Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Jacksonville to Chicago from $61

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Jacksonville to Chicago departing on 3/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Jacksonville to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
11:37 am - 11:47 pm
JAX
-
ORD
37h 10m
2 stops
Multiple Airlines Logo
5:05 am - 6:39 pm
ORD
-
JAX
12h 34m
1 stop
$228Multiple Airlines
Tue, Mar 3 - Fri, Mar 6
Frontier Logo
8:18 pm - 10:52 am
JAX
-
ORD
15h 34m
1 stop
Frontier Logo
4:40 pm - 5:08 pm
ORD
-
JAX
23h 28m
1 stop
$230Frontier
Wed, Mar 18 - Sun, Mar 22
Frontier Logo
4:29 pm - 12:34 am
JAX
-
ORD
9h 05m
2 stops
Frontier Logo
5:01 am - 5:08 pm
ORD
-
JAX
11h 07m
1 stop
$231Frontier
Thu, Mar 12 - Fri, Mar 13
Frontier Logo
4:29 pm - 1:18 pm
JAX
-
MDW
21h 49m
2 stops
Frontier Logo
6:05 am - 3:34 pm
MDW
-
JAX
8h 29m
1 stop
$236Frontier
Sun, Mar 15 - Thu, Mar 19
American Airlines Logo
7:00 am - 8:53 am
JAX
-
ORD
2h 53mnonstop
American Airlines Logo
7:45 pm - 11:09 pm
ORD
-
JAX
2h 24mnonstop
$237American Airlines
Sat, Feb 21 - Sat, Feb 28
Frontier Logo
8:18 pm - 8:07 pm
JAX
-
MDW
24h 49m
1 stop
Frontier Logo
6:00 am - 7:33 pm
MDW
-
JAX
12h 33m
1 stop
$237Frontier
Wed, Apr 8 - Mon, Apr 13
American Airlines Logo
1:22 pm - 5:58 pm
JAX
-
ORD
5h 36m
1 stop
American Airlines Logo
7:45 pm - 11:09 pm
ORD
-
JAX
2h 24mnonstop
$247American Airlines
Sat, Feb 21 - Sat, Feb 28
Delta Logo
5:30 am - 9:54 am
JAX
-
MDW
5h 24m
1 stop
Delta Logo
6:40 pm - 12:01 am
MDW
-
JAX
4h 21m
1 stop
$257Delta
Tue, Feb 24 - Wed, Feb 25
Southwest Logo
7:20 am - 8:50 am
JAX
-
MDW
2h 30mnonstop
Southwest Logo
6:50 pm - 10:05 pm
MDW
-
JAX
2h 15mnonstop
$260Southwest
Wed, Apr 29 - Mon, May 4
Southwest Logo
7:20 am - 8:50 am
JAX
-
MDW
2h 30mnonstop
Southwest Logo
8:00 am - 2:45 pm
MDW
-
JAX
5h 45m
1 stop
$270Southwest
Wed, Apr 29 - Mon, May 4

American Airlines flights from Jacksonville to Chicago

Our best American Airlines deals on Jacksonville to Chicago flight tickets
American Airlines
Feb 21
JAX7:00 amJacksonville
2h 53m
ORD8:53 amChicago O'Hare Intl
Feb 28
ORD7:45 pmChicago O'Hare Intl
2h 24m
JAX11:09 pmJacksonville
$237
American Airlines
Feb 21
JAX1:22 pmJacksonville
5h 36m
1 stop
ORD5:58 pmChicago O'Hare Intl
Feb 28
ORD7:45 pmChicago O'Hare Intl
2h 24m
JAX11:09 pmJacksonville
$247
American Airlines
Feb 21
JAX3:20 pmJacksonville
6h 55m
1 stop
ORD9:15 pmChicago O'Hare Intl
Feb 28
ORD5:00 amChicago O'Hare Intl
6h 32m
1 stop
JAX12:32 pmJacksonville
$257

Frontier flights from Jacksonville to Chicago

Our best Frontier deals on Jacksonville to Chicago flight tickets
Frontier
Mar 18
JAX8:18 pmJacksonville
15h 34m
1 stop
ORD10:52 amChicago O'Hare Intl
Mar 22
ORD4:40 pmChicago O'Hare Intl
23h 28m
1 stop
JAX5:08 pmJacksonville
$230
Frontier
Mar 12
JAX4:29 pmJacksonville
9h 05m
2 stops
ORD12:34 amChicago O'Hare Intl
Mar 13
ORD5:01 amChicago O'Hare Intl
11h 07m
1 stop
JAX5:08 pmJacksonville
$231
Frontier
Mar 15
JAX4:29 pmJacksonville
21h 49m
2 stops
MDW1:18 pmChicago Midway
Mar 19
MDW6:05 amChicago Midway
8h 29m
1 stop
JAX3:34 pmJacksonville
$236

momondo Fare Finder

 
Customize your flight search to find flights from Jacksonville to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated January 31, 2026.
Use the filters below to find and compare flights from Jacksonville to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Tue 3/3

