JAN - MDW

$152 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 7/25. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$303
Typical prices: $234-$297
Southwest
Mon 8/17Wed 8/19
JAN - MDW • 2 stops
Cheapest one-way
$152
Delta
Sat 7/25
JAN - MDW • 1 stop
Top airlines
Southwest
Cheapest • from $303 (round-trip)
Southwest
Best reviews • 7.9 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 37m (one-way)
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 100% price drop
August
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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

Mon, Aug 17 - Wed, Aug 19
Southwest Logo
5:55 am - 12:50 pm
JAN
-
MDW
6h 55m
2 stops
Southwest Logo
2:05 pm - 7:45 pm
MDW
-
JAN
5h 40m
1 stop
$303Southwest
Sat, Jul 25 - Sat, Aug 8
Southwest Logo
12:20 pm - 10:00 pm
JAN
-
MDW
9h 40m
2 stops
Southwest Logo
8:05 am - 1:55 pm
MDW
-
JAN
5h 50m
1 stop
$305Southwest
Wed, Jul 22 - Wed, Jul 29
Southwest Logo
12:20 pm - 5:05 pm
JAN
-
MDW
4h 45m
1 stop
Southwest Logo
5:05 am - 11:45 am
MDW
-
JAN
6h 40m
2 stops
$308Southwest
Sat, Jul 25 - Sat, Aug 8
Southwest Logo
12:20 pm - 10:00 pm
JAN
-
MDW
9h 40m
2 stops
Southwest Logo
7:40 am - 1:55 pm
MDW
-
JAN
6h 15m
2 stops
$310Southwest
Sat, Aug 22 - Tue, Aug 25
Southwest Logo
6:00 am - 2:15 pm
JAN
-
MDW
8h 15m
2 stops
Southwest Logo
10:10 am - 6:05 pm
MDW
-
JAN
7h 55m
2 stops
$313Southwest
Mon, Aug 17 - Wed, Aug 19
Delta Logo
3:30 pm - 10:36 pm
JAN
-
MDW
7h 06m
1 stop
Delta Logo
6:05 am - 10:37 am
MDW
-
JAN
4h 32m
1 stop
$314Delta
Thu, Sep 10 - Tue, Sep 15
Southwest Logo
5:55 am - 2:10 pm
JAN
-
MDW
8h 15m
2 stops
Southwest Logo
7:50 am - 12:50 pm
MDW
-
JAN
5h 00m
1 stop
$316Southwest
Mon, Aug 17 - Wed, Aug 19
Southwest Logo
5:55 am - 12:50 pm
JAN
-
MDW
6h 55m
2 stops
Southwest Logo
2:05 pm - 7:45 pm
MDW
-
JAN
5h 40m
1 stop
$319Southwest
Mon, Aug 17 - Wed, Aug 19
Southwest Logo
5:55 am - 2:10 pm
JAN
-
MDW
8h 15m
2 stops
Southwest Logo
11:10 am - 7:45 pm
MDW
-
JAN
8h 35m
2 stops
$321Southwest
Mon, Aug 17 - Wed, Aug 19
Southwest Logo
5:55 am - 12:50 pm
JAN
-
MDW
6h 55m
2 stops
Southwest Logo
11:10 am - 7:45 pm
MDW
-
JAN
8h 35m
2 stops
$324Southwest
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.

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 January, where tickets cost $0 (return) on average. On the other hand, the most expensive months are May and December, where the average cost of round-trip tickets is $1,458 and $587 respectively.

Find deals

Good to know

Low seasonAugust
Cheapest flight$152
Best time to beat the crowds with an average 55% drop in price.
Most popular time to fly and prices are also 55% 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 5 days, the lowest price for a flight from Jackson to Chicago Midway Airport was $152 for a one-way ticket and $303 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 $419 and an overall rating of 7.9, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $286 and an overall rating of 7.8.

  • 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.
7.9
SouthwestOverall score based on 4246 reviews
8.6Crew
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

WiFi was not working and didn’t have a beverage service

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

The seats were comfortable, and the boarding process was pretty smooth.

It was as good as it could be. Flying is not a pleasant experience these days.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

Got on the plane and sat there for an hour before departure.

Cramped seating for me. Luckily it wasn’t a long flight

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

long flights are never truly comfortable but the airline did their best. crew was great and the flight was safe.

The captain was amazing and kept us informed throughout that there would be some rough air. The flight also got delayed but we were able to actually leave on time, which was great.

The staff did not do a good job of getting everyone boarded quickly, so we missed our take off window and had to sit on the tarmac for 20+ min waiting for our turn. The plan was old. Pockets on the back of seats were torn and tearing off. One of the attendants was rude-she would ask a question but he walking away before you finished answering so she kept getting our drink orders wrong.

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

Information on your arrival and departure airports

Jackson (JAN)
Midway (MDW)