Is Southwest the cheapest airline to fly with from Denver to Chicago Midway Airport?

With an average price of $256 return, Southwest is not the cheapest airline to fly from Denver to Chicago Midway Airport with. Instead, for the lowest price, our data suggests flying with Frontier, where a return flight costs $170 on average.

Does Southwest fly direct to Chicago Midway Airport from Denver?

Yes, Southwest does offer direct flights for the route, with around 35 flights per week.

What’s the cheapest day of the week to fly from Denver to Chicago Midway Airport with Southwest?

On average, the cheapest day of the week to fly from Denver to Chicago Midway Airport with Southwest is Tuesday, when prices are around $70. The most expensive day is generally Saturday, where the average price is around $125.

What’s the cheapest month to fly from Denver to Chicago Midway Airport with Southwest?

The cheapest month for Southwest flights to Chicago Midway Airport from Denver is generally January, where plane tickets cost $94 on average. If possible, try to avoid the most expensive months of September and December, where tickets cost $247 and $264 respectively.

$71 Cheap Southwest Flights from Denver to Chicago Midway Airport

DEN - MDW

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Flight Deals

Cheap Southwest Flight Deals from Denver to Chicago Midway Airport

Here are some of the best deals found on KAYAK recently from Southwest for round-trip flights from Denver to Chicago Midway Airport 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.

Round-trip

One-way

Last minute

Direct

Recent round-trip Southwest flight deals from Denver to Chicago Midway Airport

Fri, Jan 23 - Mon, Jan 26

4:35 pm - 7:55 pmDEN-MDW

2h 20mnonstop

6:00 am - 7:50 amMDW-DEN

2h 50mnonstop

$143Southwest

Find Deal

Wed, Jan 7 - Sat, Jan 10

12:05 pm - 3:25 pmDEN-MDW

2h 20mnonstop

5:10 am - 7:00 amMDW-DEN

2h 50mnonstop

$145Southwest

Find Deal

Wed, Jan 7 - Sat, Jan 10

12:05 pm - 3:25 pmDEN-MDW

2h 20mnonstop

9:45 am - 1:15 pmMDW-DEN

4h 30m1 stop

$153Southwest

Find Deal

Tue, Feb 24 - Sat, Feb 28

7:00 am - 2:20 pmDEN-MDW

6h 20m1 stop

8:45 pm - 10:30 pmMDW-DEN

2h 45mnonstop

$155Southwest

Find Deal

Fri, Jan 23 - Mon, Jan 26

7:00 am - 10:35 amDEN-MDW

2h 35mnonstop

10:00 am - 2:35 pmMDW-DEN

5h 35m1 stop

$160Southwest

Find Deal

Wed, Jan 7 - Sat, Jan 10

7:00 am - 2:20 pmDEN-MDW

6h 20m1 stop

9:45 am - 1:15 pmMDW-DEN

4h 30m1 stop

$163Southwest

Find Deal

Thu, Dec 11 - Sat, Dec 13

10:15 am - 5:15 pmDEN-MDW

6h 00m1 stop

5:15 pm - 6:55 pmMDW-DEN

2h 40mnonstop

$167Southwest

Find Deal

Thu, Dec 18 - Mon, Dec 22

1:00 pm - 6:30 pmDEN-MDW

4h 30m1 stop

10:30 pm - 12:10 amMDW-DEN

2h 40mnonstop

$172Southwest

Find Deal

Wed, Dec 3 - Sat, Dec 6

4:45 pm - 8:05 pmDEN-MDW

2h 20mnonstop

5:15 pm - 6:55 pmMDW-DEN

2h 40mnonstop

$173Southwest

Find Deal

Thu, Dec 11 - Sat, Dec 13

10:15 am - 5:15 pmDEN-MDW

6h 00m1 stop

12:45 pm - 5:55 pmMDW-DEN

6h 10m1 stop

$177Southwest

Find Deal

Useful Info

Low season	February
High season	November
Cheapest flight	$71
Average price round-trip	$255

Best time to beat the crowds with an average 38% drop in price.

Most popular time to fly and prices are also 7% lower on average.

