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$68+ Cheap flights from Midway (MDW) to Tampa (TPA)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — TPA
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Chicago Midway to Tampa are usually found in September or October, booked 85 days in advance, depart on a Friday or Thursday and return on a Friday

Cheap flight deals from Midway to Tampa

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Tampa (TPA). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 15, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$116
(Kiwi.com)

One-way from

$68
(Kiwi.com)

Popular in

February

Cheapest in

September

Average price

$231

Good round-trip deal

$277 or less

Good one-way deal

$183 or less
Provider with most accurate pricing for Chicago Midway-Tampa flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Tampa flights.
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From Chicago Midway to Tampa
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One-way flight from Chicago Midway to Tampa
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Highest demand for flights based on searches. 18% potential increase in price ($63 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Price to beat on a round-trip flight from Chicago Midway to Tampa.
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Price to beat on a one-way flight from Chicago Midway to Tampa.
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Find flight deals from Midway to Tampa

Cheapest flights from Midway to Tampa
Explore the most affordable flight options available from Midway to Tampa. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 15, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/187:00 am
MDW
-
TPA
1 stop14h 29m
Frontier
Tue 2/246:15 am
TPA
-
MDW
1 stop13h 52m
Frontier
Deal found 1/15$110
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/176:00 am
MDW
-
TPA
1 stop17h 25m
Frontier
Tue 2/246:15 am
TPA
-
MDW
1 stop13h 52m
Frontier
Deal found 1/14$116
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1912:22 pm
MDW
-
TPA
1 stop11h 03m
Frontier
Wed 2/254:12 pm
TPA
-
MDW
1 stop25h 04m
Frontier
Deal found 1/14$118
This Kiwi.com deal was found by Cheapflights users on 1/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:00 am
MDW
-
TPA
1 stop12h 47m
Frontier
Mon 3/25:25 am
TPA
-
MDW
1 stop15h 22m
Frontier
Deal found 1/15$119
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/219:15 am
MDW
-
TPA
1 stop12h 05m
Frontier
Wed 2/254:12 pm
TPA
-
MDW
1 stop25h 04m
Frontier
Deal found 1/14$121
This Kiwi.com deal was found by Cheapflights users on 1/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/206:48 pm
MDW
-
TPA
1 stop22h 42m
Frontier
Wed 2/256:15 am
TPA
-
MDW
1 stop13h 52m
Frontier
Deal found 1/15$122
This Priceline deal was found by Cheapflights users on 1/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/31:20 pm
MDW
-
TPA
1 stop5h 41m
Frontier
Wed 2/46:30 am
TPA
-
MDW
1 stop6h 35m
Frontier
Deal found 1/13$128
This CheapOair deal was found by Cheapflights users on 1/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/219:15 am
MDW
-
TPA
1 stop12h 05m
Frontier
Sat 2/281:15 pm
TPA
-
MDW
1 stop9h 24m
Frontier
Deal found 1/15$129
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/232:19 pm
MDW
-
TPA
1 stop9h 06m
Frontier
Thu 2/265:55 am
TPA
-
MDW
1 stop11h 21m
Frontier
Deal found 1/14$131
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/116:15 am
MDW
-
TPA
1 stop13h 32m
Frontier
Wed 2/186:15 am
TPA
-
MDW
1 stop13h 52m
Frontier
Deal found 1/14$133
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/41:20 pm
MDW
-
TPA
1 stop5h 41m
Frontier
Wed 2/114:12 pm
TPA
-
MDW
1 stop20h 15m
Frontier
Deal found 1/14$135
This Kiwi.com deal was found by Cheapflights users on 1/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1212:25 pm
MDW
-
TPA
1 stop11h 00m
Frontier
Thu 2/199:53 am
TPA
-
MDW
1 stop12h 19m
Frontier
Deal found 1/13$137

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Tampa that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 15, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Tampa that are best for you.

