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$160+ 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 6/11. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — CHI
Jun 7 — Jun 141
Sun 6/7
Sun 6/14
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 May 8, 2026.

This American Airlines deal was found by Cheapflights users on 5/7. 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 7/93:39 pm
JAC
-
ORD
Nonstop3h 28m
American Airlines
Sun 7/126:51 am
ORD
-
JAC
1 stop10h 10m
American Airlines
Deal found 5/7$329
This American Airlines deal was found by Cheapflights users on 5/4. 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 6/194:14 pm
JAC
-
ORD
1 stop7h 25m
American Airlines
Sun 6/216:51 am
ORD
-
JAC
1 stop10h 07m
American Airlines
Deal found 5/4$339
This Delta deal was found by Cheapflights users on 5/7. 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 7/151:15 pm
JAC
-
ORD
1 stop7h 33m
Delta
Tue 7/281:44 pm
ORD
-
JAC
1 stop7h 20m
Delta
Deal found 5/7$349
This Delta deal was found by Cheapflights users on 5/7. 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 7/151:15 pm
JAC
-
ORD
1 stop7h 33m
Delta
Mon 7/278:27 am
ORD
-
JAC
2 stops9h 33m
Delta
Deal found 5/7$354
This United Airlines deal was found by Cheapflights users on 5/5. 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 6/47:30 am
JAC
-
ORD
Nonstop3h 10m
United Airlines
Thu 6/114:21 pm
ORD
-
JAC
Nonstop3h 21m
United Airlines
Deal found 5/5$355
This American Airlines deal was found by Cheapflights users on 5/6. 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 6/512:59 pm
JAC
-
ORD
1 stop9h 59m
American Airlines
Fri 6/126:51 am
ORD
-
JAC
1 stop10h 07m
American Airlines
Deal found 5/6$375
This Alaska Airlines deal was found by Cheapflights users on 5/4. 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 6/242:11 pm
JAC
-
ORD
1 stop8h 25m
Alaska Airlines
Sat 6/277:20 am
ORD
-
JAC
1 stop7h 11m
Alaska Airlines
Deal found 5/4$379
This Delta deal was found by Cheapflights users on 5/4. 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 6/267:00 am
JAC
-
ORD
1 stop7h 05m
Delta
Sat 6/278:36 am
ORD
-
JAC
2 stops9h 24m
Delta
Deal found 5/4$380
This Delta deal was found by Cheapflights users on 5/7. 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 7/151:15 pm
JAC
-
ORD
1 stop7h 33m
Delta
Thu 7/301:44 pm
ORD
-
JAC
1 stop7h 20m
Delta
Deal found 5/7$384
This Delta deal was found by Cheapflights users on 5/7. 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 7/81:15 pm
JAC
-
ORD
1 stop7h 33m
Delta
Fri 7/102:02 pm
ORD
-
JAC
1 stop6h 35m
Delta
Deal found 5/7$385
This Delta deal was found by Cheapflights users on 5/6. 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 5/127:00 am
JAC
-
MDW
1 stop5h 19m
Delta
Wed 6/241:49 pm
MDW
-
JAC
1 stop7h 41m
Delta
Deal found 5/6$464
This Delta deal was found by Cheapflights users on 5/4. 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 6/237:00 am
JAC
-
MDW
1 stop5h 09m
Delta
Tue 6/301:49 pm
MDW
-
JAC
1 stop7h 41m
Delta
Deal found 5/4$479

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 May 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$329
(American Airlines)

One-way from

$160
(United Airlines)

Popular in

April

Cheapest in

September

Average price

$520

Good round-trip deal

$465 or less

Good one-way deal

$235 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. 18% potential increase in price ($116 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 8, 2026.
Use the filters below to find and compare flights from Jackson to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Thu 6/11

7:30 am-11:40 am

Nonstop3h 10m

Chicago O'Hare Intl

Sat 6/13

4:21 pm-6:42 pm

Nonstop3h 21m

$355

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Tue 5/19

2:30 pm-9:23 pm

1 stop5h 53m

Chicago O'Hare Intl

Sat 5/23

4:28 pm-6:49 pm

Nonstop3h 21m

$409

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Wed 6/17

7:30 am-11:40 am

Nonstop3h 10m

Chicago O'Hare Intl

Sat 6/20

5:00 am-9:46 am

1 stop5h 46m

$409

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Wed 8/19

1:45 pm-9:42 pm

1 stop6h 57m

Chicago O'Hare Intl

Tue 8/25

9:00 am-11:22 am

Nonstop3h 22m

$419

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Fri 6/5

7:30 am-11:40 am

Nonstop3h 10m

Chicago O'Hare Intl

Fri 6/12

4:21 pm-6:42 pm

Nonstop3h 21m

$429
Quickest round-trip

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Wed 10/21

12:30 pm-4:27 pm

Nonstop2h 57m

Chicago O'Hare Intl

Sat 10/24

4:30 pm-6:52 pm

Nonstop3h 22m

$445

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Tue 6/23

7:00 am-1:09 pm

1 stop5h 09m

Chicago Midway

Tue 6/30

1:49 pm-8:30 pm

1 stop7h 41m

$479

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Tue 5/19

7:00 am-1:19 pm

1 stop5h 19m

Chicago Midway

Sat 5/23

9:23 am-4:59 pm

2 stops8h 36m

$494

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Fri 7/10

7:40 am-6:25 pm

2 stops9h 45m

Chicago Midway

Mon 7/20

1:18 pm-8:29 pm

2 stops8h 11m

$555

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Tue 5/19

7:00 am-9:09 pm

2 stops13h 09m

Chicago Midway

Fri 5/22

9:23 am-4:59 pm

2 stops8h 36m

$689

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/4

Showing 1-10 of 29 resultsSorted by cheapest first
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 May.
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, September is the cheapest month in which you can book a flight from Jackson to Chicago (average of $191). Flying from Jackson to Chicago in February 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.

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 May 8, 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
9,694 reviews

Comfort

7.3

Overall

7.4

Crew

8.1

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
United Airlines
7.4
Good
9,694 reviews
United Airlines
7.4
Good
9,694 reviews

Comfort

7.3

Overall

7.4

Crew

8.1

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
American Airlines
7.1
Good
11,666 reviews
United Airlines
7.4
Good
9,694 reviews

Comfort

7.3

Overall

7.4

Crew

8.1

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.

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 0 daily outbound flights to Chicago from 2 different airlines.

  • How long is the flight from Jackson to Chicago?

    For as low as $355, United Airlines can have you in Chicago from Jackson in 3h 10m. 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 54% 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: Copa Airlines (89%), United Airlines (87%), Lufthansa (85%).

  • What are the cheapest flights from Jackson to Chicago?

    While on average a flight from Jackson to Chicago is generally $486, our data shows the cheapest flight currently is $190. When looking at the most popular route, (Jackson Hole - Chicago O'Hare Intl), you can expect to pay $329 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, September is the cheapest month in which you can book a flight from Jackson to Chicago (average of $191). Flying from Jackson to Chicago in February 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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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 May 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$229Average$385FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$281Average$387FlexibilityNo cancel feeOn-time69%

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