$185+ Cheap flights from Midway (MDW) to Cabo San Lucas, Mexico
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 6/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
May 1 — May 81
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Cabo San Lucas 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
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Cheapest flights from Midway to Cabo San LucasExplore the most affordable flight options available from Midway to Cabo San Lucas. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 1, 2026.
Explore the most affordable flight options available from Midway to Cabo San Lucas. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 1, 2026.
This FlightHub deal was found by Cheapflights users on 3/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/32:56 pm
MDW
- SJD
1 stop21h 16m
Frontier
Sat 4/1111:27 am
SJD
- MDW
1 stop9h 02m
Frontier
Deal found 3/30![Frontier logo]()
$421
This Mytrip deal was found by Cheapflights users on 3/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/169:53 pm
MDW
- SJD
1 stop11h 38m
Volaris
Mon 6/228:16 am
SJD
- MDW
1 stop8h 48m
Volaris
Deal found 3/30![Volaris logo]()
$426
This Cheapflightsfares deal was found by Cheapflights users on 3/28. 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.
Sat 6/69:53 pm
MDW
- SJD
1 stop11h 38m
Volaris
Sun 6/148:16 am
SJD
- MDW
1 stop8h 48m
Volaris
Deal found 3/28![Volaris logo]()
$431
This Mytrip deal was found by Cheapflights users on 3/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/49:53 pm
MDW
- SJD
1 stop11h 38m
Volaris
Mon 6/87:47 pm
SJD
- MDW
2 stops22h 36m
Volaris
Deal found 3/28![Volaris logo]()
$446
This Volaris deal was found by Cheapflights users on 3/28. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/189:53 pm
MDW
- SJD
1 stop11h 38m
Volaris
Mon 6/228:16 am
SJD
- MDW
1 stop8h 48m
Volaris
Deal found 3/28![Volaris logo]()
$447
This Mytrip deal was found by Cheapflights users on 3/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/78:23 pm
MDW
- SJD
1 stop13h 08m
Volaris
Wed 6/108:16 am
SJD
- MDW
1 stop8h 48m
Volaris
Deal found 3/31![Volaris logo]()
$451
This Delta deal was found by Cheapflights users on 3/28. 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.
Sun 5/36:00 am
MDW
- SJD
1 stop7h 31m
Delta
Wed 5/612:36 pm
SJD
- MDW
1 stop7h 52m
Delta
Deal found 3/28![Delta logo]()
$452
Best flights from Midway to Cabo San LucasDiscover carefully curated flight deals from Midway to Cabo San Lucas that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 1, 2026.
Discover carefully curated flight deals from Midway to Cabo San Lucas that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 1, 2026.
This Delta deal was found by Cheapflights users on 4/1. 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 4/276:00 am
MDW
- SJD
1 stop7h 31m
Delta
Fri 5/112:36 pm
SJD
- MDW
1 stop7h 52m
Delta
Deal found 4/1![Delta logo]()
$504
This Southwest deal was found by Cheapflights users on 3/31. 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.
Sun 6/1410:25 pm
MDW
- SJD
1 stop14h 15m
Southwest
Thu 6/1811:15 am
SJD
- MDW
2 stops10h 55m
Southwest
Deal found 3/31![Southwest logo]()
$618
This Delta deal was found by Cheapflights users on 3/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:00 am
MDW
- SJD
2 stops13h 49m
Delta
Sat 5/212:36 pm
SJD
- MDW
1 stop7h 52m
Delta
Deal found 3/30![Delta logo]()
$596
This Southwest deal was found by Cheapflights users on 3/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/208:55 pm
MDW
- SJD
2 stops15h 50m
Southwest
Wed 5/2712:25 pm
SJD
- MDW
1 stop8h 55m
Southwest
Deal found 3/29![Southwest logo]()
$625
This Southwest deal was found by Cheapflights users on 4/1. 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 5/16:55 am
MDW
- SJD
1 stop7h 15m
Southwest
Thu 5/710:45 am
SJD
- MDW
1 stop9h 10m
Southwest
Deal found 4/1![Southwest logo]()
$648
This Delta deal was found by Cheapflights users on 3/31. 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 4/186:00 am
MDW
- SJD
1 stop7h 31m
Delta
Thu 4/236:01 am
SJD
- MDW
2 stops14h 27m
Delta
Deal found 3/31![Delta logo]()
$665
This Southwest deal was found by Cheapflights users on 3/27. 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.
