MDW - JAN

$154 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 4/1. 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
$297
Southwest
Tue 3/17Wed 4/8
MDW - JAN • 1 stop
Cheapest one-way
$149
Southwest
Wed 4/1
MDW - JAN • 1 stop
Top airlines
Southwest
Cheapest • from $297 (round-trip)
Southwest
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
Houston (HOU)
Cheapest • Avg $367 (round-trip)
Nashville (BNA)
Shortest trip • 4h 18m (one-way)
Insights
Insights
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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

Tue, Mar 17 - Wed, Apr 8
Southwest Logo
6:25 am - 11:30 am
MDW
-
JAN
5h 05m
1 stop
Southwest Logo
6:30 am - 11:40 am
JAN
-
MDW
5h 10m
1 stop
$297Southwest
Tue, Mar 17 - Tue, Mar 24
Southwest Logo
6:25 am - 11:30 am
MDW
-
JAN
5h 05m
1 stop
Southwest Logo
5:50 am - 2:35 pm
JAN
-
MDW
8h 45m
2 stops
$302Southwest
Tue, Mar 17 - Tue, Mar 24
Southwest Logo
10:30 am - 6:35 pm
MDW
-
JAN
8h 05m
2 stops
Southwest Logo
12:05 pm - 7:55 pm
JAN
-
MDW
7h 50m
2 stops
$307Southwest
Mon, Mar 23 - Tue, Mar 31
Delta Logo
6:07 pm - 11:24 pm
MDW
-
JAN
5h 17m
1 stop
Delta Logo
5:35 am - 9:56 am
JAN
-
MDW
4h 21m
1 stop
$309Delta
Tue, Mar 10 - Tue, Mar 31
Southwest Logo
6:25 am - 11:30 am
MDW
-
JAN
5h 05m
1 stop
Southwest Logo
12:05 pm - 7:55 pm
JAN
-
MDW
7h 50m
2 stops
$314Southwest
Sat, Apr 4 - Sat, Apr 11
Delta Logo
10:45 am - 4:20 pm
MDW
-
JAN
5h 35m
1 stop
Delta Logo
5:35 am - 9:56 am
JAN
-
MDW
4h 21m
1 stop
$321Delta
Thu, Apr 16 - Sat, Apr 18
Southwest Logo
6:55 am - 11:40 am
MDW
-
JAN
4h 45m
1 stop
Southwest Logo
6:00 am - 5:25 pm
JAN
-
MDW
11h 25m
2 stops
$326Southwest
Wed, Mar 18 - Thu, Mar 19
Southwest Logo
10:30 am - 6:35 pm
MDW
-
JAN
8h 05m
2 stops
Southwest Logo
12:20 pm - 5:40 pm
JAN
-
MDW
5h 20m
1 stop
$331Southwest
Wed, Mar 18 - Thu, Mar 19
Southwest Logo
7:45 am - 6:35 pm
MDW
-
JAN
10h 50m
1 stop
Southwest Logo
12:20 pm - 5:40 pm
JAN
-
MDW
5h 20m
1 stop
$332Southwest
Tue, Mar 10 - Tue, Mar 31
Southwest Logo
11:00 am - 8:35 pm
MDW
-
JAN
9h 35m
2 stops
Southwest Logo
12:05 pm - 7:55 pm
JAN
-
MDW
7h 50m
2 stops
$337Southwest
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 ($297) and Delta ($309).

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 3 days, the lowest price for a flight from Chicago Midway Airport to Jackson was $149 for a one-way ticket and $297 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 4295 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
7.0Food
8.6Crew
Airline reviews

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

4.0 OkayAnonymous, Feb 2026
BOI - LAS
Read more Southwest reviews

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The charges were ridiculous for an hour flight and the turbulence was very scary.

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

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

Information on your arrival and departure airports