JAN - MDW

$125 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 5/1. 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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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.
Choose your dates
Delta Logo
5:11 pm - 10:22 pmJAN-MDW
5h 11m1 stop
Delta Logo
12:48 pm - 7:20 pmMDW-JAN
6h 32m1 stop
$249Delta
Find Deal
Tue, Apr 22 - Wed, Apr 23
Delta Logo
5:40 pm - 10:22 pmJAN-MDW
4h 42m1 stop
Delta Logo
9:52 am - 2:03 pmMDW-JAN
4h 11m1 stop
$268Delta
Find Deal
Sat, Apr 19 - Wed, Apr 23
Southwest Logo
6:15 am - 11:05 amJAN-MDW
4h 50m1 stop
Southwest Logo
6:05 am - 12:40 pmMDW-JAN
6h 35m1 stop
$317Southwest
Find Deal
Sun, Sep 28 - Tue, Sep 30
Southwest Logo
6:15 am - 3:00 pmJAN-MDW
8h 45m2 stops
Southwest Logo
6:05 am - 12:40 pmMDW-JAN
6h 35m1 stop
$322Southwest
Find Deal
Sun, Sep 28 - Tue, Sep 30
Delta Logo
5:11 pm - 10:22 pmJAN-MDW
5h 11m1 stop
Delta Logo
6:45 pm - 11:02 pmMDW-JAN
4h 17m1 stop
$324Delta
Find Deal
Tue, Apr 22 - Fri, Apr 25
Delta Logo
12:11 pm - 4:12 pmJAN-MDW
4h 01m1 stop
Delta Logo
12:48 pm - 7:20 pmMDW-JAN
6h 32m1 stop
$334Delta
Find Deal
Sun, Apr 20 - Tue, Apr 22
Delta Logo
12:16 pm - 5:59 pmJAN-MDW
5h 43m1 stop
Delta Logo
9:52 am - 2:03 pmMDW-JAN
4h 11m1 stop
$343Delta
Find Deal
Sat, Apr 19 - Thu, Apr 24
Southwest Logo
8:30 pm - 1:05 amJAN-MDW
4h 35m1 stop
Southwest Logo
6:05 am - 11:35 amMDW-JAN
5h 30m1 stop
$347Southwest
Find Deal
Fri, Jun 20 - Mon, Jun 23
Delta Logo
12:16 pm - 9:40 amJAN-MDW
21h 24m2 stops
Delta Logo
9:52 am - 2:03 pmMDW-JAN
4h 11m1 stop
$352Delta
Find Deal
Sat, Apr 19 - Wed, Apr 23
Southwest Logo
6:15 am - 3:00 pmJAN-MDW
8h 45m2 stops
Southwest Logo
8:35 am - 3:15 pmMDW-JAN
6h 40m2 stops
$353Southwest
Find Deal
Sun, Sep 28 - Tue, Sep 30

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.

What is the cheapest month to fly from Jackson to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Jackson to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Jackson to Chicago Midway Airport is August, where tickets cost $325 (return) on average. On the other hand, the most expensive months are March and May, where the average cost of round-trip tickets is $723 and $623 respectively.

Good to know

Low season

March

High season

August

Cheapest flight

$125
Best time to beat the crowds but there is an average 54% increase in price.
Most popular time to fly and prices are also 31% 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 $125 for a one-way ticket and $249 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.

See more FAQs

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 4276 reviews
7.1Food
8.0Comfort
7.6Entertainment
8.6Crew
8.2Boarding
Airline reviews

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.

6.0 GoodCarolynn, Mar 2025KOA - SMF
Read more Southwest reviews

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.

1.5 hour delay, poor service, no compassion from the crew. Terrible experience

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

Short flight with plenty of open seats. Drinks and snacks were still provided even on such a short flight. <1 hr

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

Great experience flying Southwest. The crew was really kind and helpful, and very friendly with our toddler.

Very good. Sad to learn Southwest is going start to charge for bags

Our flight was diverted from being a non-stop to getting within 150 miles and requiring another plane. We heard 4 or 5 different versions from SW as to why we had to stop, then wait for a replacement plane. Five hour delay, weather did not come up as a single excuse.... communication was not clear and well explained. No one really took charge!

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

WiFi on the flight was not working. Thus, entertainment options were limited.

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.

Terrible and im avoiding them in the future. My initial flight was delayed causing me to rebook my flight and when speaking with the representative to rebook I explained this is the second time my flights were delayed and they did nothing to help me. I wasn't booked to comfort plus or given a voucher or anything. I was almost late for my meeting that I needed to attend on Monday because of the games delta played delaying my flights even more and putting me in the very back of the plane next to an extremely intoxicated passenger

Flights on time. .Ride was as comfortable as can be expected in steerage. Luggage arrived at destination. Attendants were fairly friendly.

Great staff. Wifi is terrible. Signing up for skylines is a painstaking process. Had to call customer service just to get my flight itinerary and confirmation sent to me. Consistent delays. A well staffed company that is run so poorly. Upper management needs to be renewed.

The WiFi didn't seem as fast as it normally is

Thank you for not flipping the plane on the run way. You guys get a 5 star rating for the flight!!!

The crew was wonderful and attentive. The seats near exit row were restrictive. Offer healthy snacks please

Delta is a premier airline so my expectations are most always met.

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

Information on your arrival and departure airports

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