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 3/4. 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
$303
Delta
Tue 5/5Tue 5/12
JAN - MDW • 1 stop
Cheapest one-way
$149
Delta
Wed 3/4
JAN - MDW • 1 stop
Top airlines
Delta
Cheapest • from $303 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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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
5:11 pm - 10:29 pm
JAN
-
MDW
5h 18m
1 stop
Delta Logo
10:35 am - 3:53 pm
MDW
-
JAN
5h 18m
1 stop
$303Delta
Tue, May 5 - Tue, May 12
Delta Logo
5:11 pm - 10:29 pm
JAN
-
MDW
5h 18m
1 stop
Delta Logo
6:00 am - 10:02 am
MDW
-
JAN
4h 02m
1 stop
$321Delta
Thu, Feb 19 - Thu, Feb 26
Delta Logo
7:47 am - 11:59 am
JAN
-
MDW
4h 12m
1 stop
Delta Logo
6:00 am - 10:10 am
MDW
-
JAN
4h 10m
1 stop
$325Delta
Sat, Feb 14 - Sat, Feb 21
Southwest Logo
12:25 pm - 6:50 pm
JAN
-
MDW
6h 25m
1 stop
Southwest Logo
1:55 pm - 9:10 pm
MDW
-
JAN
7h 15m
2 stops
$326Southwest
Sat, Feb 14 - Sat, Feb 21
Southwest Logo
12:25 pm - 6:50 pm
JAN
-
MDW
6h 25m
1 stop
Southwest Logo
12:30 pm - 9:10 pm
MDW
-
JAN
8h 40m
1 stop
$327Southwest
Thu, Feb 19 - Thu, Feb 26
Southwest Logo
4:15 pm - 9:25 pm
JAN
-
MDW
5h 10m
1 stop
Southwest Logo
9:45 am - 7:20 pm
MDW
-
JAN
9h 35m
2 stops
$336Southwest
Sat, Feb 14 - Sat, Feb 21
Southwest Logo
6:05 am - 5:10 pm
JAN
-
MDW
11h 05m
2 stops
Southwest Logo
1:55 pm - 9:10 pm
MDW
-
JAN
7h 15m
2 stops
$337Southwest
Tue, Mar 10 - Mon, Mar 16
Southwest Logo
7:05 pm - 11:55 pm
JAN
-
MDW
4h 50m
1 stop
Southwest Logo
11:35 am - 7:40 pm
MDW
-
JAN
8h 05m
1 stop
$350Southwest
Tue, Mar 10 - Mon, Mar 16
Southwest Logo
12:05 pm - 8:50 pm
JAN
-
MDW
8h 45m
2 stops
Southwest Logo
11:35 am - 7:40 pm
MDW
-
JAN
8h 05m
1 stop
$355Southwest
Fri, Apr 10 - Sun, Apr 12
Delta Logo
12:55 pm - 4:55 pm
JAN
-
MDW
4h 00m
1 stop
Delta Logo
6:00 am - 10:08 am
MDW
-
JAN
4h 08m
1 stop
$367Delta
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 ($303) and Southwest ($326).

Good to know

Low seasonAugust
Cheapest flight$149
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 $149 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 $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 4269 reviews
7.5Entertainment
8.1Boarding
7.0Food
8.0Comfort
8.6Crew
Airline reviews

Great vacation. Can't wait till next year for another one.

10.0 ExcellentJohn, Jan 2026
SAT - PHX
Read more Southwest reviews

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

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

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

We got exit row seats both flights. Everything was running on time

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

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

There was no wifi available on this flight. And there were no screens, no onboard entertainment, no entertainment options at all. It was like travelling in the 1990s again, except without even a main screen for options. Seats, as usual, were tight and uncomfortable.

Good seat comfort ORF to ATL. Bad seat ATL to SEA (terrible lumbar support, hard, ouch)..

Because I was moved to an exit row, the snacks in economy comfort, the selection of snacks was better.

I upgraded to first. Quick and easy boarding. Comfortable seat with power and a nice IPA.

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

Information on your arrival and departure airports