$135+ Cheap flights from Pensacola (PNS) 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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — MDW
Sep 19 — Sep 261
Round-trip
1 adult, Economy
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Find cheap flights from Pensacola 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 Pensacola to Midway
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Cheapest flights from Pensacola to MidwayExplore the most affordable flight options available from Pensacola to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 20, 2026.
Explore the most affordable flight options available from Pensacola to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 20, 2026.
This Southwest deal was found by Cheapflights users on 8/19. 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 9/199:40 am -
1 stop4h 40m
Wed 9/302:00 pm -
1 stop3h 35m
Deal found 8/19![Southwest logo]()
$290
This Southwest deal was found by Cheapflights users on 8/17. 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 9/167:55 am -
1 stop5h 35m
Wed 9/232:00 pm -
1 stop3h 35m
Deal found 8/17![Southwest logo]()
$294
This Delta deal was found by Cheapflights users on 8/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:26 am -
1 stop6h 49m
Mon 9/286:05 am -
1 stop6h 34m
Deal found 8/18![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 8/19. 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 9/297:55 am -
2 stops7h 30m
Thu 10/16:05 pm -
1 stop4h 45m
Deal found 8/19![Southwest logo]()
$304
This Southwest deal was found by Cheapflights users on 8/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1610:30 am -
1 stop4h 35m
Mon 10/194:30 pm -
1 stop4h 00m
Deal found 8/18![Southwest logo]()
$310
This Southwest deal was found by Cheapflights users on 8/17. 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 9/123:35 pm -
1 stop3h 45m
Fri 9/185:55 am -
1 stop7h 10m
Deal found 8/17![Southwest logo]()
$315
This Delta deal was found by Cheapflights users on 8/17. 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 9/55:00 pm -
1 stop5h 36m
Wed 9/94:30 pm -
1 stop5h 11m
Deal found 8/17![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 8/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:30 pm -
1 stop5h 14m
Sat 9/194:30 pm -
1 stop5h 11m
Deal found 8/18![Delta logo]()
$321
This Southwest deal was found by Cheapflights users on 8/19. 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 9/252:40 pm -
2 stops8h 45m
Sun 9/277:55 am -
1 stop3h 45m
Deal found 8/19![Southwest logo]()
$324
Best flights from Pensacola to MidwayDiscover carefully curated flight deals from Pensacola to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 20, 2026.
Discover carefully curated flight deals from Pensacola to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 20, 2026.
This Southwest deal was found by Cheapflights users on 8/19. 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 9/199:40 am -
1 stop4h 40m
Wed 9/302:00 pm -
1 stop3h 35m
Deal found 8/19![Southwest logo]()
$290
This Southwest deal was found by Cheapflights users on 8/19. 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 9/293:00 pm -
1 stop5h 45m
Thu 10/16:05 pm -
1 stop4h 45m
Deal found 8/19![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 8/16. 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 10/156:05 pm -
1 stop5h 50m
Mon 10/194:30 pm -
1 stop4h 00m
Deal found 8/16![Southwest logo]()
$299
This Southwest deal was found by Cheapflights users on 8/19. 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 9/227:55 am -
2 stops7h 30m
Tue 9/292:00 pm -
1 stop3h 35m
Deal found 8/19![Southwest logo]()
$300
This Southwest deal was found by Cheapflights users on 8/15. 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 9/102:40 pm -
2 stops8h 45m
Mon 9/145:30 am -
1 stop8h 00m
Deal found 8/15![Southwest logo]()
$304
This Southwest deal was found by Cheapflights users on 8/17. 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 9/269:40 am -
2 stops10h 55m
Tue 9/298:15 am -
2 stops5h 50m
Deal found 8/17![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 8/19. 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 11/47:55 am -
2 stops6h 35m
Sun 11/85:05 am -
2 stops8h 35m
Deal found 8/19![Southwest logo]()
$329
This Southwest deal was found by Cheapflights users on 8/17. 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 8/3110:05 am -
1 stop6h 50m
Wed 9/22:00 pm -
1 stop3h 35m
Deal found 8/17![Southwest logo]()
$334
Last-minute flights from Pensacola to MidwayDiscover last-minute flight deals from Pensacola to Midway. Data last updated August 20, 2026 and is based on user searches.
Discover last-minute flight deals from Pensacola to Midway. Data last updated August 20, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/17. 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 9/510:50 am -
1 stop5h 10m
Mon 9/217:55 am -
1 stop4h 15m
Deal found 8/17![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 8/17. 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 9/114:20 pm -
1 stop6h 05m
Fri 9/185:55 am -
1 stop7h 10m
Deal found 8/17![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 8/17. 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 9/123:35 pm -
1 stop3h 45m
Fri 9/185:55 am -
1 stop7h 10m
Deal found 8/17![Southwest logo]()
$315
This Delta deal was found by Cheapflights users on 8/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:30 pm -
1 stop5h 14m
Sat 9/194:30 pm -
1 stop5h 11m
Deal found 8/18![Delta logo]()
$321
This Southwest deal was found by Cheapflights users on 8/17. 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 9/167:55 am -
1 stop5h 35m
Wed 9/232:00 pm -
1 stop3h 35m
Deal found 8/17![Southwest logo]()
$294
This Southwest deal was found by Cheapflights users on 8/19. 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 9/199:40 am -
1 stop4h 40m
Wed 9/302:00 pm -
1 stop3h 35m
Deal found 8/19![Southwest logo]()
$290
This Delta deal was found by Cheapflights users on 8/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:26 am -
1 stop6h 49m
Mon 9/286:05 am -
1 stop6h 34m
Deal found 8/18![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 8/19. 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 9/252:40 pm -
2 stops8h 45m
Sun 9/277:55 am -
1 stop3h 45m
Deal found 8/19![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 8/19. 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 9/297:55 am -
2 stops7h 30m
Thu 10/16:05 pm -
1 stop4h 45m
Deal found 8/19![Southwest logo]()
$304
One-way flights from Pensacola to MidwaySearch for one-way flight options from Pensacola to Midway. Find affordable one-way fares based on user searches. Data last updated August 20, 2026.
