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$45+ Cheap flights from Clearwater, FL 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from Clearwater to Chicago Midway are usually found in April or May, booked 87 days in advance, depart on a Friday or Tuesday and return on a Tuesday

Cheap flight deals from Clearwater to Midway

Keep the following information in mind while searching for Clearwater to Midway flight deals. Data was last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$82
(Frontier)

One-way from

$45
(Trip.com)

Popular in

October

Cheapest in

April

Average price

$211
Provider with most accurate pricing for Tampa-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Tampa-Chicago (CHI) flights.
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From Clearwater to Chicago Midway
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One-way flight from Clearwater to Chicago Midway
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Highest demand for flights based on searches. 20% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Find flight deals from Clearwater to Midway

Cheapest flights from Clearwater to Midway
Explore the most affordable flight options available from Clearwater to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/18. 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.
Thu 4/179:51 amTPA - MDW
Nonstop2h 52mFrontier
Sun 4/205:15 amMDW - TPA
Nonstop2h 41mFrontier
Deal found 2/18$81
This Southwest deal was found by Cheapflights users on 2/20. 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 3/267:05 amTPA - MDW
Nonstop2h 50mSouthwest
Tue 4/83:45 pmMDW - TPA
Nonstop2h 35mSouthwest
Deal found 2/20$193
This Delta deal was found by Cheapflights users on 2/20. 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.
Wed 4/306:00 amTPA - MDW
1 stop4h 07mDelta
Wed 4/303:02 pmMDW - TPA
1 stop4h 47mDelta
Deal found 2/20$209

Find flights from Clearwater to Midway within your budget

Customize your flight search to find flights from Clearwater 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 February 20, 2025.

Fly from

Clearwater

Fly to

Midway

Route

Depart

Return

Price

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 4/17

9:51 am-11:43 am

Nonstop2h 52m

Chicago Midway

Sun 4/20

5:15 am-8:56 am

Nonstop2h 41m

$81

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 3/26

7:05 am-8:55 am

Nonstop2h 50m

Chicago Midway

Tue 4/8

3:45 pm-7:20 pm

Nonstop2h 35m

$193

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 4/30

6:00 am-9:07 am

1 stop4h 07m

Chicago Midway

Wed 4/30

3:02 pm-8:49 pm

1 stop4h 47m

$209

TampaChicago

TPA - MDW

TPAMDW

Tampa

Mon 3/17

7:38 pm-9:34 pm

Nonstop2h 56m

$45

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 3/25

7:05 am-8:55 am

Nonstop2h 50m

$95

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 4/30

6:00 am-9:07 am

1 stop4h 07m

$105

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 5/20

11:15 am-3:37 pm

3 stops29h 22m

$165

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Best time to book a flight from Clearwater to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Clearwater 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.

Travel insights for flights from Clearwater to Midway

Get recent, data-driven insights about flights from Clearwater to Midway including ideal travel times, pricing trends, and more.

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

Use this chart to determine the optimal time to book a round-trip flight from Clearwater to Midway. Price data was last updated on February 14, 2025.

To ensure you get the cheapest price possible for a flight from Clearwater to Chicago Midway Airport, you should look to book at least 87 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, April is the cheapest month in which you can book a flight from Clearwater to Chicago Midway Airport (average of $160). Flying from Clearwater 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 CL9 to MDW?

Find hourly flight availability from Clearwater 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 February 20, 2025.

When flying from Clearwater to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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

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

Travelers seeking maximum savings on their Clearwater to Chicago Midway Airport flight should consider departing on Thursday evenings when fares are most often at their lowest. Wednesday 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 February 20, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Frontier from Clearwater to Chicago to help guide your decision. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

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
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

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
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

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
3,355 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

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 Clearwater to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    One-way options have recently been found by users for as low as $45 on Frontier. Other airlines that offer cheap prices include Southwest from $95 and Delta from $105 one-way.

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

    Looking at all options, your cheapest flight can be booked for $44. While the most popular route (Tampa - Chicago Midway) can be booked for $68 on average our data indicates $191 when flying from Clearwater to Chicago Midway Airport.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Clearwater to Chicago Midway Airport (average of $160). Flying from Clearwater 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 Clearwater?

Book flights to Clearwater 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 Clearwater to Midway

Discover the top 4 airlines that operate flights from Clearwater 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$67Average$103FlexibilityNo cancel feeOn-time65%
FrontierCheapest$70Average$150FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$158Average$367FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$386FlexibilityNo cancel feeOn-timeN/A
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