$52+ Cheap flights from Valparaiso, FL (VPS) 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — MDW
Nov 29 — Dec 61
Round-trip
1 adult, Economy
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Find cheap flights from Valparaiso 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 Valparaiso to Midway
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Cheapest flights from Valparaiso to MidwayExplore the most affordable flight options available from Valparaiso to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2026.
Explore the most affordable flight options available from Valparaiso to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/25. 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.
Fri 11/67:30 am -
Nonstop2h 18m
Mon 11/91:08 pm -
Nonstop2h 11m
Deal found 10/25![Allegiant Air logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/23:36 pm -
Nonstop2h 18m
Fri 11/610:38 am -
Nonstop2h 11m
Deal found 10/27![Allegiant Air logo]()
$219
This CheapOair deal was found by Cheapflights users on 10/30. 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 11/67:30 am -
Nonstop2h 18m
Fri 11/1310:38 am -
Nonstop2h 11m
Deal found 10/30![Allegiant Air logo]()
$223
This Southwest deal was found by Cheapflights users on 10/27. 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 12/811:10 am -
1 stop6h 00m
Thu 12/107:05 am -
1 stop6h 20m
Deal found 10/27![Southwest logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Fri 11/137:30 am -
Nonstop2h 18m
Tue 11/176:08 am -
3 stops54h 51m
Deal found 10/29![Multiple Airlines logo]()
$300
This Southwest deal was found by Cheapflights users on 10/27. 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 12/72:05 pm -
1 stop8h 40m
Thu 12/107:05 am -
1 stop6h 20m
Deal found 10/27![Southwest logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/11:46 pm -
1 stop22h 50m
Fri 11/610:38 am -
Nonstop2h 11m
Deal found 10/27![Allegiant Air logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 11/2511:37 am -
2 stops20h 37m
Mon 11/306:51 pm -
Nonstop2h 05m
Deal found 10/26![Multiple Airlines logo]()
$347
This Southwest deal was found by Cheapflights users on 10/26. 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 12/32:05 pm -
1 stop8h 40m
Sun 12/65:20 am -
1 stop8h 05m
Deal found 10/26![Southwest logo]()
$356
Best flights from Valparaiso to MidwayDiscover carefully curated flight deals from Valparaiso to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 30, 2026.
Discover carefully curated flight deals from Valparaiso to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 30, 2026.
This Southwest deal was found by Cheapflights users on 10/27. 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 12/87:00 am -
1 stop5h 55m
Thu 12/1011:30 am -
2 stops9h 45m
Deal found 10/27![Southwest logo]()
$305
This Southwest deal was found by Cheapflights users on 10/27. 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 12/72:05 pm -
1 stop8h 40m
Thu 12/107:05 am -
1 stop6h 20m
Deal found 10/27![Southwest logo]()
$305
This Southwest deal was found by Cheapflights users on 10/26. 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 12/32:05 pm -
1 stop8h 40m
Sun 12/65:20 am -
1 stop8h 05m
Deal found 10/26![Southwest logo]()
$356
This Southwest deal was found by Cheapflights users on 10/26. 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 12/296:00 pm -
1 stop6h 20m
Fri 1/17:05 am -
1 stop6h 20m
Deal found 10/26![Southwest logo]()
$379
This Southwest deal was found by Cheapflights users on 10/25. 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 11/246:00 pm -
1 stop6h 20m
Tue 12/111:30 am -
2 stops9h 45m
Deal found 10/25![Southwest logo]()
$402
Last-minute flights from Valparaiso to MidwayDiscover last-minute flight deals from Valparaiso to Midway. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Valparaiso to Midway. Data last updated October 30, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/11:46 pm -
1 stop22h 50m
Fri 11/610:38 am -
Nonstop2h 11m
Deal found 10/27![Allegiant Air logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/23:36 pm -
Nonstop2h 18m
Fri 11/610:38 am -
Nonstop2h 11m
Deal found 10/27![Allegiant Air logo]()
$219
This Cheapflightsfares deal was found by Cheapflights users on 10/25. 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.
