$209+ Cheap flights from Charlottesville (CHO) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHO — CHI
Nov 19 — Nov 261
Round-trip
1 adult, Economy
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Find cheap flights from Charlottesville 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
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 Charlottesville to Chicago
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Best
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One-way
Cheapest flights from Charlottesville to ChicagoExplore the most affordable flight options available from Charlottesville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2026.
Explore the most affordable flight options available from Charlottesville to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2026.
This American Airlines deal was found by Cheapflights users on 10/16. 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 11/267:11 am -
Nonstop2h 09m
Thu 12/32:48 pm -
Nonstop2h 02m
Deal found 10/16![American Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 10/17. 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 12/16:48 pm -
Nonstop2h 10m
Tue 12/82:45 pm -
Nonstop2h 05m
Deal found 10/17![American Airlines logo]()
$340
This United Airlines deal was found by Cheapflights users on 10/17. 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.
Tue 11/246:15 am -
1 stop6h 23m
Tue 12/110:25 am -
Nonstop2h 04m
Deal found 10/17![United Airlines logo]()
$362
This American Airlines deal was found by Cheapflights users on 10/19. 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 11/66:42 pm -
Nonstop2h 10m
Wed 11/115:19 am -
1 stop5h 27m
Deal found 10/19![American Airlines logo]()
$369
This United Airlines deal was found by Cheapflights users on 10/15. 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.
Tue 11/246:15 am -
1 stop6h 23m
Mon 11/306:55 am -
Nonstop2h 07m
Deal found 10/15![United Airlines logo]()
$377
This Delta deal was found by Cheapflights users on 10/19. 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 11/62:30 pm -
1 stop7h 13m
Wed 11/115:30 am -
1 stop7h 21m
Deal found 10/19![Delta logo]()
$379
This American Airlines deal was found by Cheapflights users on 10/17. 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 11/247:11 am -
Nonstop2h 09m
Tue 12/18:45 pm -
Nonstop2h 10m
Deal found 10/17![American Airlines logo]()
$380
Best flights from Charlottesville to ChicagoDiscover carefully curated flight deals from Charlottesville to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 20, 2026.
Discover carefully curated flight deals from Charlottesville to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 20, 2026.
This United Airlines deal was found by Cheapflights users on 10/16. 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.
Sat 3/278:15 pm -
1 stop4h 09m
Wed 3/312:00 pm -
Nonstop1h 58m
Deal found 10/16![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 10/18. 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 12/102:36 pm -
1 stop5h 49m
Mon 12/145:30 am -
1 stop4h 42m
Deal found 10/18![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 10/18. 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.
Thu 1/142:15 pm -
Nonstop2h 15m
Mon 1/188:40 am -
1 stop4h 07m
Deal found 10/18![United Airlines logo]()
$349
This United Airlines deal was found by Cheapflights users on 10/18. 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.
Sat 10/316:42 am -
Nonstop2h 11m
Wed 11/42:10 pm -
Nonstop2h 04m
Deal found 10/18![United Airlines logo]()
$414
This United Airlines deal was found by Cheapflights users on 10/14. 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.
Thu 11/56:46 am -
Nonstop2h 11m
Mon 11/96:55 am -
Nonstop2h 07m
Deal found 10/14![United Airlines logo]()
$439
This United Airlines deal was found by Cheapflights users on 10/16. 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.
Wed 11/183:15 pm -
1 stop4h 39m
Sun 11/228:50 am -
1 stop4h 05m
Deal found 10/16![United Airlines logo]()
$459
This United Airlines deal was found by Cheapflights users on 10/15. 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.
Fri 10/306:46 am -
Nonstop2h 11m
Sun 11/110:25 am -
Nonstop2h 03m
Deal found 10/15![United Airlines logo]()
$479
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Thu 10/298:05 pm -
1 stop4h 56m
Wed 11/46:04 am -
1 stop6h 51m
Deal found 10/19![United Airlines logo]()
$534
This United Airlines deal was found by Cheapflights users on 10/15. 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.
