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$61+ Cheap flights from Tampa (TPA) to Midway (MDW)

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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
TPA — MDW
Mar 30 — Apr 61
Sun 3/30
Sun 4/6
1 adult, Economy
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Cheapflights Tip: The best prices from Tampa to Chicago Midway are usually found in May or April, booked 87 days in advance, depart on a Friday or Tuesday and return on a Tuesday

Cheap flight deals from Tampa to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Tampa (TPA) to Midway (MDW). 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 March 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$122
(Frontier)

One-way from

$61
(Frontier)

Popular in

February

Cheapest in

May

Average price

$209

Good round-trip deal

$154 or less

Good one-way deal

$101 or less
Provider with most accurate pricing for Tampa-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Tampa-Chicago Midway flights.
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From Tampa to Chicago Midway
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One-way flight from Tampa to Chicago Midway
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2025
Search Deals
Price to beat on a round-trip flight from Tampa to Chicago Midway.
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Price to beat on a one-way flight from Tampa to Chicago Midway.
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Find flight deals from Tampa to Midway

Cheapest flights from Tampa to Midway
Explore the most affordable flight options available from Tampa to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 25, 2025.

This CheapOair deal was found by Cheapflights users on 3/24. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/128:45 pmTPA - MDW
Nonstop2h 51mFrontier
Tue 4/155:03 pmMDW - TPA
Nonstop2h 43mFrontier
Deal found 3/24$138
This Southwest deal was found by Cheapflights users on 3/23. 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.
Tue 4/228:50 amTPA - MDW
1 stop6h 45mSouthwest
Tue 4/299:40 amMDW - TPA
Nonstop2h 35mSouthwest
Deal found 3/23$193
This Delta deal was found by Cheapflights users on 3/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/238:49 amTPA - MDW
1 stop4h 46mDelta
Wed 4/305:59 pmMDW - TPA
1 stop4h 25mDelta
Deal found 3/24$197

Cheapflights Fare Finder

Customize your flight search to find flights from Tampa to Midway 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 March 25, 2025.
Use the filters below to find and compare flights from Tampa to Chicago Midway Airport that are best for you.

Fly from

Tampa

Fly to

Midway

Route

Depart

Return

Price

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 4/12

8:45 pm-10:36 pm

Nonstop2h 51m

Chicago Midway

Tue 4/15

5:03 pm-8:46 pm

Nonstop2h 43m

$138

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 4/22

8:50 am-2:35 pm

1 stop6h 45m

Chicago Midway

Tue 4/29

9:40 am-1:15 pm

Nonstop2h 35m

$193

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 4/23

8:49 am-12:35 pm

1 stop4h 46m

Chicago Midway

Wed 4/30

5:59 pm-11:24 pm

1 stop4h 25m

$197

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 4/12

8:45 pm-10:36 pm

Nonstop2h 51m

$68

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 6/4

7:25 pm-9:10 pm

Nonstop2h 45m

$88

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 6/28

5:20 am-9:54 am

1 stop5h 34m

$109

TampaChicago

TPA - MDW

TPAMDW

Tampa

Mon 6/2

5:20 am-7:14 pm

2 stops14h 54m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

Compare providers for flights from Tampa to Midway

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 Tampa to Midway in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*2 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
Trip.comPrice Accuracy1 starTrust Score*3 stars
CheapOairPrice Accuracy1 starTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust 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 Tampa-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Tampa-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Tampa-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Tampa-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub 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 Tampa-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

The best insider tips for Tampa to Chicago Midway Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Tampa to Chicago Midway Airport trip
Airlines
Frontier

Frontier's UpFront Plus offers a guaranteed empty middle seat for extra comfort.


Bring a power bank as Frontier offers no in-seat power or Wi-Fi.

Read more about Frontierby Marisa Garcia
Southwest

Enjoy free snacks and non-alcoholic drinks, plus a free drink on special occasions.


Two free checked bags included, even oversized like skis or golf clubs.

Read more about Southwestby Marisa Garcia
Airports
TPA

TPA's Blue Express Curbside lanes streamline drop-offs for travelers without checked bags, offering a quick path to security and gates.

Read more about TPAby Ramsey Qubein
MDW

Use the Orange Line train for a quick, affordable ride from MDW to downtown Chicago in under 30 minutes.

Read more about MDWby Ramsey Qubein
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Frontier and Southwest

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
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

Best time to book a flight from Tampa to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Tampa 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 Tampa to Chicago Midway Airport

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

Use this chart to determine the optimal time to book a round-trip flight from Tampa to Midway. Price data was last updated on March 21, 2025.

The best time to book flights from Tampa to Chicago Midway Airport is 87 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 Tampa to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Tampa to Chicago Midway Airport (average of $160). Flying from Tampa to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 TPA to MDW?

Find hourly flight availability from Tampa to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 25, 2025.

It’s optimal to fly from Tampa to Chicago Midway Airport in the evening. By choosing this option you can save up to 43% on the cost of your flight, compared to a flight at noon.

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

Use this chart to determine the cheapest time to fly round-trip from Tampa to Midway. Price data was last updated on March 16, 2025.

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

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated March 25, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Frontier from Tampa to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,272 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Delta
8.0
Very good
7,890 reviews
Southwest
8.0
Very good
4,272 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Frontier
6.0
Okay
3,273 reviews
Southwest
8.0
Very good
4,272 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Tampa to Midway. 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 from for flights from Tampa to Chicago Midway?

    Tampa (TPA) is the airport you will fly out of if you book a flight from Tampa to Chicago Midway. You should not have trouble finding flights to Chicago Midway from Tampa; the airport handles an average of 5 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 4 airlines have flights from the Tampa airport to Chicago Midway. It is only a 4.9 mi journey to Tampa (TPA) from Tampa’s city center.

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

    Our cheapest airline available from Tampa to Chicago Midway Airport is Frontier. Our recent data shows that you can find tickets from as low as $122 on this airline. Additional options worth looking into are Delta and Southwest, starting at $197 and $203 round-trip. Frontier is 38% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Tampa to Chicago Midway Airport one-way?

    $61 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Southwest and Delta, with prices starting from $88 and $129, respectively.

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

    Looking for the cheapest flight from Tampa to Chicago Midway Airport? While on average our users pay $223, our data indicates the cheapest price to be $39. The most popular route (Tampa - Chicago Midway), is priced around $156.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Tampa to Midway 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 Tampa to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Tampa to Chicago Midway Airport (average of $160). Flying from Tampa to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Top 4 airlines flying from Tampa to Midway

Discover the top 4 airlines that operate flights from Tampa to Midway. 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 March 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$67Average$155FlexibilityNo cancel feeOn-time65%
FrontierCheapest$75Average$155FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$159Average$315FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$352FlexibilityNo cancel feeOn-timeN/A
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