MDW - JAN

$149 Find Cheap Flights from Chicago Midway Airport to Jackson - 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 Midway to Jackson departing on 8/19. 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
$303
Delta
Sat 8/15Sat 8/22
MDW - JAN • 1 stop
Cheapest one-way
$149
Delta
Wed 8/19
MDW - JAN • 1 stop
Top airlines
Delta
Cheapest • from $303 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Midway and Jackson. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Houston (HOU)
Cheapest • Avg $377 (round-trip)
Nashville (BNA)
Shortest trip • 3h 35m (one-way)
Insights
Insights
Insights
Insights
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 Jackson!
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, Aug 15 - Sat, Aug 22
Delta Logo
10:56 am - 4:16 pm
MDW
-
JAN
5h 20m
1 stop
Delta Logo
5:01 pm - 10:36 pm
JAN
-
MDW
5h 35m
1 stop
$303Delta
Sat, Aug 15 - Sat, Aug 22
Southwest Logo
1:45 pm - 7:05 pm
MDW
-
JAN
5h 20m
1 stop
Southwest Logo
6:00 am - 2:15 pm
JAN
-
MDW
8h 15m
2 stops
$308Southwest
Sat, Aug 15 - Sat, Aug 22
Southwest Logo
7:40 am - 1:55 pm
MDW
-
JAN
6h 15m
2 stops
Southwest Logo
6:00 am - 2:15 pm
JAN
-
MDW
8h 15m
2 stops
$313Southwest
Thu, Aug 6 - Mon, Aug 10
Delta Logo
6:05 am - 12:12 pm
MDW
-
JAN
6h 07m
1 stop
Delta Logo
7:49 am - 11:51 am
JAN
-
MDW
4h 02m
1 stop
$325Delta
Thu, Aug 6 - Mon, Aug 10
Southwest Logo
5:25 am - 12:00 pm
MDW
-
JAN
6h 35m
1 stop
Southwest Logo
12:40 pm - 7:30 pm
JAN
-
MDW
6h 50m
2 stops
$330Southwest
Thu, Aug 6 - Mon, Aug 10
Southwest Logo
9:00 am - 6:00 pm
MDW
-
JAN
9h 00m
2 stops
Southwest Logo
12:40 pm - 7:30 pm
JAN
-
MDW
6h 50m
2 stops
$335Southwest
Thu, Jul 30 - Wed, Aug 5
Delta Logo
6:00 am - 10:00 am
MDW
-
JAN
4h 00m
1 stop
Delta Logo
5:32 am - 9:59 am
JAN
-
MDW
4h 27m
1 stop
$345Delta
Thu, Jul 30 - Wed, Aug 5
Southwest Logo
1:00 pm - 10:00 pm
MDW
-
JAN
9h 00m
2 stops
Southwest Logo
1:30 pm - 8:10 pm
JAN
-
MDW
6h 40m
1 stop
$350Southwest
Thu, Jul 30 - Wed, Aug 5
Southwest Logo
2:45 pm - 10:00 pm
MDW
-
JAN
7h 15m
2 stops
Southwest Logo
7:05 am - 3:20 pm
JAN
-
MDW
8h 15m
2 stops
$355Southwest
Fri, Aug 7 - Mon, Aug 10
Delta Logo
6:05 am - 10:37 am
MDW
-
JAN
4h 32m
1 stop
Delta Logo
5:01 pm - 10:36 pm
JAN
-
MDW
5h 35m
1 stop
$356Delta
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.

Which airlines provide the cheapest flights from Chicago Midway Airport to Jackson?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 5 days.

In the past 5 days, the cheapest round-trip tickets from Chicago Midway Airport to Jackson were found on Delta ($303) and Southwest ($308).

Find deals

Good to know

Cheapest flight$149
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 5 days, the lowest price for a flight from Chicago Midway Airport to Jackson was $149 for a one-way ticket and $303 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.
7.9
SouthwestOverall score based on 4250 reviews
8.0Comfort
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

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

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Excellent experience. WiFi worked on this leg of My trip

wifi wasn't working correctly so couldn't watch live tv

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)