Thu 12/1010:35 am -
2 stops10h 35m
Mon 12/148:52 am -
1 stop4h 03m
Deal found 10/15![United Airlines logo]()
$543
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Tue 11/248:05 pm -
1 stop4h 56m
Fri 11/277:50 pm -
2 stops17h 05m
Deal found 10/19![United Airlines logo]()
$543
Last-minute flights from Charlottesville to ChicagoDiscover last-minute flight deals from Charlottesville to Chicago. Data last updated October 20, 2026 and is based on user searches.
Discover last-minute flight deals from Charlottesville to Chicago. Data last updated October 20, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/15. 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.
Tue 10/276:46 am -
Nonstop2h 11m
Thu 10/2910:25 am -
Nonstop2h 03m
Deal found 10/15![United Airlines logo]()
$746
This American Airlines deal was found by Cheapflights users on 10/16. 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 10/281:13 pm -
1 stop5h 38m
Sat 10/315:00 am -
1 stop6h 48m
Deal found 10/16![American Airlines logo]()
$434
This United Airlines deal was found by Cheapflights users on 10/18. 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.
Wed 10/282:03 pm -
Nonstop2h 16m
Sat 10/316:55 am -
Nonstop2h 05m
Deal found 10/18![United Airlines logo]()
$449
This Delta deal was found by Cheapflights users on 10/16. 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 10/286:00 am -
2 stops9h 36m
Sat 10/315:27 am -
1 stop4h 47m
Deal found 10/16![Delta logo]()
$614
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Thu 10/2910:59 am -
1 stop4h 39m
Wed 11/410:25 am -
Nonstop2h 03m
Deal found 10/19![United Airlines logo]()
$524
One-way flights from Charlottesville to ChicagoSearch for one-way flight options from Charlottesville to Chicago. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
Search for one-way flight options from Charlottesville to Chicago. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
This United Airlines deal was found by Cheapflights users on 10/18. 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.
Fri 11/276:35 am -
Nonstop2h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![United Airlines logo]()
$209
This American Airlines deal was found by Cheapflights users on 10/16. 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 12/166:20 pm -
Nonstop2h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![American Airlines logo]()
$289
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Sat 12/266:30 am -
Nonstop2h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![United Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 10/16. 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 12/268:00 pm -
1 stop4h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 10/15. 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 12/166:00 am -
2 stops8h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 10/17. 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 11/167:00 am -
2 stops7h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Delta logo]()
$384
This Delta deal was found by Cheapflights users on 10/15. 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 11/62:30 pm -
2 stops7h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Delta logo]()
$395
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Thu 4/810:30 am -
2 stops5h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![United Airlines logo]()
$445
Find flight deals from Charlottesville to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Charlottesville (CHO) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $339 (American Airlines) |
One-way from | $209 (United Airlines) |
Popular in | October |
Cheapest in | January |
Average price | $561 |
Good round-trip deal | $385 or less |
Good one-way deal | $362 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Charlottesville 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 October 20, 2026.
