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$201+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — MDW
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
1 adult, Economy
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Cheap 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 February 3, 2026.

This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/112:41 pm
JAC
-
MDW
1 stop6h 50m
Delta
Wed 3/189:30 am
MDW
-
JAC
2 stops10h 32m
Delta
Deal found 2/1$350
This Delta deal was found by Cheapflights users on 2/2. 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 2/122:35 pm
JAC
-
MDW
1 stop6h 56m
Delta
Mon 2/166:00 am
MDW
-
JAC
1 stop8h 25m
Delta
Deal found 2/2$413
This Delta deal was found by Cheapflights users on 2/2. 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 2/2$496
This Delta deal was found by Cheapflights users on 2/2. 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 2/137:20 am
JAC
-
MDW
2 stops9h 17m
Delta
Mon 2/166:00 am
MDW
-
JAC
1 stop8h 25m
Delta
Deal found 2/2$514
This Delta deal was found by Cheapflights users on 2/3. 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 2/272:35 pm
JAC
-
MDW
1 stop6h 56m
Delta
Mon 3/26:00 am
MDW
-
JAC
1 stop8h 25m
Delta
Deal found 2/3$586

Find 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 February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$350
(Delta)

One-way from

$201
(Delta)

Popular in

January

Cheapest in

September

Average price

$359
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
One-way flight from Jackson Hole to Chicago Midway
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 February 2026
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 February 3, 2026.
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

Wed 3/11

2:41 pm-10:31 pm

1 stop6h 50m

Chicago Midway

Wed 3/18

9:30 am-7:02 pm

2 stops10h 32m

$350

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Thu 2/19

2:35 pm-10:31 pm

1 stop6h 56m

Chicago Midway

Mon 2/23

6:00 am-1:25 pm

1 stop8h 25m

$496

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Fri 2/13

7:20 am-5:37 pm

2 stops9h 17m

Chicago Midway

Mon 2/16

6:00 am-1:25 pm

1 stop8h 25m

$514

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Fri 2/27

2:35 pm-10:31 pm

1 stop6h 56m

Chicago Midway

Mon 3/2

9:34 am-7:04 pm

2 stops10h 30m

$716

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Tue 2/17

2:35 pm-10:33 pm

1 stop6h 58m

Chicago Midway

Sat 2/21

11:45 am-7:04 pm

2 stops8h 19m

$933

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Wed 3/4

2:35 pm-10:31 pm

1 stop6h 56m

$201

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Wed 7/8

7:09 am-1:07 pm

1 stop4h 58m

$291

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Thu 7/9

7:09 am-1:07 pm

1 stop4h 58m

$421

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Sat 7/11

7:09 am-1:07 pm

1 stop4h 58m

$490

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Sun 3/22

12:17 pm-8:53 am

3 stops43h 36m

$684

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 13 results
1
2

Compare providers for flights from Jackson to Midway

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 Midway in February.
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 Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Jackson-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 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 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 6h 50m. 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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