Fri 5/86:00 am
MDW
- SJD
2 stops9h 25m
Southwest
Mon 5/181:25 pm
SJD
- MDW
2 stops8h 05m
Southwest
Deal found 3/27![Southwest logo]()
$677
This Delta deal was found by Cheapflights users on 3/31. 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 5/56:00 am
MDW
- SJD
2 stops13h 48m
Delta
Sun 5/106:02 am
SJD
- MDW
2 stops13h 07m
Delta
Deal found 3/31![Delta logo]()
$708
This KAYAK deal was found by Cheapflights users on 3/29. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/178:55 pm
MDW
- SJD
2 stops13h 55m
Southwest
Mon 6/2211:15 am
SJD
- MDW
3 stops20h 25m
Southwest
Deal found 3/29![Southwest logo]()
$743
This Delta deal was found by Cheapflights users on 3/28. 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 4/246:00 am
MDW
- SJD
1 stop7h 31m
Delta
Mon 4/276:01 am
SJD
- MDW
2 stops14h 27m
Delta
Deal found 3/28![Delta logo]()
$780
This Delta deal was found by Cheapflights users on 3/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/56:00 am
MDW
- SJD
2 stops13h 49m
Delta
Sat 4/118:35 am
SJD
- MDW
2 stops11h 56m
Delta
Deal found 3/29![Delta logo]()
$814
Last-minute flights from Midway to Cabo San LucasDiscover last-minute flight deals from Midway to Cabo San Lucas. Data last updated April 1, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Cabo San Lucas. Data last updated April 1, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 3/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/75:53 pm
MDW
- SJD
2 stops22h 27m
Volaris
Tue 4/147:37 pm
SJD
- MDW
2 stops21h 27m
Volaris
Deal found 3/31![Volaris logo]()
$611
This Delta deal was found by Cheapflights users on 3/31. 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 4/76:00 am
MDW
- SJD
1 stop7h 30m
Delta
Tue 4/1412:36 pm
SJD
- MDW
1 stop7h 52m
Delta
Deal found 3/31![Delta logo]()
$749
This Mytrip deal was found by Cheapflights users on 3/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/711:00 am
MDW
- SJD
3 stops27h 50m
Multiple Airlines
Tue 4/143:10 pm
SJD
- MDW
3 stops25h 54m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$927
This Southwest deal was found by Cheapflights users on 3/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:55 am
MDW
- SJD
1 stop7h 15m
Southwest
Mon 4/1311:40 am
SJD
- MDW
1 stop10h 00m
Southwest
Deal found 3/29![Southwest logo]()
$839
This Delta deal was found by Cheapflights users on 4/1. 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.
Thu 4/96:00 am
MDW
- SJD
1 stop7h 30m
Delta
Sun 4/126:03 am
SJD
- MDW
2 stops14h 28m
Delta
Deal found 4/1![Delta logo]()
$1,287
This Southwest deal was found by Cheapflights users on 3/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/105:10 am
MDW
- SJD
2 stops10h 15m
Southwest
Mon 4/1312:25 pm
SJD
- MDW
2 stops8h 20m
Southwest
Deal found 3/29![Southwest logo]()
$844
This Southwest deal was found by Cheapflights users on 3/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:00 am
MDW
- SJD
1 stop8h 45m
Southwest
Thu 4/163:05 pm
SJD
- MDW
1 stop11h 55m
Southwest
Deal found 3/30![Southwest logo]()
$794
One-way flights from Midway to Cabo San LucasSearch for one-way flight options from Midway to Cabo San Lucas. Find affordable one-way fares based on user searches. Data last updated April 1, 2026.
Search for one-way flight options from Midway to Cabo San Lucas. Find affordable one-way fares based on user searches. Data last updated April 1, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/218:23 pm
MDW
- SJD
1 stop13h 08m
Volaris
Deal found 3/29![Volaris logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 3/28. 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 4/276:20 am
MDW
- SJD
2 stops34h 34m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$186
This Volaris deal was found by Cheapflights users on 3/29. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/49:53 pm
MDW
- SJD
1 stop11h 38m
Volaris
Deal found 3/29![Volaris logo]()
$187
This Volaris deal was found by Cheapflights users on 3/27. 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 Volaris is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/279:53 pm
MDW
- SJD
1 stop11h 38m
Volaris
Deal found 3/27![Volaris logo]()
$188
This Mytrip deal was found by Cheapflights users on 3/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/58:48 pm
MDW
- SJD
1 stop16h 44m
Volaris
Deal found 3/28![Volaris logo]()
$200
This Delta deal was found by Cheapflights users on 3/31. 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.
