What are the cheapest airlines flying from Jacksonville, North Carolina to Chicago round-trip?

According to our current data, American Airlines ($297), and Delta ($331) offers the cheapest pricing from Jacksonville, North Carolina to Chicago. These flights start at 36% lower than the current average price 3 months from now.

What is the cheapest day to fly from Jacksonville, North Carolina to Chicago?

Travelers seeking maximum savings on their Jacksonville, North Carolina to Chicago flight should consider departing on Thursday mornings when fares are most often at their lowest. Saturday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What is the cheapest month to fly from Jacksonville, North Carolina to Chicago?

Our data shows that May tends to be the cheapest month to fly to Chicago from Jacksonville, North Carolina. Users have commonly found prices around $466 for the month, but tickets can be as low as $256. Due to multiple factors, prepare for potentially higher prices in November.

What airport do you fly from for flights from Jacksonville to Chicago?

Jacksonville Albert J Ellis (OAJ) is the airport you will fly out of if you book a flight from Jacksonville to Chicago. You should not have trouble finding flights to Chicago from Albert J Ellis; the airport handles an average of 0 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 1 airline has flights from the Jacksonville airport to Chicago. It is only a 11.3 mi journey to Albert J Ellis (OAJ) from Jacksonville’s city center.

Can I find deals for flights from Jacksonville to Chicago that include hotel bookings?

Yes. In addition to deals on Jacksonville to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Jacksonville to Chicago?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Jacksonville to Chicago.

Can I find deals for business class flights from Jacksonville to Chicago?

Yes. Cheapflights offers flight deals from Jacksonville to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$297+ Flights from Jacksonville, NC to Chicago

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Cheap flight deals from Jacksonville to Chicago

Round-trip from	$297 (American Airlines)
Popular in	November
Cheapest in	May
Average price	$597

From Jacksonville Albert J Ellis to Chicago (CHI)

Search Deals

Highest demand for flights based on searches. 8% potential increase in price ($41 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 4% potential price decrease ($23 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in August 2025

Search Deals

Find flight deals from Jacksonville to Chicago

Cheapest flights from Jacksonville to Chicago
Explore the most affordable flight options available from Jacksonville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on agosto 1, 2025.

mié. 8/277:17 pmOAJ - ORD

1 stop4h 42mAmerican Airlines

sáb. 8/308:35 amORD - OAJ

1 stop4h 41mAmerican Airlines

Deal found 7/31

$297

jue. 12/46:25 pmOAJ - ORD

1 stop6h 28mDelta

lun. 12/87:10 amORD - OAJ

1 stop5h 30mDelta

Deal found 7/31

$331

sáb. 8/164:30 pmOAJ - MDW

1 stop5h 42mDelta

mié. 8/2010:31 amMDW - OAJ

1 stop4h 16mDelta

Deal found 7/31

$394

Best flights from Jacksonville to Chicago
Discover carefully curated flight deals from Jacksonville to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated agosto 1, 2025.

mié. 8/277:17 pmOAJ - ORD

1 stop4h 42mAmerican Airlines

sáb. 8/308:35 amORD - OAJ

1 stop4h 41mAmerican Airlines

Deal found 7/31

$297

jue. 12/46:25 pmOAJ - ORD

1 stop6h 28mDelta

lun. 12/87:10 amORD - OAJ

1 stop5h 30mDelta

Deal found 7/31

$331

sáb. 8/164:30 pmOAJ - MDW

1 stop5h 42mDelta

mié. 8/2010:31 amMDW - OAJ

1 stop4h 16mDelta

Deal found 7/31

$394

Last-minute flights from Jacksonville to Chicago
Discover last-minute flight deals from Jacksonville to Chicago. Data last updated agosto 1, 2025 and is based on user searches.

