Cheap Flights from Jacksonville to Chicago

Cheapest flights from Jacksonville to Chicago

Flaut.Travel was designed and developed by a team dedicated to making the process of searching, comparing and booking airline tickets as easy and convenient as possible. Our service helps travelers to find and buy the cheapest flights from Jacksonville to Chicago. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.

Cheapest one way flight

$134

United Airlines

1 transfer

8h 17m

12/02/2025

The cheapest one-way flight from Jacksonville to Chicago departs on 12/02/2025, is operated by United Airlines and costs $134

Cheapest round trip flight

$339

American Airlines

Direct flight

5h 23m

11/27/2025

The cheapest roundtrip flight from Jacksonville to Chicago departs on 11/27/2025, is operated by American Airlines and costs $339

The fastest flight

3h 1m

Fastest flight from Jacksonville to Chicago takes 3h 1m

Direct flights

Once a week

There are direct flights on this route 1 day a week: Sa

Earliest flight

6:42 AM

Latest flight

5:45 PM

Direct flights count

45

Distance

1390km

Timezone difference

1h

The distance between Jacksonville and Chicago is 1390km (862 miles). There are 45 direct flights from Jacksonville to Chicago. The time difference between Jacksonville and Chicago is 1h. Flights from Jacksonville begin at 6:42 AM. The latest flight from Jacksonville departs at 5:45 PM

Remember that on average the ideal time to book flights is 2 months before departure!

Airfare from Jacksonville to Chicago by month

We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from Jacksonville to Chicago

November 2025

Lowest price

on average:

$310

Avg Price

Airlines operating on route

The route Jacksonville — Chicago is served by many carriers — 4 in total, including United Airlines, American Airlines, Southwest Airlines, and Frontier Airlines. This gives passengers wide opportunities: from finding the lowest fare (from $134) to selecting flights by schedule or service class. Our service aggregates data from multiple booking systems so you can compare offers in one place. This saves time and money: no need to check dozens of sites — just pick the right option and book online.

Starting at $134

Starting at $187

Starting at $209

Starting at $200

Direct Flights from Jacksonville to Chicago

A direct flight is the most convenient and comfortable way to fly from Jacksonville to Chicago, despite the fact that sometimes flights with transfers can cost significantly less.

Jacksonville — Chicago

JAX — CHI

11/26/2025

Departure

Direct flight

UA411

Starting at $486

Jacksonville — Chicago

JAX — CHI

11/29/2025

Departure

Direct flight

AA4718

Starting at $546

Jacksonville — Chicago

JAX — CHI

12/02/2025

Departure

Direct flight

WN1173

Starting at $209

Jacksonville — Chicago

JAX — CHI

01/03/2026

Departure

Direct flight

AA4618

Starting at $383

Schedule of direct flights from Jacksonville to Chicago

A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Jacksonville to Chicago:

Unable to find information about the schedule of direct flights from

Jacksonville airports overview

Jacksonville International Airport

•

JAX

18km

Serves Jacksonville and northeastern Florida with domestic flights and connections to major U.S. hubs; convenient for downtown, the beaches, and nearby military bases.

•

Chicago airports overview

Merrill C Meigs

•

CGX

3km

Former single-runway general aviation facility on Chicago’s lakefront adjacent to downtown, serving business and private flights until its abrupt closure in 2003.

DuPage Airport

•

DPA

52km

General aviation reliever near Chicago in West Chicago, Illinois, serving corporate, private and flight-training traffic with hangars, FBO services and maintenance, convenient for access to the western suburbs.

Chicago Midway International Airport

•

MDW

14km

Serving Chicago’s Southwest Side and downtown, it handles mainly domestic flights with a strong presence of low-cost carriers and easy connections via the 'L' Orange Line and nearby expressways.

O'Hare International Airport

•

ORD

26km

Chicago Executive Airport

•

PWK

35km

Chicago Rockford International Airport

•

RFD

140km

Serving Rockford and northern Illinois, the airport handles domestic passenger flights and is a major cargo hub. Convenient ground links provide access to the Chicago metro and surrounding communities.

•

Frequently asked questions (FAQ)

Answers to questions about the route that travelers are most interested in.

How much is the cheapest flight ticket from Jacksonville to Chicago?

The cheapest flight ticket from Jacksonville to Chicago according to data for the last 48 hours costs $134

When is the best time to buy air tickets on the route Jacksonville — Chicago?

Often the best time to buy tickets from Jacksonville to Chicago is 2 months before departure.

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

Based on statistics over the past years, the lowest prices for flights from Jacksonville to Chicago can be found flying in these months: November.

How long does it take to fly from Jacksonville to Chicago?

The fastest flights from Jacksonville to Chicago start from 3 hours 1 minute in the air.

Which airline can fly direct from Jacksonville to Chicago?

The following airlines operate direct flights on the route Jacksonville — Chicago: United Airlines, American Airlines, Southwest Airlines

Special offers and sales on air tickets from Jacksonville to Chicago

We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.

We couldn't find any special offers for flights from Jacksonville to Chicago

Alternative routes

Gainesville ➜ Chicago•Lakeland ➜ Chicago•Orlando ➜ Chicago•Savannah ➜ Chicago•Sarasota ➜ Chicago•Tallahassee ➜ Chicago•Tampa ➜ Chicago•Jacksonville ➜ Appleton•Jacksonville ➜ Kalamazoo•Jacksonville ➜ Champaign•Jacksonville ➜ Fort Wayne•Jacksonville ➜ Indianapolis•Jacksonville ➜ Lansing•Jacksonville ➜ Milwaukee•Jacksonville ➜ Muskegon•Jacksonville ➜ South Bend

•••••••••••••••••••

Cheapest one way flight

$134

United Airlines

1 transfer

8h 17m

12/02/2025

The cheapest one-way flight from Jacksonville to Chicago departs on 12/02/2025, is operated by United Airlines and costs $134

Cheapest round trip flight

$339

American Airlines

Direct flight

5h 23m

11/27/2025

The cheapest roundtrip flight from Jacksonville to Chicago departs on 11/27/2025, is operated by American Airlines and costs $339

The fastest flight