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Midway

$55+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
TPA — MDW
Oct 19 — Oct 261
Sun 10/19
Sun 10/26
1 adult, Economy
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Cheapflights Tip: The best prices from Tampa to Chicago Midway are usually found in January or December, booked 87 days in advance, depart on a Friday or Thursday 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 September 19, 2025.

Round-trip from

$100
(Priceline)

One-way from

$55
(Priceline)

Popular in

June

Cheapest in

January

Average price

$248

Good round-trip deal

$95 or less

Good one-way deal

$78 or less
From Tampa to Chicago Midway
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One-way flight from Tampa to Chicago Midway
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Highest demand for flights based on searches. 15% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 19, 2025.

This Priceline deal was found by Cheapflights users on 9/17. 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.
Fri 10/172:22 pmTPA - MDW
Nonstop2h 47mFrontier
Mon 10/209:45 amMDW - TPA
Nonstop2h 37mFrontier
Deal found 9/17$100
This Priceline deal was found by Cheapflights users on 9/17. 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.
Sun 10/199:57 amTPA - MDW
Nonstop2h 47mFrontier
Sun 10/265:20 amMDW - TPA
Nonstop2h 35mFrontier
Deal found 9/17$101
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/143:11 pmTPA - MDW
Nonstop2h 46mFrontier
Sun 11/166:06 pmMDW - TPA
Nonstop2h 35mFrontier
Deal found 9/17$103
This Frontier deal was found by Cheapflights users on 9/16. 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.
Fri 11/143:11 pmTPA - MDW
Nonstop2h 46mFrontier
Mon 11/176:06 pmMDW - TPA
Nonstop2h 35mFrontier
Deal found 9/16$104
This CheapOair deal was found by Cheapflights users on 9/17. 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 10/129:57 amTPA - MDW
Nonstop2h 47mFrontier
Sun 10/195:20 amMDW - TPA
Nonstop2h 35mFrontier
Deal found 9/17$107
This Frontier deal was found by Cheapflights users on 9/17. 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.
Sat 10/118:15 amTPA - MDW
1 stop9h 58mFrontier
Sun 10/125:20 amMDW - TPA
Nonstop2h 35mFrontier
Deal found 9/17$112
This Frontier deal was found by Cheapflights users on 9/17. 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.
Sat 10/188:15 amTPA - MDW
1 stop9h 58mFrontier
Sun 10/195:20 amMDW - TPA
Nonstop2h 35mFrontier
Deal found 9/17$115
This Priceline deal was found by Cheapflights users on 9/17. 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.
Thu 10/29:31 amTPA - MDW
1 stop7h 27mFrontier
Sun 10/56:21 amMDW - TPA
Nonstop2h 36mFrontier
Deal found 9/17$121
This Priceline deal was found by Cheapflights users on 9/17. 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.
Fri 10/32:10 pmTPA - MDW
1 stop7h 36mFrontier
Sun 10/56:21 amMDW - TPA
Nonstop2h 36mFrontier
Deal found 9/17$122
This CheapOair deal was found by Cheapflights users on 9/17. 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.
Fri 10/318:43 amTPA - MDW
1 stop10h 56mFrontier
Sun 11/26:06 pmMDW - TPA
Nonstop2h 35mFrontier
Deal found 9/17$123

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 September 19, 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

Tue 11/11

7:15 pm-9:00 pm

Nonstop2h 45m

Chicago Midway

Wed 11/12

6:00 pm-9:35 pm

Nonstop2h 35m

$137

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 9/25

6:00 am-3:58 pm

1 stop10h 58m

Chicago Midway

Tue 9/30

2:32 pm-8:06 pm

1 stop4h 34m

$144

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 10/22

7:30 am-1:38 pm

1 stop7h 08m

Chicago Midway

Sat 10/25

6:15 am-6:19 pm

1 stop11h 04m

$144

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 10/22

7:05 pm-8:45 pm

Nonstop2h 40m

Chicago Midway

Sat 10/25

5:45 pm-9:15 pm

Nonstop2h 30m

$147

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 11/7

9:30 pm-11:10 pm

Nonstop2h 40m

Chicago Midway

Tue 11/11

9:05 am-12:40 pm

Nonstop2h 35m

$148

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 11/4

7:15 pm-9:00 pm

Nonstop2h 45m

Chicago Midway

Tue 11/11

10:15 am-6:10 pm

2 stops6h 55m

$152

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 10/3

10:55 am-12:44 pm

Nonstop2h 49m

Chicago Midway

Sun 10/5

6:21 am-9:57 am

Nonstop2h 36m

$153

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 10/14

6:35 pm-10:05 pm

1 stop4h 30m

Chicago Midway

Tue 10/21

10:10 am-3:50 pm

1 stop4h 40m

$157

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 11/27

9:25 am-3:10 pm

1 stop6h 45m

Chicago Midway

Tue 12/2

7:10 am-10:45 am

Nonstop2h 35m

$157

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 11/4

4:30 pm-6:15 pm

Nonstop2h 45m

$69

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/18

Showing 1-10 of 17 results
1
2

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

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 September 12, 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 September 19, 2025.

It’s optimal to fly from Tampa to Chicago Midway Airport in the evening. By choosing this option you can save up to 25% 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 September 14, 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.

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 September 19, 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
4,242 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

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
7,964 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

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
5.8
Fair
3,171 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

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 2 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 45m. There are 998 mi between Tampa and Chicago Midway Airport. This flight may include one or multiple stops.

  • 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 $53 on this airline. Additional options worth looking into are Delta and Southwest, starting at $138 and $159 round-trip. Frontier is 77% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the most reliable airlines from Tampa to Chicago Midway Airport?

    The top 3 most reliable airlines when flying from Tampa to Chicago Midway Airport are Southwest (74%), Frontier (73%) and United Airlines (0%).

  • 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 $173, our data indicates the cheapest price to be $44. The most popular route (Tampa - Chicago Midway), is priced around $100.

  • 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 Chicago Midway Airport?

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

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Alternative routes for Tampa to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$53Average$165FlexibilityNo cancel feeOn-time62%
DeltaCheapest$138Average$212FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$159Average$294FlexibilityNo cancel feeOn-time63%

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