Sun 5/36:00 am
MDW
- SJD
1 stop7h 31m
Delta
Deal found 3/31![Delta logo]()
$204
This Mytrip deal was found by Cheapflights users on 3/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/158:23 pm
MDW
- SJD
2 stops16h 30m
Volaris
Deal found 3/31![Volaris logo]()
$205
This Delta deal was found by Cheapflights users on 3/31. 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.
Sun 5/319:23 am
MDW
- SJD
2 stops29h 07m
Delta
Deal found 3/31![Delta logo]()
$210
Find flight deals from Midway to Cabo San Lucas
Keep the following information in mind while searching for Midway to Cabo San Lucas flight deals. Data was last updated April 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $426 (Mytrip) |
One-way from | $185 (Cheapflightsfares) |
Popular in | December |
Cheapest in | October |
Average price | $692 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Cabo San Lucas 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 April 1, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Cabo San Lucas that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Mon 4/27
6:00 am-11:31 am
1 stop7h 31m
San José del Cabo Los Cabos
Fri 5/1
12:36 pm-10:28 pm
1 stop7h 52m
$504
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Sat 4/25
6:00 am-5:49 pm
2 stops13h 49m
San José del Cabo Los Cabos
Sat 5/2
12:36 pm-10:28 pm
1 stop7h 52m
$596
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Sun 6/14
10:25 pm-10:40 am
1 stop14h 15m
San José del Cabo Los Cabos
Thu 6/18
11:15 am-12:10 am
2 stops10h 55m
$618
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Wed 5/20
8:55 pm-10:45 am
2 stops15h 50m
San José del Cabo Los Cabos
Wed 5/27
12:25 pm-11:20 pm
1 stop8h 55m
$625
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Fri 5/1
6:55 am-12:10 pm
1 stop7h 15m
San José del Cabo Los Cabos
Thu 5/7
10:45 am-9:55 pm
1 stop9h 10m
$648
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Sat 4/18
6:00 am-11:31 am
1 stop7h 31m
San José del Cabo Los Cabos
Thu 4/23
6:01 am-10:28 pm
2 stops14h 27m
$665
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Fri 5/8
6:00 am-1:25 pm
2 stops9h 25m
San José del Cabo Los Cabos
Mon 5/18
1:25 pm-11:30 pm
2 stops8h 05m
$677
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Tue 5/5
6:00 am-5:48 pm
2 stops13h 48m
San José del Cabo Los Cabos
Sun 5/10
6:02 am-9:09 pm
2 stops13h 07m
$708
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Wed 6/17
8:55 pm-8:50 am
2 stops13h 55m
San José del Cabo Los Cabos
Mon 6/22
11:15 am-9:40 am
3 stops20h 25m
$743
ChicagoSan José del Cabo
MDW - SJD
MDWSJD
Chicago Midway
Fri 4/24
6:00 am-11:31 am
1 stop7h 31m
San José del Cabo Los Cabos
Mon 4/27
6:01 am-10:28 pm
2 stops14h 27m
$780
Showing 1-10 of 20 resultsSorted by cheapest first
Best time to book a flight from Midway to Cabo San Lucas
Have a flexible travel schedule? Discover the best time to fly to Cabo San Lucas from Midway with our price prediction graph.
MDW-SJD
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 Chicago Midway Airport to Cabo San Lucas
MDW-C4B
MDW-SJD
What is the cheapest time of day to fly from MDW to C4B?
Find hourly flight availability from Midway to Cabo San Lucas. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 1, 2026.
When flying from Chicago Midway Airport to Cabo San Lucas, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
How much does it cost to fly round-trip from Chicago Midway Airport to Cabo San Lucas?
Reviews of airlines servicing Cabo San Lucas
Get insights into the airlines that provide service to Cabo San Lucas. 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 Cabo San Lucas. Reviews last updated April 1, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Cabo San Lucas, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Midway to Cabo San Lucas. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Midway to Cabo San Lucas
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Complete your trip
Complete your trip to Cabo San Lucas by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Cabo San Lucas by cabin class
Find flights from Midway to Cabo San Lucas, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Cabo San Lucas flights
Browse other Midway and Cabo San Lucas flight options. Last updated on April 1, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on April 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Midway to Cabo San Lucas flights
Consider these flights traveling from Midway to Cabo San Lucas.
Top airline flying from Midway to Cabo San Lucas
Discover the top airline that operate flights from Midway to Cabo San Lucas. 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 April 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$475 | Average$667 | FlexibilityNo cancel fee | On-time63% |