JAX - CHI

$111 Find Cheap Flights from Jacksonville to Chicago - Compare and Save

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Everything you should know

Cheapest round-trip
$198
Typical prices: $290-$441
Frontier
Sat 10/6Sat 10/13
JAX - ORD • 1 stop
Cheapest non-stop
$327
Typical prices: $301-$444
American Airlines
Tue 10/23Fri 10/26
JAX - ORD • Non-stop
Nonstop flights
You can fly direct with United Airlines, American Airlines and Southwest. Average duration is 2h 51m
Direct flights
+1
Direct flights
+1
Top routes
Cheapest • 4% average savings
Most popular
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 14 weeks in advance save around 45% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 14% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $242 (round-trip)
Shortest trip • 4h 45m (one-way)
Insights
Insights
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Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Jacksonville to Chicago (JAX-CHI)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Jacksonville to Chicago

Fri, Sep 25 - Mon, Sep 28
Frontier Logo
7:46 pm - 6:23 pmJAX  Jacksonville-ORD Chicago O'Hare Intl
23h 37m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
7:28 pm - 7:01 pmORD  Chicago O'Hare Intl-JAX Jacksonville
22h 33m1 stop Atlanta Hartsfield-Jackson
$197Frontier
Tue, Oct 6 - Tue, Oct 13
Frontier Logo
7:46 pm - 11:51 amJAX  Jacksonville-ORD Chicago O'Hare Intl
17h 05m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
7:44 pm - 6:46 pmORD  Chicago O'Hare Intl-JAX Jacksonville
22h 02m1 stop Atlanta Hartsfield-Jackson
$198Frontier
Mon, Oct 5 - Sat, Oct 10
Multiple Airlines Logo
3:46 pm - 3:20 pmJAX  Jacksonville-ORD Chicago O'Hare Intl
24h 34m1 stop Fort Lauderdale
Multiple Airlines Logo
6:00 am - 6:46 pmORD  Chicago O'Hare Intl-JAX Jacksonville
11h 46m1 stop Atlanta Hartsfield-Jackson
$236Multiple Airlines
Thu, Sep 24 - Mon, Sep 28
Multiple Airlines Logo
3:00 pm - 2:45 pmJAX  Jacksonville-ORD Chicago O'Hare Intl
24h 45m1 stop Fort Lauderdale
Multiple Airlines Logo
7:28 pm - 7:01 pmORD  Chicago O'Hare Intl-JAX Jacksonville
22h 33m1 stop Atlanta Hartsfield-Jackson
$238Multiple Airlines
Fri, Oct 23 - Mon, Oct 26
American Airlines Logo
6:36 am - 8:29 amJAX  Jacksonville-ORD Chicago O'Hare Intl
2h 53mnonstop
American Airlines Logo
7:30 pm - 10:59 pmORD  Chicago O'Hare Intl-JAX Jacksonville
2h 29mnonstop
$327American Airlines
Fri, Oct 16 - Mon, Oct 19
American Airlines Logo
6:36 am - 8:29 amJAX  Jacksonville-ORD Chicago O'Hare Intl
2h 53mnonstop
American Airlines Logo
8:20 am - 11:49 amORD  Chicago O'Hare Intl-JAX Jacksonville
2h 29mnonstop
$327American Airlines
Tue, Oct 6 - Fri, Oct 9
Southwest Logo
12:45 pm - 2:05 pmJAX  Jacksonville-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
2:55 pm - 6:15 pmMDW  Chicago Midway-JAX Jacksonville
2h 20mnonstop
$327Southwest
Tue, Oct 6 - Tue, Oct 13
Southwest Logo
12:45 pm - 2:05 pmJAX  Jacksonville-MDW Chicago Midway
2h 20mnonstop
Southwest Logo
6:00 pm - 9:20 pmMDW  Chicago Midway-JAX Jacksonville
2h 20mnonstop
$327Southwest
Wed, Oct 28 - Tue, Nov 3
United Airlines Logo
3:40 pm - 5:29 pmJAX  Jacksonville-ORD Chicago O'Hare Intl
2h 49mnonstop
United Airlines Logo
8:00 pm - 11:42 pmORD  Chicago O'Hare Intl-JAX Jacksonville
2h 42mnonstop
$343United Airlines
Wed, Nov 11 - Sat, Nov 14
United Airlines Logo
12:35 pm - 2:29 pmJAX  Jacksonville-ORD Chicago O'Hare Intl
2h 54mnonstop
United Airlines Logo
10:44 am - 2:20 pmORD  Chicago O'Hare Intl-JAX Jacksonville
2h 36mnonstop
$343United Airlines
Booking Insights

Price, demand and travel trends for Jacksonville to Chicago flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Jacksonville to Chicago with more confidence.

