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Midway

$86+ 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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
TPA — MDW
Jun 24 — Jul 11
Wed 6/24
Wed 7/1
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 Tampa to Chicago Midway are usually found in October or August, booked 71 days in advance, depart on a Friday or Wednesday and return on a Friday

Cheap 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 May 25, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/20. 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 9/247:00 am
TPA
-
MDW
1 stop4h 58m
Frontier
Tue 9/2912:03 pm
MDW
-
TPA
1 stop9h 54m
Frontier
Deal found 5/20$178
This Southwest deal was found by Cheapflights users on 5/22. 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 6/304:40 pm
TPA
-
MDW
1 stop4h 15m
Southwest
Tue 7/78:15 pm
MDW
-
TPA
Nonstop2h 40m
Southwest
Deal found 5/22$181
This Kiwi.com deal was found by Cheapflights users on 5/20. 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 7/41:18 pm
TPA
-
MDW
1 stop9h 53m
Frontier
Tue 7/76:05 am
MDW
-
TPA
1 stop14h 11m
Frontier
Deal found 5/20$183
This Southwest deal was found by Cheapflights users on 5/20. 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.
Wed 7/89:55 pm
TPA
-
MDW
Nonstop2h 40m
Southwest
Tue 7/148:15 pm
MDW
-
TPA
Nonstop2h 35m
Southwest
Deal found 5/20$189
This Delta deal was found by Cheapflights users on 5/22. 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 7/86:20 am
TPA
-
MDW
1 stop4h 45m
Delta
Tue 7/1411:05 am
MDW
-
TPA
1 stop5h 50m
Delta
Deal found 5/22$197
This Kiwi.com deal was found by Cheapflights users on 5/20. 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 9/247:00 am
TPA
-
MDW
1 stop4h 58m
Frontier
Mon 9/2812:03 pm
MDW
-
TPA
1 stop9h 54m
Frontier
Deal found 5/20$203
This Southwest deal was found by Cheapflights users on 5/21. 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 8/135:15 am
TPA
-
MDW
Nonstop2h 40m
Southwest
Tue 8/189:05 am
MDW
-
TPA
1 stop7h 00m
Southwest
Deal found 5/21$205
This Delta deal was found by Cheapflights users on 5/20. 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.
Tue 6/235:15 am
TPA
-
MDW
1 stop5h 54m
Delta
Wed 7/812:41 pm
MDW
-
TPA
1 stop5h 14m
Delta
Deal found 5/20$209

Find 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 May 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$178
(Kiwi.com)

One-way from

$86
(Southwest)

Popular in

March

Cheapest in

October

Average price

$292

Good round-trip deal

$284 or less

Good one-way deal

$165 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.
Search Deals
From Tampa to Chicago Midway
Search Deals
One-way flight from Tampa to Chicago Midway
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Tampa to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Tampa to Chicago Midway.
Search Deals

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 May 25, 2026.
Use the filters below to find and compare flights from Tampa to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 8/4

3:40 pm-8:10 pm

1 stop5h 30m

Chicago Midway

Tue 8/18

6:05 pm-9:40 pm

Nonstop2h 35m

$199

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 7/25

9:20 pm-11:05 pm

Nonstop2h 45m

Chicago Midway

Tue 7/28

5:25 am-8:55 am

Nonstop2h 30m

$225

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 7/4

8:25 am-2:35 pm

2 stops7h 10m

Chicago Midway

Wed 7/8

5:20 pm-10:40 pm

1 stop4h 20m

$250
Quickest round-trip

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 10/9

10:55 pm-12:30 am

Nonstop2h 35m

Chicago Midway

Mon 10/12

5:00 am-8:30 am

Nonstop2h 30m

$265

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 7/7

4:32 pm-10:15 pm

1 stop6h 43m

Chicago Midway

Wed 7/15

11:05 am-4:48 pm

1 stop4h 43m

$271

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 7/1

9:55 pm-11:35 pm

Nonstop2h 40m

Chicago Midway

Tue 7/7

5:25 am-8:55 am

Nonstop2h 30m

$286

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sun 7/12

7:10 am-8:50 am

Nonstop2h 40m

Chicago Midway

Wed 7/15

7:25 am-1:20 pm

1 stop4h 55m

$287

TampaChicago

TPA - MDW

TPAMDW

Tampa

Mon 7/13

8:00 am-9:40 am

Nonstop2h 40m

Chicago Midway

Fri 7/17

5:15 pm-8:50 pm

Nonstop2h 35m

$311

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 7/31

5:20 am-7:00 am

Nonstop2h 40m

Chicago Midway

Sun 8/2

5:30 am-9:00 am

Nonstop2h 30m

$311

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 8/7

2:10 pm-7:45 pm

2 stops6h 35m

Chicago Midway

Sat 8/15

7:45 am-12:55 pm

1 stop4h 10m

$321

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/22

Showing 1-10 of 22 resultsSorted by cheapest first
1
2
3

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
eDreamsPrice Accuracy2 starsTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice 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 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.

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?

The best time to book flights from Tampa to Chicago Midway Airport is 69 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, October is the cheapest month in which you can book a flight from Tampa to Chicago Midway Airport (average of $196). Flying from Tampa to Chicago Midway Airport in March is currently the most expensive (average of $372). 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 May 25, 2026.

It’s optimal to fly from Tampa to Chicago Midway Airport at noon. By choosing this option you can save up to 33% on the cost of your flight, compared to a flight in the morning.

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 May 23, 2026.

Travelers seeking maximum savings on their Tampa to Chicago Midway Airport flight should consider departing on Sunday 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.

How much does it cost to fly round-trip from Tampa to Chicago Midway Airport?

The best insider tips for Tampa to Chicago Midway Airport 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 Tampa to Chicago Midway Airport trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW and TPA

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 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 May 25, 2026.
Read through reviews of airlines operating flights from Tampa to Chicago Midway Airport, such as Southwest,JetBlue, andFrontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,269 reviews

Comfort

8.0

Overall

7.9

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,269 reviews
Southwest
7.9
Good
4,269 reviews

Comfort

8.0

Overall

7.9

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
JetBlue
7.2
Good
2,979 reviews
Southwest
7.9
Good
4,269 reviews

Comfort

8.0

Overall

7.9

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,936 reviews
Southwest
7.9
Good
4,269 reviews

Comfort

8.0

Overall

7.9

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 3 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 3 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.

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

    Departing from Tampa to Chicago Midway Airport will take you 5h 30m. There are 998 mi between Tampa and Chicago Midway Airport.

  • 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 $46 on this airline. Additional options worth looking into are Southwest and JetBlue, starting at $169 and $202 round-trip. Frontier is 84% cheaper than the average price of flights available within the next 90 days to this destination.

  • 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 $280, our data indicates the cheapest price to be $120. The most popular route (Tampa - Chicago Midway), is priced around $189.

  • 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, October is the cheapest month in which you can book a flight from Tampa to Chicago Midway Airport (average of $196). Flying from Tampa to Chicago Midway Airport in March is currently the most expensive (average of $372). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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Top 3 airlines flying from Tampa to Midway

Discover the top 3 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 May 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$169FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$169Average$315FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$202Average$350FlexibilityNo cancel feeOn-time62%

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