JAN - MDW

$129 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 6/3. 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

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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Flights Deals

Cheap Flight Deals 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.

Recent round-trip flight deals from Jackson to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from Jackson to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
8:30 pm - 1:05 amJAN-MDW
4h 35m1 stop
Southwest Logo
8:10 am - 1:05 pmMDW-JAN
4h 55m1 stop
$294Southwest
Find Deal
Thu, Jun 26 - Tue, Jul 1
Southwest Logo
8:30 pm - 1:05 amJAN-MDW
4h 35m1 stop
Southwest Logo
6:00 am - 1:05 pmMDW-JAN
7h 05m2 stops
$299Southwest
Find Deal
Thu, Jun 26 - Tue, Jul 1
Southwest Logo
12:25 pm - 9:40 pmJAN-MDW
9h 15m2 stops
Southwest Logo
6:00 am - 1:05 pmMDW-JAN
7h 05m2 stops
$312Southwest
Find Deal
Thu, Jun 26 - Tue, Jul 1
Southwest Logo
12:40 pm - 5:50 pmJAN-MDW
5h 10m1 stop
Southwest Logo
5:45 am - 11:20 amMDW-JAN
5h 35m1 stop
$317Southwest
Find Deal
Sun, Aug 10 - Thu, Aug 14
Southwest Logo
12:40 pm - 9:35 pmJAN-MDW
8h 55m2 stops
Southwest Logo
5:45 am - 11:20 amMDW-JAN
5h 35m1 stop
$322Southwest
Find Deal
Sun, Aug 10 - Thu, Aug 14
Southwest Logo
1:45 pm - 9:05 pmJAN-MDW
7h 20m1 stop
Southwest Logo
10:50 am - 5:45 pmMDW-JAN
6h 55m1 stop
$327Southwest
Find Deal
Wed, Jul 16 - Fri, Jul 18
Southwest Logo
1:45 pm - 9:05 pmJAN-MDW
7h 20m1 stop
Southwest Logo
5:35 am - 11:35 amMDW-JAN
6h 00m2 stops
$333Southwest
Find Deal
Wed, Jul 16 - Fri, Jul 18
Southwest Logo
8:30 pm - 1:05 amJAN-MDW
4h 35m1 stop
Southwest Logo
6:05 am - 11:35 amMDW-JAN
5h 30m1 stop
$339Southwest
Find Deal
Fri, Jun 20 - Mon, Jun 23
Delta Logo
5:55 am - 11:53 amJAN-MDW
5h 58m1 stop
Delta Logo
6:00 am - 12:25 pmMDW-JAN
6h 25m1 stop
$407Delta
Find Deal
Tue, May 13 - Sat, May 17
Delta Logo
10:40 am - 2:54 pmJAN-MDW
4h 14m1 stop
Delta Logo
1:05 pm - 6:04 pmMDW-JAN
4h 59m1 stop
$413Delta
Find Deal
Mon, Sep 8 - Wed, Sep 10
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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.

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 season

August

High season

August

Cheapest flight

$129
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly and prices are also 32% 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 $129 for a one-way ticket and $294 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, Delta or Southwest?

    The two airlines most popular with KAYAK users for flights from Jackson to Chicago are Delta and Southwest. With an average price for the route of $496 and an overall rating of 8.0, Delta is the most popular choice. Southwest is also a great choice for the route, with an average price of $396 and an overall rating of 8.0.

  • 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.

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 4295 reviews
8.2Boarding
8.6Crew
7.6Entertainment
7.1Food
8.0Comfort
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

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

Information on your arrival and departure airports

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