Find cheap Southwest flights to Chicago Midway Airport
RDU — MDW
Aug 26 — Sep 21
Round-trip
1 adult, Economy
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Cheapest Southwest flights from USA to MidwayExplore the most affordable Southwest flight options available from USA to Midway. Find the lowest fares with prices last updated on July 27, 2026.
Explore the most affordable Southwest flight options available from USA to Midway. Find the lowest fares with prices last updated on July 27, 2026.
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/157:30 pm
BWI
- MDW
Nonstop2h 00m
Southwest
Wed 8/195:15 pm
MDW
- BWI
Nonstop1h 55m
Southwest
Deal found 7/22![Southwest logo]()
$206
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:15 pm
BWI
- MDW
1 stop4h 05m
Southwest
Thu 8/201:00 pm
MDW
- BWI
1 stop3h 10m
Southwest
Deal found 7/22![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/254:10 pm
LGA
- MDW
Nonstop2h 30m
Southwest
Tue 9/17:05 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Deal found 7/27![Southwest logo]()
$207
Best Southwest flights from USA to MidwayDiscover carefully curated Southwest flight deals from USA to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 27, 2026.
Discover carefully curated Southwest flight deals from USA to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 27, 2026.
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/128:30 am
BWI
- MDW
2 stops6h 40m
Southwest
Mon 9/145:30 am
MDW
- BWI
1 stop4h 25m
Southwest
Deal found 7/26![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:25 am
LGA
- MDW
Nonstop2h 20m
Southwest
Sun 9/65:25 am
MDW
- LGA
Nonstop2h 00m
Southwest
Deal found 7/22![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:45 pm
LGA
- MDW
1 stop5h 05m
Southwest
Tue 9/87:15 am
MDW
- LGA
1 stop7h 35m
Southwest
Deal found 7/24![Southwest logo]()
$227
Direct Southwest flights from USA to MidwayExplore non-stop Southwest flight options from USA to Midway based on user searches, and compare prices and availability for your desired travel dates. Data last updated July 27, 2026.
Explore non-stop Southwest flight options from USA to Midway based on user searches, and compare prices and availability for your desired travel dates. Data last updated July 27, 2026.
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:00 pm
BWI
- MDW
Nonstop2h 00m
Southwest
Sat 9/55:55 am
MDW
- BWI
Nonstop1h 45m
Southwest
Deal found 7/22![Southwest logo]()
$206
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/254:10 pm
LGA
- MDW
Nonstop2h 30m
Southwest
Tue 9/17:05 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Deal found 7/27![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:25 am
DCA
- MDW
Nonstop1h 55m
Southwest
Tue 9/88:15 pm
MDW
- DCA
Nonstop1h 50m
Southwest
Deal found 7/24![Southwest logo]()
$216
Last-minute Southwest flights from USA to MidwayDiscover last-minute Southwest flight deals from USA to Midway. Data last updated July 27, 2026 and is based on user searches.
Discover last-minute Southwest flight deals from USA to Midway. Data last updated July 27, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/157:30 pm
BWI
- MDW
Nonstop2h 00m
Southwest
Wed 8/195:15 pm
MDW
- BWI
Nonstop1h 55m
Southwest
Deal found 7/22![Southwest logo]()
$206
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/177:15 pm
BWI
- MDW
1 stop4h 05m
Southwest
Thu 8/201:00 pm
MDW
- BWI
1 stop3h 10m
Southwest
Deal found 7/22![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/254:10 pm
LGA
- MDW
Nonstop2h 30m
Southwest
Tue 9/17:05 pm
MDW
- LGA
Nonstop2h 05m
Southwest
Deal found 7/27![Southwest logo]()
$207
One-way Southwest flights to MidwaySearch for one-way Southwest flight options to Midway. Find affordable one-way fares based on user searches. Data last updated July 27, 2026.
Search for one-way Southwest flight options to Midway. Find affordable one-way fares based on user searches. Data last updated July 27, 2026.
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/76:30 am
BWI
- MDW
Nonstop2h 00m
Southwest
Deal found 7/26![Southwest logo]()
$89
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:30 pm
BWI
- MDW
Nonstop2h 00m
Southwest
Deal found 7/22![Southwest logo]()
$94
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/69:00 pm
DCA
- MDW
Nonstop2h 05m
Southwest
Deal found 7/23![Southwest logo]()
$94
Flights to Chicago Midway Airport with Southwest at a glance
Find detailed information about Southwest flights from USA to Midway. Explore the options provided by Southwest to plan your journey from USA to Midway. Data last updated July 27, 2026.
Cheapflights Insights
Find cheap Southwest flights to Chicago Midway Airport
US0-MDW
BWI-MDW
DCA-MDW
LGA-MDW
How long is the flight to Chicago Midway Airport with Southwest?
On average, Southwest flights from the United States to Chicago Midway Airport take 2 hours 2 minutes. Flights to Chicago Midway Airport from other popular cities in the United States will vary in length. Below are a few examples of popular routes and their flight times.
Southwest weekly flight availability to Chicago Midway Airport
The most flights to Chicago Midway Airport operated by Southwest are scheduled on a Monday (239 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (188 on average).
When is the best time to book a flight to Chicago Midway Airport with Southwest?
The best time to book a flight to Chicago Midway Airport with Southwest is 39 days before departure. On average, fares are higher if you book 2 days before departure.
When is the cheapest time to fly to Chicago Midway Airport with Southwest?
Users looking for the cheapest Southwest fares to Chicago Midway Airport should consider flying on Wednesday at noon, when prices are typically cheapest. Budget-minded travellers will want to avoid Sunday at noon, when prices are usually at their highest.
FAQs about flights to Chicago Midway Airport with Southwest
Reviews of Southwest
See what Cheapflights users have to say about their Southwest experience.
Overview
Reviews
Southwest
4,229 reviews
Overview
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Recent reviews
10.0
|Jul 2026Good
8.0
|Jun 2026One delay in a 2 layover flight=a good trip. The crew was great.
6.0
|Jun 2026The seats were super cramped and couldn’t move without hitting other passengers
8.0
|Jun 2026The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.
10.0
|Jun 2026On time and no problems
1 out of 1410
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