MDW - JAN

$174 Find Cheap Flights from Chicago Midway Airport to Jackson

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Jackson departing on 1/14. 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
$174
Southwest
Wed 1/14Wed 1/21
MDW - JAN • 1 stop
Cheapest one-way
$184
Delta
Fri 1/2
MDW - JAN • 1 stop
Top airlines
Southwest
Cheapest • from $174 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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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, Jan 14 - Wed, Jan 21
Southwest Logo
10:05 am - 2:40 pm
MDW
-
JAN
4h 35m1 stop
Southwest Logo
1:25 pm - 6:05 pm
JAN
-
MDW
4h 40m1 stop
$174Southwest
Wed, Jan 14 - Wed, Jan 21
Southwest Logo
1:20 pm - 8:00 pm
MDW
-
JAN
6h 40m2 stops
Southwest Logo
6:40 am - 1:30 pm
JAN
-
MDW
6h 50m1 stop
$179Southwest
Wed, Jan 14 - Wed, Jan 21
Southwest Logo
6:50 am - 2:40 pm
MDW
-
JAN
7h 50m2 stops
Southwest Logo
6:40 am - 4:30 pm
JAN
-
MDW
9h 50m2 stops
$184Southwest
Mon, Jan 12 - Wed, Jan 14
Southwest Logo
6:15 am - 12:40 pm
MDW
-
JAN
6h 25m1 stop
Southwest Logo
6:10 pm - 10:55 pm
JAN
-
MDW
4h 45m1 stop
$220Southwest
Mon, Jan 12 - Wed, Jan 14
Southwest Logo
6:50 am - 2:40 pm
MDW
-
JAN
7h 50m2 stops
Southwest Logo
6:10 pm - 10:55 pm
JAN
-
MDW
4h 45m1 stop
$225Southwest
Mon, Jan 12 - Wed, Jan 14
Southwest Logo
12:15 pm - 8:00 pm
MDW
-
JAN
7h 45m2 stops
Southwest Logo
6:40 am - 4:30 pm
JAN
-
MDW
9h 50m2 stops
$230Southwest
Thu, Jan 15 - Sun, Jan 18
Delta Logo
6:45 am - 11:17 am
MDW
-
JAN
4h 32m1 stop
Delta Logo
5:32 am - 10:27 am
JAN
-
MDW
4h 55m1 stop
$260Delta
Thu, Jan 15 - Sun, Jan 18
Southwest Logo
8:15 am - 3:40 pm
MDW
-
JAN
7h 25m2 stops
Southwest Logo
1:25 pm - 6:05 pm
JAN
-
MDW
4h 40m1 stop
$345Southwest
Thu, Jan 15 - Sun, Jan 18
Southwest Logo
7:45 am - 3:40 pm
MDW
-
JAN
7h 55m2 stops
Southwest Logo
6:40 am - 1:10 pm
JAN
-
MDW
6h 30m2 stops
$350Southwest
Fri, May 8 - Sun, May 10
Southwest Logo
6:55 am - 11:40 am
MDW
-
JAN
4h 45m1 stop
Southwest Logo
5:55 am - 10:35 am
JAN
-
MDW
4h 40m1 stop
$367Southwest
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.

What’s the cheapest day of the week to fly from Chicago Midway Airport to Jackson?

The average price of all round-trip flights from Chicago Midway Airport to Jackson clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago Midway Airport to Jackson, look for departures on Wednesdays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Jackson, Wednesday is the cheapest day to fly and Sunday is the most expensive.

Good to know

Low seasonApril
Cheapest flight$174
Best time to beat the crowds with an average 43% drop in price.
Most popular time to fly with an average 24% 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 $174 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.

  • Which airline alliances offer flights from Chicago Midway Airport to Jackson?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Jackson.

  • Which is the best airline for flights from Chicago to Jackson, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Jackson are Southwest and Delta. With an average price for the route of $476 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $456 and an overall rating of 7.9.

  • 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 airlines 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 4251 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

10.0 ExcellentDavid, Nov 2025
BUF - PHX
Read more Southwest reviews

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

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

Information on your arrival and departure airports