How much is a round-trip flight from Jacksonville to Chicago?

Round-trip flights from Jacksonville to Chicago start at $198. Prices are below average for this route right now, with typical round-trip fares ranging from $290 to $441. The lowest price found in the past 5 days was $198 on Frontier.

What is the cheapest Jacksonville to Chicago flight route?

There's little price difference between Jacksonville to Chicago routes. They average around $350 round-trip, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Jacksonville to Chicago?

Wednesday is the cheapest day of the week to fly from Jacksonville to Chicago, it is 10% cheaper than the average day. Monday is the most expensive day with flight prices 14% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is the cheapest month to fly from Jacksonville to Chicago?

  • September is the cheapest month to fly from Jacksonville to Chicago at $310 round-trip.
  • November ($390) and March ($385) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 25% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Jacksonville to Chicago the cheapest?

Flights from Jacksonville to Chicago are cheapest 14 weeks before departure. Booking in this window typically costs about 45% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from Jacksonville to Chicago

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, ORD and MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Marisa Garcia

Marisa Garcia

Expert on JAX

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Key details for Jacksonville to Chicago flights

Low season

February

Cheapest flight

$111
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Jacksonville to Chicago O'Hare Intl Airport

When to book flights from Jacksonville to Chicago

Are your dates flexible? Find out the best times to travel from Jacksonville to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Jacksonville to Chicago flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Where are the art installations at JAX?

    JAX has art installations before and after security as well as in the baggage claim area. It also has several artworks in the Haskell Art Gallery. Located in the center courtyard after security, this gallery showcases art pieces made by local artists.

  • What is the best method of public transportation to JAX from Jacksonville?

    Currently, no bus or train offers transportation services from Jacksonville’s city center to JAX. Only cabs do. If you’d like to travel from Jacksonville’s city center to JAX via public transportation, you’ll have to settle for a cab.

  • Does ORD have an on-site hotel?

    ORD does have an on-site hotel, the Hilton Chicago O’Hare International Airport hotel. Located directly across from terminals 1, 2, and 3, this hotel is a short walking distance from the terminals. As a guest at the Hilton, you’ll have a great time, as it boasts great amenities and superb staff.

  • Where can I shower at ORD?

    In case you want to shower before leaving ORD, visit the Health Club. Located between terminal 2 and the parking garage, this club has super clean showers you can use. You will also have access to a sauna, steam room, jacuzzi, and pool - everything you need to relax before your flight.

  • Which airlines offer extra legroom and free seat selection on Jacksonville to Chicago flights?

    Among airlines operating Jacksonville to Chicago flights:

    • United Airlines: offers extra legroom; offers free seat selection
    • American Airlines: offers extra legroom; offers free seat selection
    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • What airlines are available from Jacksonville to Chicago?

    3 airlines operate flights between Jacksonville and Chicago. The airlines offering nonstop flights on this route include:

    • United Airlines
    • American Airlines
    • Southwest

  • Which airports can I use when flying from Jacksonville to Chicago?

    Flights from Jacksonville to Chicago usually depart from Jacksonville (JAX) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • Which airlines include bags at no extra cost on Jacksonville to Chicago flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • United Airlines: a cabin bag and a checked bag in Economy Class
    • American Airlines: a cabin bag and a checked bag in Economy Class
    • Southwest: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

  • What cabin classes can I book on flights from Jacksonville to Chicago?

    Two cabin classes are available on flights from Jacksonville to Chicago:

    • Economy Class
    • First Class

  • How much can I save by taking a layover when flying from Jacksonville to Chicago?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $242 round-trip via Philadelphia (PHL), compared to $365 for nonstop.

  • What is the standard checked-bag allowance on flights from Jacksonville to Chicago?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $40–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which airports do connecting flights from Jacksonville to Chicago pass through?

    One-stop flights from Jacksonville to Chicago most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 86% of one-stop connections
    • Charlotte Douglas (CLT) - 4% of one-stop connections
    • Nashville Intl (BNA) - 2% of one-stop connections
    • Fort Lauderdale (FLL) - 2% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Jacksonville to Chicago?

    Yes. Being flexible with your travel dates can save you up to 22% on the Jacksonville to Chicago route. Wednesday is the cheapest departure day at $324 round-trip on average, while Monday is the most expensive at $411, a difference of $87. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How are flight departures from Jacksonville to Chicago spread across the day?

    Morning is the busiest departure period on Jacksonville to Chicago flights, with 43% of flights leaving in that window. Afternoon departures account for 43%, evening flights for 14%, and night flights for 0%.

  • What popular places can I visit in Chicago?

    Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago on KAYAK.

  • What are the earliest and latest flights from Jacksonville to Chicago?

