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$150+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — CHI
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This American Airlines deal was found by Cheapflights users on 1/27. 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 2/191:44 pm
JAC
-
ORD
Nonstop3h 13m
American Airlines
Mon 2/239:54 am
ORD
-
JAC
Nonstop3h 24m
American Airlines
Deal found 1/27$311
This Alaska Airlines deal was found by Cheapflights users on 1/28. 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.
Thu 3/1211:48 am
JAC
-
ORD
1 stop11h 11m
Alaska Airlines
Fri 3/133:54 pm
ORD
-
JAC
1 stop20h 14m
Alaska Airlines
Deal found 1/28$319
This United Airlines deal was found by Cheapflights users on 1/28. 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 2/194:27 pm
JAC
-
ORD
1 stop6h 32m
United Airlines
Mon 2/239:00 am
ORD
-
JAC
Nonstop3h 29m
United Airlines
Deal found 1/28$321
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Tue 4/141:25 pm
JAC
-
ORD
2 stops16h 59m
American Airlines
Tue 4/216:05 am
ORD
-
JAC
1 stop7h 33m
American Airlines
Deal found 1/27$332
This Delta deal was found by Cheapflights users on 1/27. 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 2/191:05 pm
JAC
-
ORD
1 stop7h 47m
Delta
Mon 2/239:48 am
ORD
-
JAC
2 stops10h 16m
Delta
Deal found 1/27$336
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Fri 2/131:44 pm
JAC
-
ORD
Nonstop3h 13m
American Airlines
Mon 2/169:54 am
ORD
-
JAC
Nonstop3h 24m
American Airlines
Deal found 1/27$339
This Delta deal was found by Cheapflights users on 1/27. 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.
Tue 4/141:00 pm
JAC
-
MDW
2 stops8h 28m
Delta
Tue 4/216:00 am
MDW
-
JAC
2 stops11h 09m
Delta
Deal found 1/27$342
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Fri 2/134:27 pm
JAC
-
ORD
1 stop5h 25m
United Airlines
Mon 2/169:00 am
ORD
-
JAC
Nonstop3h 29m
United Airlines
Deal found 1/27$349
This Delta deal was found by Cheapflights users on 1/28. 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 2/192:35 pm
JAC
-
ORD
1 stop8h 21m
Delta
Sun 2/226:45 am
ORD
-
JAC
1 stop7h 40m
Delta
Deal found 1/28$351
This Delta deal was found by Cheapflights users on 1/28. 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 2/192:35 pm
JAC
-
MDW
1 stop6h 56m
Delta
Mon 2/236:00 am
MDW
-
JAC
1 stop8h 25m
Delta
Deal found 1/28$466
This Delta deal was found by Cheapflights users on 1/28. 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 7/27:09 am
JAC
-
MDW
1 stop4h 58m
Delta
Mon 7/62:00 pm
MDW
-
JAC
1 stop6h 38m
Delta
Deal found 1/28$629
This Delta deal was found by Cheapflights users on 1/26. 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 4/241:00 pm
JAC
-
MDW
2 stops8h 28m
Delta
Sun 4/266:00 am
MDW
-
JAC
2 stops11h 09m
Delta
Deal found 1/26$761

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$311
(American Airlines)

One-way from

$150
(Alaska Airlines)

Popular in

January

Cheapest in

September

Average price

$532

Good round-trip deal

$387 or less

Good one-way deal

$298 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. 6% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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 2/19

1:44 pm-5:57 pm

Nonstop3h 13m

Chicago O'Hare Intl

Mon 2/23

9:54 am-12:18 pm

Nonstop3h 24m

$311

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Thu 3/12

11:48 am-11:59 pm

1 stop11h 11m

Chicago O'Hare Intl

Fri 3/13

3:54 pm-11:08 am

1 stop20h 14m

$319

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Fri 4/24

1:00 pm-9:18 pm

1 stop7h 18m

Chicago O'Hare Intl

Sun 4/26

2:09 pm-7:01 pm

1 stop5h 52m

$331

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Tue 4/14

2:35 pm-9:20 pm

1 stop5h 45m

Chicago O'Hare Intl

Tue 4/21

10:49 am-3:24 pm

1 stop5h 35m

$331

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Thu 2/19

2:40 pm-10:52 pm

1 stop7h 12m

Chicago O'Hare Intl

Mon 2/23

7:10 am-1:21 pm

1 stop7h 11m

$331

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Tue 4/14

1:25 pm-7:24 am

2 stops16h 59m

Chicago O'Hare Intl

Tue 4/21

8:53 pm-12:38 pm

2 stops16h 45m

$334

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Tue 4/14

1:00 pm-10:28 pm

2 stops8h 28m

Chicago Midway

Tue 4/21

6:00 am-4:09 pm

2 stops11h 09m

$342

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Fri 2/13

4:27 pm-10:52 pm

1 stop5h 25m

Chicago O'Hare Intl

Mon 2/16

9:00 am-11:29 am

Nonstop3h 29m

$349

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Thu 4/30

1:00 pm-9:18 pm

1 stop7h 18m

Chicago O'Hare Intl

Sun 5/3

2:09 pm-7:01 pm

1 stop5h 52m

$351

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Thu 2/19

2:35 pm-11:56 pm

1 stop8h 21m

Chicago O'Hare Intl

Sun 2/22

6:45 am-1:25 pm

1 stop7h 40m

$351

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 33 results
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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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Jackson-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 January 29, 2026.

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 January 29, 2026.

The most flights from JAC to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 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 January 29, 2026.
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
9,215 reviews

Comfort

7.3

Crew

8.1

Boarding

7.7

Food

6.6

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,215 reviews
United Airlines
7.4
Good
9,215 reviews

Comfort

7.3

Crew

8.1

Boarding

7.7

Food

6.6

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
American Airlines
7.2
Good
11,205 reviews
United Airlines
7.4
Good
9,215 reviews

Comfort

7.3

Crew

8.1

Boarding

7.7

Food

6.6

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 2 daily outbound flights to Chicago from 2 different airlines.

  • How long is the flight from Jackson to Chicago?

    For as low as $311, American Airlines can have you in Chicago from Jackson in 3h 13m. 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 56% 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 (100%), United Airlines (70%), Emirates (69%).

  • What are the cheapest flights from Jackson to Chicago?

    While on average a flight from Jackson to Chicago is generally $639, our data shows the cheapest flight currently is $150. When looking at the most popular route, (Jackson Hole - Chicago O'Hare Intl), you can expect to pay $321 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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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$191Average$385FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$289Average$411FlexibilityNo cancel feeOn-time69%

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