Use the filters below to find and compare flights from Charlottesville to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
CharlottesvilleChicago
CHO Charlottesville Albemarle - ORD Chicago O'Hare Intl
CHOORD
Charlottesville Albemarle
Mon 11/16
10:59 am-5:00 pm
1 stop7h 01m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$299
CharlottesvilleChicago
CHO Charlottesville Albemarle - ORD Chicago O'Hare Intl
CHOORD
Charlottesville Albemarle
Fri 11/6
2:40 pm-9:39 pm
1 stop7h 59m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$299
CharlottesvilleChicago
CHO Charlottesville Albemarle - ORD Chicago O'Hare Intl
CHOORD
Charlottesville Albemarle
Sat 12/26
6:30 am-7:45 am
Nonstop2h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$339
Quickest round-trip
CharlottesvilleChicago
CHO Charlottesville Albemarle - ORD Chicago O'Hare Intl
CHOORD
Charlottesville Albemarle
Thu 4/8
8:35 am-9:45 am
Nonstop2h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$339
CharlottesvilleChicago
CHO Charlottesville Albemarle - ORD Chicago O'Hare Intl
CHOORD
Charlottesville Albemarle
Sat 12/26
8:00 pm-11:59 pm
1 stop4h 59m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$349
CharlottesvilleChicago
CHO Charlottesville Albemarle - ORD Chicago O'Hare Intl
CHOORD
Charlottesville Albemarle
Sat 3/27
8:15 pm-11:24 pm
1 stop4h 09m
Chicago O'Hare Intl
Wed 3/31
2:00 pm-4:58 pm
Nonstop1h 58m
$349
CharlottesvilleChicago
CHO Charlottesville Albemarle - ORD Chicago O'Hare Intl
CHOORD
Charlottesville Albemarle
Thu 1/14
2:15 pm-3:30 pm
Nonstop2h 15m
Chicago O'Hare Intl
Mon 1/18
8:40 am-1:47 pm
1 stop4h 07m
$349
CharlottesvilleChicago
CHO Charlottesville Albemarle - ORD Chicago O'Hare Intl
CHOORD
Charlottesville Albemarle
Thu 12/10
2:36 pm-7:25 pm
1 stop5h 49m
Chicago O'Hare Intl
Mon 12/14
5:30 am-11:12 am
1 stop4h 42m
$359
CharlottesvilleChicago
CHO Charlottesville Albemarle - ORD Chicago O'Hare Intl
CHOORD
Charlottesville Albemarle
Sat 10/31
6:42 am-7:53 am
Nonstop2h 11m
Chicago O'Hare Intl
Wed 11/4
2:10 pm-5:14 pm
Nonstop2h 04m
$414
CharlottesvilleChicago
CHO Charlottesville Albemarle - ORD Chicago O'Hare Intl
CHOORD
Charlottesville Albemarle
Thu 11/5
6:46 am-7:57 am
Nonstop2h 11m
Chicago O'Hare Intl
Mon 11/9
6:55 am-10:02 am
Nonstop2h 07m
$439
Showing 1-10 of 15 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on Charlottesville-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Charlottesville-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Charlottesville-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Charlottesville-Chicago 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 Charlottesville-Chicago 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 Charlottesville to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Charlottesville with our price prediction graph.
CHO-CHI
CHO-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 Charlottesville to Chicago
CHO-CHI
CHO-ORD
What is the cheapest month to book a flight from Charlottesville to Chicago?
Currently, November is the cheapest month in which you can book a flight from Charlottesville to Chicago (average of $292). Flying from Charlottesville to Chicago in October is currently the most expensive (average of $549). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHO to CHI?
Find hourly flight availability from Charlottesville 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 October 20, 2026.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 15% on flights from Charlottesville to Chicago by exploring options for tickets at noon.
How much does it cost to fly round-trip from Charlottesville to Chicago?
Airfare is typical for this route at the moment.
Charlottesville to Chicago flights typically cost between $312 and $473 in November.The cheapest round-trip price found within the last 5 days was $339 on American Airlines (Nov 26-Dec 3).
How far ahead should I book a flight from Charlottesville to Chicago?
To ensure you get the cheapest price possible for a flight from Charlottesville to Chicago, you should look to book at least 28 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated October 20, 2026.
Peruse reviews from past customers who have flown with United Airlines and American Airlines from Charlottesville to Chicago 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.
Boarding
7.7
Food
6.7
Crew
8.1
Overall
7.3
Comfort
7.3
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Boarding
7.7
Food
6.7
Crew
8.1
Overall
7.3
Comfort
7.3
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Boarding
7.7
Food
6.7
Crew
8.1
Overall
7.3
Comfort
7.3
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Related info for your journey
Find useful and relevant information for your journey from Charlottesville 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
Merrillville
Lansing
Valparaiso
Hammond
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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 October 20, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
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Charlottesville and Chicago flights
Browse other Charlottesville and Chicago flight options. Last updated on October 20, 2026.
Other flights from Charlottesville
Browse through other flights departing from Charlottesville. Flights are based on user searches made on Cheapflights and were last updated on October 20, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Charlottesville to Chicago
Discover the top 2 airlines that operate flights from Charlottesville 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 October 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$418 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$288 | Average$417 | FlexibilityNo cancel fee | On-time71% |