Flight from Denver to Chicago Midway Airport

(price for this month)

When to Book Flights with Southwest from Denver to Chicago Midway Airport

Average price per month

Flight prices as travel date approaches

Is Southwest the cheapest airline to fly with from Denver to Chicago Midway Airport?
With an average price of $256 return, Southwest is not the cheapest airline to fly from Denver to Chicago Midway Airport with. Instead, for the lowest price, our data suggests flying with Frontier, where a return flight costs $170 on average.
What is the cheapest Southwest flight from Denver to Chicago Midway Airport?
In the last 3 days, the lowest price for a flight with Southwest from Denver to Chicago Midway Airport was $105 for a return flight and $78 for a one-way flight.
Does Southwest fly direct to Chicago Midway Airport from Denver?
Yes, Southwest does offer direct flights for the route, with around 35 flights per week.
What’s the cheapest day of the week to fly from Denver to Chicago Midway Airport with Southwest?
On average, the cheapest day of the week to fly from Denver to Chicago Midway Airport with Southwest is Tuesday, when prices are around $70. The most expensive day is generally Saturday, where the average price is around $125.
What’s the cheapest month to fly from Denver to Chicago Midway Airport with Southwest?
The cheapest month for Southwest flights to Chicago Midway Airport from Denver is generally January, where plane tickets cost $94 on average. If possible, try to avoid the most expensive months of September and December, where tickets cost $247 and $264 respectively.

8.0

Very good4,236 verified ratings

7.5Entertainment

8.1Boarding

8.6Crew

7.0Food

8.0Comfort

Pros +

Cons -

Show reviews that mention

10.0 Wonderful

Stacy, Oct 2025

SMF-DEN

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

2.0 Poor

Verified traveler, Oct 2025

DAL-LIT

Delayed 5.5 hours

10.0 Wonderful

Verified traveler, Oct 2025

BOS-BWI

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

8.0 Very good

Verified traveler, Oct 2025

MHT-MDW

Getting worse with new changes.

4.0 Mediocre

Jeff, Oct 2025

MCI-SAN

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

4.0 Mediocre

Thomas, Oct 2025

STL-CMH

Internet was not functioning.

2.0 Poor

Thomas, Oct 2025

SAT-STL

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

10.0 Wonderful

Lynda, Oct 2025

VPS-BNA

On time. Communication good. Smooth flight

2.0 Poor

Princess, Oct 2025

MSY-DAL

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

6.0 Okay

Thomas, Oct 2025

DAL-SAT

Late again.

Everything you need to know for your flight from Denver to Chicago Midway Airport

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Cabin class types available on flights to Chicago Midway Airport

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DEN - MDW

$71 Find Cheap Southwest Flights from Denver to Chicago Midway Airport

Search hundreds of travel sites at once for deals on Southwest flights from Denver to Chicago Midway Airport

Cheap Southwest Flight Deals from Denver to Chicago Midway Airport

Recent round-trip Southwest flight deals from Denver to Chicago Midway Airport

Recent one-way Southwest flight deals from Denver to Chicago Midway Airport

Recent last minute Southwest flight deals from Denver to Chicago Midway Airport

Recent direct Southwest flight deals from Denver to Chicago Midway Airport

Good to know

When to Book Flights with Southwest from Denver to Chicago Midway Airport

FAQs for flying to Chicago Midway Airport with Southwest

Is Southwest the cheapest airline to fly with from Denver to Chicago Midway Airport?

What is the cheapest Southwest flight from Denver to Chicago Midway Airport?

Does Southwest fly direct to Chicago Midway Airport from Denver?

What’s the cheapest day of the week to fly from Denver to Chicago Midway Airport with Southwest?

What’s the cheapest month to fly from Denver to Chicago Midway Airport with Southwest?

Southwest Customer Reviews

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Everything you need to know for your flight from Denver to Chicago Midway Airport

Cabin class types available on flights to Chicago Midway Airport

Cabin classes available on flights to Denver. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

Complete your trip to Chicago Midway Airport with a hotel stay or car rental

Flights to other popular destinations

The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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Top Southwest flights

The most popular destinations for flights with Southwest according to clicks from KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.