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$319+ Cheap flights from Jackson (JAC) to Midway (MDW)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — MDW
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
1 adult, Economy
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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 October 27, 2025.

This Delta deal was found by Cheapflights users on 10/25. 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 12/912:55 pmJAC - MDW
2 stops9h 52mDelta
Tue 12/169:59 amMDW - JAC
2 stops12h 30mDelta
Deal found 10/25$319
This Delta deal was found by Cheapflights users on 10/25. 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 11/76:55 pmJAC - MDW
2 stops13h 45mDelta
Tue 11/1110:47 amMDW - JAC
2 stops11h 42mDelta
Deal found 10/25$424
This Delta deal was found by Cheapflights users on 10/27. 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 10/287:30 amJAC - MDW
2 stops9h 55mDelta
Tue 11/46:00 amMDW - JAC
2 stops9h 47mDelta
Deal found 10/27$484
This Delta deal was found by Cheapflights users on 10/26. 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.
Mon 11/107:00 amJAC - MDW
2 stops10h 18mDelta
Fri 11/146:00 amMDW - JAC
2 stops12h 10mDelta
Deal found 10/26$571
This Delta deal was found by Cheapflights users on 10/26. 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.
Sat 11/157:00 amJAC - MDW
2 stops10h 18mDelta
Mon 11/176:00 amMDW - JAC
2 stops12h 10mDelta
Deal found 10/26$589
This Delta deal was found by Cheapflights users on 10/25. 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 11/46:55 pmJAC - MDW
2 stops13h 50mDelta
Sun 11/99:41 amMDW - JAC
2 stops12h 48mDelta
Deal found 10/25$724
This Delta deal was found by Cheapflights users on 10/26. 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.
Thu 11/207:00 amJAC - MDW
2 stops10h 18mDelta
Mon 11/249:41 amMDW - JAC
2 stops12h 48mDelta
Deal found 10/26$1,039
This Delta deal was found by Cheapflights users on 10/25. 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.
Sat 11/227:00 amJAC - MDW
2 stops10h 18mDelta
Sat 11/299:41 amMDW - JAC
2 stops8h 29mDelta
Deal found 10/25$1,569

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 October 27, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$319
(Delta)

Popular in

November

Cheapest in

September

Average price

$425
Provider with most accurate pricing for Jackson Hole-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Jackson Hole-Chicago Midway flights.
Search Deals
From Jackson Hole to Chicago Midway
Search Deals
Highest demand for flights based on searches. 24% potential increase in price ($164 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($56 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 27, 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

Tue 12/9

12:55 pm-11:47 pm

2 stops9h 52m

Chicago Midway

Tue 12/16

9:59 am-9:29 pm

2 stops12h 30m

$319

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Fri 11/7

6:55 pm-9:40 am

2 stops13h 45m

Chicago Midway

Tue 11/11

10:47 am-9:29 pm

2 stops11h 42m

$424

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Mon 11/10

7:00 am-6:18 pm

2 stops10h 18m

Chicago Midway

Fri 11/14

6:00 am-5:10 pm

2 stops12h 10m

$571

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Sat 11/15

7:00 am-6:18 pm

2 stops10h 18m

Chicago Midway

Mon 11/17

6:00 am-5:10 pm

2 stops12h 10m

$589

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Thu 4/2

5:30 pm-8:54 am

2 stops14h 24m

Chicago Midway

Mon 4/6

9:20 am-7:03 pm

2 stops10h 43m

$766

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Thu 11/20

7:00 am-6:18 pm

2 stops10h 18m

Chicago Midway

Mon 11/24

9:41 am-9:29 pm

2 stops12h 48m

$1,039

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Sat 11/22

7:00 am-6:18 pm

2 stops10h 18m

Chicago Midway

Sat 11/29

9:41 am-5:10 pm

2 stops8h 29m

$1,569

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Mon 11/3

7:30 am-5:43 pm

2 stops9h 13m

$356

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Sat 11/22

7:00 am-6:18 pm

2 stops10h 18m

$485

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

  • Most accurate provider: When it comes to deals on Jackson-Chicago Midway Airport flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Jackson-Chicago Midway Airport flight deals on Cheapflights vs. Expedia 90-95% of the time. Price accuracy is based on data collected from Jackson-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Jackson-Chicago Midway Airport flights, Cheapflights users trust Expedia the most. Expedia 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 Midway Airport 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 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 52m. 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.

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
Porter
Benton Harbor

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