App
Customer Support
MXN
Find Bookings
Worldwide Coverage
Worldwide Coverage
Flights to over 5,000 cities
One-stop Service Guarantee
One-stop Service Guarantee
Price guaranteed upon confirmed payment, booking guaranteed once tickets issued
Secure Payment
Secure Payment
Convenient & reliable booking and payment system

Cheap flight deals from Jacksonville to Chicago Starting at MXN$1,258

We've found these cheap flights for you. You can book one-way or round-trip flight tickets.

  • One way
  • Round-trip
      • Cheapest nonstop
        JAX04:35 pm
        2h 40m
        Nonstop
        MDW06:15 pm
        Wed, Feb 26|Jacksonville - Chicago|Southwest Airlines
        MXN$2,407MXN$3,175
        24% OFF
        24% OFF
        MXN$3,175MXN$2,407

        Choose Southwest Airlines flights from Jacksonville to Chicago. The one-way direct flight with Southwest Airlines departs from Jacksonville International Airport on Wed, Feb 26, arriving at Midway International Airport. One-way Prices start from MXN$2,407 including taxes and charges.

      • JAX05:20 pm
        2h 30m
        Nonstop
        MDW06:50 pm
        Thu, Feb 27|Jacksonville - Chicago|Southwest Airlines
        MXN$2,413MXN$3,175
        24% OFF
        24% OFF
        MXN$3,175MXN$2,413

        Choose Southwest Airlines flights from Jacksonville to Chicago. The one-way direct flight with Southwest Airlines departs from Jacksonville International Airport on Thu, Feb 27, arriving at Midway International Airport. One-way Prices start from MXN$2,413 including taxes and charges.

      • JAX10:26 pm
        9h 16m
        1 stop
        ORD06:42 am
        Thu, May 1|Jacksonville - Chicago|Frontier Airlines
        MXN$1,258MXN$3,175
        60% OFF
        60% OFF
        MXN$3,175MXN$1,258

        Choose Frontier Airlines flights from Jacksonville to Chicago. The one-way connecting flight with Frontier Airlines departs from Jacksonville International Airport on Thu, May 1, arriving at O'Hare International Airport. One-way Prices start from MXN$1,258 including taxes and charges.

      • JAX09:42 am
        11h 9m
        1 stop
        MDW07:51 pm
        Tue, Apr 1|Jacksonville - Chicago|Frontier Airlines
        MXN$1,410
        MXN$1,410

        Choose Frontier Airlines flights from Jacksonville to Chicago. The one-way connecting flight with Frontier Airlines departs from Jacksonville International Airport on Tue, Apr 1, arriving at Midway International Airport. One-way Prices start from MXN$1,410 including taxes and charges.

      • JAX10:26 pm
        9h 16m
        1 stop
        ORD06:42 am
        Thu, May 8|Jacksonville - Chicago|Frontier Airlines
        MXN$1,675
        MXN$1,675

        Choose Frontier Airlines flights from Jacksonville to Chicago. The one-way connecting flight with Frontier Airlines departs from Jacksonville International Airport on Thu, May 8, arriving at O'Hare International Airport. One-way Prices start from MXN$1,675 including taxes and charges.

      • JAX09:42 am
        11h 9m
        1 stop
        MDW07:51 pm
        Tue, Apr 8|Jacksonville - Chicago|Frontier Airlines
        MXN$1,743
        MXN$1,743

        Choose Frontier Airlines flights from Jacksonville to Chicago. The one-way connecting flight with Frontier Airlines departs from Jacksonville International Airport on Tue, Apr 8, arriving at Midway International Airport. One-way Prices start from MXN$1,743 including taxes and charges.

      • JAX07:30 am
        5h 39m
        1 stop
        ORD12:09 pm
        Tue, Apr 15|Jacksonville - Chicago|Delta Air Lines
        MXN$2,081
        MXN$2,081

        Choose Delta Air Lines flights from Jacksonville to Chicago. The one-way connecting flight with Delta Air Lines departs from Jacksonville International Airport on Tue, Apr 15, arriving at O'Hare International Airport. One-way Prices start from MXN$2,081 including taxes and charges.

      • JAX06:59 pm
        5h 50m
        1 stop
        ORD11:49 pm
        Wed, Feb 26|Jacksonville - Chicago|Delta Air Lines
        MXN$2,092
        MXN$2,092

        Choose Delta Air Lines flights from Jacksonville to Chicago. The one-way connecting flight with Delta Air Lines departs from Jacksonville International Airport on Wed, Feb 26, arriving at O'Hare International Airport. One-way Prices start from MXN$2,092 including taxes and charges.

