HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$67+ 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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
TPA — MDW
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Tampa to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Tampa to Chicago Midway are usually found in January or March, booked 87 days in advance, depart on a Friday or Monday and return on a Friday

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 November 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$127
(Kiwi.com)

One-way from

$67
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$261

Good round-trip deal

$110 or less

Good one-way deal

$163 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. 16% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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

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 November 26, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/26. 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 12/245:45 amTPA - MDW
1 stop17h 27mFrontier
Wed 12/316:12 amMDW - TPA
1 stop17h 14mFrontier
Deal found 11/26$146
This FlightHub deal was found by Cheapflights users on 11/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3012:40 pmTPA - MDW
1 stop8h 15mFrontier
Wed 1/75:10 pmMDW - TPA
1 stop5h 18mFrontier
Deal found 11/25$161
This Frontier deal was found by Cheapflights users on 11/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3012:40 pmTPA - MDW
1 stop8h 15mFrontier
Mon 1/56:12 amMDW - TPA
1 stop11h 38mFrontier
Deal found 11/25$162
This Frontier deal was found by Cheapflights users on 11/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:48 amTPA - MDW
1 stop11h 24mFrontier
Mon 1/56:12 amMDW - TPA
1 stop11h 38mFrontier
Deal found 11/25$163
This CheapOair deal was found by Cheapflights users on 11/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/216:00 amTPA - MDW
1 stop8h 59mFrontier
Sun 1/410:50 pmMDW - TPA
1 stop29h 41mFrontier
Deal found 11/23$164
This Kiwi.com deal was found by Cheapflights users on 11/25. 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 12/309:03 pmTPA - MDW
2 stops26h 09mMultiple Airlines
Wed 1/75:10 pmMDW - TPA
1 stop5h 18mMultiple Airlines
Deal found 11/25$165
This Kiwi.com deal was found by Cheapflights users on 11/26. 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 12/245:45 amTPA - MDW
1 stop17h 27mMultiple Airlines
Wed 12/316:12 amMDW - TPA
2 stops12h 56mMultiple Airlines
Deal found 11/26$169
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:48 amTPA - MDW
1 stop11h 24mFrontier
Sun 1/410:50 pmMDW - TPA
1 stop29h 41mFrontier
Deal found 11/24$174
This CheapOair deal was found by Cheapflights users on 11/25. 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 12/137:00 amTPA - MDW
1 stop29h 08mFrontier
Wed 12/172:49 pmMDW - TPA
1 stop7h 40mFrontier
Deal found 11/25$183
This FlightHub deal was found by Cheapflights users on 11/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/77:00 amTPA - MDW
1 stop29h 08mFrontier
Tue 12/92:49 pmMDW - TPA
1 stop7h 40mFrontier
Deal found 11/25$186
This CheapOair deal was found by Cheapflights users on 11/24. 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 12/137:00 amTPA - MDW
1 stop29h 08mFrontier
Sun 1/410:50 pmMDW - TPA
1 stop29h 41mFrontier
Deal found 11/24$188
This Southwest deal was found by Cheapflights users on 11/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/117:15 pmTPA - MDW
Nonstop2h 45mSouthwest
Mon 1/196:45 amMDW - TPA
Nonstop2h 45mSouthwest
Deal found 11/24$196

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 November 26, 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

