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$211+ Cheap flights from Jackson (JAC) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Jackson to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Jackson (JAC) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 15, 2025.

Round-trip from

$259
(United Airlines)

One-way from

$211
(United Airlines)

Popular in

March

Cheapest in

September

Average price

$289

Good round-trip deal

$368 or less

Good one-way deal

$305 or less
From Jackson Hole to Chicago (CHI)
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One-way flight from Jackson Hole to Chicago (CHI)
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Highest demand for flights based on searches. 6% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Jackson Hole to Chicago (CHI).
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Price to beat on a one-way flight from Jackson Hole to Chicago (CHI).
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Find flight deals from Jackson to Chicago

Cheapest flights from Jackson to Chicago
Explore the most affordable flight options available from Jackson to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/291:10 pmJAC - ORD
Nonstop3h 09mAmerican Airlines
Wed 11/55:18 amORD - JAC
1 stop7h 58mAmerican Airlines
Deal found 9/14$259
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/23:19 pmJAC - ORD
Nonstop3h 15mAmerican Airlines
Sun 10/510:10 amORD - JAC
Nonstop3h 11mAmerican Airlines
Deal found 9/14$264
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/291:00 pmJAC - ORD
1 stop7h 43mDelta
Wed 11/51:55 pmORD - JAC
1 stop5h 20mDelta
Deal found 9/14$269
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/24:18 pmJAC - ORD
1 stop5h 21mUnited Airlines
Sun 10/59:05 amORD - JAC
Nonstop3h 15mUnited Airlines
Deal found 9/14$274
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2312:35 pmJAC - ORD
Nonstop3h 15mUnited Airlines
Thu 1/19:04 amORD - JAC
Nonstop3h 30mUnited Airlines
Deal found 9/14$280
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/305:56 pmJAC - ORD
1 stop5h 03mUnited Airlines
Sat 10/44:20 pmORD - JAC
Nonstop3h 12mUnited Airlines
Deal found 9/15$289
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/81:06 pmJAC - ORD
1 stop7h 15mAmerican Airlines
Mon 11/1010:12 pmORD - JAC
2 stops15h 04mAmerican Airlines
Deal found 9/15$325
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/254:18 pmJAC - ORD
1 stop5h 21mUnited Airlines
Mon 9/299:05 amORD - JAC
Nonstop3h 15mUnited Airlines
Deal found 9/15$334
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/67:30 amJAC - MDW
2 stops9h 13mDelta
Tue 11/1110:47 amMDW - JAC
2 stops11h 42mDelta
Deal found 9/13$474
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/156:57 pmJAC - MDW
2 stops13h 43mDelta
Wed 9/171:08 pmMDW - JAC
2 stops9h 21mDelta
Deal found 9/14$671
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/217:20 amJAC - MDW
2 stops9h 48mDelta
Mon 11/249:41 amMDW - JAC
2 stops12h 48mDelta
Deal found 9/13$684
This Delta deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1712:57 pmJAC - MDW
2 stops9h 35mDelta
Wed 11/199:41 amMDW - JAC
2 stops12h 48mDelta
Deal found 9/13$730

Cheapflights Fare Finder

 
Customize your flight search to find flights from Jackson 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, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
Use the filters below to find and compare flights from Jackson to Chicago that are best for you.

