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 9/30Wed 10/3
JAN - MDW • 1 stop
Cheapest one-way
$155
Typical prices: $259-$378
Delta
Wed 10/3
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
Baltimore/Washington (BWI)
Cheapest • Avg $347 (round-trip)
Nashville Intl (BNA)
Shortest trip • 4h 17m (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

Wed, Sep 30 - Sat, Oct 3
Southwest Logo
1:30 pm - 8:10 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
6h 40m1 stop Nashville Intl
Southwest Logo
8:40 am - 2:45 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
6h 05m1 stop Nashville Intl
$309Southwest
Wed, Sep 30 - Wed, Oct 7
Southwest Logo
6:40 pm - 11:15 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
4h 35m1 stop Houston Hobby
Southwest Logo
6:25 am - 12:15 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
5h 50m1 stop Houston Hobby
$309Southwest
Wed, Sep 30 - Sat, Oct 3
Southwest Logo
7:05 am - 3:20 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
8h 15m2 stops Houston Hobby Dallas Love Field
Southwest Logo
8:40 am - 2:45 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
6h 05m1 stop Nashville Intl
$314Southwest
Wed, Sep 30 - Wed, Oct 7
Southwest Logo
7:05 am - 3:20 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
8h 15m2 stops Houston Hobby Dallas Love Field
Southwest Logo
6:25 am - 12:15 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
5h 50m1 stop Houston Hobby
$314Southwest
Wed, Sep 30 - Sat, Oct 3
Southwest Logo
7:05 am - 4:00 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
8h 55m2 stops Houston Hobby Austin Bergstrom
Southwest Logo
6:55 am - 2:45 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
7h 50m2 stops Baltimore/Washington Nashville Intl
$319Southwest
Wed, Sep 30 - Wed, Oct 7
Southwest Logo
7:05 am - 3:20 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
8h 15m2 stops Houston Hobby Dallas Love Field
Southwest Logo
12:15 pm - 8:00 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
7h 45m2 stops Austin Bergstrom Houston Hobby
$319Southwest
Fri, Sep 25 - Mon, Sep 28
Delta Logo
5:12 pm - 10:44 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
5h 32m1 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
Fri, Oct 2 - Mon, Oct 5
Southwest Logo
5:55 am - 3:40 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
9h 45m2 stops Houston Hobby Austin Bergstrom
Southwest Logo
4:30 pm - 7:50 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
3h 20m1 stop Nashville Intl
$352Southwest
Fri, Feb 26 - Sun, Feb 28
Southwest Logo
7:20 pm - 12:35 amJAN  Jackson-Evers Intl-MDW Chicago Midway
5h 15m1 stop Houston Hobby
Southwest Logo
5:00 am - 11:00 amMDW  Chicago Midway-JAN Jackson-Evers Intl
6h 00m1 stop Houston Hobby
$366Southwest
Sat, Oct 31 - Mon, Nov 9
Delta Logo
4:00 pm - 10:33 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
6h 33m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:13 pm - 11:05 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
5h 52m1 stop Atlanta Hartsfield-Jackson
$367Delta
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 from Jackson to Chicago Midway Airport 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 start at $309. Prices are below average for this route right now, with typical round-trip fares ranging 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?

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

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Key details for Jackson to Chicago Midway Airport flights

Low season

February

Cheapest flight

$155
Most popular time to fly with an average 18% increase in price.
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 route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • 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).

  • 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.

  • 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) - 58% of one-stop connections
    • Houston Hobby (HOU) - 25% of one-stop connections
    • Nashville Intl (BNA) - 8% of one-stop connections
    • Baltimore/Washington (BWI) - 8% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

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

    Yes. Being flexible with your travel dates can save you up to 67% on the Jackson to Chicago Midway Airport route. 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.

  • 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.

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

    A nonstop flight from Jackson to Chicago Midway Airport takes 0h 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.

  • 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 $2,336. That means the highest observed fare was about 8x 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 $203, which is 40% below the typical average for this route.

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

    Flying via Nashville Intl (BNA) gives the shortest average 1-stop total travel time at 4h 17m, compared with 4h 56m via Atlanta Hartsfield-Jackson (ATL) and 6h 12m via Houston Hobby (HOU).

  • 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

  • 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.

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 can be flexible, aim for a Wednesday departure instead of Sunday. On this route, Wednesday flights average $336 - about $671 less than Sunday (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

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

Information on your arrival and departure airports

Jackson (JAN)
Midway (MDW)