HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kissimmee

$39+ Cheap flights from Connecticut to Kissimmee, FL

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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — MCO
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Connecticut to Kissimmee 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.

Cheap flight deals from Connecticut to Kissimmee

Keep the following information in mind while searching for Connecticut to Kissimmee flight deals. Data was last updated August 14, 2025.

Round-trip from

$78
(Cheapflightsfares)

One-way from

$39
(Breeze Airways)

Popular in

April

Cheapest in

March

Average price

$196
From Connecticut to Kissimmee
Search Deals
One-way flight from Connecticut to Kissimmee
Search Deals
High demand for flights, 0% potential price rise
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 August 2025
Search Deals

Find flight deals from Connecticut to Kissimmee

Cheapest flights from Connecticut to Kissimmee
Explore the most affordable flight options available from Connecticut to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 8/14. 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.
Mon 8/257:30 amHVN - MCO
Nonstop2h 44mAvelo Airlines
Sat 8/304:59 pmMCO - HVN
Nonstop2h 45mAvelo Airlines
Deal found 8/14$78
This CheapOair deal was found by Cheapflights users on 8/14. 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.
Mon 9/223:40 pmHVN - MCO
Nonstop2h 45mAvelo Airlines
Fri 9/267:10 pmMCO - HVN
Nonstop2h 40mAvelo Airlines
Deal found 8/14$81
This CheapOair deal was found by Cheapflights users on 8/14. 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 9/74:57 pmHVN - MCO
Nonstop3h 04mBreeze Airways
Thu 9/114:23 pmMCO - HVN
Nonstop2h 45mBreeze Airways
Deal found 8/14$82
This CheapOair deal was found by Cheapflights users on 8/14. 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 9/263:40 pmHVN - MCO
Nonstop2h 45mAvelo Airlines
Fri 10/35:15 pmMCO - HVN
Nonstop2h 40mAvelo Airlines
Deal found 8/14$83
This FlightHub deal was found by Cheapflights users on 8/14. 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.
Mon 9/158:52 pmBDL - MCO
Nonstop3h 05mFrontier
Sun 9/215:00 pmMCO - BDL
Nonstop2h 52mFrontier
Deal found 8/14$85
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
Sat 8/302:45 pmBDL - MCO
Nonstop3h 00mMultiple Airlines
Thu 9/47:04 pmMCO - BDL
1 stop4h 00mMultiple Airlines
Deal found 8/11$86
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
Sun 8/316:15 pmBDL - MCO
Nonstop2h 58mMultiple Airlines
Thu 9/47:04 pmMCO - BDL
1 stop4h 00mMultiple Airlines
Deal found 8/11$87
This FlightHub deal was found by Cheapflights users on 8/12. 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.
Sat 8/232:45 pmBDL - MCO
Nonstop3h 00mSpirit Airlines
Thu 8/288:39 amMCO - BDL
Nonstop2h 42mSpirit Airlines
Deal found 8/12$88
This CheapOair deal was found by Cheapflights users on 8/14. 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 8/234:00 pmHVN - MCO
Nonstop3h 00mBreeze Airways
Thu 8/286:00 amMCO - HVN
Nonstop2h 45mBreeze Airways
Deal found 8/14$88
This Cheapflightsfares deal was found by Cheapflights users on 8/12. 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 8/286:15 pmBDL - MCO
Nonstop2h 58mSpirit Airlines
Sun 8/318:39 amMCO - BDL
Nonstop2h 42mSpirit Airlines
Deal found 8/12$89
This Expedia deal was found by Cheapflights users on 8/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/246:15 pmBDL - MCO
Nonstop2h 58mSpirit Airlines
Thu 8/288:39 amMCO - BDL
Nonstop2h 42mSpirit Airlines
Deal found 8/12$90
This Cheapflightsfares deal was found by Cheapflights users on 8/12. 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 8/2111:05 amBDL - MCO
Nonstop3h 01mFrontier
Thu 8/287:25 amMCO - BDL
Nonstop2h 55mFrontier
Deal found 8/12$91

Cheapflights Fare Finder

 
Customize your flight search to find flights from Connecticut to Kissimmee 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 August 14, 2025.
Use the filters below to find and compare flights from Connecticut to Kissimmee that are best for you.