Search for one-way flight options from Pensacola to Midway. Find affordable one-way fares based on user searches. Data last updated August 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/15. 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.
Wed 11/188:58 am -
2 stops12h 55m
Deal found 8/15![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 11/178:48 am -
2 stops37h 05m
Deal found 8/17![Multiple Airlines logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Wed 9/167:35 pm -
2 stops22h 11m
Deal found 8/16![Multiple Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/151:20 pm -
2 stops28h 31m
Deal found 8/16![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/171:25 pm -
2 stops10h 18m
Deal found 8/18![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 10/131:20 pm -
2 stops10h 23m
Deal found 8/15![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Mon 9/141:25 pm -
2 stops28h 21m
Deal found 8/16![Multiple Airlines logo]()
$148
Find flight deals from Pensacola to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Pensacola (PNS) 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 August 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $290 (Southwest) |
One-way from | $135 (Kiwi.com) |
Popular in | March |
Cheapest in | June |
Average price | $429 |
Good round-trip deal | $636 or less |
Good one-way deal | $246 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Pensacola 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 August 20, 2026.
Use the filters below to find and compare flights from Pensacola to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Sat 9/19
9:40 am-2:20 pm
1 stop4h 40m
Chicago Midway
Wed 9/30
2:00 pm-5:35 pm
1 stop3h 35m
$290
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Tue 9/29
3:00 pm-8:45 pm
1 stop5h 45m
Chicago Midway
Thu 10/1
6:05 pm-10:50 pm
1 stop4h 45m
$299
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Thu 10/15
6:05 pm-11:55 pm
1 stop5h 50m
Chicago Midway
Mon 10/19
4:30 pm-8:30 pm
1 stop4h 00m
$299
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Tue 9/22
7:55 am-3:25 pm
2 stops7h 30m
Chicago Midway
Tue 9/29
2:00 pm-5:35 pm
1 stop3h 35m
$300
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Thu 9/10
2:40 pm-11:25 pm
2 stops8h 45m
Chicago Midway
Mon 9/14
5:30 am-1:30 pm
1 stop8h 00m
$304
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Sat 9/26
9:40 am-8:35 pm
2 stops10h 55m
Chicago Midway
Tue 9/29
8:15 am-2:05 pm
2 stops5h 50m
$309
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Wed 11/4
7:55 am-2:30 pm
2 stops6h 35m
Chicago Midway
Sun 11/8
5:05 am-1:40 pm
2 stops8h 35m
$329
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Mon 8/31
10:05 am-4:55 pm
1 stop6h 50m
Chicago Midway
Wed 9/2
2:00 pm-5:35 pm
1 stop3h 35m
$334
Cheapest one-way
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Wed 9/16
5:30 pm-10:44 pm
1 stop5h 14m
$150
PensacolaChicago
PNS Pensacola - MDW Chicago Midway
PNSMDW
Pensacola
Tue 2/16
5:45 pm-10:10 pm
1 stop4h 25m
$150
Showing 1-10 of 19 resultsSorted by cheapest first
Compare providers for flights from Pensacola 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 Pensacola to Midway in August.
| 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 Pensacola-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 Pensacola-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Pensacola-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Pensacola-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 Pensacola-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 Pensacola to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Pensacola with our price prediction graph.
PNS-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 Pensacola to Chicago Midway Airport
What is the cheapest time of day to fly from PNS to MDW?
Find hourly flight availability from Pensacola 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 August 20, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Pensacola to Chicago Midway Airport as you normally would.
How much does it cost to fly round-trip from Pensacola to Chicago Midway Airport?
Airfare is typical for this route at the moment.
Pensacola to Chicago Midway Airport flights typically cost between $263 and $554 in September.The cheapest round-trip price found within the last 5 days was $290 on Southwest (Sep 19-Sep 30).
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 August 20, 2026.
See what other customers who have flown with Southwest and Delta from Pensacola to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Pensacola 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
Lansing
Merrillville
Valparaiso
Hammond
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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 August 20, 2026.
Pensacola and Midway flights
Browse other Pensacola and Midway flight options. Last updated on August 20, 2026.
Other flights from Pensacola
Browse through other flights departing from Pensacola. Flights are based on user searches made on Cheapflights and were last updated on August 20, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Pensacola to Midway
Discover the top 2 airlines that operate flights from Pensacola 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 August 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$228 | Average$429 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$237 | Average$397 | FlexibilityNo cancel fee | On-time63% |