JAN - MDW

$163 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 2/12. 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 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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Everything you should know

Cheapest round-trip
$271
Delta
Thu 2/12Mon 2/16
JAN - MDW • 1 stop
Cheapest one-way
$163
Southwest
Thu 2/12
JAN - MDW • 1 stop
Top airlines
Delta
Cheapest • from $271 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
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

Thu, Feb 12 - Mon, Feb 16
Delta Logo
7:47 am - 11:59 am
JAN
-
MDW
4h 12m1 stop
Delta Logo
6:40 pm - 11:07 pm
MDW
-
JAN
4h 27m1 stop
$271Delta
Tue, May 5 - Tue, May 12
Delta Logo
5:11 pm - 10:29 pm
JAN
-
MDW
5h 18m1 stop
Delta Logo
10:35 am - 3:53 pm
MDW
-
JAN
5h 18m1 stop
$295Delta
Fri, Feb 20 - Mon, Feb 23
Southwest Logo
4:50 pm - 10:45 pm
JAN
-
MDW
5h 55m1 stop
Southwest Logo
10:45 am - 6:05 pm
MDW
-
JAN
7h 20m1 stop
$346Southwest
Sun, Mar 22 - Thu, Mar 26
Southwest Logo
5:30 am - 3:10 pm
JAN
-
MDW
9h 40m2 stops
Southwest Logo
5:05 am - 11:45 am
MDW
-
JAN
6h 40m2 stops
$350Southwest
Fri, Feb 20 - Mon, Feb 23
Southwest Logo
5:20 am - 2:30 pm
JAN
-
MDW
9h 10m2 stops
Southwest Logo
4:10 pm - 8:55 pm
MDW
-
JAN
4h 45m1 stop
$351Southwest
Fri, Feb 20 - Mon, Feb 23
Southwest Logo
11:50 am - 7:00 pm
JAN
-
MDW
7h 10m2 stops
Southwest Logo
12:20 pm - 8:55 pm
MDW
-
JAN
8h 35m2 stops
$357Southwest
Sun, Mar 22 - Thu, Mar 26
Southwest Logo
5:30 am - 10:40 am
JAN
-
MDW
5h 10m1 stop
Southwest Logo
5:05 am - 11:45 am
MDW
-
JAN
6h 40m2 stops
$364Southwest
Sat, May 23 - Tue, May 26
Delta Logo
5:35 pm - 9:45 pm
JAN
-
MDW
4h 10m1 stop
Delta Logo
10:35 am - 3:53 pm
MDW
-
JAN
5h 18m1 stop
$367Delta
Fri, Feb 20 - Sun, Feb 22
Southwest Logo
11:50 am - 5:20 pm
JAN
-
MDW
5h 30m2 stops
Southwest Logo
6:15 am - 11:10 am
MDW
-
JAN
4h 55m1 stop
$372Southwest
Fri, Feb 6 - Sun, Feb 8
Delta Logo
5:32 am - 9:53 am
JAN
-
MDW
4h 21m1 stop
Delta Logo
6:00 am - 11:22 am
MDW
-
JAN
5h 22m1 stop
$377Delta
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.

Which airlines provide the cheapest flights from Jackson to Chicago Midway Airport?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Jackson to Chicago Midway Airport were found on Delta ($271) and Southwest ($346).

Which airlines fly non-stop between Jackson and Chicago Midway Airport?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Jackson to Chicago Midway Airport.

There are 2 airlines that fly nonstop from Jackson to Chicago Midway Airport. They are Delta and Southwest. The cheapest airline for this route is Delta, with the best round-trip deal found costing $196. On average, the best prices for this route can be found at Delta.

Good to know

Low seasonAugust
Cheapest flight$163
Best time to beat the crowds with an average 42% drop in price.
Most popular time to fly and prices are also 42% 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 $163 for a one-way ticket and $271 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 $350 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 4249 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
Airline reviews

The flight crew was extremely rude and especially not helpful when our flight was delayed.

2.0 MediocreMatthew, Jan 2026
DAL - SAN
Read more Southwest reviews

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.

Air travel sucks. It continues to be awful for all airlines. No shame on delta alone.

It was Delta, but the flight attendants were stressful and disrespectful. I am a diamond member a travel weekly. I have not had a negative thing to share in quite some time. But this was noticeable.

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

Flight was late from Newark to Atlanta, I asked flight attendant to please let my family of 3 out first when we landed to Atlanta because we were late for our connecting flight to Quito. She didn't and we were late for 5 minutes we couldn't board the plane and spend hours trying to get another flight with customer service for the next day.

I really liked the legroom. I am 6’4”.a at For some reason our seats were not together and using the app to fix it didn’t work. Passengers were nice enough to move for us but you should absolutely ensure a parent sits with their child.

Late delayed flight delays boarding and delays leaving and delays on arrival too. Cramped plane no room no food.

DTW line is too long. The flights from DTW to BWI are always delayed for unknown reasons.

Delta canceled our flight and we had to scramble to find another airline to get home. Phoenix is not a delta hub so they didn’t have another plane. It would have been a red eye though Salt Lake City. Getting in at 5am. No bueno.

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

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

Information on your arrival and departure airports