11:37 am-11:47 pm

2 stops37h 10m

Chicago O'Hare Intl

Fri 3/6

5:05 am-6:39 pm

1 stop12h 34m

$228

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Wed 3/18

8:18 pm-10:52 am

1 stop15h 34m

Chicago O'Hare Intl

Sun 3/22

4:40 pm-5:08 pm

1 stop23h 28m

$230

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Thu 3/12

4:29 pm-12:34 am

2 stops9h 05m

Chicago O'Hare Intl

Fri 3/13

5:01 am-5:08 pm

1 stop11h 07m

$231

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sun 3/15

4:29 pm-1:18 pm

2 stops21h 49m

Chicago Midway

Thu 3/19

6:05 am-3:34 pm

1 stop8h 29m

$236

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Sat 2/21

7:00 am-8:53 am

Nonstop2h 53m

Chicago O'Hare Intl

Sat 2/28

7:45 pm-11:09 pm

Nonstop2h 24m

$237

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 4/8

8:18 pm-8:07 pm

1 stop24h 49m

Chicago Midway

Mon 4/13

6:00 am-7:33 pm

1 stop12h 33m

$237

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Sat 2/21

1:22 pm-5:58 pm

1 stop5h 36m

Chicago O'Hare Intl

Sat 2/28

7:45 pm-11:09 pm

Nonstop2h 24m

$247

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Tue 2/24

5:30 am-9:54 am

1 stop5h 24m

Chicago Midway

Wed 2/25

6:40 pm-12:01 am

1 stop4h 21m

$257

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 4/29

7:20 am-8:50 am

Nonstop2h 30m

Chicago Midway

Mon 5/4

6:50 pm-10:05 pm

Nonstop2h 15m

$260

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Wed 4/29

7:20 am-8:50 am

Nonstop2h 30m

Chicago Midway

Mon 5/4

8:00 am-2:45 pm

1 stop5h 45m

$270

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from Jacksonville to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Jacksonville and Chicago?

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Jacksonville, with most prices found around $287. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Jacksonville to Chicago during August average around $295.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $410. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Jacksonville to Chicago for around $678.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Jacksonville to Chicago during this time can be as low as $406. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $534.

What is the cheapest Jacksonville to Chicago flight route?

Fly from Jacksonville to Chicago O'Hare Intl for the best Jacksonville - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Jacksonville when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $358 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Jacksonville for as low as $280 on momondo.

What cabin class options are available on Jacksonville to Chicago flights?

There are 4 cabin classes available to choose from on Jacksonville to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Jacksonville to Chicago flights?

No. A direct flight is the cheapest option for a flight between Jacksonville to Chicago.

How have Jacksonville to Chicago flight prices changed over time?

As of January 2026, prices for Jacksonville to Chicago flights are approximately 34% cheaper when compared to flights at the same time last year.

When to book flights from Jacksonville to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Jacksonville to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Jacksonville to Chicago (JAX to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Jacksonville to Chicago

Best Price Found

$208

Fastest flight time

2h 20m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Jacksonville in the past 72 hours is $208. The best round-trip flight deal from Jacksonville to Chicago found on momondo in the last 72 hours is $341.
The fastest flight from Jacksonville to Chicago takes 2h 20m
Direct flights go from Jacksonville to Chicago every day.
There are 3 airports in Chicago. From Jacksonville there are direct flights to Chicago Midway (MDW).
Search flight deals

  • How far is Jacksonville to Chicago by plane?

    The straight-line distance from Jacksonville to Chicago is 863.3 mi. In terms of flight time, this usually takes a little over 2h 20m.

  • When did momondo last update prices for flights from Jacksonville Airport to Chicago?

    Prices for flights from Jacksonville Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Jacksonville Airport to Chicago?

  • How old do you have to be to fly from Jacksonville Airport to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Jacksonville Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Jacksonville to Chicago?

  • What is the most popular airline from Jacksonville to Chicago?

Best airlines flying from Jacksonville to Chicago

Compare and see reviews for airlines that fly from Jacksonville to Chicago with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $121Free CancellationRating
7.9
8,130 reviews
Search Delta flights
FrontierPriceFrom $136Free CancellationRating
5.7
3,054 reviews
Search Frontier flights
American AirlinesPriceFrom $179Free CancellationRating
7.2
11,213 reviews
Search American Airlines flights
SouthwestPriceFrom $203Free CancellationRating
8.0
4,267 reviews
Search Southwest flights
United AirlinesPriceFrom $217Free CancellationRating
7.4
9,219 reviews
Search United Airlines flights

  • Southwest Flights From Jacksonville to Chicago

    Southwest flies from Jacksonville to Chicago around 4 times per week, with 4,267 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Jacksonville to Chicago in the last 72 hours was $203 (round-trip), much lower than the average airfare cost of $370 for Southwest flights on this route.

  • United Airlines Flights From Jacksonville to Chicago

    Another popular option for Jacksonville to Chicago flights is United Airlines (7.4/10, 9,219 ratings). United Airlines flies from Jacksonville to Chicago around 13 times per week, with deals starting from $217 round-trip and rising to an average price of around $382.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Jacksonville to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Jacksonville to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Jacksonville to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Jacksonville with this policy.

How can momondo help me find flights from Jacksonville to Chicago?

Once you have performed a search for Jacksonville to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Jacksonville to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Jacksonville to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Mon 3/2
Mon 3/9
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport