$210+ Cheap flights from Williamsburg, VA to Chicago (CHI)
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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — CHI
Sep 24 — Oct 11
Round-trip
1 adult, Economy
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Find cheap flights from Williamsburg to Chicago 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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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 Williamsburg to Chicago
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Cheapest flights from Williamsburg to ChicagoExplore the most affordable flight options available from Williamsburg to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 25, 2026.
Explore the most affordable flight options available from Williamsburg to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 25, 2026.
This American Airlines deal was found by Cheapflights users on 8/21. 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.
Wed 9/306:00 am -
1 stop7h 14m
Thu 10/18:59 am -
1 stop5h 38m
Deal found 8/21![American Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 8/20. 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.
Thu 9/176:00 am -
1 stop7h 14m
Sun 9/205:18 am -
1 stop4h 15m
Deal found 8/20![American Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 8/20. 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.
Fri 9/46:59 pm -
1 stop5h 53m
Tue 9/811:53 am -
1 stop4h 30m
Deal found 8/20![American Airlines logo]()
$495
This American Airlines deal was found by Cheapflights users on 8/22. 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.
Thu 10/16:00 am -
1 stop7h 14m
Wed 10/144:45 pm -
1 stop6h 38m
Deal found 8/22![American Airlines logo]()
$499
This American Airlines deal was found by Cheapflights users on 8/23. 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.
Wed 9/26:59 pm -
1 stop5h 53m
Sat 9/58:54 am -
1 stop5h 22m
Deal found 8/23![American Airlines logo]()
$501
This American Airlines deal was found by Cheapflights users on 8/22. 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.
Thu 10/112:27 pm -
1 stop4h 33m
Fri 10/94:45 pm -
1 stop6h 38m
Deal found 8/22![American Airlines logo]()
$509
This American Airlines deal was found by Cheapflights users on 8/22. 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.
Thu 10/112:27 pm -
1 stop6h 11m
Tue 10/134:45 pm -
1 stop5h 43m
Deal found 8/22![American Airlines logo]()
$544
This American Airlines deal was found by Cheapflights users on 8/20. 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.
Sat 8/2212:36 pm -
1 stop5h 14m
Mon 8/248:54 am -
1 stop7h 29m
Deal found 8/20![American Airlines logo]()
$559
This American Airlines deal was found by Cheapflights users on 8/22. 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.
Sat 10/36:00 am -
2 stops10h 30m
Wed 10/144:45 pm -
1 stop6h 38m
Deal found 8/22![American Airlines logo]()
$573
This American Airlines deal was found by Cheapflights users on 8/22. 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.
Sat 10/36:00 am -
2 stops10h 30m
Mon 10/125:00 am -
1 stop4h 45m
Deal found 8/22![American Airlines logo]()
$583
This American Airlines deal was found by Cheapflights users on 8/22. 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.
Sun 10/45:00 am -
1 stop5h 00m
Fri 10/911:00 pm -
2 stops10h 50m
Deal found 8/22![American Airlines logo]()
$590
Best flights from Williamsburg to ChicagoDiscover carefully curated flight deals from Williamsburg to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 25, 2026.
Discover carefully curated flight deals from Williamsburg to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 25, 2026.
This American Airlines deal was found by Cheapflights users on 8/22. 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.
Tue 10/131:00 pm -
1 stop5h 51m
Thu 10/155:00 am -
1 stop4h 45m
Deal found 8/22![American Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 8/23. 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.
Fri 11/135:00 am -
1 stop5h 00m
Sun 11/159:00 am -
1 stop6h 13m
Deal found 8/23![American Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 8/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:55 pm -
1 stop5h 13m
Sun 11/15:19 am -
1 stop5h 05m
Deal found 8/25![American Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 8/24. 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.
Tue 9/2212:27 pm -
1 stop6h 11m
Thu 9/248:05 am -
1 stop6h 32m
Deal found 8/24![American Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 8/20. 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.
Thu 9/176:00 am -
1 stop7h 14m
Sun 9/205:18 am -
1 stop4h 15m
Deal found 8/20![American Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 8/22. 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.
Sun 9/611:14 am -
1 stop5h 48m
Thu 9/105:20 am -
1 stop5h 41m
Deal found 8/22![American Airlines logo]()
$495
This American Airlines deal was found by Cheapflights users on 8/24. 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.
Thu 9/1012:27 pm -
1 stop4h 33m
Sun 9/135:18 am -
1 stop4h 15m
Deal found 8/24![American Airlines logo]()
$495
This American Airlines deal was found by Cheapflights users on 8/21. 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.
