MDW - JAN

$160 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 5/19. 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

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$342
Southwest
Wed 5/6Thu 5/14
MDW - JAN • 1 stop
Cheapest one-way
$160
Southwest
Tue 5/19
MDW - JAN • 1 stop
Top airlines
Cheapest • from $342 (round-trip)
Best reviews • 8.0 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
Cheapest • Avg $369 (round-trip)
Shortest trip • 4h 18m (one-way)
Insights
Insights
Insights
Insights
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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

Wed, May 6 - Thu, May 14
Southwest Logo
7:25 am - 12:20 pm
MDW
-
JAN
4h 55m
1 stop
Southwest Logo
12:15 pm - 5:00 pm
JAN
-
MDW
4h 45m
1 stop
$342Southwest
Wed, May 6 - Thu, May 14
Southwest Logo
11:35 am - 8:20 pm
MDW
-
JAN
8h 45m
2 stops
Southwest Logo
12:15 pm - 5:00 pm
JAN
-
MDW
4h 45m
1 stop
$347Southwest
Thu, Jun 4 - Mon, Jun 8
Southwest Logo
5:00 am - 10:45 am
MDW
-
JAN
5h 45m
1 stop
Southwest Logo
11:25 am - 9:55 pm
JAN
-
MDW
10h 30m
1 stop
$352Southwest
Tue, Apr 28 - Thu, Apr 30
Southwest Logo
7:25 am - 12:20 pm
MDW
-
JAN
4h 55m
1 stop
Southwest Logo
5:45 am - 10:25 am
JAN
-
MDW
4h 40m
1 stop
$353Southwest
Tue, Apr 28 - Thu, Apr 30
Southwest Logo
11:35 am - 8:20 pm
MDW
-
JAN
8h 45m
2 stops
Southwest Logo
5:45 am - 10:25 am
JAN
-
MDW
4h 40m
1 stop
$358Southwest
Tue, Apr 28 - Thu, Apr 30
Southwest Logo
9:10 am - 5:30 pm
MDW
-
JAN
8h 20m
2 stops
Southwest Logo
5:45 am - 2:55 pm
JAN
-
MDW
9h 10m
2 stops
$363Southwest
Wed, Jun 10 - Mon, Jun 15
Southwest Logo
1:10 pm - 8:40 pm
MDW
-
JAN
7h 30m
1 stop
Southwest Logo
5:10 am - 10:40 am
JAN
-
MDW
5h 30m
1 stop
$367Southwest
Wed, May 6 - Thu, May 14
Southwest Logo
11:35 am - 8:20 pm
MDW
-
JAN
8h 45m
2 stops
Southwest Logo
12:15 pm - 6:15 pm
JAN
-
MDW
6h 00m
2 stops
$372Southwest
Wed, Jun 10 - Mon, Jun 15
Southwest Logo
11:25 am - 6:45 pm
MDW
-
JAN
7h 20m
2 stops
Southwest Logo
11:25 am - 8:05 pm
JAN
-
MDW
8h 40m
2 stops
$377Southwest
Sun, May 17 - Wed, May 20
Southwest Logo
5:00 am - 11:55 am
MDW
-
JAN
6h 55m
2 stops
Southwest Logo
6:20 pm - 11:05 pm
JAN
-
MDW
4h 45m
1 stop
$378Southwest
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 72 hours.

In the past 3 days, the cheapest round-trip tickets from Chicago Midway Airport to Jackson were found on Southwest ($342) and Delta ($403).

Good to know

Cheapest flight$160
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 $160 for a one-way ticket and $342 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 4343 reviews
8.6Crew
8.0Comfort
7.0Food
7.5Entertainment
8.1Boarding
Airline reviews

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

4.0 Okaysangeetha, Apr 2026
AUS - SJC
Read more Southwest reviews

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Had a great flight. Delayed takeoff, but comfortable. Snacks were good.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I liked it better when you were truer to your roots Am paying more for less fun

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

Information on your arrival and departure airports