JAN - MDW

$184 Find Cheap Flights from Jackson to Chicago Midway Airport - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Jackson to Midway departing on 8/18. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$239
Typical prices: $236-$428
Delta
Thu 8/20Sat 8/22
JAN - MDW • 1 stop
Cheapest one-way
$184
Delta
Tue 8/18
JAN - MDW • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Jackson and Midway. You'll need at least 1 connection.
Insights
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Top layover airports
Nashville (BNA)
Cheapest • Avg $286 (round-trip)
Atlanta (ATL)
Shortest trip • 4h 37m (one-way)
Insights
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Insights
When to travel
January
Cheapest • 100% price drop
August
Most popular
Good to know
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+1
+1
Good to know
Good to know
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Jackson to Midway (JAN-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Jackson to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Jackson to Midway

Thu, Aug 20 - Sat, Aug 22
Delta Logo
3:30 pm - 10:36 pm
JAN
-
MDW
7h 06m
1 stop
Delta Logo
10:56 am - 4:16 pm
MDW
-
JAN
5h 20m
1 stop
$239Delta
Sat, Aug 8 - Sat, Aug 15
Southwest Logo
12:25 pm - 5:40 pm
JAN
-
MDW
5h 15m
1 stop
Southwest Logo
1:45 pm - 7:05 pm
MDW
-
JAN
5h 20m
1 stop
$304Southwest
Sat, Aug 8 - Sat, Aug 15
Southwest Logo
6:00 am - 2:05 pm
JAN
-
MDW
8h 05m
2 stops
Southwest Logo
8:05 am - 1:55 pm
MDW
-
JAN
5h 50m
1 stop
$309Southwest
Sat, Aug 8 - Sat, Aug 15
Southwest Logo
6:00 am - 2:10 pm
JAN
-
MDW
8h 10m
2 stops
Southwest Logo
7:40 am - 1:55 pm
MDW
-
JAN
6h 15m
2 stops
$314Southwest
Wed, Aug 26 - Sat, Aug 29
Delta Logo
3:30 pm - 10:36 pm
JAN
-
MDW
7h 06m
1 stop
Delta Logo
6:11 am - 11:59 am
MDW
-
JAN
5h 48m
1 stop
$325Delta
Wed, Aug 26 - Sat, Aug 29
Southwest Logo
7:05 am - 3:20 pm
JAN
-
MDW
8h 15m
2 stops
Southwest Logo
1:45 pm - 7:05 pm
MDW
-
JAN
5h 20m
1 stop
$330Southwest
Wed, Aug 26 - Sat, Aug 29
Southwest Logo
1:30 pm - 9:50 pm
JAN
-
MDW
8h 20m
2 stops
Southwest Logo
7:40 am - 1:55 pm
MDW
-
JAN
6h 15m
2 stops
$335Southwest
Sat, Aug 8 - Sat, Aug 15
Southwest Logo
12:25 pm - 5:40 pm
JAN
-
MDW
5h 15m
1 stop
Southwest Logo
1:45 pm - 7:05 pm
MDW
-
JAN
5h 20m
1 stop
$367Southwest
Sat, Aug 8 - Sat, Aug 15
Southwest Logo
6:00 am - 2:05 pm
JAN
-
MDW
8h 05m
2 stops
Southwest Logo
8:05 am - 1:55 pm
MDW
-
JAN
5h 50m
1 stop
$372Southwest
Sat, Aug 8 - Sat, Aug 15
Southwest Logo
6:00 am - 2:05 pm
JAN
-
MDW
8h 05m
2 stops
Southwest Logo
9:05 am - 7:05 pm
MDW
-
JAN
10h 00m
2 stops
$377Southwest
Booking Insights

KAYAK's insights & trends for Jackson to Midway flights

Get data-powered insights and trends into flights from Jackson to Midway to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Jackson to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Jackson to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Jackson to Chicago Midway Airport is January, where tickets cost $0 (return) on average. On the other hand, the most expensive months are May and December, where the average cost of round-trip tickets is $1,458 and $587 respectively.

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Good to know

Low seasonAugust
Cheapest flight$184
Best time to beat the crowds with an average 55% drop in price.
Most popular time to fly and prices are also 55% lower on average.
Flight from Jackson to Chicago Midway Airport

When to book flights from Jackson to Midway

Are your dates flexible? Find out the best times to travel from Jackson to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Jackson to Chicago Midway Airport flights

  • What is the cheapest flight from Jackson to Chicago Midway Airport?

    In the last 5 days, the lowest price for a flight from Jackson to Chicago Midway Airport was $184 for a one-way ticket and $239 for a round-trip.

  • Do I need a passport to fly between Jackson and Chicago Midway Airport?

    No

  • Which aircraft models fly most regularly from Jackson to Chicago Midway Airport?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Jackson to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Jackson and Chicago Midway Airport.

  • Which is the best airline for flights from Jackson to Chicago, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Jackson to Chicago are Southwest and Delta. With an average price for the route of $426 and an overall rating of 7.9, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $286 and an overall rating of 7.8.

  • How does KAYAK find such low prices on flights from Jackson to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Jackson to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Jackson to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Jackson is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Jackson to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Jackson with another airline. Booking your flights between Jackson and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Jackson to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Jackson up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Everything you need to know for your flight from Jackson to Midway

Information on your arrival and departure airports

Jackson (JAN)
Midway (MDW)