MDW - JAN

$297 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 11/24. 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
Delta
Tue 12/2Sat 12/6
MDW - JAN • 1 stop
Cheapest one-way
$149
Delta
Mon 11/24
MDW - JAN • 1 stop
Top airlines
Delta
Cheapest • from $297 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
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Airline reviews
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We hope you love your trip to Jackson!
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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, Dec 2 - Sat, Dec 6
Delta Logo
5:13 pm - 11:02 pmMDW-JAN
5h 49m1 stop
Delta Logo
5:48 am - 9:54 amJAN-MDW
4h 06m1 stop
$297Delta
Find Deal
Tue, Feb 3 - Tue, Feb 10
Southwest Logo
6:15 am - 12:40 pmMDW-JAN
6h 25m1 stop
Southwest Logo
6:40 am - 1:10 pmJAN-MDW
6h 30m2 stops
$302Southwest
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Tue, Feb 3 - Tue, Feb 10
Southwest Logo
1:20 pm - 8:00 pmMDW-JAN
6h 40m2 stops
Southwest Logo
6:40 am - 1:10 pmJAN-MDW
6h 30m2 stops
$307Southwest
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Tue, Dec 16 - Tue, Dec 23
Southwest Logo
7:00 am - 12:25 pmMDW-JAN
5h 25m1 stop
Southwest Logo
6:05 pm - 11:05 pmJAN-MDW
5h 00m1 stop
$309Southwest
Find Deal
Tue, Dec 16 - Tue, Dec 23
Southwest Logo
6:40 am - 3:05 pmMDW-JAN
8h 25m2 stops
Southwest Logo
6:05 pm - 11:05 pmJAN-MDW
5h 00m1 stop
$314Southwest
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Tue, Jan 6 - Sat, Jan 10
Southwest Logo
9:50 am - 5:35 pmMDW-JAN
7h 45m1 stop
Southwest Logo
6:00 am - 1:50 pmJAN-MDW
7h 50m1 stop
$318Southwest
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Mon, Feb 2 - Tue, Feb 10
Southwest Logo
12:15 pm - 8:00 pmMDW-JAN
7h 45m2 stops
Southwest Logo
6:40 am - 4:30 pmJAN-MDW
9h 50m2 stops
$319Southwest
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Thu, Jan 8 - Thu, Jan 15
Southwest Logo
10:05 am - 2:40 pmMDW-JAN
4h 35m1 stop
Southwest Logo
4:15 pm - 9:25 pmJAN-MDW
5h 10m1 stop
$321Southwest
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Mon, Jan 5 - Thu, Jan 8
Southwest Logo
9:35 am - 7:35 pmMDW-JAN
10h 00m1 stop
Southwest Logo
1:25 pm - 6:05 pmJAN-MDW
4h 40m1 stop
$326Southwest
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Thu, Jan 8 - Thu, Jan 15
Southwest Logo
10:05 am - 8:00 pmMDW-JAN
9h 55m2 stops
Southwest Logo
5:35 am - 2:20 pmJAN-MDW
8h 45m2 stops
$331Southwest
Find Deal
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 seasonMay
Cheapest flight$149
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly with an average 22% 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 $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.

  • 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 $452 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 4248 reviews
8.6Crew
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
Airline reviews

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

10.0 ExcellentIlevba, Nov 2025DCA - DAL
Read more Southwest reviews

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.

Tried watching free movie and it kept freezing so I couldn’t finish.

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

Flight delayed then cancelled. Misplaced luggage. Still do not have. Rented car 1100 mile drive. I had to buy some overnight Hotels clothes toiletries gas food at my expense. Still not home. Not sure where luggage is. Over 4 hours on hold to Felta

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

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

Information on your arrival and departure airports