Fri 1/9

7:15 am-9:05 am

Nonstop2h 50m

Chicago Midway

Wed 2/18

6:10 am-11:45 am

1 stop4h 35m

$171

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 2/12

6:40 am-8:25 am

Nonstop2h 45m

Chicago Midway

Sun 2/15

9:55 am-3:00 pm

1 stop4h 05m

$191

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 1/8

6:30 pm-10:05 pm

1 stop4h 35m

Chicago Midway

Mon 1/12

1:25 pm-9:05 pm

2 stops6h 40m

$195

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 2/27

6:55 pm-8:40 pm

Nonstop2h 45m

Chicago Midway

Sun 3/1

5:25 am-9:10 am

Nonstop2h 45m

$197

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 1/20

4:25 pm-10:55 pm

2 stops7h 30m

Chicago Midway

Sat 1/24

6:40 am-4:05 pm

1 stop8h 25m

$202

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 12/12

9:30 pm-11:10 pm

Nonstop2h 40m

Chicago Midway

Mon 12/15

9:05 am-12:40 pm

Nonstop2h 35m

$210

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 1/16

3:05 pm-7:35 pm

1 stop5h 30m

Chicago Midway

Sun 1/18

10:15 am-5:45 pm

2 stops6h 30m

$218

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 12/30

3:55 pm-9:10 pm

1 stop6h 15m

Chicago Midway

Wed 1/7

7:50 am-11:30 am

Nonstop2h 40m

$222

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 12/12

7:06 pm-11:47 pm

1 stop5h 41m

Chicago Midway

Mon 12/15

6:00 am-12:47 pm

1 stop5h 47m

$233

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 12/31

2:55 pm-7:05 pm

1 stop5h 10m

Chicago Midway

Mon 1/5

9:00 am-12:35 pm

Nonstop2h 35m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

Showing 1-10 of 20 results
1
2

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
Trip.comPrice Accuracy2 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
JustAirTicketPrice Accuracy-Trust Score*1 star

*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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Tampa-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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?

Use this chart to determine the optimal time to book a round-trip flight from Tampa to Midway. Price data was last updated on November 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, March is the cheapest month in which you can book a flight from Tampa to Chicago Midway Airport (average of $41). Flying from Tampa to Chicago Midway Airport in July is currently the most expensive (average of $126). 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 November 26, 2025.

It’s optimal to fly from Tampa to Chicago Midway Airport in the evening. By choosing this option you can save up to 32% 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 November 2, 2025.

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.

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
Airports
TPA

TPA's Blue Express Curbside lets travelers without checked bags quickly reach their gate, bypassing crowded areas.

Read more about TPAby Ramsey Qubein
MDW

The Orange Line train connects MDW to downtown Chicago in under 30 minutes, offering a convenient and cost-effective option.

Read more about MDWby 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 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 November 26, 2025.
Read through reviews of airlines operating flights from Tampa to Chicago Midway Airport, such as Southwest, Delta, and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

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
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

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
7.9
Good
8,000 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

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
5.8
Fair
3,100 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

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 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 2h 50m. There are 998 mi between Tampa and Chicago Midway Airport. All flights are typically nonstop.

  • 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 Delta and Southwest, starting at $98 and $175 round-trip. Frontier is 80% 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 $202, our data indicates the cheapest price to be $50. The most popular route (Tampa - Chicago Midway), is priced around $157.

  • 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, March is the cheapest month in which you can book a flight from Tampa to Chicago Midway Airport (average of $41). Flying from Tampa to Chicago Midway Airport in July is currently the most expensive (average of $126). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Tampa to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Tampa to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Orlando to O'Hare Intl flights
Miami to O'Hare Intl flights
Orlando to Midway flights
Jacksonville to O'Hare Intl flights
Fort Myers to O'Hare Intl flights
Miami to Midway flights
Fort Lauderdale to Midway flights
West Palm Beach to O'Hare Intl flights
Sarasota to O'Hare Intl flights
Jacksonville to Midway flights
Fort Myers to Midway flights
Pensacola to O'Hare Intl flights
West Palm Beach to Midway flights
Sarasota to Midway flights
Gainesville to O'Hare Intl flights
Orlando Sanford Intl to Rockford flights
Key West to O'Hare Intl flights
Pensacola to Midway flights
Panama City to O'Hare Intl flights
Daytona Beach to O'Hare Intl flights
Valparaiso to O'Hare Intl flights
Tallahassee to O'Hare Intl flights
Key West to Midway flights
Gainesville to Midway flights
Daytona Beach to Midway flights
St Petersburg to Rockford flights
Melbourne to O'Hare Intl flights
Melbourne to Midway flights
Panama City to Midway flights
Tampa to Rockford flights
Valdosta to O'Hare Intl flights
Valparaiso to Midway flights
Tallahassee to Midway flights
Punta Gorda to Rockford flights
Fort Lauderdale to Rockford flights
Orlando to Rockford flights
Fort Myers to Rockford flights
Pensacola to Rockford flights

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 November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$153FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$196FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$173Average$299FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.