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

With an average price of $365 return, Southwest is not the cheapest airline to fly from Chicago Midway Airport to Tampa with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $167 on average.

Does Southwest fly direct to Tampa from Chicago Midway Airport?

Yes, Southwest does offer direct flights for the route, with around 21 flights per week.

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

On average, the cheapest day of the week to fly from Chicago Midway Airport to Tampa with Southwest is Friday, when prices are around $88. The most expensive day is generally Wednesday, where the average price is around $146.

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

The cheapest month for Southwest flights to Tampa from Chicago Midway Airport is generally May, where plane tickets cost $128 on average. If possible, try to avoid the most expensive months of December and June, where tickets cost $279 and $418 respectively.

$69 Cheap Southwest Flights from Chicago Midway Airport to Tampa

Flight Deals

Cheap Southwest Flight Deals from Chicago Midway Airport to Tampa

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

Tue, Jan 13 - Tue, Jan 20

5:40 pm - 9:15 pmMDW-TPA

2h 35mnonstop

7:15 am - 9:05 amTPA-MDW

2h 50mnonstop

$158Southwest

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Tue, Jan 13 - Tue, Jan 20

10:10 am - 1:50 pmMDW-TPA

2h 40mnonstop

6:30 pm - 10:05 pmTPA-MDW

4h 35m1 stop

$168Southwest

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Tue, Jan 13 - Tue, Jan 20

1:25 pm - 5:00 pmMDW-TPA

2h 35mnonstop

4:25 pm - 10:55 pmTPA-MDW

7h 30m2 stops

$173Southwest

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Wed, Oct 29 - Mon, Nov 10

2:15 pm - 5:45 pmMDW-TPA

2h 30mnonstop

9:30 pm - 11:10 pmTPA-MDW

2h 40mnonstop

$177Southwest

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Thu, Oct 30 - Thu, Nov 6

5:35 am - 9:05 amMDW-TPA

2h 30mnonstop

9:30 pm - 11:10 pmTPA-MDW

2h 40mnonstop

$178Southwest

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Mon, Jan 12 - Thu, Jan 15

7:50 am - 11:30 amMDW-TPA

2h 40mnonstop

11:05 am - 12:55 pmTPA-MDW

2h 50mnonstop

$179Southwest

Find Deal

Tue, Jan 13 - Tue, Jan 20

1:25 pm - 8:15 pmMDW-TPA

5h 50m1 stop

4:25 pm - 10:55 pmTPA-MDW

7h 30m2 stops

$189Southwest

Find Deal

Mon, Jan 12 - Thu, Jan 15

7:50 am - 11:30 amMDW-TPA

2h 40mnonstop

6:50 am - 11:00 amTPA-MDW

5h 10m1 stop

$195Southwest

Find Deal

Thu, Oct 30 - Sun, Nov 2

5:35 am - 9:05 amMDW-TPA

2h 30mnonstop

5:50 am - 7:30 amTPA-MDW

2h 40mnonstop

$197Southwest

Find Deal

Sat, Oct 25 - Wed, Oct 29

12:50 pm - 7:30 pmMDW-TPA

5h 40m1 stop

11:35 am - 1:10 pmTPA-MDW

2h 35mnonstop

$198Southwest

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Useful Info

Low season	July
High season	February
Cheapest flight	$69
Average price round-trip	$208

Best time to beat the crowds with an average 15% drop in price.

Most popular time to fly with an average 51% increase in price.

Flight from Chicago Midway Airport to Tampa

(price for this month)

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

Average price per month

Flight prices as travel date approaches

Is Southwest the cheapest airline to fly with from Chicago Midway Airport to Tampa?
With an average price of $365 return, Southwest is not the cheapest airline to fly from Chicago Midway Airport to Tampa with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $167 on average.
What is the cheapest Southwest flight from Chicago Midway Airport to Tampa?
In the last 3 days, the lowest price for a flight with Southwest from Chicago Midway Airport to Tampa was $75 for a return flight and $55 for a one-way flight.
Does Southwest fly direct to Tampa from Chicago Midway Airport?
Yes, Southwest does offer direct flights for the route, with around 21 flights per week.
What’s the cheapest day of the week to fly from Chicago Midway Airport to Tampa with Southwest?
On average, the cheapest day of the week to fly from Chicago Midway Airport to Tampa with Southwest is Friday, when prices are around $88. The most expensive day is generally Wednesday, where the average price is around $146.
What’s the cheapest month to fly from Chicago Midway Airport to Tampa with Southwest?
The cheapest month for Southwest flights to Tampa from Chicago Midway Airport is generally May, where plane tickets cost $128 on average. If possible, try to avoid the most expensive months of December and June, where tickets cost $279 and $418 respectively.

8.0

Very good4,248 verified ratings

8.6Crew

8.1Boarding

8.0Comfort

7.5Entertainment

7.0Food

Pros +

Cons -

Show reviews that mention

10.0 Wonderful

Gabriel, Sep 2025

DEN-SMF

Connecting flight is on time and boarding was a breeze!

10.0 Wonderful

Gabriel, Sep 2025

LGA-DEN

Easy boarding process. No delays!

10.0 Wonderful

Melissa, Sep 2025

MDW-DTW

Excellent

10.0 Wonderful

Melissa, Sep 2025

MSY-MDW

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

10.0 Wonderful

Robert, Sep 2025

RNO-LAS

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

4.0 Mediocre

Ashish, Sep 2025

PHX-OGG

Southwest airlines boarding process is the worst. Period.

8.0 Very good

Verified traveler, Sep 2025

LAS-DTW

Good

10.0 Wonderful

Verified traveler, Sep 2025

CLT-BWI

Always liked SW

10.0 Wonderful

Lynda, Sep 2025

MDW-OKC

Clear communication

10.0 Wonderful

Lynda, Sep 2025

BNA-MDW

On time-smooth flights-clear communication

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

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Return flight deals

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Cabin class types available on flights to Tampa

First Class flights from Chicago Midway Airport to Tampa

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MDW - TPA

$69 Find Cheap Southwest Flights from Chicago Midway Airport to Tampa

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

Cheap Southwest Flight Deals from Chicago Midway Airport to Tampa

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

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

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

Recent direct Southwest flight deals from Chicago Midway Airport to Tampa

Good to know

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

FAQs for flying to Tampa with Southwest

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

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

Does Southwest fly direct to Tampa from Chicago Midway Airport?

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

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

Southwest Customer Reviews

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

Cabin class types available on flights to Tampa

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

Complete your trip to Tampa 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.

Find deals for your return flight

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.