mar. 8/56:00 pmOAJ - ORD

1 stop4h 31mAmerican Airlines

mar. 8/1210:26 amORD - OAJ

1 stop5h 15mAmerican Airlines

Deal found 7/30

$395

sáb. 8/164:30 pmOAJ - MDW

1 stop5h 42mDelta

mié. 8/2010:31 amMDW - OAJ

1 stop4h 16mDelta

Deal found 7/31

$394

mié. 8/277:17 pmOAJ - ORD

1 stop4h 42mAmerican Airlines

sáb. 8/308:35 amORD - OAJ

1 stop4h 41mAmerican Airlines

Deal found 7/31

$297

mié. 8/275:55 amOAJ - ORD

2 stops11h 18mDelta

vie. 8/297:15 amORD - OAJ

2 stops7h 32mDelta

Deal found 7/31

$1,195

Cheapflights Fare Finder

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

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

mié. 8/27

7:17 pm-10:59 pm

1 stop4h 42m

Chicago O'Hare Intl

sáb. 8/30

8:35 am-2:16 pm

1 stop4h 41m

$297

JacksonvilleChicago

OAJ - ORD

OAJORD

Jacksonville Albert J Ellis

jue. 12/4

6:25 pm-11:53 pm

1 stop6h 28m

Chicago O'Hare Intl

lun. 12/8

7:10 am-1:40 pm

1 stop5h 30m

$331

JacksonvilleChicago

OAJ - MDW

OAJMDW

Jacksonville Albert J Ellis

sáb. 8/16

4:30 pm-9:12 pm

1 stop5h 42m

Chicago Midway

mié. 8/20

10:31 am-3:47 pm

1 stop4h 16m

$394

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Best time to book a flight from Jacksonville to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Jacksonville with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Jacksonville to Chicago

What is the cheapest month to book a flight from Jacksonville, North Carolina to Chicago?

Currently, August is the cheapest month in which you can book a flight from Jacksonville, North Carolina to Chicago (average of $245). Flying from Jacksonville, North Carolina to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from OAJ to CHI?

When flying from Jacksonville, North Carolina to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Jacksonville to Chicago, such as Delta and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

7,981 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Delta

8.0

Very good

7,981 reviews

Delta

8.0

Very good

7,981 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,981 reviews

Reviews

1 / 20

10.0

Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

What airport do you fly from for flights from Jacksonville to Chicago?
Jacksonville Albert J Ellis (OAJ) is the airport you will fly out of if you book a flight from Jacksonville to Chicago. You should not have trouble finding flights to Chicago from Albert J Ellis; the airport handles an average of 0 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 1 airline has flights from the Jacksonville airport to Chicago. It is only a 11.3 mi journey to Albert J Ellis (OAJ) from Jacksonville’s city center.
What are the cheapest airlines flying from Jacksonville, North Carolina to Chicago round-trip?
According to our current data, American Airlines ($297), and Delta ($331) offers the cheapest pricing from Jacksonville, North Carolina to Chicago. These flights start at 36% lower than the current average price 3 months from now.
Can I find deals for flights from Jacksonville to Chicago that include hotel bookings?
Yes. In addition to deals on Jacksonville to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Jacksonville to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Jacksonville to Chicago.
Can I find deals for business class flights from Jacksonville to Chicago?
Yes. Cheapflights offers flight deals from Jacksonville to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Jacksonville, North Carolina to Chicago?
Currently, August is the cheapest month in which you can book a flight from Jacksonville, North Carolina to Chicago (average of $245). Flying from Jacksonville, North Carolina to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top airline flying from Jacksonville to Chicago

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$336	Average$440	FlexibilityNo cancel fee	On-time71%

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$297+ Cheap flights from Jacksonville, NC (OAJ) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/27. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Jacksonville to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Jacksonville to Chicago

Round-trip from

Popular in

Cheapest in

Average price

Find flight deals from Jacksonville to Chicago

Cheapest flights from Jacksonville to ChicagoExplore the most affordable flight options available from Jacksonville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on agosto 1, 2025.

Explore the most affordable flight options available from Jacksonville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on agosto 1, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Jacksonville to Chicago that are best for you.

Best time to book a flight from Jacksonville to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Jacksonville with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Jacksonville to Chicago

What is the cheapest month to book a flight from Jacksonville, North Carolina to Chicago?

What is the cheapest time of day to fly from OAJ to CHI?

Find hourly flight availability from Jacksonville to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated agosto 1, 2025.

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Jacksonville to Chicago, such as Delta and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Jacksonville to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What airport do you fly from for flights from Jacksonville to Chicago?

What are the cheapest airlines flying from Jacksonville, North Carolina to Chicago round-trip?

Can I find deals for flights from Jacksonville to Chicago that include hotel bookings?

How can I find direct flights from Jacksonville to Chicago?

Can I find deals for business class flights from Jacksonville to Chicago?

What is the cheapest month to book a flight from Jacksonville, North Carolina to Chicago?

Traveling to a place near Chicago?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Jacksonville to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top airline flying from Jacksonville to Chicago

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Book with Flexibility

Travel Smart

Cheapest flights from Jacksonville to Chicago
Explore the most affordable flight options available from Jacksonville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on agosto 1, 2025.