$147+ Cheap flights from Colorado Springs (COS) to Midway (MDW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
COS — MDW
Oct 12 — Oct 191
Round-trip
1 adult, Economy
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Find cheap flights from Colorado Springs to Midway 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 Colorado Springs to Midway
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Best
Last-minute
One-way
Cheapest flights from Colorado Springs to MidwayExplore the most affordable flight options available from Colorado Springs to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 12, 2026.
Explore the most affordable flight options available from Colorado Springs to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 12, 2026.
This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/222:05 pm -
Nonstop2h 20m
Tue 10/273:35 pm -
Nonstop2h 35m
Deal found 9/11![Southwest logo]()
$293
This Southwest deal was found by Cheapflights users on 9/9. 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.
Thu 10/12:05 pm -
Nonstop2h 20m
Mon 10/55:15 am -
1 stop6h 00m
Deal found 9/9![Southwest logo]()
$303
This Southwest deal was found by Cheapflights users on 9/7. 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.
Tue 9/296:15 am -
1 stop4h 45m
Tue 10/136:05 am -
1 stop4h 40m
Deal found 9/7![Southwest logo]()
$308
This Delta deal was found by Cheapflights users on 9/10. 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 10/271:31 pm -
1 stop8h 02m
Thu 10/2912:49 pm -
1 stop8h 27m
Deal found 9/10![Delta logo]()
$313
This Delta deal was found by Cheapflights users on 9/10. 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.
Sat 11/71:26 pm -
1 stop8h 07m
Tue 11/101:31 pm -
2 stops9h 51m
Deal found 9/10![Delta logo]()
$318
This Southwest deal was found by Cheapflights users on 9/8. 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.
Thu 10/12:05 pm -
Nonstop2h 20m
Tue 10/66:00 am -
1 stop5h 35m
Deal found 9/8![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 9/10. 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 10/22:05 pm -
Nonstop2h 20m
Sat 10/311:15 am -
Nonstop2h 35m
Deal found 9/10![Southwest logo]()
$325
This Delta deal was found by Cheapflights users on 9/10. 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.
Fri 10/231:31 pm -
1 stop8h 02m
Thu 10/296:04 am -
1 stop7h 26m
Deal found 9/10![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 9/9. 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.
Mon 10/58:10 pm -
1 stop8h 30m
Tue 10/63:35 pm -
Nonstop2h 35m
Deal found 9/9![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 9/10. 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.
Thu 10/155:00 pm -
1 stop6h 20m
Tue 10/2011:30 am -
2 stops9h 25m
Deal found 9/10![Southwest logo]()
$334
Best flights from Colorado Springs to MidwayDiscover carefully curated flight deals from Colorado Springs to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 12, 2026.
Discover carefully curated flight deals from Colorado Springs to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 12, 2026.
This Southwest deal was found by Cheapflights users on 9/9. 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.
Thu 10/12:05 pm -
Nonstop2h 20m
Tue 10/611:30 am -
2 stops9h 25m
Deal found 9/9![Southwest logo]()
$308
This Delta deal was found by Cheapflights users on 9/10. 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.
Sat 11/76:00 am -
1 stop8h 17m
Tue 11/101:05 pm -
1 stop8h 45m
Deal found 9/10![Delta logo]()
$313
This Southwest deal was found by Cheapflights users on 9/10. 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 10/22:05 pm -
Nonstop2h 20m
Sat 10/35:10 am -
1 stop7h 20m
Deal found 9/10![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 9/10. 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.
Thu 10/155:00 pm -
1 stop6h 20m
Tue 10/2011:30 am -
2 stops9h 25m
Deal found 9/10![Southwest logo]()
$334
This Delta deal was found by Cheapflights users on 9/8. 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 10/71:31 pm -
1 stop8h 02m
Thu 10/156:04 am -
1 stop7h 26m
Deal found 9/8![Delta logo]()
$381
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:31 pm -
1 stop8h 02m
Wed 10/286:04 am -
1 stop7h 26m
Deal found 9/11![Delta logo]()
$393
This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:40 pm -
1 stop7h 30m
Sun 11/155:15 am -
1 stop6h 55m
Deal found 9/11![Southwest logo]()
$397
Last-minute flights from Colorado Springs to MidwayDiscover last-minute flight deals from Colorado Springs to Midway. Data last updated September 12, 2026 and is based on user searches.
Discover last-minute flight deals from Colorado Springs to Midway. Data last updated September 12, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 9/9. 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.
Sat 9/1910:40 am -
Nonstop2h 20m
Sat 9/2610:10 am -
Nonstop2h 30m
Deal found 9/9![Southwest logo]()
$471
This Southwest deal was found by Cheapflights users on 9/9. 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.
Sat 9/1910:40 am -
Nonstop2h 20m
Tue 9/226:00 am -
1 stop7h 40m
Deal found 9/9![Southwest logo]()
$489
This Southwest deal was found by Cheapflights users on 9/9. 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.