Fly from

Midway

Fly to

Tampa

Route

Depart

Return

Price

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 2/17

4:55 pm-10:50 pm

1 stop4h 55m

Tampa

Wed 2/18

7:15 am-9:05 am

Nonstop2h 50m

$167

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 2/24

10:15 am-5:45 pm

2 stops6h 30m

Tampa

Wed 4/1

2:45 pm-7:25 pm

1 stop5h 40m

$182

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Tue 5/5

5:55 am-9:25 am

Nonstop2h 30m

Tampa

Sat 5/9

5:55 am-12:10 pm

2 stops7h 15m

$191

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Mon 2/23

1:28 pm-9:46 pm

1 stop7h 18m

Tampa

Thu 2/26

5:40 am-12:46 pm

1 stop8h 06m

$199

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Mon 2/16

6:40 pm-12:01 am

1 stop4h 21m

Tampa

Mon 2/23

1:47 pm-5:45 pm

1 stop4h 58m

$206

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Fri 2/13

7:45 am-4:38 pm

1 stop7h 53m

Tampa

Mon 2/16

7:35 pm-7:07 pm

1 stop24h 32m

$208

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Thu 3/5

7:00 pm-12:10 am

1 stop4h 10m

Tampa

Mon 3/9

5:20 am-9:00 am

1 stop4h 40m

$213

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Fri 2/20

4:35 pm-12:05 am

1 stop6h 30m

Tampa

Wed 2/25

10:00 am-4:40 pm

1 stop7h 40m

$217

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Wed 2/25

10:15 am-5:45 pm

2 stops6h 30m

Tampa

Fri 2/27

7:40 am-1:30 pm

1 stop6h 50m

$222

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 2/28

6:15 pm-9:55 pm

Nonstop2h 40m

Tampa

Mon 3/2

6:50 am-11:00 am

1 stop5h 10m

$224

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/15

Showing 1-10 of 19 results
1
2

Compare providers for flights from Midway to Tampa

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Tampa in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Tampa flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Chicago Midway Airport-Tampa flight deals on Cheapflights vs. CheapOair >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Tampa flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Tampa flights, Cheapflights users trust CheapOair the most. CheapOair has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Tampa flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Tampa

Have a flexible travel schedule? Discover the best time to fly to Tampa from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

How far ahead should I book a flight from Chicago Midway Airport to Tampa?

Use this chart to determine the optimal time to book a round-trip flight from Midway to Tampa. Price data was last updated on January 9, 2026.

The best time to book flights from Chicago Midway Airport to Tampa is 85 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago Midway Airport to Tampa?

Currently, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Tampa (average of $56). Flying from Chicago Midway Airport to Tampa in June is currently the most expensive (average of $166). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to TPA?

Find hourly flight availability from Midway to Tampa. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 15, 2026.

It’s typically best to fly out from Chicago Midway Airport to Tampa in the afternoon. Doing so could potentially save you 35% on the flight price compared to flying in the evening, which is usually more expensive.

What is the cheapest day to fly from Chicago Midway Airport to Tampa?

Use this chart to determine the cheapest time to fly round-trip from Midway to Tampa. Price data was last updated on January 10, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to Tampa flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

The best insider tips for Chicago Midway Airport to Tampa flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Tampa trip
Airports
MDW

Use the 'L' train for a cheap and quick 30-minute ride to MDW from downtown Chicago.

Read more about MDWBy Ramsey Qubein
TPA

TPA's Blue Express Curbside helps travelers without checked bags quickly access transportation or exit the airport.

Read more about TPABy Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW and TPA

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

Reviews of airlines servicing Tampa

Get insights into the airlines that provide service to Tampa. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Tampa. Reviews last updated January 15, 2026.
Get a feel of what it's like to fly with Southwest and Frontier from Chicago Midway Airport to Tampa by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,258 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,258 reviews
Southwest
8.0
Very good
4,258 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Frontier
5.7
Fair
3,057 reviews
Southwest
8.0
Very good
4,258 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from Midway to Tampa. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Tampa from Chicago Midway?

    For a flight from Chicago Midway to Tampa, you will be flying into Tampa. Tampa (TPA) is just 4.9 mi from the center of the city. Tampa is the only Tampa airport and it handles 4 inbound flights from Chicago Midway per day. 2 airlines have flights to Tampa from Chicago Midway on a regular basis.

  • How long is the flight from Chicago Midway Airport to Tampa?

    Departing from Chicago Midway Airport to Tampa will take you 4h 55m. Chicago Midway Airport and Tampa are separated by a distance of 998 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago Midway Airport to Tampa round-trip?

    Currently priced at $74, Frontier will fly you from Chicago Midway Airport to Tampa and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on Southwest for as low as $177. Users have found that Frontier is 73% cheaper than the other options available to this destination.

  • What are the cheapest flights from Chicago Midway Airport to Tampa?

    While on average a flight from Chicago Midway Airport to Tampa is generally $320, our data shows the cheapest flight currently is $118. When looking at the most popular route, (Chicago Midway - Tampa), you can expect to pay $140 for that flight.

  • Can I find deals for flights from Midway to Tampa that include hotel bookings?

    Yes. In addition to deals on Midway to Tampa flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Tampa?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Tampa.

  • Can I find deals for business class flights from Midway to Tampa?

    Yes. Cheapflights offers flight deals from Midway to Tampa by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Tampa?

    Currently, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Tampa (average of $56). Flying from Chicago Midway Airport to Tampa in June is currently the most expensive (average of $166). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Tampa?

Book flights to Tampa if you plan to visit one of these locations
St. Petersburg
Tarpon Springs
Spring Hill
Wesley Chapel
Seminole
Saint Pete Beach
Holmes Beach
Oldsmar
Ruskin
Dunedin
Safety Harbor
Palm Harbor
Treasure Island
Zephyrhills
Largo
New Port Richey
Anna Maria
Port Richey
Pinellas Park
Crystal River

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Alternative routes for Midway to Tampa

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Top 2 airlines flying from Midway to Tampa

Discover the top 2 airlines that operate flights from Midway to Tampa. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$74Average$221FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$177Average$350FlexibilityNo cancel feeOn-time63%

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