Find cheap Southwest flights to Chicago Midway Airport
CHI — MDW
Nov 6 — Nov 131
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 October 7, 2026.
Explore the most affordable Southwest flight options available from USA to Midway. Find the lowest fares with prices last updated on October 7, 2026.
This Southwest deal was found by Cheapflights users on 10/6. 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 11/55:25 pm -
Nonstop1h 55m
Mon 11/95:30 am -
Nonstop1h 55m
Deal found 10/6![Southwest logo]()
$163
This Southwest deal was found by Cheapflights users on 10/4. 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 11/31:35 pm -
Nonstop1h 55m
Wed 11/188:10 am -
Nonstop1h 55m
Deal found 10/4![Southwest logo]()
$164
This Southwest deal was found by Cheapflights users on 10/7. 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 11/2110:15 am -
Nonstop1h 40m
Sun 11/228:05 am -
Nonstop1h 35m
Deal found 10/7![Southwest logo]()
$171
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 October 7, 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 October 7, 2026.
This Southwest deal was found by Cheapflights users on 10/7. 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.
Fri 11/67:30 pm -
Nonstop1h 55m
Tue 11/101:15 pm -
2 stops6h 15m
Deal found 10/7![Southwest logo]()
$178
This Southwest deal was found by Cheapflights users on 10/7. 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 12/35:30 pm -
Nonstop1h 55m
Mon 12/71:15 pm -
2 stops6h 10m
Deal found 10/7![Southwest logo]()
$178
This Southwest deal was found by Cheapflights users on 10/7. 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 11/911:40 am -
Nonstop2h 10m
Thu 11/123:50 pm -
Nonstop1h 55m
Deal found 10/7![Southwest logo]()
$185
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 October 7, 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 October 7, 2026.
This Southwest deal was found by Cheapflights users on 10/6. 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 11/55:25 pm -
Nonstop1h 55m
Mon 11/95:30 am -
Nonstop1h 55m
Deal found 10/6![Southwest logo]()
$163
This Southwest deal was found by Cheapflights users on 10/4. 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 11/31:35 pm -
Nonstop1h 55m
Wed 11/188:10 am -
Nonstop1h 55m
Deal found 10/4![Southwest logo]()
$164
This Southwest deal was found by Cheapflights users on 10/7. 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 11/2110:15 am -
Nonstop1h 40m
Sun 11/228:05 am -
Nonstop1h 35m
Deal found 10/7![Southwest logo]()
$171
Last-minute Southwest flights from USA to MidwayDiscover last-minute Southwest flight deals from USA to Midway. Data last updated October 7, 2026 and is based on user searches.
Discover last-minute Southwest flight deals from USA to Midway. Data last updated October 7, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/6. 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 11/55:25 pm -
Nonstop1h 55m
Mon 11/95:30 am -
Nonstop1h 55m
Deal found 10/6![Southwest logo]()
$163
This Southwest deal was found by Cheapflights users on 10/4. 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 11/31:35 pm -
Nonstop1h 55m
Wed 11/188:10 am -
Nonstop1h 55m
Deal found 10/4![Southwest logo]()
$164
This Southwest deal was found by Cheapflights users on 10/7. 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 11/2110:15 am -
Nonstop1h 40m
Sun 11/228:05 am -
Nonstop1h 35m
Deal found 10/7![Southwest logo]()
$171
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 October 7, 2026.
Search for one-way Southwest flight options to Midway. Find affordable one-way fares based on user searches. Data last updated October 7, 2026.
This Southwest deal was found by Cheapflights users on 10/6. 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 11/2110:15 am -
Nonstop1h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Southwest logo]()
$86
This Southwest deal was found by Cheapflights users on 10/7. 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.
Fri 10/308:15 pm -
1 stop3h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Southwest logo]()
$92
This Southwest deal was found by Cheapflights users on 10/6. 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 10/311:55 pm -
Nonstop2h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Southwest logo]()
$93
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 October 7, 2026.
Cheapflights Insights
Find cheap Southwest flights to Chicago Midway Airport
US0-MDW
ATL-MDW
MSP-MDW
PHL-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 16 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 Friday (223 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (165 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 68 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
4,214 reviews
Overview
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Recent reviews
10.0
|Sep 2026Changed flight which was easy. Gate Agent booked me from extra leg room seat on original flight to row 15 on new flight that did not have extra leg room - even though it was an exit row. The row in front of me with extra leg room had an empty seat.
4.0
|Sep 2026It was a red eye overnight which I prefer. But this time the seat was SOOOO uncomfortable that sleeping was difficult and painful
10.0
|Sep 2026I still think the aircraft should load from the back and window seats first for all passengers. It's so much easier and efficient to board when you do not have to worry about hitting Anyone already seated.
10.0
|Aug 2026great
10.0
|Jul 2026Good
1 out of 1405
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