MDW - JAN

$179 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 5/23. 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
$333
Southwest
Sat 5/30Tue 6/2
MDW - JAN • 1 stop
Cheapest one-way
$179
Southwest
Sat 5/23
MDW - JAN • 2 stops
Top airlines
Cheapest • from $333 (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 $370 (round-trip)
Shortest trip • 4h 08m (one-way)
Insights
Insights
Insights
Insights
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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, May 30 - Tue, Jun 2
Southwest Logo
5:00 am - 11:45 am
MDW
-
JAN
6h 45m
1 stop
Southwest Logo
1:00 pm - 4:45 pm
JAN
-
MDW
3h 45m
1 stop
$333Southwest
Sat, May 30 - Tue, Jun 2
Southwest Logo
11:00 am - 5:35 pm
MDW
-
JAN
6h 35m
2 stops
Southwest Logo
1:00 pm - 4:45 pm
JAN
-
MDW
3h 45m
1 stop
$338Southwest
Sat, May 30 - Tue, Jun 2
Southwest Logo
7:45 am - 5:35 pm
MDW
-
JAN
9h 50m
2 stops
Southwest Logo
6:30 am - 3:25 pm
JAN
-
MDW
8h 55m
2 stops
$343Southwest
Thu, May 28 - Mon, Jun 1
Delta Logo
6:23 am - 12:12 pm
MDW
-
JAN
5h 49m
1 stop
Delta Logo
5:06 pm - 9:09 pm
JAN
-
MDW
4h 03m
1 stop
$347Delta
Wed, Jun 10 - Mon, Jun 15
Southwest Logo
3:10 pm - 6:45 pm
MDW
-
JAN
3h 35m
1 stop
Southwest Logo
5:10 am - 3:55 pm
JAN
-
MDW
10h 45m
1 stop
$358Southwest
Thu, May 7 - Tue, May 12
Southwest Logo
6:55 am - 11:40 am
MDW
-
JAN
4h 45m
1 stop
Southwest Logo
6:20 pm - 11:05 pm
JAN
-
MDW
4h 45m
1 stop
$363Southwest
Wed, Jun 10 - Mon, Jun 15
Southwest Logo
5:05 am - 11:45 am
MDW
-
JAN
6h 40m
2 stops
Southwest Logo
11:25 am - 9:55 pm
JAN
-
MDW
10h 30m
1 stop
$364Southwest
Thu, May 7 - Sat, May 16
Southwest Logo
6:55 am - 11:40 am
MDW
-
JAN
4h 45m
1 stop
Southwest Logo
6:10 pm - 10:45 pm
JAN
-
MDW
4h 35m
1 stop
$372Southwest
Thu, May 7 - Tue, May 12
Southwest Logo
6:55 am - 11:40 am
MDW
-
JAN
4h 45m
1 stop
Southwest Logo
1:00 pm - 9:50 pm
JAN
-
MDW
8h 50m
2 stops
$377Southwest
Thu, May 14 - Sat, May 16
Delta Logo
6:23 am - 12:43 pm
MDW
-
JAN
6h 20m
1 stop
Delta Logo
5:00 pm - 9:09 pm
JAN
-
MDW
4h 09m
1 stop
$378Delta
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 ($333) and Delta ($347).

Good to know

Cheapest flight$179
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 $179 for a one-way ticket and $333 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 4328 reviews
8.6Crew
7.0Food
8.0Comfort
8.1Boarding
7.5Entertainment
Airline reviews

The new boarding process was easy and straightforward. Very pleasant.

10.0 ExcellentAnonymous, Apr 2026
LAS - OKC
Read more Southwest reviews

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

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.

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

Information on your arrival and departure airports