JAN - MDW

$149 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 3/25. 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$271
Delta
Tue 5/5Tue 5/12
JAN - MDW • 1 stop
Cheapest one-way
$149
Southwest
Wed 3/25
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
+1
Nonstop flights
Not available
There are currently no direct flights between Jackson and Midway. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Nashville (BNA)
Cheapest • Avg $286 (round-trip)
Atlanta (ATL)
Shortest trip • 4h 25m (one-way)
Insights
Insights
Insights
Insights
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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

Tue, May 5 - Tue, May 12
Delta Logo
5:02 pm - 10:28 pm
JAN
-
MDW
5h 26m
1 stop
Delta Logo
10:55 am - 4:16 pm
MDW
-
JAN
5h 21m
1 stop
$271Delta
Mon, Apr 13 - Wed, Apr 15
Delta Logo
5:02 pm - 10:28 pm
JAN
-
MDW
5h 26m
1 stop
Delta Logo
6:00 am - 12:08 pm
MDW
-
JAN
6h 08m
1 stop
$287Delta
Tue, May 5 - Tue, May 12
Delta Logo
5:02 pm - 10:28 pm
JAN
-
MDW
5h 26m
1 stop
Delta Logo
6:23 am - 12:44 pm
MDW
-
JAN
6h 21m
1 stop
$297Delta
Mon, Apr 13 - Thu, Apr 16
Delta Logo
5:02 pm - 10:28 pm
JAN
-
MDW
5h 26m
1 stop
Delta Logo
6:00 am - 12:08 pm
MDW
-
JAN
6h 08m
1 stop
$303Delta
Mon, Apr 13 - Tue, Apr 14
Southwest Logo
5:45 am - 10:25 am
JAN
-
MDW
4h 40m
1 stop
Southwest Logo
7:25 am - 12:20 pm
MDW
-
JAN
4h 55m
1 stop
$319Southwest
Mon, Apr 13 - Tue, Apr 14
Southwest Logo
12:15 pm - 5:00 pm
JAN
-
MDW
4h 45m
1 stop
Southwest Logo
11:35 am - 8:20 pm
MDW
-
JAN
8h 45m
2 stops
$325Southwest
Mon, Apr 13 - Tue, Apr 14
Southwest Logo
12:15 pm - 8:35 pm
JAN
-
MDW
8h 20m
2 stops
Southwest Logo
8:15 am - 5:30 pm
MDW
-
JAN
9h 15m
2 stops
$330Southwest
Thu, Apr 23 - Sat, Apr 25
Southwest Logo
5:45 am - 2:55 pm
JAN
-
MDW
9h 10m
2 stops
Southwest Logo
5:00 am - 11:45 am
MDW
-
JAN
6h 45m
1 stop
$341Southwest
Sun, Apr 12 - Wed, Apr 15
Delta Logo
5:35 am - 9:56 am
JAN
-
MDW
4h 21m
1 stop
Delta Logo
6:00 am - 12:08 pm
MDW
-
JAN
6h 08m
1 stop
$343Delta
Sun, Apr 12 - Wed, Apr 15
Southwest Logo
5:55 am - 10:35 am
JAN
-
MDW
4h 40m
1 stop
Southwest Logo
11:35 am - 8:20 pm
MDW
-
JAN
8h 45m
2 stops
$345Southwest
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 ($319).

Good to know

Low seasonAugust
Cheapest flight$149
Best time to beat the crowds with an average 46% drop in price.
Most popular time to fly and prices are also 46% 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 $149 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 $406 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 4301 reviews
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
Airline reviews

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

2.0 MediocreAnonymous, Feb 2026
BWI - PBI
Read more Southwest reviews

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

I have not flown Southwest in awhile and had a very pleasant experience. From ticketing to boarding to the flight. The flight left on time and landed ahead of schedule. It won't be so long next time!!

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The charges were ridiculous for an hour flight and the turbulence was very scary.

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

Seat was extremely hard which made even a short 1 hour 20 minute flight fairly uncomfortable.

Everything was good except wifi and a leaking drink chiller. The floor was all wet and my bag was soaked. Did not notice until debarking. Have not heard back from Delta. Even though this was leg one of an international flight in first class, they denied access to their Sky Club - very disappointing!

The staff was fine. The plane was extremely tight, and I paid for the wifi and it did not work at all. I was actually going to ask for a refund.

two hour delay and the Delta representative on the PA system was unable to understand

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

Flight was delayed due to crew being not on time

Flight crew issues delayed my flight by 2 1/2 hours. Causing me to miss my connection.

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

Information on your arrival and departure airports