    These are the earliest and latest flight times available from Jacksonville to Chicago:

    • Earliest: departs at 6:00 am and lands at 8:51 am
    • Latest: departs at 7:55 pm and lands at 10:46 pm.

    The flight takes about 2h 51m.

  • How expensive are last-minute Jacksonville to Chicago flights?

    Last-minute fares on this route - booked within 2 weeks of departure - run 51% above the route average of $360. Book 14 weeks before departure for the lowest fares.

  • How long is a flight from Jacksonville to Chicago?

    A nonstop flight from Jacksonville to Chicago takes 2h 51m, covering 852 miles.

  • Do I need a passport to fly from Jacksonville to Chicago?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

  • Have flight prices from Jacksonville to Chicago changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $198 to $1,662. That means the highest observed fare was about 8x higher than the lowest one.

  • How are flight prices from Jacksonville to Chicago looking right now?

    One-way fares from Jacksonville to Chicago are currently lower than usual. Average one-way flight prices are about $147, which is 36% below the typical average for this route.

  • How much time can I save by choosing a different layover airport from Jacksonville to Chicago?

    Flying via Charlotte Douglas (CLT) gives the shortest average 1-stop total travel time at 4h 45m, compared with 6h 03m via Nashville Intl (BNA) and 6h 44m via Atlanta Hartsfield-Jackson (ATL).

  • What is the time difference between Jacksonville and Chicago?

    Chicago is 1 hour behind Jacksonville (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

    · Routes Car & Truck Rentals
    · Europcar
    · Hertz
    · Dollar
    · Ace

    Near Chicago Midway Airport (MDW) — daily rates from around $32:

    · Hertz
    · Dollar
    · Budget
    · Alamo
    · Rent-A-Wreck

    Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

    · Alamo
    · Enterprise Rent-A-Car
    · Budget
    · Avis
    · National

  • How much should I expect to pay for a Jacksonville to Chicago flight?

    Round-trip flights from Jacksonville to Chicago range from $290 to $441, with an average of $360 over the past 12 months. Anything below $290 counts as a good deal.

  • Which airlines offer Wi-Fi on Jacksonville to Chicago flights?

    Two airlines offer in-flight Wi-Fi on Jacksonville to Chicago flights:

    • • American Airlines
    • • JetBlue

    Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

Your guide to booking Jacksonville to Chicago flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Wednesday departure instead of Monday. On this route, Wednesday flights average $324 - about $87 less than Monday (21% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 14 weeks before you fly. On this route, that window historically saves about 45% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Jacksonville to Chicago trip for September. Fares historically average $310 round-trip in that month - typically $80 less than the most expensive month, which is November (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Philadelphia Airport (PHL) can be cheaper than flying direct. The cheapest layover option averages $242 round-trip on this route - about $123 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.
    - DoubleTree by Hilton Chicago Midway Airport
    - Holiday Inn Chicago - Midway Airport S by IHG
    - Skylark Motel
  • On the day you’re scheduled to fly from Jacksonville International Airport (JAX) to Chicago, you should reach the airport 2 hours ahead of your flight to have enough time to go through the airport’s security checkpoints. Besides being able to go through the airport’s security checkpoints in time for your flight, you’ll also have adequate time to explore the airport.
  • JAX features numerous on-site parking garages. It is also surrounded by several off-site garages. If you intend to leave your car at JAX, you should consider doing so at one of the off-site garages near the airport because these garages are cheaper than the on-site ones. Regardless of the type of garage you choose, you can rest assured of finding your car intact when you return, as both on-site and off-site garages feature effective security.
  • While waiting for your flight to Chicago from JAX, you can enjoy relaxing spa services at Comfort Zone Spa, a highly-reviewed spa with locations pre- and post-security. At either of the locations run by this company, you’ll have a truly relaxing experience with their well-trained professionals and state-of-the-art spa equipment.
  • In Chicago, you will land at either Chicago Midway International Airport (MDW) or O’Hare International Airport (ORD). When booking your flight, consider booking one that lands at MDW. This airport is closer to Chicago and has less passenger traffic than ORD.
  • If you’d like to breastfeed your infant before departing MDW, you can use the airport’s lactation room found in concourse C next to the yoga room. Apart from breastfeeding your baby, you can also change diapers as it features a changing table and a strategically placed bin. The room is also suitable for pumping for later use as it boasts a power outlet you can use to charge your breast pump.

Prefer to fly direct from Jacksonville to Chicago?

 
Find which airlines fly direct from Jacksonville Airport to Chicago, which days they fly and book direct flights.

Direct departures

Jacksonville to Chicago

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Direct returns

Chicago to Jacksonville

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

More options for your flight from Jacksonville to Chicago

Complete your trip to Chicago with a hotel stay or car rental