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$109+ 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 6/4. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$211
(American Airlines)

One-way from

$109
(Alaska Airlines)

Popular in

March

Cheapest in

December

Average price

$605

Good round-trip deal

$399 or less

Good one-way deal

$269 or less
Provider with most accurate pricing for Jackson Hole-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Jackson Hole-Chicago (CHI) flights.
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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. 1% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This American Airlines deal was found by Cheapflights users on 5/1. 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 6/61:10 pmJAC - ORD
Nonstop3h 02mAmerican Airlines
Thu 6/121:22 pmORD - JAC
Nonstop3h 06mAmerican Airlines
Deal found 5/1$211
This Delta deal was found by Cheapflights users on 4/30. 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 6/411:40 amJAC - ORD
1 stop5h 40mDelta
Sat 6/71:30 pmORD - JAC
1 stop7h 46mDelta
Deal found 4/30$240
This United Airlines deal was found by Cheapflights users on 4/30. 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 6/105:48 pmJAC - ORD
1 stop5h 37mUnited Airlines
Fri 6/135:02 amORD - JAC
1 stop5h 41mUnited Airlines
Deal found 4/30$248
This Delta deal was found by Cheapflights users on 4/30. 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 6/276:53 pmJAC - MDW
2 stops12h 48mDelta
Sun 7/612:44 pmMDW - JAC
1 stop8h 32mDelta
Deal found 4/30$464
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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.
Sun 6/112:09 pmJAC - ORD
2 stops29h 46mAlaska Airlines
Sun 6/85:58 pmORD - JAC
3 stops19h 20mAlaska Airlines
Deal found 4/30$1,245

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 1, 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

Fri 6/6

1:10 pm-5:12 pm

Nonstop3h 02m

Chicago O'Hare Intl

Thu 6/12

1:22 pm-3:28 pm

Nonstop3h 06m

$211

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Wed 6/4

11:40 am-6:20 pm

1 stop5h 40m

Chicago O'Hare Intl

Sat 6/7

1:30 pm-8:16 pm

1 stop7h 46m

$240

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Tue 6/10

5:48 pm-12:25 am

1 stop5h 37m

Chicago O'Hare Intl

Fri 6/13

5:02 am-9:43 am

1 stop5h 41m

$248

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Fri 6/27

6:53 pm-8:41 am

2 stops12h 48m

Chicago Midway

Sun 7/6

12:44 pm-8:16 pm

1 stop8h 32m

$464

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Sun 6/1

12:09 pm-6:55 pm

2 stops29h 46m

Chicago O'Hare Intl

Sun 6/8

5:58 pm-12:18 pm

3 stops19h 20m

$1,245

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Wed 6/4

11:40 am-10:23 pm

1 stop9h 43m

$109

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Wed 6/18

7:37 am-11:43 am

Nonstop3h 06m

$124

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Wed 6/4

11:40 am-11:58 pm

2 stops11h 18m

$139

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Fri 6/27

3:29 pm-7:39 pm

Nonstop3h 10m

$265

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Fri 6/27

6:53 pm-8:41 am

2 stops12h 48m

$305

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 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 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, 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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

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.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

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).

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 1, 2025.
Read reviews from past customers who have flown Alaska Airlines, Delta and United Airlines from Jackson to Chicago. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

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

    Cheapflights users have booked flights from Jackson to Chicago round-trip from $211. Other airlines that can offer you cheap pricing are Delta, from $240, and United Airlines, from $248. American Airlines is priced at 56% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Jackson to Chicago one-way?

    One-way options have recently been found by users for as low as $109 on Alaska Airlines. Other airlines that offer cheap prices include United Airlines from $124 and Delta from $134 one-way.

  • 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: Emirates (89%), Lufthansa (89%), United Airlines (67%).

  • What are the cheapest flights from Jackson to Chicago?

    While on average a flight from Jackson to Chicago is generally $604, our data shows the cheapest flight currently is $193. When looking at the most popular route, (Jackson Hole - Chicago O'Hare Intl), you can expect to pay $232 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 Jackson?

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

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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 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$349Average$474FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$359Average$421FlexibilityNo cancel feeOn-time71%

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