Cheap flights from Clearwater, FL to Midway (MDW)
MCO — MDW
Dec 3 — Dec 101
Round-trip
1 adult, Economy
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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 Clearwater to Chicago Midway are usually found in December or May, booked 57 days in advance, depart on a Thursday or Friday and return on a Wednesday
Find flight deals from Clearwater to Midway
Keep the following information in mind while searching for Clearwater to Midway flight deals. Data was last updated November 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Popular in | October |
Cheapest in | December |
Average price | $321 |
Cheapflights Insights
Everything you need to know about your flight from Clearwater to Chicago Midway Airport
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 November 3, 2026.
It’s optimal to fly from Clearwater to Chicago Midway Airport in the evening. By choosing this option you can save up to 15% on the cost of your flight, compared to a flight at noon.
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 October 31, 2026.
Travelers seeking maximum savings on their Clearwater to Chicago Midway Airport flight should consider departing on Saturday evenings when fares are most often at their lowest. Sunday afternoons 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 November 3, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andJetBlue from Clearwater to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on November 3, 2026.
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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 7,457,451 searches. Data last updated November 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$79 | Average$230 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$98 | Average$219 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$199 | Average$398 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$244 | Average$360 | FlexibilityNo cancel fee | On-time62% |