Mon 9/214:20 pm -
1 stop4h 45m
Sun 9/2710:15 am -
Nonstop2h 30m
Deal found 9/9![Southwest logo]()
$520
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/221:25 pm -
1 stop8h 19m
Tue 9/296:05 am -
1 stop7h 09m
Deal found 9/11![Delta logo]()
$511
One-way flights from Colorado Springs to MidwaySearch for one-way flight options from Colorado Springs to Midway. Find affordable one-way fares based on user searches. Data last updated September 12, 2026.
Search for one-way flight options from Colorado Springs to Midway. Find affordable one-way fares based on user searches. Data last updated September 12, 2026.
This Southwest deal was found by Cheapflights users on 9/8. 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.
Tue 10/2012:40 pm -
Nonstop2h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Southwest logo]()
$147
This Delta deal was found by Cheapflights users on 9/9. 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 12/81:40 pm -
1 stop8h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Delta logo]()
$157
This Delta deal was found by Cheapflights users on 9/10. 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.
Sat 11/78:17 am -
2 stops13h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Delta logo]()
$162
This Delta deal was found by Cheapflights users on 9/10. 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.
Mon 12/71:40 pm -
1 stop8h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Delta logo]()
$167
This Delta deal was found by Cheapflights users on 9/10. 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 12/98:00 am -
2 stops13h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Delta logo]()
$172
This Delta deal was found by Cheapflights users on 9/9. 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.
Fri 12/111:40 pm -
1 stop8h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Delta logo]()
$173
This Southwest deal was found by Cheapflights users on 9/8. 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 10/712:40 pm -
Nonstop2h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/101:40 pm -
1 stop8h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 9/10. 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.
Sat 10/175:40 am -
2 stops11h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Southwest logo]()
$192
This Delta deal was found by Cheapflights users on 9/8. 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 10/61:31 pm -
1 stop8h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Delta logo]()
$200
This Southwest deal was found by Cheapflights users on 9/10. 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.
Tue 10/1312:40 pm -
Nonstop2h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Southwest logo]()
$201
Find flight deals from Colorado Springs to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Colorado Springs (COS) 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 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $293 (Southwest) |
One-way from | $147 (Southwest) |
Popular in | March |
Cheapest in | April |
Average price | $361 |
Good round-trip deal | $444 or less |
Good one-way deal | $250 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Colorado Springs 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 7,457,451 searches. Data last updated September 12, 2026.
Use the filters below to find and compare flights from Colorado Springs to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Tue 11/10
1:31 pm-10:54 pm
1 stop8h 23m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$157
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Tue 12/8
1:40 pm-11:05 pm
1 stop8h 25m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$157
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Mon 12/7
1:40 pm-10:55 pm
1 stop8h 15m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$157
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Tue 1/5
6:55 am-4:15 pm
2 stops8h 20m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$162
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Sat 12/5
8:00 am-10:55 pm
2 stops13h 55m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$162
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Sat 11/7
6:00 am-2:30 pm
2 stops7h 30m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$162
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Wed 12/9
8:00 am-10:55 pm
2 stops13h 55m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$162
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Fri 12/11
1:40 pm-10:55 pm
1 stop8h 15m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$173
Quickest round-trip
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Tue 3/9
1:35 pm-9:00 pm
1 stop6h 25m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$196
Colorado SpringsChicago
COS Colorado Springs - MDW Chicago Midway
COSMDW
Colorado Springs
Thu 3/11
9:10 pm-5:45 am
1 stop7h 35m
Chicago Midway
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$241
Showing 1-10 of 18 resultsSorted by cheapest first
Compare providers for flights from Colorado Springs to Midway
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Colorado Springs to Midway in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Colorado Springs-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Colorado Springs-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Colorado Springs-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Colorado Springs-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Colorado Springs-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Colorado Springs to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Colorado Springs with our price prediction graph.
COS-MDW
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 Colorado Springs to Chicago Midway Airport
What is the cheapest month to book a flight from Colorado Springs to Chicago Midway Airport?
Currently, April is the cheapest month in which you can book a flight from Colorado Springs to Chicago Midway Airport (average of $288). Flying from Colorado Springs to Chicago Midway Airport in March is currently the most expensive (average of $671). 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 COS to MDW?
Find hourly flight availability from Colorado Springs 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 12, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Colorado Springs to Chicago Midway Airport as you normally would.
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 12, 2026.
Peruse reviews from past customers who have flown with Southwest from Colorado Springs to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
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 Colorado Springs 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 September 12, 2026.
Colorado Springs and Midway flights
Browse other Colorado Springs and Midway flight options. Last updated on September 12, 2026.
Other flights from Colorado Springs
Browse through other flights departing from Colorado Springs. Flights are based on user searches made on Cheapflights and were last updated on September 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Colorado Springs to Midway
Discover the top airline that operate flights from Colorado Springs 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 September 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$240 | Average$385 | FlexibilityNo cancel fee | On-time63% |