JAN - MDW

$122 Find Cheap Flights from Jackson to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Jackson to Midway departing on 12/2. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Jackson to Chicago, 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 Jackson to Chicago, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Jackson to Midway (JAN-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Jackson to Midway 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 Jackson to Midway

Sat, Oct 4 - Tue, Oct 7
Delta Logo
3:10 pm - 9:10 pmJAN-MDW
6h 00m1 stop
Delta Logo
6:00 am - 10:01 amMDW-JAN
4h 01m1 stop
$250Delta
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Sat, Oct 4 - Tue, Oct 7
Southwest Logo
3:20 pm - 8:20 pmJAN-MDW
5h 00m1 stop
Southwest Logo
5:30 am - 12:30 pmMDW-JAN
7h 00m2 stops
$255Southwest
Find Deal
Tue, Oct 21 - Sat, Oct 25
Southwest Logo
6:30 am - 2:05 pmJAN-MDW
7h 35m2 stops
Southwest Logo
6:30 am - 2:45 pmMDW-JAN
8h 15m2 stops
$260Southwest
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Thu, Sep 25 - Mon, Sep 29
Southwest Logo
2:10 pm - 7:50 pmJAN-MDW
5h 40m1 stop
Southwest Logo
5:40 am - 1:30 pmMDW-JAN
7h 50m1 stop
$262Southwest
Find Deal
Tue, Oct 21 - Sat, Oct 25
Southwest Logo
6:30 am - 1:35 pmJAN-MDW
7h 05m1 stop
Southwest Logo
7:00 am - 12:10 pmMDW-JAN
5h 10m1 stop
$275Southwest
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Thu, Oct 16 - Mon, Oct 20
Southwest Logo
8:05 pm - 12:45 amJAN-MDW
4h 40m1 stop
Southwest Logo
5:30 am - 11:20 amMDW-JAN
5h 50m1 stop
$312Southwest
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Fri, Oct 24 - Tue, Oct 28
Delta Logo
5:58 pm - 10:14 pmJAN-MDW
4h 16m1 stop
Delta Logo
5:04 pm - 10:50 pmMDW-JAN
5h 46m1 stop
$317Delta
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Sat, Oct 4 - Tue, Oct 7
Southwest Logo
10:30 am - 7:05 pmJAN-MDW
8h 35m2 stops
Southwest Logo
5:30 am - 12:30 pmMDW-JAN
7h 00m2 stops
$325Southwest
Find Deal
Thu, Sep 25 - Mon, Sep 29
Southwest Logo
5:40 am - 1:45 pmJAN-MDW
8h 05m2 stops
Southwest Logo
6:30 am - 1:30 pmMDW-JAN
7h 00m2 stops
$332Southwest
Find Deal
Sat, Oct 4 - Tue, Oct 7
Southwest Logo
10:30 am - 7:05 pmJAN-MDW
8h 35m2 stops
Southwest Logo
5:30 am - 12:30 pmMDW-JAN
7h 00m2 stops
$345Southwest
Find Deal
Booking Insights

KAYAK's insights & trends for Jackson to Midway flights

Get data-powered insights and trends into flights from Jackson to Midway to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Jackson, Mississippi to Chicago Midway Airport?

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

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

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

Good to know

Low seasonAugust
Cheapest flight$122
Best time to beat the crowds with an average 38% drop in price.
Most popular time to fly and prices are also 38% lower on average.
Flight from Jackson to Chicago Midway Airport

When to book flights from Jackson to Midway

Are your dates flexible? Find out the best times to travel from Jackson to Midway 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 Jackson to Chicago Midway Airport flights

  • What is the cheapest flight from Jackson to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Jackson to Chicago Midway Airport was $122 for a one-way ticket and $250 for a round-trip.

  • Do I need a passport to fly between Jackson and Chicago Midway Airport?

    No

  • Which aircraft models fly most regularly from Jackson to Chicago Midway Airport?

    We unfortunately don’t have that data for this specific route.

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

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

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

    The two airlines most popular with KAYAK users for flights from Jackson to Chicago are Southwest and Delta. With an average price for the route of $392 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 $356 and an overall rating of 7.9.

  • How does KAYAK find such low prices on flights from Jackson to Chicago Midway Airport?

    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 Jackson to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Jackson to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Jackson 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 Jackson to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to Jackson with another airline. Booking your flights between Jackson and MDW 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 Jackson to Chicago Midway Airport?

    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 Chicago Midway Airport from Jackson 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 Jackson to Midway

 
See real verified KAYAK customer reviews for airlines flying from Jackson to Chicago. 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 Jackson to Midway? 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 4244 reviews
7.0Food
8.6Crew
8.1Boarding
8.0Comfort
7.5Entertainment
Airline reviews

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

6.0 GoodCarl, Aug 2025MSY - BWI
Read more Southwest reviews

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

I was uncomfortably cold on the plane. Other than that it was uneventful and therefore as enjoyable as a plane ride can be.

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

Information on your arrival and departure airports

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