Fly from

Connecticut

Fly to

Kissimmee

Route

Depart

Return

Price

New HavenOrlando

HVN - MCO

HVNMCO

Tweed-New Haven

Wed 8/27

1:05 pm-3:49 pm

Nonstop2h 44m

Orlando

Sat 8/30

12:15 pm-3:00 pm

Nonstop2h 45m

$78

New HavenOrlando

HVN - MCO

HVNMCO

Tweed-New Haven

Fri 9/12

3:40 pm-6:25 pm

Nonstop2h 45m

Orlando

Mon 9/15

7:10 pm-9:50 pm

Nonstop2h 40m

$78

New HavenOrlando

HVN - MCO

HVNMCO

Tweed-New Haven

Mon 9/15

3:40 pm-6:25 pm

Nonstop2h 45m

Orlando

Thu 9/18

7:55 pm-10:35 pm

Nonstop2h 40m

$78

New HavenOrlando

HVN - MCO

HVNMCO

Tweed-New Haven

Mon 8/25

4:20 pm-7:04 pm

Nonstop2h 44m

Orlando

Sat 8/30

12:15 pm-3:00 pm

Nonstop2h 45m

$78

New HavenOrlando

HVN - MCO

HVNMCO

Tweed-New Haven

Mon 9/22

3:40 pm-6:25 pm

Nonstop2h 45m

Orlando

Fri 9/26

7:10 pm-9:50 pm

Nonstop2h 40m

$81

New HavenOrlando

HVN - MCO

HVNMCO

Tweed-New Haven

Tue 9/23

2:42 pm-5:46 pm

Nonstop3h 04m

Orlando

Tue 9/30

11:12 am-1:57 pm

Nonstop2h 45m

$82

New HavenOrlando

HVN - MCO

HVNMCO

Tweed-New Haven

Sun 9/7

4:57 pm-8:01 pm

Nonstop3h 04m

Orlando

Thu 9/11

4:23 pm-7:08 pm

Nonstop2h 45m

$82

New HavenOrlando

HVN - MCO

HVNMCO

Tweed-New Haven

Mon 8/25

7:54 pm-10:54 pm

Nonstop3h 00m

Orlando

Sun 8/31

6:00 am-8:45 am

Nonstop2h 45m

$88

New HavenOrlando

HVN - MCO

HVNMCO

Tweed-New Haven

Sat 8/23

4:00 pm-7:00 pm

Nonstop3h 00m

Orlando

Thu 8/28

6:00 am-8:45 am

Nonstop2h 45m

$88

New HavenOrlando

HVN - MCO

HVNMCO

Tweed-New Haven

Sat 8/23

4:00 pm-7:00 pm

Nonstop3h 00m

Orlando

Sun 8/31

6:00 am-8:45 am

Nonstop2h 45m

$88

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Connecticut to Kissimmee

Have a flexible travel schedule? Discover the best time to fly to Kissimmee from Connecticut 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 Connecticut to Kissimmee

What is the cheapest month to book a flight from Connecticut to Kissimmee?

Currently, May is the cheapest month in which you can book a flight from Connecticut to Kissimmee (average of $206). Flying from Connecticut to Kissimmee in November is currently the most expensive (average of $289). 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 CT to K1S?

Find hourly flight availability from Connecticut to Kissimmee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

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

Weekly flight availability from Connecticut to Kissimmee

Explore weekly flight availability from Connecticut to Kissimmee. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 14, 2025.

The most flights from USCT to K1S are scheduled on a Monday (9 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

Related info for your journey

Find useful and relevant information for your journey from Connecticut to Kissimmee. 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 Connecticut to Kissimmee one-way?

