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$53+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MDW
Dec 27 — Jan 31
Fri 12/27
Fri 1/3
1 adult, Economy
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The best prices from Clearwater to Chicago Midway are usually found in April or May, booked 89 days in advance, depart on a Tuesday or Thursday and return on a Tuesday

Cheap flight deals from Clearwater to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Clearwater (CL9) 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 December 22, 2024.

Round-trip from

$105
(FlightHub)

One-way from

$54
(Cheapflightsfares)

Popular in

October

Cheapest in

April

Average price

$184
From Clearwater to Chicago Midway
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One-way flight from Clearwater to Chicago Midway
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High demand for flights, 21% potential price rise
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Best time to find cheap flights, 2% potential price drop
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Average for round-trip flights in December 2024
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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 December 22, 2024.

This Kiwi.com deal was found by Cheapflights users on 12/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/318:46 pmTPA - MDW
Nonstop2h 47mFrontier
Mon 1/62:20 pmMDW - TPA
1 stop6h 04mFrontier
Deal found 12/21$152
This Delta deal was found by Cheapflights users on 12/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3111:38 amTPA - MDW
1 stop5h 32mDelta
Mon 1/62:08 pmMDW - TPA
2 stops20h 07mDelta
Deal found 12/21$343
This Southwest deal was found by Cheapflights users on 12/20. 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.
Fri 12/275:55 pmTPA - MDW
Nonstop2h 40mSouthwest
Thu 1/306:10 pmMDW - TPA
Nonstop2h 35mSouthwest
Deal found 12/20$508

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 December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 2/6

10:44 am-6:26 pm

1 stop8h 42m

Chicago Midway

Sun 2/9

8:45 am-12:31 pm

Nonstop2h 46m

$105

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 2/5

2:30 pm-4:15 pm

Nonstop2h 45m

Chicago Midway

Mon 2/10

5:25 am-9:05 am

Nonstop2h 40m

$163

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 2/5

8:40 am-1:05 pm

1 stop5h 25m

Chicago Midway

Tue 2/11

6:00 am-11:20 am

1 stop4h 20m

$196

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sun 1/5

9:01 pm-11:14 pm

1 stop27h 13m

Chicago Midway

Tue 1/7

5:24 pm-10:00 am

2 stops15h 36m

$289

TampaChicago

TPA - MDW

TPAMDW

Tampa

Mon 3/3

7:09 pm-11:58 pm

1 stop5h 49m

$53

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 1/22

5:55 pm-7:45 pm

Nonstop2h 50m

$79

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 2/19

8:00 am-11:59 am

1 stop4h 59m

$98

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 1/25

6:23 am-8:31 am

3 stops27h 08m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

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 December 20, 2024.

To ensure you get the cheapest price possible for a flight from Clearwater to Chicago Midway Airport, you should look to book at least 89 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 December 22, 2024.

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 December 16, 2024.

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. Monday afternoons 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 December 22, 2024.
Peruse reviews from past customers who have flown with Southwest, Frontier and Delta 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
4,804 reviews

Boarding

8.2

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.1
Very good
4,804 reviews
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Delta
8.0
Very good
8,597 reviews
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Frontier
6.1
Okay
3,472 reviews
Southwest
8.1
Very good
4,804 reviews

Boarding

8.2

Crew

8.7

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

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 $54 on Frontier. Other airlines that offer cheap prices include Southwest from $79 and Delta from $98 one-way.

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

    Looking at all options, your cheapest flight can be booked for $57. While the most popular route (Tampa - Chicago Midway) can be booked for $88 on average our data indicates $196 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.

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Alternative routes for Clearwater to Midway

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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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$67Average$155FlexibilityNo cancel feeOn-time65%
FrontierCheapest$70Average$148FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$158Average$355FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$372FlexibilityNo cancel feeOn-timeN/A
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