Sat 9/511:19 am -
1 stop6h 24m
Wed 9/96:29 am -
1 stop4h 32m
Deal found 8/21![American Airlines logo]()
$495
This American Airlines deal was found by Cheapflights users on 8/22. 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.
Sun 10/47:54 pm -
1 stop5h 05m
Wed 10/1412:05 pm -
1 stop6h 25m
Deal found 8/22![American Airlines logo]()
$499
This American Airlines deal was found by Cheapflights users on 8/22. 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 10/54:33 pm -
1 stop7h 27m
Fri 10/94:45 pm -
1 stop6h 38m
Deal found 8/22![American Airlines logo]()
$509
This American Airlines deal was found by Cheapflights users on 8/22. 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.
Wed 10/74:33 pm -
1 stop7h 27m
Fri 10/94:45 pm -
1 stop6h 38m
Deal found 8/22![American Airlines logo]()
$509
This American Airlines deal was found by Cheapflights users on 8/22. 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.
Thu 10/112:27 pm -
1 stop4h 33m
Fri 10/94:45 pm -
1 stop6h 38m
Deal found 8/22![American Airlines logo]()
$509
Last-minute flights from Williamsburg to ChicagoDiscover last-minute flight deals from Williamsburg to Chicago. Data last updated August 25, 2026 and is based on user searches.
Discover last-minute flight deals from Williamsburg to Chicago. Data last updated August 25, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/23. 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.
Thu 8/276:07 am -
1 stop7h 08m
Sat 8/296:49 am -
1 stop4h 20m
Deal found 8/23![American Airlines logo]()
$559
This American Airlines deal was found by Cheapflights users on 8/23. 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.
Wed 9/26:59 pm -
1 stop5h 53m
Sat 9/58:54 am -
1 stop5h 22m
Deal found 8/23![American Airlines logo]()
$501
This American Airlines deal was found by Cheapflights users on 8/21. 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.
Sat 9/511:19 am -
1 stop6h 24m
Wed 9/96:29 am -
1 stop4h 32m
Deal found 8/21![American Airlines logo]()
$495
This American Airlines deal was found by Cheapflights users on 8/22. 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.
Sun 9/68:30 am -
2 stops6h 45m
Thu 9/105:20 am -
1 stop5h 41m
Deal found 8/22![American Airlines logo]()
$815
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/76:07 am -
1 stop7h 08m
Fri 9/115:20 am -
1 stop5h 41m
Deal found 8/21![American Airlines logo]()
$636
This American Airlines deal was found by Cheapflights users on 8/24. 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.
Tue 9/812:36 pm -
1 stop6h 06m
Sat 9/1211:48 am -
2 stops6h 03m
Deal found 8/24![American Airlines logo]()
$883
This American Airlines deal was found by Cheapflights users on 8/20. 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.
Thu 9/176:00 am -
1 stop7h 14m
Sun 9/205:18 am -
1 stop4h 15m
Deal found 8/20![American Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 8/21. 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.
Wed 9/306:00 am -
1 stop7h 14m
Thu 10/18:59 am -
1 stop5h 38m
Deal found 8/21![American Airlines logo]()
$419
One-way flights from Williamsburg to ChicagoSearch for one-way flight options from Williamsburg to Chicago. Find affordable one-way fares based on user searches. Data last updated August 25, 2026.
Search for one-way flight options from Williamsburg to Chicago. Find affordable one-way fares based on user searches. Data last updated August 25, 2026.
This American Airlines deal was found by Cheapflights users on 8/24. 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.
Fri 9/257:16 pm -
1 stop5h 43m
Deal found 8/24![American Airlines logo]()
$210
This American Airlines deal was found by Cheapflights users on 8/24. 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.
Thu 9/247:16 pm -
1 stop5h 43m
Deal found 8/24![American Airlines logo]()
$250
This American Airlines deal was found by Cheapflights users on 8/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:36 pm -
1 stop6h 06m
Deal found 8/25![American Airlines logo]()
$251
This American Airlines deal was found by Cheapflights users on 8/24. 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.
Sat 9/266:00 am -
2 stops10h 06m
Deal found 8/24![American Airlines logo]()
$555
Find flight deals from Williamsburg to Chicago
Keep the following information in mind while searching for Williamsburg to Chicago flight deals. Data was last updated August 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $419 (American Airlines) |
One-way from | $210 (American Airlines) |
Cheapflights Fare Finder
Customize your flight search to find flights from Williamsburg to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 25, 2026.
