$146+ Cheap flights from Colorado Springs (COS) 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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
COS — MDW
Jun 4 — Jun 111
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
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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 May 5, 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 May 5, 2026.
This Southwest deal was found by Cheapflights users on 5/1. 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.
Sat 6/69:25 am
COS
- MDW
Nonstop2h 25m
Southwest
Tue 6/95:25 pm
MDW
- COS
1 stop7h 20m
Southwest
Deal found 5/1![Southwest logo]()
$301
This Delta deal was found by Cheapflights users on 5/1. 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.
Wed 6/31:55 pm
COS
- MDW
1 stop6h 14m
Delta
Sat 6/61:22 pm
MDW
- COS
2 stops10h 00m
Delta
Deal found 5/1![Delta logo]()
$306
This Delta deal was found by Cheapflights users on 5/5. 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 8/2511:27 am
COS
- MDW
1 stop5h 34m
Delta
Sat 8/294:39 pm
MDW
- COS
1 stop6h 15m
Delta
Deal found 5/5![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 5/4. 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 10/211:30 pm
COS
- MDW
Nonstop2h 20m
Southwest
Sun 10/256:00 am
MDW
- COS
1 stop4h 30m
Southwest
Deal found 5/4![Southwest logo]()
$329
This Southwest deal was found by Cheapflights users on 5/5. 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 6/22:30 pm
COS
- MDW
1 stop6h 15m
Southwest
Sat 6/65:25 am
MDW
- COS
1 stop4h 20m
Southwest
Deal found 5/5![Southwest logo]()
$339
This Southwest deal was found by Cheapflights users on 5/5. 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 6/87:55 pm
COS
- MDW
1 stop8h 30m
Southwest
Fri 6/124:55 pm
MDW
- COS
1 stop6h 45m
Southwest
Deal found 5/5![Southwest logo]()
$341
This Delta deal was found by Cheapflights users on 5/1. 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.
Tue 8/256:00 am
COS
- MDW
2 stops11h 05m
Delta
Fri 8/2810:35 am
MDW
- COS
2 stops12h 54m
Delta
Deal found 5/1![Delta logo]()
$342
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 May 5, 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 May 5, 2026.
This Delta deal was found by Cheapflights users on 5/4. 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 8/251:21 pm
COS
- MDW
1 stop8h 15m
Delta
Sat 8/294:39 pm
MDW
- COS
1 stop6h 15m
Delta
Deal found 5/4![Delta logo]()
$331
This Southwest deal was found by Cheapflights users on 5/3. 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 7/86:00 am
COS
- MDW
1 stop6h 25m
Southwest
Wed 7/225:35 pm
MDW
- COS
1 stop6h 20m
Southwest
Deal found 5/3![Southwest logo]()
$371
This Delta deal was found by Cheapflights users on 5/1. 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.
Fri 8/711:10 am
COS
- MDW
1 stop6h 08m
Delta
Tue 8/119:20 am
MDW
- COS
2 stops8h 54m
Delta
Deal found 5/1![Delta logo]()
$336
This Southwest deal was found by Cheapflights users on 5/3. 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 6/31:10 pm
COS
- MDW
1 stop9h 10m
Southwest
Mon 6/85:20 am
MDW
- COS
1 stop6h 10m
Southwest
Deal found 5/3![Southwest logo]()
$371
This Southwest deal was found by Cheapflights users on 5/1. 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.
Sat 6/69:25 am
COS
- MDW
Nonstop2h 25m
Southwest
Tue 6/94:05 pm
MDW
- COS
Nonstop2h 30m
Southwest
Deal found 5/1![Southwest logo]()
$375
This Delta deal was found by Cheapflights users on 5/5. 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 6/266:00 am
COS
- MDW
2 stops11h 18m
Delta
Sun 6/286:00 am
MDW
- COS
1 stop7h 35m
Delta
Deal found 5/5![Delta logo]()
$376
This Southwest deal was found by Cheapflights users on 5/1. 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.
Thu 5/288:00 pm
COS
- MDW
1 stop8h 25m
Southwest
Tue 6/210:15 am
MDW
- COS
1 stop8h 50m
Southwest
Deal found 5/1![Southwest logo]()
$381
This Southwest deal was found by Cheapflights users on 5/5. 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 6/2612:20 pm
COS
- MDW
2 stops11h 15m
Southwest
Sun 6/288:20 pm
MDW
- COS
2 stops15h 10m
Southwest
Deal found 5/5![Southwest logo]()
$397
This Southwest deal was found by Cheapflights users on 5/2. 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 6/114:55 pm
COS
- MDW
2 stops7h 05m
Southwest
Wed 6/173:10 pm
MDW
- COS
2 stops7h 35m
Southwest
Deal found 5/2![Southwest logo]()
$401
This Southwest deal was found by Cheapflights users on 5/4. 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 6/52:35 pm
COS
- MDW
1 stop9h 00m
Southwest
Sun 6/75:25 am
MDW
- COS
1 stop8h 15m
Southwest
Deal found 5/4![Southwest logo]()
$418
Last-minute flights from Colorado Springs to MidwayDiscover last-minute flight deals from Colorado Springs to Midway. Data last updated May 5, 2026 and is based on user searches.
Discover last-minute flight deals from Colorado Springs to Midway. Data last updated May 5, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/5. 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 6/22:30 pm
COS
- MDW
1 stop6h 15m
Southwest
Sat 6/65:25 am
MDW
- COS
1 stop4h 20m
Southwest
Deal found 5/5![Southwest logo]()
$339
This Delta deal was found by Cheapflights users on 5/1. 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.
