$350+ Cheap flights from Chicago (CHI) to Pisa (PSA)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PSA
Oct 10 — Oct 171
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Pisa 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 Chicago to Pisa
Cheapest
Best
Last-minute
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Cheapest flights from Chicago to PisaExplore the most affordable flight options available from Chicago to Pisa. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 10, 2026.
Explore the most affordable flight options available from Chicago to Pisa. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 10, 2026.
This KAYAK deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:15 pm -
1 stop33h 55m
Sat 10/318:00 pm -
1 stop27h 45m
Deal found 9/9![Scandinavian Airlines logo]()
$917
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:30 pm -
2 stops18h 25m
Sat 10/3110:35 pm -
1 stop23h 20m
Deal found 9/9![Multiple Airlines logo]()
$925
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/218:50 pm -
1 stop15h 45m
Fri 10/28:30 pm -
1 stop22h 55m
Deal found 9/9![American Airlines logo]()
$967
This FlightHub deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/214:30 pm -
2 stops20h 05m
Fri 10/28:30 pm -
2 stops26h 40m
Deal found 9/9![British Airways logo]()
$976
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:20 pm -
2 stops33h 35m
Sat 11/281:50 pm -
1 stop31h 20m
Deal found 9/7![Multiple Airlines logo]()
$1,022
This United Airlines deal was found by Cheapflights users on 9/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/214:05 pm -
1 stop18h 55m
Fri 10/210:35 am -
2 stops17h 05m
Deal found 9/6![United Airlines logo]()
$1,081
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/253:55 pm -
1 stop20h 50m
Tue 12/296:15 am -
2 stops17h 30m
Deal found 9/9![Multiple Airlines logo]()
$1,113
This KLM deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/211:19 pm -
2 stops17h 56m
Fri 10/23:40 pm -
2 stops30h 44m
Deal found 9/9![KLM logo]()
$2,005
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/219:59 am -
2 stops21h 16m
Mon 9/283:25 pm -
2 stops34h 08m
Deal found 9/9![Delta logo]()
$6,007
Best flights from Chicago to PisaDiscover carefully curated flight deals from Chicago to Pisa that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 10, 2026.
Discover carefully curated flight deals from Chicago to Pisa that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 10, 2026.
This KAYAK deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:15 pm -
1 stop33h 55m
Sat 10/318:00 pm -
1 stop27h 45m
Deal found 9/9![Scandinavian Airlines logo]()
$917
This United Airlines deal was found by Cheapflights users on 9/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:30 pm -
1 stop16h 30m
Fri 10/210:35 am -
2 stops28h 24m
Deal found 9/5![United Airlines logo]()
$1,081
This KLM deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/201:29 pm -
2 stops18h 11m
Sat 10/310:15 pm -
1 stop23h 00m
Deal found 9/8![KLM logo]()
$1,223
This oojo deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/207:15 pm -
1 stop32h 40m
Sat 10/38:00 pm -
1 stop27h 10m
Deal found 9/9![Scandinavian Airlines logo]()
$1,188
This KLM deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/211:19 pm -
2 stops17h 56m
Fri 10/23:40 pm -
2 stops30h 44m
Deal found 9/9![KLM logo]()
$2,005
This Delta deal was found by Cheapflights users on 9/6. 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 9/219:59 am -
2 stops21h 16m
Mon 9/283:25 pm -
2 stops34h 08m
Deal found 9/6![Delta logo]()
$6,041
Last-minute flights from Chicago to PisaDiscover last-minute flight deals from Chicago to Pisa. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Pisa. Data last updated September 10, 2026 and is based on user searches.
This oojo deal was found by Cheapflights users on 9/5. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/207:15 pm -
1 stop32h 40m
Sat 10/38:00 pm -
1 stop27h 10m
Deal found 9/5![Scandinavian Airlines logo]()
$1,138
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/218:50 pm -
1 stop15h 45m
Fri 10/28:30 pm -
1 stop22h 55m
Deal found 9/9![American Airlines logo]()
$967
This FlightHub deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/214:30 pm -
2 stops20h 05m
Fri 10/28:30 pm -
2 stops26h 40m
Deal found 9/9![British Airways logo]()
$976
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:30 pm -
1 stop16h 30m
Fri 10/210:35 am -
2 stops28h 24m
Deal found 9/7![United Airlines logo]()
$1,081
This KLM deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KLM is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/211:19 pm -
2 stops17h 56m
Fri 10/23:40 pm -
2 stops30h 44m
Deal found 9/9![KLM logo]()
$2,005
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/219:59 am -
2 stops21h 16m
Mon 9/283:25 pm -
2 stops34h 08m
Deal found 9/9![Delta logo]()
$6,007
This KAYAK deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:15 pm -
1 stop33h 55m
Sat 10/318:00 pm -
1 stop27h 45m
Deal found 9/9![Scandinavian Airlines logo]()
$917
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:30 pm -
2 stops18h 25m
Sat 10/3110:35 pm -
1 stop23h 20m
Deal found 9/9![Multiple Airlines logo]()
$925
One-way flights from Chicago to PisaSearch for one-way flight options from Chicago to Pisa. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
Search for one-way flight options from Chicago to Pisa. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:30 pm -
3 stops54h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/243:30 pm -
3 stops41h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$467
This Expedia deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:44 pm -
2 stops42h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![KLM logo]()
$503
This FlightHub deal was found by Cheapflights users on 9/5. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2010:35 pm -
2 stops52h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Aer Lingus logo]()
$547
This oojo deal was found by Cheapflights users on 9/5. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/207:15 pm -
1 stop32h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Scandinavian Airlines logo]()
$555
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:30 pm -
2 stops33h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Delta logo]()
$582
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/277:10 pm -
2 stops56h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Delta logo]()
$596
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:30 am -
2 stops16h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Delta logo]()
$632
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:31 pm -
2 stops33h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Delta logo]()
$823
This Travelocity deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/47:00 am -
2 stops19h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Multiple Airlines logo]()
$870
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/299:29 am -
2 stops17h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Delta logo]()
$873
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:09 pm -
2 stops58h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Delta logo]()
$1,401
Find flight deals from Chicago to Pisa
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Pisa (PSA). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 10, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $860 (Mytrip) |
One-way from | $350 (Kiwi.com) |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Pisa that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 10, 2026.