Use the filters below to find and compare flights from Williamsburg to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Newport NewsChicago
PHF Newport News Intl - ORD Chicago O'Hare Intl
PHFORD
Newport News Intl
Tue 10/13
1:00 pm-5:51 pm
1 stop5h 51m
Chicago O'Hare Intl
Thu 10/15
5:00 am-10:45 am
1 stop4h 45m
$419
Newport NewsChicago
PHF Newport News Intl - ORD Chicago O'Hare Intl
PHFORD
Newport News Intl
Fri 11/13
5:00 am-9:00 am
1 stop5h 00m
Chicago O'Hare Intl
Sun 11/15
9:00 am-4:13 pm
1 stop6h 13m
$419
Newport NewsChicago
PHF Newport News Intl - ORD Chicago O'Hare Intl
PHFORD
Newport News Intl
Fri 10/30
7:55 pm-12:08 am
1 stop5h 13m
Chicago O'Hare Intl
Sun 11/1
5:19 am-11:24 am
1 stop5h 05m
$419
Newport NewsChicago
PHF Newport News Intl - ORD Chicago O'Hare Intl
PHFORD
Newport News Intl
Tue 9/22
12:27 pm-5:38 pm
1 stop6h 11m
Chicago O'Hare Intl
Thu 9/24
8:05 am-3:37 pm
1 stop6h 32m
$429
Newport NewsChicago
PHF Newport News Intl - ORD Chicago O'Hare Intl
PHFORD
Newport News Intl
Thu 9/17
6:00 am-12:14 pm
1 stop7h 14m
Chicago O'Hare Intl
Sun 9/20
5:18 am-10:33 am
1 stop4h 15m
$429
Newport NewsChicago
PHF Newport News Intl - ORD Chicago O'Hare Intl
PHFORD
Newport News Intl
Sun 9/6
11:14 am-4:02 pm
1 stop5h 48m
Chicago O'Hare Intl
Thu 9/10
5:20 am-12:01 pm
1 stop5h 41m
$495
Quickest round-trip
Newport NewsChicago
PHF Newport News Intl - ORD Chicago O'Hare Intl
PHFORD
Newport News Intl
Thu 9/10
12:27 pm-4:00 pm
1 stop4h 33m
Chicago O'Hare Intl
Sun 9/13
5:18 am-10:33 am
1 stop4h 15m
$495
Newport NewsChicago
PHF Newport News Intl - ORD Chicago O'Hare Intl
PHFORD
Newport News Intl
Sat 9/5
11:19 am-4:43 pm
1 stop6h 24m
Chicago O'Hare Intl
Wed 9/9
6:29 am-12:01 pm
1 stop4h 32m
$495
Newport NewsChicago
PHF Newport News Intl - ORD Chicago O'Hare Intl
PHFORD
Newport News Intl
Sun 10/4
7:54 pm-11:59 pm
1 stop5h 05m
Chicago O'Hare Intl
Wed 10/14
12:05 pm-7:30 pm
1 stop6h 25m
$499
Newport NewsChicago
PHF Newport News Intl - ORD Chicago O'Hare Intl
PHFORD
Newport News Intl
Mon 10/5
4:33 pm-11:00 pm
1 stop7h 27m
Chicago O'Hare Intl
Fri 10/9
4:45 pm-12:23 am
1 stop6h 38m
$509
Showing 1-10 of 16 resultsSorted by cheapest first
Best time to book a flight from Williamsburg to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Williamsburg with our price prediction graph.
PHF-ORD
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 Williamsburg to Chicago
W11-CHI
PHF-ORD
What is the cheapest time of day to fly from W11 to CHI?
Find hourly flight availability from Williamsburg to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 25, 2026.
A simple way to save on the total cost of your ticket is to fly from Williamsburg to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 8% on your trip compared to booking a flight in the morning.
Weekly flight availability from Williamsburg to Chicago
Explore weekly flight availability from Williamsburg to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 25, 2026.
The most flights from W11 to CHI are scheduled on a Sunday (33 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (27 on average).
What is the cheapest day to fly from Williamsburg to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Williamsburg to Chicago. Price data was last updated on August 22, 2026.
Travelers seeking maximum savings on their Williamsburg to Chicago flight should consider departing on Saturday at noon when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Williamsburg to Chicago. 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?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Alternative routes for Williamsburg to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 25, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Williamsburg to Chicago by cabin class
Find flights from Williamsburg to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Williamsburg and Chicago flights
Browse other Williamsburg and Chicago flight options. Last updated on August 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Williamsburg to Chicago
Discover the top 6 airlines that operate flights from Williamsburg to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$72 | Average$369 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$126 | Average$352 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$178 | Average$399 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$251 | Average$393 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$253 | Average$442 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$260 | Average$260 | FlexibilityNo cancel fee | On-timeN/A |