JAN - MDW

$155 Find Cheap Flights from Jackson to Chicago Midway Airport - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$309
Typical prices: $366-$587
Southwest
Sun 1/7Sat 1/13
JAN - MDW • 1 stop
Cheapest one-way
$155
Typical prices: $259-$378
Southwest
Wed 11/7
JAN - MDW • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Jackson and Chicago Midway Airport. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
October
Cheapest • 37% price drop
August
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Houston Hobby (HOU)
Cheapest • Avg $390 (round-trip)
Atlanta Hartsfield-Jackson (ATL)
Shortest trip • 4h 45m (one-way)
Insights
Insights
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We hope you love your trip to Chicago Midway Airport!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Jackson to Midway (JAN-MDW)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Jackson to Midway

Thu, Jan 7 - Wed, Jan 13
Southwest Logo
12:55 pm - 6:20 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
5h 25m1 stop Nashville Intl
Southwest Logo
1:20 pm - 5:30 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
4h 10m1 stop Nashville Intl
$309Southwest
Thu, Nov 12 - Tue, Nov 17
Delta Logo
3:50 pm - 10:54 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
7h 04m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 10:29 amMDW  Chicago Midway-JAN Jackson-Evers Intl
4h 29m1 stop Atlanta Hartsfield-Jackson
$309Delta
Wed, Oct 21 - Tue, Oct 27
Delta Logo
3:33 pm - 10:33 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
7h 00m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:04 am - 10:25 amMDW  Chicago Midway-JAN Jackson-Evers Intl
4h 21m1 stop Atlanta Hartsfield-Jackson
$309Delta
Mon, Oct 26 - Wed, Oct 28
Delta Logo
5:02 pm - 10:33 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
5h 31m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:04 am - 12:14 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
6h 10m1 stop Atlanta Hartsfield-Jackson
$309Delta
Thu, Nov 12 - Tue, Nov 17
Southwest Logo
8:15 pm - 1:10 amJAN  Jackson-Evers Intl-MDW Chicago Midway
4h 55m1 stop Houston Hobby
Southwest Logo
9:55 am - 7:55 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
10h 00m2 stops Nashville Intl Houston Hobby
$314Southwest
Thu, Jan 7 - Wed, Jan 13
Southwest Logo
12:55 pm - 6:20 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
5h 25m1 stop Nashville Intl
Southwest Logo
12:25 pm - 7:50 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
7h 25m2 stops Dallas Love Field Houston Hobby
$314Southwest
Wed, Oct 21 - Tue, Oct 27
Southwest Logo
12:55 pm - 10:00 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
9h 05m2 stops Nashville Intl Lambert-St Louis
Southwest Logo
6:25 am - 12:15 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
5h 50m1 stop Houston Hobby
$314Southwest
Wed, Oct 21 - Tue, Oct 27
Southwest Logo
12:55 pm - 10:00 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
9h 05m2 stops Nashville Intl Lambert-St Louis
Southwest Logo
12:15 pm - 8:00 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
7h 45m2 stops Austin Bergstrom Houston Hobby
$319Southwest
Thu, Jan 7 - Wed, Jan 13
Southwest Logo
12:55 pm - 9:20 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
8h 25m2 stops Nashville Intl Baltimore/Washington
Southwest Logo
10:05 am - 5:30 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
7h 25m2 stops Lambert-St Louis Nashville Intl
$319Southwest
Sat, Nov 7 - Mon, Nov 9
Delta Logo
11:10 am - 3:17 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
4h 07m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:13 pm - 11:05 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
5h 52m1 stop Atlanta Hartsfield-Jackson
$329Delta
Booking Insights

Price, demand and travel trends for Jackson to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

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

Round-trip flights from Jackson to Chicago Midway Airport typically range from $366 to $587. The lowest price found in the past 5 days was $309, on Southwest.

What's the cheapest day of the week to fly from Jackson to Chicago Midway Airport?

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Jackson to Chicago Midway Airport. It’s 27% cheaper than the average day, while Sunday is the most expensive, with prices 120% higher.

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Key details for Jackson to Chicago Midway Airport flights

Low season

February

Cheapest flight

$155
One-way 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

Your Jackson to Chicago Midway Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What cabin classes can I book on flights from Jackson to Chicago Midway Airport?

    Only Economy Class is available on flights from Jackson to Chicago Midway Airport.

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

    A nonstop flight from Jackson to Chicago Midway Airport takes 00m, covering 667 miles.

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

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Jackson to Chicago Midway Airport flight?

    Round-trip flights from Jackson to Chicago Midway Airport range from $366 to $587, with an average of $456 over the past 12 months. Anything below $366 counts as a good deal.

  • Have flight prices from Jackson to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $309 to $1,594. That means the highest observed fare was about 5x higher than the lowest one.

  • How are flight prices from Jackson to Chicago Midway Airport looking right now?

    One-way fares from Jackson to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $191, which is 43% below the typical average for this route.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • Which airports can I use when flying from Jackson to Chicago Midway Airport?

    Flights from Jackson to Chicago Midway Airport usually depart from Jackson-Evers Intl (JAN) and arrive at Chicago Midway (MDW).

  • Which airports do connecting flights from Jackson to Chicago Midway Airport pass through?

    One-stop flights from Jackson to Chicago Midway Airport most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 60% of one-stop connections
    • Nashville Intl (BNA) - 15% of one-stop connections
    • Houston Hobby (HOU) - 15% of one-stop connections
    • Baltimore/Washington (BWI) - 10% of one-stop connections

  • Can I save money by using flexible dates for flights from Jackson to Chicago Midway Airport?

    Yes. Flexible dates can save you up to 67% on flights from Jackson to Chicago Midway Airport. Wednesday is the cheapest departure day at $336 round-trip on average, while Sunday is the most expensive at $1,007, a difference of $671.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How much time can I save by choosing a different layover airport from Jackson to Chicago Midway Airport?

    Flying via Atlanta Hartsfield-Jackson (ATL) gives the shortest average 1-stop total travel time at 4h 45m, compared with 5h 31m via Houston Hobby (HOU) and 6h via Nashville Intl (BNA).

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

Your guide to booking Jackson to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Wednesday departure and avoid flying on Sunday. On this route, Wednesday flights average $336, about $671 less than Sunday fares (67% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Jackson to Chicago Midway Airport trip for October. Fares historically average $286 round-trip in that month - typically $336 less than the most expensive month, which is May (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel

More options for your flight from Jackson to Midway

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