JAN - MDW

$168 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 12/31. 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

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$309
Typical prices: $370-$573
Southwest
Sat 8/29Wed 9/2
JAN - MDW • 1 stop
Cheapest one-way
$168
Southwest
Thu 12/31
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
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $437 (round-trip)
Shortest trip • 5h 00m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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

Sat, Aug 29 - Wed, Sep 2
Southwest Logo
12:25 pm - 5:40 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
5h 15m1 stop Houston Hobby
Southwest Logo
2:40 pm - 6:05 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
3h 25m1 stop Nashville Intl
$309Southwest
Sat, Aug 29 - Wed, Sep 2
Southwest Logo
12:25 pm - 5:40 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
5h 15m1 stop Houston Hobby
Southwest Logo
11:10 am - 7:45 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
8h 35m2 stops Dallas Love Field Houston Hobby
$314Southwest
Wed, Sep 2 - Sat, Sep 5
Delta Logo
5:32 am - 9:59 amJAN  Jackson-Evers Intl-MDW Chicago Midway
4h 27m1 stop Atlanta Hartsfield-Jackson
Delta Logo
10:56 am - 4:16 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
5h 20m1 stop Atlanta Hartsfield-Jackson
$315Delta
Sat, Aug 29 - Wed, Sep 2
Southwest Logo
6:00 am - 2:05 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
8h 05m2 stops Houston Hobby Austin Bergstrom
Southwest Logo
11:10 am - 7:45 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
8h 35m2 stops Dallas Love Field Houston Hobby
$319Southwest
Sun, Sep 6 - Tue, Sep 22
Delta Logo
10:36 am - 3:44 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
5h 08m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:11 pm - 11:21 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
6h 10m1 stop Atlanta Hartsfield-Jackson
$322Delta
Sat, Aug 29 - Mon, Aug 31
Southwest Logo
12:25 pm - 5:40 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
5h 15m1 stop Houston Hobby
Southwest Logo
5:25 am - 12:00 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
6h 35m1 stop Houston Hobby
$322Southwest
Sun, Sep 6 - Wed, Sep 23
Delta Logo
10:36 am - 3:44 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
5h 08m1 stop Atlanta Hartsfield-Jackson
Delta Logo
10:48 am - 4:29 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
5h 41m1 stop Atlanta Hartsfield-Jackson
$322Delta
Sun, Sep 6 - Sat, Sep 19
Delta Logo
3:30 pm - 10:36 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
7h 06m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:30 pm - 9:34 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
5h 04m1 stop Atlanta Hartsfield-Jackson
$322Delta
Sat, Sep 5 - Sat, Sep 12
Delta Logo
5:01 pm - 10:36 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
5h 35m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 11:46 amMDW  Chicago Midway-JAN Jackson-Evers Intl
5h 41m1 stop Atlanta Hartsfield-Jackson
$322Delta
Sun, Sep 6 - Mon, Sep 21
Delta Logo
6:00 am - 10:10 amJAN  Jackson-Evers Intl-MDW Chicago Midway
4h 10m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 10:23 amMDW  Chicago Midway-JAN Jackson-Evers Intl
4h 18m1 stop Atlanta Hartsfield-Jackson
$322Delta
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.

How much is a round-trip flight from Jackson, Mississippi to Chicago Midway Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Jackson, Mississippi to Chicago Midway Airport departing in August.

Flight prices are below average for this route right now.

Flights to Chicago Midway Airport from Jackson, Mississippi usually cost between $432 and $639 in August.
The lowest price found in the past 5 days was $309 on Southwest (Aug 29-Sep 2).

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.

Good to know

Low season

November

Cheapest flight

$168
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly and prices are also 28% 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 $168 for a one-way ticket and $309 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.

  • 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