    To fly one-way, consider booking your trip with Breeze Airways, which is currently one of the cheapest options available, starting at $39. Avelo Airlines flights start at $42 while deals on Spirit Airlines start at $58 one-way.

  • What are the most popular routes from Connecticut to Kissimmee?

    The most popular flight routes from Connecticut to Kissimmee are New York John F Kennedy Intl - Orlando, Newark - Orlando and New York LaGuardia - Orlando.

  • What are the most reliable airlines from Connecticut to Kissimmee?

    No one likes to see their flight delayed. When booking a flight from Connecticut to Kissimmee consider choosing Breeze Airways (85%), Frontier (80%) or Southwest (70%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Connecticut to Kissimmee?

    Looking at all options, your cheapest flight can be booked for $58. While the most popular route (New York John F Kennedy Intl - Orlando) can be booked for $75 on average our data indicates $177 when flying from Connecticut to Kissimmee.

  • Can I find deals for flights from Connecticut to Kissimmee that include hotel bookings?

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

  • How can I find direct flights from Connecticut to Kissimmee?

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

  • Can I find deals for business class flights from Connecticut to Kissimmee?

    Yes. Cheapflights offers flight deals from Connecticut to Kissimmee 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 Connecticut to Kissimmee?

    Currently, May is the cheapest month in which you can book a flight from Connecticut to Kissimmee (average of $206). Flying from Connecticut to Kissimmee in November is currently the most expensive (average of $289). 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

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 Connecticut to Kissimmee

See prices for flight routes from nearby airports that may be better suited for you.
Newark to Fort Lauderdale flights
LaGuardia to Fort Lauderdale flights
John F Kennedy Intl to Miami flights
Newark to Miami flights
LaGuardia to Miami flights
John F Kennedy Intl to Orlando flights
John F Kennedy Intl to Fort Lauderdale flights
Newark to Orlando flights
LaGuardia to Orlando flights
John F Kennedy Intl to West Palm Beach flights
Dulles Intl to Miami flights
LaGuardia to Tampa flights
Newark to Tampa flights
Los Angeles to Orlando flights
Philadelphia to Orlando flights
Baltimore to Fort Lauderdale flights
Dallas/Fort Worth to Orlando flights
Los Angeles to Miami flights
John F Kennedy Intl to Tampa flights
Boston to Orlando flights
Atlanta to Miami flights
Boston to Fort Lauderdale flights
O'Hare Intl to Fort Lauderdale flights
Philadelphia to Fort Lauderdale flights
Baltimore to Orlando flights
Reagan-National to Miami flights
Atlanta to Fort Lauderdale flights
Baltimore to Miami flights
Los Angeles to Fort Lauderdale flights
O'Hare Intl to Miami flights
O'Hare Intl to Orlando flights
Dulles Intl to Orlando flights
Dallas/Fort Worth to Fort Lauderdale flights
Hartford to Orlando flights
Dallas/Fort Worth to Miami flights
Cleveland to Orlando flights
Denver to Orlando flights
Reagan-National to Orlando flights
Philadelphia to Miami flights
San Francisco to Miami flights
Boston to Miami flights
Providence to Orlando flights
Newark to West Palm Beach flights
Minneapolis to Orlando flights
Cincinnati to Orlando flights
LaGuardia to West Palm Beach flights
Seattle to Orlando flights
Islip to Orlando flights
Detroit to Orlando flights
Detroit to Fort Lauderdale flights

Top 9 airlines flying from Connecticut to Kissimmee

Discover the top 9 airlines that operate flights from Connecticut to Kissimmee. 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$142FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$54Average$159FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$55Average$182FlexibilityNo cancel feeOn-time65%
Avelo AirlinesCheapest$59Average$159FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$104Average$270FlexibilityNo cancel feeOn-time62%
DeltaCheapest$113Average$324FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$158Average$306FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$172Average$307FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$203Average$380FlexibilityNo cancel feeOn-time69%

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.