Fri 11/67:30 am -
Nonstop2h 18m
Mon 11/91:08 pm -
Nonstop2h 11m
Deal found 10/25![Allegiant Air logo]()
$154
This CheapOair deal was found by Cheapflights users on 10/30. 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 11/67:30 am -
Nonstop2h 18m
Fri 11/1310:38 am -
Nonstop2h 11m
Deal found 10/30![Allegiant Air logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Fri 11/61:39 pm -
2 stops28h 08m
Mon 11/91:08 pm -
Nonstop2h 11m
Deal found 10/25![Multiple Airlines logo]()
$356
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Fri 11/137:30 am -
Nonstop2h 18m
Tue 11/176:08 am -
3 stops54h 51m
Deal found 10/29![Multiple Airlines logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/243:37 pm -
Nonstop2h 24m
Tue 12/112:33 pm -
2 stops43h 20m
Deal found 10/25![Multiple Airlines logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 11/2511:37 am -
2 stops20h 37m
Mon 11/306:51 pm -
Nonstop2h 05m
Deal found 10/26![Multiple Airlines logo]()
$347
One-way flights from Valparaiso to MidwaySearch for one-way flight options from Valparaiso to Midway. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
Search for one-way flight options from Valparaiso to Midway. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This Jetabroad deal was found by Cheapflights users on 10/26. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:30 am -
Nonstop2h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Allegiant Air logo]()
$52
This Super.com deal was found by Cheapflights users on 10/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:30 am -
Nonstop2h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Allegiant Air logo]()
$99
This Southwest deal was found by Cheapflights users on 10/25. 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 11/215:25 pm -
1 stop7h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Southwest logo]()
$149
This Southwest deal was found by Cheapflights users on 10/26. 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 11/267:00 am -
2 stops7h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Southwest logo]()
$154
This Southwest deal was found by Cheapflights users on 10/26. 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 12/306:00 pm -
1 stop6h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Southwest logo]()
$180
This Southwest deal was found by Cheapflights users on 10/26. 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 12/296:00 pm -
1 stop6h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Southwest logo]()
$198
This Delta deal was found by Cheapflights users on 10/25. 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 1/15:12 pm -
1 stop5h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Delta logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 12/292:40 pm -
3 stops28h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Multiple Airlines logo]()
$287
This Southwest deal was found by Cheapflights users on 10/26. 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 11/62:10 pm -
2 stops8h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Southwest logo]()
$295
Find flight deals from Valparaiso to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Valparaiso (VPS) 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 October 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $299 (Southwest) |
One-way from | $52 (Jetabroad) |
Popular in | October |
Cheapest in | August |
Average price | $543 |
Good round-trip deal | $161 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Valparaiso 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 October 30, 2026.
Use the filters below to find and compare flights from Valparaiso to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Sat 11/21
5:25 pm-12:25 am
1 stop7h 00m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$149
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Wed 12/30
6:00 pm-12:20 am
1 stop6h 20m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$180
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Tue 12/29
6:00 pm-12:20 am
1 stop6h 20m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$198
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Fri 1/1
5:12 pm-10:22 pm
1 stop5h 10m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$261
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Tue 12/8
7:00 am-12:55 pm
1 stop5h 55m
Chicago Midway
Thu 12/10
11:30 am-9:15 pm
2 stops9h 45m
$305
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Mon 12/7
2:05 pm-10:45 pm
1 stop8h 40m
Chicago Midway
Thu 12/10
7:05 am-1:25 pm
1 stop6h 20m
$305
Quickest round-trip
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Sat 11/28
6:08 pm-8:32 pm
Nonstop2h 24m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$314
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Thu 12/3
2:05 pm-10:45 pm
1 stop8h 40m
Chicago Midway
Sun 12/6
5:20 am-1:25 pm
1 stop8h 05m
$356
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Tue 12/29
6:00 pm-12:20 am
1 stop6h 20m
Chicago Midway
Fri 1/1
7:05 am-1:25 pm
1 stop6h 20m
$379
ValparaisoChicago
VPS Valparaiso Destin-Ft Walton Beach - MDW Chicago Midway
VPSMDW
Valparaiso Destin-Ft Walton Beach
Sat 1/2
7:00 am-6:30 pm
2 stops11h 30m
Chicago Midway
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$402
Showing 1-10 of 14 resultsSorted by cheapest first
Compare providers for flights from Valparaiso 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 Valparaiso to Midway in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Valparaiso, Florida-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 Valparaiso, Florida-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Valparaiso, Florida-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Valparaiso, Florida-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 Valparaiso, Florida-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 Valparaiso to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Valparaiso with our price prediction graph.
VPS-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 Valparaiso to Chicago Midway Airport
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 October 30, 2026.
Get a feel of what it's like to fly with Allegiant Air from Valparaiso 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.
Entertainment
5.5
Comfort
6.9
Crew
8.1
Boarding
7.7
Overall
7.3
Food
5.9
Reviews
1 / 20
2.0
MediocreNic,Aug 2026
SRQ - ALB
Entertainment
5.5
Comfort
6.9
Crew
8.1
Boarding
7.7
Overall
7.3
Food
5.9
Reviews
1 / 20
2.0
MediocreNic,Aug 2026
SRQ - ALB
Related info for your journey
Find useful and relevant information for your journey from Valparaiso 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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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 October 30, 2026.
Valparaiso and Midway flights
Browse other Valparaiso and Midway flight options. Last updated on October 30, 2026.
Other flights from Valparaiso
Browse through other flights departing from Valparaiso. Flights are based on user searches made on Cheapflights and were last updated on October 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Valparaiso to Midway
Discover the top airline that operate flights from Valparaiso 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 October 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$104 | Average$161 | FlexibilityNo cancel fee | On-time88% |