Wed 6/31:55 pm
COS
- MDW
1 stop6h 14m
Delta
Sat 6/61:22 pm
MDW
- COS
2 stops10h 00m
Delta
Deal found 5/1![Delta logo]()
$306
This Southwest deal was found by Cheapflights users on 5/1. 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.
Sat 6/69:25 am
COS
- MDW
Nonstop2h 25m
Southwest
Tue 6/95:25 pm
MDW
- COS
1 stop7h 20m
Southwest
Deal found 5/1![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 5/5. 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 6/64:50 pm
COS
- MDW
1 stop5h 50m
Southwest
Mon 6/85:20 am
MDW
- COS
1 stop6h 10m
Southwest
Deal found 5/5![Southwest logo]()
$351
This Southwest deal was found by Cheapflights users on 5/5. 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 6/87:55 pm
COS
- MDW
1 stop8h 30m
Southwest
Fri 6/124:55 pm
MDW
- COS
1 stop6h 45m
Southwest
Deal found 5/5![Southwest logo]()
$341
This Southwest deal was found by Cheapflights users on 5/5. 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 6/166:10 pm
COS
- MDW
1 stop4h 55m
Southwest
Fri 6/196:25 pm
MDW
- COS
2 stops7h 50m
Southwest
Deal found 5/5![Southwest logo]()
$344
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 May 5, 2026.
Search for one-way flight options from Colorado Springs to Midway. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
This Southwest deal was found by Cheapflights users on 5/5. 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 9/1210:40 am
COS
- MDW
Nonstop2h 20m
Southwest
Deal found 5/5![Southwest logo]()
$146
This Delta deal was found by Cheapflights users on 5/3. 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 7/16:20 pm
COS
- MDW
2 stops13h 54m
Delta
Deal found 5/3![Delta logo]()
$151
This Southwest deal was found by Cheapflights users on 5/5. 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 6/96:10 pm
COS
- MDW
1 stop4h 55m
Southwest
Deal found 5/5![Southwest logo]()
$154
This Southwest deal was found by Cheapflights users on 5/4. 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 6/18:00 pm
COS
- MDW
1 stop8h 25m
Southwest
Deal found 5/4![Southwest logo]()
$156
This Southwest deal was found by Cheapflights users on 5/1. 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 10/162:15 pm
COS
- MDW
Nonstop2h 20m
Southwest
Deal found 5/1![Southwest logo]()
$176
This Delta deal was found by Cheapflights users on 5/1. 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.
Fri 10/301:40 pm
COS
- MDW
1 stop7h 05m
Delta
Deal found 5/1![Delta logo]()
$186
This Southwest deal was found by Cheapflights users on 5/2. 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 5/288:00 pm
COS
- MDW
1 stop8h 25m
Southwest
Deal found 5/2![Southwest logo]()
$196
This Southwest deal was found by Cheapflights users on 5/1. 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.
Sat 6/279:55 am
COS
- MDW
2 stops6h 05m
Southwest
Deal found 5/1![Southwest logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 5/295:16 pm
COS
- MDW
2 stops48h 43m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$206
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 May 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $301 (Southwest) |
One-way from | $146 (Southwest) |
Popular in | November |
Cheapest in | April |
Average price | $407 |
Good round-trip deal | $361 or less |
Good one-way deal | $261 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 2,558,603 searches. Data last updated May 5, 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 - MDW
COSMDW
Colorado Springs
Tue 8/25
1:21 pm-10:36 pm
1 stop8h 15m
Chicago Midway
Sat 8/29
4:39 pm-9:54 pm
1 stop6h 15m
$331
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Fri 8/7
11:10 am-6:18 pm
1 stop6h 08m
Chicago Midway
Tue 8/11
9:20 am-5:14 pm
2 stops8h 54m
$336
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Wed 7/8
6:00 am-1:25 pm
1 stop6h 25m
Chicago Midway
Wed 7/22
5:35 pm-10:55 pm
1 stop6h 20m
$371
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Wed 6/3
1:10 pm-11:20 pm
1 stop9h 10m
Chicago Midway
Mon 6/8
5:20 am-10:30 am
1 stop6h 10m
$371
Quickest round-trip
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Sat 6/6
9:25 am-12:50 pm
Nonstop2h 25m
Chicago Midway
Tue 6/9
4:05 pm-5:35 pm
Nonstop2h 30m
$375
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Fri 6/26
6:00 am-6:18 pm
2 stops11h 18m
Chicago Midway
Sun 6/28
6:00 am-12:35 pm
1 stop7h 35m
$376
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Thu 5/28
8:00 pm-5:25 am
1 stop8h 25m
Chicago Midway
Tue 6/2
10:15 am-6:05 pm
1 stop8h 50m
$381
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Fri 6/26
12:20 pm-12:35 am
2 stops11h 15m
Chicago Midway
Sun 6/28
8:20 pm-10:30 am
2 stops15h 10m
$397
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Thu 6/11
4:55 pm-1:00 am
2 stops7h 05m
Chicago Midway
Wed 6/17
3:10 pm-9:45 pm
2 stops7h 35m
$401
Colorado SpringsChicago
COS - MDW
COSMDW
Colorado Springs
Fri 6/5
2:35 pm-12:35 am
1 stop9h 00m
Chicago Midway
Sun 6/7
5:25 am-12:40 pm
1 stop8h 15m
$418
Showing 1-10 of 21 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 May.
| 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
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 May 5, 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.
Overall
7.9
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
7.9
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
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 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
Lansing
Merrillville
Hammond
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 May 5, 2026.
Colorado Springs and Midway flights
Browse other Colorado Springs and Midway flight options. Last updated on May 5, 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 May 5, 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 2,558,603 searches. Data last updated May 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$227 | Average$371 | FlexibilityNo cancel fee | On-time63% |