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$154+ 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This United Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/3112:35 pmJAC - ORD
Nonstop3h 15mUnited Airlines
Sun 1/49:04 amORD - JAC
Nonstop3h 30mUnited Airlines
Deal found 12/16$374
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Sun 12/281:30 pmJAC - ORD
Nonstop3h 41mAmerican Airlines
Tue 12/309:55 amORD - JAC
Nonstop3h 18mAmerican Airlines
Deal found 12/16$514
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Sun 12/282:30 pmJAC - ORD
1 stop5h 49mUnited Airlines
Tue 12/301:55 pmORD - JAC
1 stop7h 57mUnited Airlines
Deal found 12/16$626
This Delta deal was found by Cheapflights users on 12/16. 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 12/312:31 pmJAC - MDW
1 stop6h 51mDelta
Sun 1/46:00 amMDW - JAC
1 stop8h 21mDelta
Deal found 12/16$671
This Alaska Airlines deal was found by Cheapflights users on 12/16. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/314:15 pmJAC - ORD
2 stops35h 47mAlaska Airlines
Sun 1/42:12 pmORD - JAC
2 stops26h 23mAlaska Airlines
Deal found 12/16$1,110
This Delta deal was found by Cheapflights users on 12/16. 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.
Sun 12/287:00 amJAC - ORD
2 stops13h 14mDelta
Tue 12/307:00 amORD - JAC
2 stops11h 00mDelta
Deal found 12/16$1,220
This Delta deal was found by Cheapflights users on 12/16. 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.
Sun 12/282:31 pmJAC - MDW
1 stop6h 51mDelta
Tue 12/306:00 amMDW - JAC
1 stop8h 21mDelta
Deal found 12/16$1,269

Find 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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$364
(United Airlines)

One-way from

$154
(American Airlines)

Popular in

January

Cheapest in

September

Average price

$529

Good round-trip deal

$433 or less

Good one-way deal

$259 or less
Provider with most accurate pricing for Jackson Hole-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Jackson Hole-Chicago (CHI) flights.
Search Deals
From Jackson Hole to Chicago (CHI)
Search Deals
One-way flight from Jackson Hole to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Jackson Hole to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Jackson Hole to Chicago (CHI).
Search Deals

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 December 18, 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

Thu 1/8

1:42 pm-6:15 pm

Nonstop3h 33m

Chicago O'Hare Intl

Sun 1/11

6:54 am-2:42 pm

1 stop8h 48m

$248

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Thu 1/8

2:40 pm-11:58 pm

1 stop8h 18m

Chicago O'Hare Intl

Sun 1/11

9:00 am-11:22 am

Nonstop3h 22m

$329

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Thu 1/8

12:58 pm-9:52 pm

1 stop7h 54m

Chicago O'Hare Intl

Sun 1/11

1:50 pm-7:06 pm

1 stop6h 16m

$330

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Tue 12/30

4:20 pm-11:59 pm

1 stop6h 39m

Chicago O'Hare Intl

Sat 1/3

8:45 am-1:24 pm

1 stop5h 39m

$359

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Wed 1/14

2:40 pm-11:59 pm

1 stop8h 19m

Chicago O'Hare Intl

Sun 1/18

9:00 am-11:22 am

Nonstop3h 22m

$364

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Wed 12/31

12:35 pm-4:50 pm

Nonstop3h 15m

Chicago O'Hare Intl

Sun 1/4

9:04 am-11:34 am

Nonstop3h 30m

$374

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Wed 12/31

2:31 pm-10:22 pm

1 stop6h 51m

Chicago Midway

Sun 1/4

6:00 am-1:21 pm

1 stop8h 21m

$671

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Sun 3/29

2:45 pm-10:29 pm

1 stop6h 44m

Chicago Midway

Tue 3/31

9:32 am-4:47 pm

2 stops8h 15m

$1,003

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Sun 3/29

2:45 pm-10:29 pm

1 stop6h 44m

Chicago Midway

Wed 4/1

6:30 am-4:47 pm

2 stops11h 17m

$1,075

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Mon 3/30

7:20 am-5:55 pm

2 stops9h 35m

Chicago Midway

Wed 4/1

6:30 am-4:47 pm

2 stops11h 17m

$1,080

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 26 results
1
2
3

Compare providers for flights from Jackson to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Jackson to Chicago in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Jackson-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Jackson-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Jackson-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Jackson-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Jackson-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, June is the cheapest month in which you can book a flight from Jackson to Chicago (average of $193). Flying from Jackson to Chicago in July is currently the most expensive (average of $447). 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 December 18, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Jackson to Chicago as you normally would.

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 December 18, 2025.

The most flights from JAC to CHI are scheduled on a Thursday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

How much does it cost to fly round-trip from Jackson to Chicago?

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 December 18, 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
9,091 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Food

6.6

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

BOS - EWR

Seems like every United flight has a delay and it’s always someone else’s fault. Step up and take some accountability
United Airlines
7.4
Good
9,091 reviews
United Airlines
7.4
Good
9,091 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Food

6.6

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

BOS - EWR

Seems like every United flight has a delay and it’s always someone else’s fault. Step up and take some accountability
American Airlines
7.2
Good
11,054 reviews
United Airlines
7.4
Good
9,091 reviews

Boarding

7.7

Overall

7.4

Comfort

7.3

Crew

8.1

Entertainment

7.1

Food

6.6

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

BOS - EWR

Seems like every United flight has a delay and it’s always someone else’s fault. Step up and take some accountability

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 3 daily outbound flights to Chicago from 2 different airlines.

  • How long is the flight from Jackson to Chicago?

    For as low as $248, American Airlines can have you in Chicago from Jackson in 3h 33m. 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 $191. Another airline that can offer you cheap pricing is United Airlines. American Airlines is priced at 57% 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: Qatar Airways (89%), American Airlines (82%), United Airlines (68%).

  • What are the cheapest flights from Jackson to Chicago?

    While on average a flight from Jackson to Chicago is generally $416, our data shows the cheapest flight currently is $195. When looking at the most popular route, (Jackson Hole - Chicago O'Hare Intl), you can expect to pay $319 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, June is the cheapest month in which you can book a flight from Jackson to Chicago (average of $193). Flying from Jackson to Chicago in July is currently the most expensive (average of $447). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$191Average$385FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$283Average$421FlexibilityNo cancel feeOn-time69%

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