angeles

Flights
from $116 26 May 2025

Jacksonville - Miami NK 1123 Spirit Airlines Airbus A319

13:00 Jacksonville

in a way 1 hours 13 min Direct

14:13 Fort Lauderdale Executive Airport

Flights
from $148 26 May 2025

Jacksonville - Chicago UA 3559 United Airlines Embraer 175

23:48 Jacksonville

in a way 2 hours 12 min Direct

02:00 O'Hare

Flights
from $158 22 May 2025

Jacksonville - San Francisco WN 5571 Southwest Airlines Boeing 737-700

01:20 Jacksonville

in a way 7 hours 0 min Direct

08:20 Auckland Airport

Flights
from $155 26 May 2025

All flights from Jacksonville

Flights from United States to Chicago

Here are the cheapest flight bookings from United States to Chicago made by users of our website. If you didn’t find your flight destination, use the search bar at the top of the page.

New York - Chicago UA 761 United Airlines Boeing 737-800

13:00 LaGuardia

in a way 2 hours 0 min Direct

15:00 O'Hare

Flights
from $33 20 May 2025

Los Angeles - Chicago UA 910 United Airlines Boeing 737-800

10:23 Los Angeles

in a way 3 hours 37 min Direct

14:00 O'Hare

Flights
from $48 20 May 2025

Miami - Chicago AA 2796 American Airlines Boeing 767-300

17:05 Miami

in a way 2 hours 55 min Direct

20:00 O'Hare

Flights
from $36 22 May 2025

Miami - Chicago WN 1626 Southwest Airlines Boeing 737

13:35 Fort Lauderdale Executive Airport

in a way 3 hours 0 min Direct

16:35 Chicago Midway

Flights
from $36 22 May 2025

San Francisco - Chicago UA 1800 United Airlines Airbus A319

04:15 San Francisco

in a way 3 hours 45 min Direct

08:00 O'Hare

Flights
from $83 20 May 2025

All flights to Chicago

Tips for buying a ticket

Jacksonville – Chicago – Jacksonville round-trip route are always cheaper than tickets purchased there and back separately.

Cheap flights from Jacksonville to Chicago — Chicago city

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