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$295+ Cheap flights from Jackson (JAC) to Midway (MDW)

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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — MDW
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
1 adult, Economy
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Cheap flight deals from Jackson to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Jackson (JAC) to Midway (MDW). 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 septiembre 11, 2025.

Round-trip from

$489
(Delta)

One-way from

$465
(Delta)

Popular in

March

Cheapest in

September

Average price

$289
From Jackson Hole to Chicago Midway
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One-way flight from Jackson Hole to Chicago Midway
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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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Find flight deals from Jackson to Midway

Cheapest flights from Jackson to Midway
Explore the most affordable flight options available from Jackson to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 11, 2025.

This Delta deal was found by Cheapflights users on 9/9. 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.
vie. 10/246:55 pmJAC - MDW
2 stops13h 45mDelta
vie. 10/319:20 amMDW - JAC
2 stops8h 28mDelta
Deal found 9/9$454
This Delta deal was found by Cheapflights users on 9/9. 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.
jue. 11/67:30 amJAC - MDW
2 stops9h 13mDelta
mar. 11/1110:47 amMDW - JAC
2 stops11h 42mDelta
Deal found 9/9$464
This Delta deal was found by Cheapflights users on 9/10. 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.
vie. 11/217:20 amJAC - MDW
2 stops9h 58mDelta
lun. 11/249:41 amMDW - JAC
2 stops12h 48mDelta
Deal found 9/10$489
This Delta deal was found by Cheapflights users on 9/10. 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.
jue. 9/258:00 amJAC - MDW
2 stops9h 35mDelta
lun. 9/2912:43 pmMDW - JAC
1 stop8h 06mDelta
Deal found 9/10$525
This Delta deal was found by Cheapflights users on 9/10. 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.
mié. 10/17:30 amJAC - MDW
2 stops9h 05mDelta
sáb. 10/49:35 amMDW - JAC
2 stops11h 14mDelta
Deal found 9/10$555
This Delta deal was found by Cheapflights users on 9/9. 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.
mar. 9/168:00 amJAC - MDW
1 stop8h 35mDelta
jue. 9/189:35 amMDW - JAC
2 stops11h 14mDelta
Deal found 9/9$924
This Delta deal was found by Cheapflights users on 9/9. 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.
sáb. 11/2212:57 pmJAC - MDW
2 stops9h 35mDelta
sáb. 11/299:41 amMDW - JAC
2 stops12h 48mDelta
Deal found 9/9$960

Cheapflights Fare Finder

 
Customize your flight search to find flights from Jackson to Midway 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 septiembre 11, 2025.
Use the filters below to find and compare flights from Jackson to Chicago Midway Airport that are best for you.

Fly from

Jackson

Fly to

Midway

Route

Depart

Return

Price

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

vie. 11/21

7:20 am-6:18 pm

2 stops9h 58m

Chicago Midway

lun. 11/24

9:41 am-9:29 pm

2 stops12h 48m

$489

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

jue. 9/25

8:00 am-6:35 pm

2 stops9h 35m

Chicago Midway

lun. 9/29

12:43 pm-7:49 pm

1 stop8h 06m

$525

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

mié. 10/1

7:30 am-5:35 pm

2 stops9h 05m

Chicago Midway

sáb. 10/4

9:35 am-7:49 pm

2 stops11h 14m

$555

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

sáb. 11/22

7:20 am-6:18 pm

2 stops9h 58m

Chicago Midway

sáb. 11/29

9:41 am-9:29 pm

2 stops12h 48m

$1,029

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

vie. 10/10

7:30 am-5:43 pm

2 stops9h 13m

Chicago Midway

lun. 10/13

1:08 pm-9:29 pm

2 stops9h 21m

$1,661

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

jue. 10/16

7:30 am-5:43 pm

2 stops9h 13m

Chicago Midway

dom. 10/19

9:20 am-6:15 pm

2 stops9h 55m

$1,950

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

sáb. 1/31

7:15 am-9:46 pm

2 stops13h 31m

$295

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

jue. 10/30

6:55 pm-9:45 am

2 stops13h 50m

$379

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

mar. 10/21

6:55 pm-9:40 am

2 stops13h 45m

$465

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

sáb. 1/31

7:20 pm-1:08 pm

3 stops40h 48m

$628

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 11 results
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Best time to book a flight from Jackson to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway 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.

Related info for your journey

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

    Most people fly from Jackson Hole (JAC) if they book a flight from Jackson to Chicago Midway. On average, Jackson Hole has 0 outbound flights to Chicago Midway per day from 0 airlines. Jackson Hole is conveniently located just 8.8 mi from Jackson’s city center.

  • How long is the flight from Jackson to Chicago Midway Airport?

    Delta can get you from Jackson to Chicago Midway Airport in just under 9h 58m. Your travel time can differ by up to . Airlines will cover a distance of 1170 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Jackson to Midway 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 Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Jackson to Chicago Midway Airport (average of $160). Flying from Jackson to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 Midway Airport?

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

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