      • JAX12:05 pm
        7h 36m
        1 stop
        ORD06:41 pm
        Tue, May 20|Jacksonville - Chicago|Delta Air Lines
        MXN$2,092
        MXN$2,092

        Choose Delta Air Lines flights from Jacksonville to Chicago. The one-way connecting flight with Delta Air Lines departs from Jacksonville International Airport on Tue, May 20, arriving at O'Hare International Airport. One-way Prices start from MXN$2,092 including taxes and charges.

      • JAX05:30 am
        4h 5m
        1 stop
        ORD08:35 am
        Wed, Apr 16|Jacksonville - Chicago|Delta Air Lines
        MXN$2,100
        MXN$2,100

        Choose Delta Air Lines flights from Jacksonville to Chicago. The one-way connecting flight with Delta Air Lines departs from Jacksonville International Airport on Wed, Apr 16, arriving at O'Hare International Airport. One-way Prices start from MXN$2,100 including taxes and charges.

      • JAX01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Sat, Mar 1|Jacksonville - Chicago|Southwest Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Jacksonville to Chicago Flight Time

Flight info.
Departure
Arrival
Weekly Schedule

  1. UA457

    United Airlines

    04:33 pm

    JAX

    2.8h

    Nonstop

    06:20 pm

    ORD

    SMTWTFS
    Search

  2. WN4816

    Southwest Airlines

    04:35 pm

    JAX

    2.7h

    Nonstop

    06:15 pm

    MDW

    SMTWTFS
    Search

  3. AA548

    American Airlines

    05:05 am

    JAX

    1.4h

    06:32 am

    CLT

    SMTWTFS
    Search

  4. AA2843

    American Airlines

    07:50 am

    CLT

    2.2h

    09:01 am

    ORD

    SMTWTFS

  5. DL2722

    Delta Air Lines

    05:30 am

    JAX

    1.2h

    06:44 am

    ATL

    SMTWT-S
    Search

  6. DL1063

    Delta Air Lines

    08:22 am

    ATL

    2.0h

    09:23 am

    MDW

    SMTWTFS

  7. DL2722

    Delta Air Lines

    05:30 am

    JAX

    1.2h

    06:44 am

    ATL

    SMTWT-S
    Search

  8. DL1178

    Delta Air Lines

    07:25 am

    ATL

    2.2h

    08:39 am

    ORD

    SMTWT-S

  9. WN699

    Southwest Airlines

    06:35 am

    JAX

    1.8h

    07:20 am

    BNA

    SMTWTFS
    Search

  10. WN983

    Southwest Airlines

    09:40 am

    BNA

    1.8h

    11:30 am

    ORD

    SMTWT-S

  11. DL2627

    Delta Air Lines

    06:46 pm

    JAX

    1.4h

    08:08 pm

    ATL

    SMTWT-S
    Search

  12. DL1076

    Delta Air Lines

    08:50 pm

    ATL

    1.9h

    09:46 pm

    MDW

    SMTWTFS

  13. DL2331

    Delta Air Lines

    08:10 pm

    JAX

    1.3h

    09:30 pm

    ATL

    S--WT-S
    Search

  14. DL1199

    Delta Air Lines

    10:45 pm

    ATL

    2.1h

    11:54 pm

    ORD

    SMTWTFS

  15. UA2850

    United Airlines

    11:25 am

    JAX

    2.8h

    Nonstop

    01:13 pm

    ORD

    SMTWTFS
    Search

  16. AA4707

    American Airlines

    11:48 am

    JAX

    1.9h

    01:44 pm

    DCA

    SMTWT-S
    Search

  17. AA3180

    American Airlines

    02:54 pm

    DCA

    2.3h

    04:14 pm

    ORD

    SMTWTFS
Find more flights and airlines

When is the cheapest time to fly from Jacksonville to Chicago?

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

  • When are flight tickets from Jacksonville (JAX) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Jacksonville to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Jacksonville (JAX) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around MXN$7,502.

  • How long does it take to fly from Jacksonville (JAX) to Chicago (CHI) and what is the distance?

    It takes around 4 hours 51 minutes to fly from Jacksonville (JAX) to Chicago (CHI).

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.

  • What are the most popular airlines that fly from Jacksonville (JAX) to Chicago (CHI)?

    Airlines with flights from Jacksonville (JAX) to Chicago (CHI): Alaska Airlines, American Airlines, United Airlines, Qatar Airways, Southwest Airlines and Air Canada.

How to find a cheap flight from Jacksonville to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Jacksonville to Chicago. Book your flights at the right time and save more.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Info | Jacksonville to Chicago

Cheapest nonstop flight priceMXN$1,258
Cheapest round-trip ticket priceMXN$4,096
Off-season for travelDecember
Peak season for travelNovember
Flight distance1,382.54 km
Average flight time4 hours 51 minutes
Popular airlineUnited Airlines

Contact Us

About

Other Services

Payment Methods
Our Partners
Copyright © 2025 Trip.com Travel Singapore Pte. Ltd. All rights reserved
Site Operator: Trip.com Travel Singapore Pte. Ltd.