Use the filters below to find and compare flights from Chicago to Pisa that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoPisa
MDW Chicago Midway - PSA Pisa Gal Galilei
MDWPSA
Chicago Midway
Sat 10/24
3:30 pm-3:45 pm
3 stops41h 15m
Pisa Gal Galilei
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$467
ChicagoPisa
MDW Chicago Midway - PSA Pisa Gal Galilei
MDWPSA
Chicago Midway
Sat 10/24
6:44 pm-7:50 pm
2 stops42h 06m
Pisa Gal Galilei
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$503
ChicagoPisa
ORD Chicago O'Hare Intl - PSA Pisa Gal Galilei
ORDPSA
Chicago O'Hare Intl
Sun 9/20
10:35 pm-9:50 am
2 stops52h 15m
Pisa Gal Galilei
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$547
ChicagoPisa
ORD Chicago O'Hare Intl - PSA Pisa Gal Galilei
ORDPSA
Chicago O'Hare Intl
Sun 9/20
7:15 pm-10:55 am
1 stop32h 40m
Pisa Gal Galilei
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$555
ChicagoPisa
ORD Chicago O'Hare Intl - PSA Pisa Gal Galilei
ORDPSA
Chicago O'Hare Intl
Wed 10/28
5:30 pm-9:15 am
2 stops33h 45m
Pisa Gal Galilei
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$582
ChicagoPisa
ORD Chicago O'Hare Intl - PSA Pisa Gal Galilei
ORDPSA
Chicago O'Hare Intl
Tue 10/27
7:10 pm-9:15 am
2 stops56h 05m
Pisa Gal Galilei
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$596
Quickest round-trip
ChicagoPisa
ORD Chicago O'Hare Intl - PSA Pisa Gal Galilei
ORDPSA
Chicago O'Hare Intl
Thu 10/29
10:30 am-9:15 am
2 stops16h 45m
Pisa Gal Galilei
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$632
ChicagoPisa
MDW Chicago Midway - PSA Pisa Gal Galilei
MDWPSA
Chicago Midway
Wed 10/28
5:31 pm-9:15 am
2 stops33h 44m
Pisa Gal Galilei
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$823
ChicagoPisa
MDW Chicago Midway - PSA Pisa Gal Galilei
MDWPSA
Chicago Midway
Thu 10/29
9:29 am-9:15 am
2 stops17h 46m
Pisa Gal Galilei
Wed 12/31
12:00 am-5:00 pm
Nonstop0h 00m
$873
ChicagoPisa
ORD Chicago O'Hare Intl - PSA Pisa Gal Galilei
ORDPSA
Chicago O'Hare Intl
Fri 10/23
7:15 pm-12:10 pm
1 stop33h 55m
Pisa Gal Galilei
Sat 10/31
8:00 pm-5:45 pm
1 stop27h 45m
$917
Showing 1-10 of 16 resultsSorted by cheapest first
Compare providers for flights from Chicago to Pisa
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 Chicago to Pisa in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Pisa flights, users find the pricing of Ovago to be most consistent on Cheapflights vs. Ovago Users can find the same prices on Chicago-Pisa flight deals on Cheapflights vs. Ovago >95% of the time. Price accuracy is based on data collected from Chicago-Pisa flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Pisa flights, Cheapflights users trust Ovago the most. Ovago 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 Chicago-Pisa 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 Chicago to Pisa
Have a flexible travel schedule? Discover the best time to fly to Pisa from Chicago with our price prediction graph.
CHI-PSA
ORD-PSA
MDW-PSA
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 to Pisa
CHI-PSA
ORD-PSA
MDW-PSA
No data available for this route at this time. Please check back soon.
Related info for your journey
Find useful and relevant information for your journey from Chicago to Pisa. 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 Pisa?
Book flights to Pisa if you plan to visit one of these locationsLa Spezia
Livorno
Monterosso al Mare
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Chicago and Pisa flights
Browse other Chicago and Pisa flight options. Last updated on September 10, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on September 10, 2026.
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Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Chicago to Pisa
Discover the top airline that operate flights from Chicago to Pisa. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$458 | Average$859 | FlexibilityNo cancel fee | On-time70% |