MDW - JAN

$184 Find Cheap Flights from Chicago Midway Airport to Jackson

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Jackson departing on 5/25. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Jackson

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Jackson, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Jackson, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$309
Typical prices: $346-$466
Delta
Sat 2/14Mon 2/16
MDW - JAN • 1 stop
Cheapest one-way
$184
Delta
Mon 5/25
MDW - JAN • 1 stop
Top airlines
Delta
Cheapest • from $309 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Jackson (MDW-JAN)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Jackson 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 Midway to Jackson

Sat, Feb 14 - Mon, Feb 16
Delta Logo
4:13 pm - 11:07 pm
MDW
-
JAN
6h 54m
1 stop
Delta Logo
5:30 am - 11:59 am
JAN
-
MDW
6h 29m
1 stop
$309Delta
Mon, Mar 2 - Wed, Apr 1
Delta Logo
6:40 pm - 11:07 pm
MDW
-
JAN
4h 27m
1 stop
Delta Logo
5:35 am - 12:02 pm
JAN
-
MDW
6h 27m
1 stop
$321Delta
Mon, Mar 2 - Wed, Apr 1
Southwest Logo
8:15 am - 3:40 pm
MDW
-
JAN
7h 25m
2 stops
Southwest Logo
5:50 am - 10:45 am
JAN
-
MDW
4h 55m
1 stop
$326Southwest
Mon, Mar 2 - Wed, Apr 1
Southwest Logo
12:50 pm - 8:55 pm
MDW
-
JAN
8h 05m
2 stops
Southwest Logo
12:05 pm - 7:55 pm
JAN
-
MDW
7h 50m
2 stops
$331Southwest
Wed, Mar 11 - Sat, Mar 14
Southwest Logo
6:25 am - 11:30 am
MDW
-
JAN
5h 05m
1 stop
Southwest Logo
12:20 pm - 5:50 pm
JAN
-
MDW
5h 30m
1 stop
$344Southwest
Fri, Apr 3 - Tue, Apr 7
Southwest Logo
4:05 pm - 7:40 pm
MDW
-
JAN
3h 35m
1 stop
Southwest Logo
6:30 am - 2:55 pm
JAN
-
MDW
8h 25m
2 stops
$349Southwest
Mon, Feb 23 - Mon, Mar 2
Southwest Logo
12:50 pm - 8:55 pm
MDW
-
JAN
8h 05m
2 stops
Southwest Logo
4:15 pm - 9:25 pm
JAN
-
MDW
5h 10m
1 stop
$355Southwest
Thu, May 28 - Sun, May 31
Delta Logo
6:00 am - 11:20 am
MDW
-
JAN
5h 20m
1 stop
Delta Logo
5:35 pm - 9:45 pm
JAN
-
MDW
4h 10m
1 stop
$367Delta
Wed, Feb 11 - Tue, Feb 17
Southwest Logo
6:15 am - 12:40 pm
MDW
-
JAN
6h 25m
1 stop
Southwest Logo
4:15 pm - 9:25 pm
JAN
-
MDW
5h 10m
1 stop
$372Southwest
Fri, Apr 3 - Tue, Apr 7
Southwest Logo
11:15 am - 7:40 pm
MDW
-
JAN
8h 25m
2 stops
Southwest Logo
6:30 am - 2:55 pm
JAN
-
MDW
8h 25m
2 stops
$374Southwest
Booking Insights

KAYAK's insights & trends for Midway to Jackson flights

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

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

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

Good to know

Low seasonApril
Cheapest flight$184
Best time to beat the crowds with an average 44% drop in price.
Most popular time to fly with an average 22% increase in price.
Flight from Chicago Midway Airport to Jackson

When to book flights from Midway to Jackson

Are your dates flexible? Find out the best times to travel from Midway to Jackson 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 Chicago Midway Airport to Jackson flights

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Jackson was $184 for a one-way ticket and $309 for a round-trip.

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

    No, a passport isn't needed to fly from Chicago Midway Airport to Jackson. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Chicago Midway Airport to Jackson?

    Chicago Midway Airport airport is called Chicago Midway and the only airport in Jackson is Jackson-Evers Intl.

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

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

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

    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 Chicago Midway Airport to Jackson.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Jackson from Chicago Midway Airport 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 Chicago Midway Airport to Jackson?

    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 Jackson with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and JAN 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 Chicago Midway Airport to Jackson?

    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 Jackson from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Midway to Jackson

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Jackson. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Jackson? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4268 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Jackson (JAN)