Fly from

Jackson

Fly to

Chicago

Route

Depart

Return

Price

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Wed 10/29

1:00 pm-9:43 pm

1 stop7h 43m

Chicago O'Hare Intl

Wed 11/5

1:55 pm-6:15 pm

1 stop5h 20m

$269

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Tue 12/23

12:35 pm-4:50 pm

Nonstop3h 15m

Chicago O'Hare Intl

Thu 1/1

9:04 am-11:34 am

Nonstop3h 30m

$280

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Tue 9/30

5:56 pm-11:59 pm

1 stop5h 03m

Chicago O'Hare Intl

Sat 10/4

4:20 pm-6:32 pm

Nonstop3h 12m

$289

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Thu 9/25

4:08 pm-11:17 pm

1 stop6h 09m

Chicago O'Hare Intl

Sun 9/28

10:10 am-12:21 pm

Nonstop3h 11m

$334

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Thu 9/25

4:08 pm-11:52 pm

1 stop6h 44m

Chicago O'Hare Intl

Mon 9/29

6:55 am-4:07 pm

1 stop10h 12m

$344

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Thu 9/25

5:56 pm-11:59 pm

1 stop5h 03m

Chicago O'Hare Intl

Sun 9/28

9:05 am-11:20 am

Nonstop3h 15m

$379

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Sat 11/8

1:00 pm-11:58 pm

2 stops9h 58m

Chicago O'Hare Intl

Mon 11/10

9:46 am-9:29 pm

2 stops12h 43m

$398

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Thu 10/9

5:56 pm-11:59 pm

1 stop5h 03m

Chicago O'Hare Intl

Sat 10/11

4:20 pm-6:32 pm

Nonstop3h 12m

$399

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Thu 11/6

7:30 am-5:43 pm

2 stops9h 13m

Chicago Midway

Tue 11/11

10:47 am-9:29 pm

2 stops11h 42m

$474

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Fri 11/21

7:20 am-6:08 pm

2 stops9h 48m

Chicago Midway

Mon 11/24

9:41 am-9:29 pm

2 stops12h 48m

$684

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 32 results
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Best time to book a flight from Jackson to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Jackson 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 Jackson to Chicago

What is the cheapest month to book a flight from Jackson to Chicago?

Currently, August is the cheapest month in which you can book a flight from Jackson to Chicago (average of $245). Flying from Jackson 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 JAC to CHI?

Find hourly flight availability from Jackson 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 September 15, 2025.

One of the essential ways to save on airfare from Jackson to Chicago is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 20% on airfare.

Weekly flight availability from Jackson to Chicago

Explore weekly flight availability from Jackson to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 15, 2025.

The most flights from JAC to CHI are scheduled on a Monday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated September 15, 2025.
See what other customers who have flown with United Airlines and American Airlines from Jackson to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,929 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Crew

8.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,929 reviews
United Airlines
7.4
Good
8,929 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Crew

8.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,929 reviews

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Crew

8.1

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Jackson 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 Jackson to Chicago?

    Located just 8.8 mi from the city center, Jackson Hole is the airport most travelers will use when flying to Chicago from Jackson. Booking flights from Jackson Hole (JAC) to Chicago should be relatively easy as there are 8 daily outbound flights to Chicago from 2 different airlines.

  • How long is the flight from Jackson to Chicago?

    For as low as $280, Delta can have you in Chicago from Jackson in 3h 15m. The distance from Jackson to Chicago is about 1159 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Jackson to Chicago round-trip?

    Cheapflights users have booked flights from Jackson to Chicago round-trip from $229. Another airline that can offer you cheap pricing is United Airlines. American Airlines is priced at 50% lower than the current average price of a flight leaving 3 months from now.

  • What are the most reliable airlines from Jackson to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Jackson to Chicago on time: United Airlines (75%), Lufthansa (72%), Emirates (72%).

  • What are the cheapest flights from Jackson to Chicago?

    While on average a flight from Jackson to Chicago is generally $771, our data shows the cheapest flight currently is $167. When looking at the most popular route, (Jackson Hole - Chicago O'Hare Intl), you can expect to pay $259 for that flight.

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

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

  • How can I find direct flights from Jackson to Chicago?

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

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

    Yes. Cheapflights offers flight deals from Jackson 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 Jackson to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Jackson to Chicago (average of $245). Flying from Jackson 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Jackson to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Jackson to Chicago

Discover the top 2 airlines that operate flights from Jackson to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$229Average$404FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$297Average$461FlexibilityNo cancel feeOn-time69%

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