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$102+ Cheap flights from Philadelphia (PHL) 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 8/8. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — CHI
Aug 11 — Aug 181
Tue 8/11
Tue 8/18
1 adult, Economy
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Find cheap flights from Philadelphia to Chicago with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Philadelphia to Chicago are usually found in January or September, booked 66 days in advance, depart on a Friday or Thursday and return on a Friday

Cheap flight deals from Philadelphia to Chicago

Cheapest flights from Philadelphia to Chicago
Explore the most affordable flight options available from Philadelphia to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 12, 2026.

This Frontier deal was found by Cheapflights users on 7/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:30 am
PHL
-
ORD
1 stop12h 29m
Frontier
Sun 9/66:00 am
ORD
-
PHL
Nonstop2h 17m
Frontier
Deal found 7/9$213
This Southwest deal was found by Cheapflights users on 7/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:15 am
PHL
-
MDW
2 stops9h 10m
Southwest
Tue 8/2512:35 pm
MDW
-
PHL
2 stops8h 15m
Southwest
Deal found 7/9$213
This Frontier deal was found by Cheapflights users on 7/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:05 pm
PHL
-
ORD
Nonstop2h 42m
Frontier
Mon 8/108:58 pm
ORD
-
PHL
Nonstop2h 23m
Frontier
Deal found 7/12$214
This Southwest deal was found by Cheapflights users on 7/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:35 pm
PHL
-
MDW
1 stop4h 20m
Southwest
Mon 8/319:20 am
MDW
-
PHL
2 stops11h 40m
Southwest
Deal found 7/9$214
This Kiwi.com deal was found by Cheapflights users on 7/10. 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.
Wed 9/28:35 am
PHL
-
ORD
2 stops12h 33m
Frontier
Tue 9/81:59 pm
ORD
-
PHL
1 stop7h 34m
Frontier
Deal found 7/10$215
This Kiwi.com deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/31:32 pm
PHL
-
MDW
1 stop9h 31m
Frontier
Fri 8/711:06 am
MDW
-
PHL
1 stop7h 14m
Frontier
Deal found 7/10$215
This Kiwi.com deal was found by Cheapflights users on 7/11. 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 8/286:00 am
PHL
-
ORD
Nonstop2h 29m
Frontier
Sun 8/301:59 pm
ORD
-
PHL
1 stop7h 34m
Frontier
Deal found 7/11$216
This Southwest deal was found by Cheapflights users on 7/10. 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 8/277:10 am
PHL
-
MDW
2 stops7h 35m
Southwest
Thu 8/272:55 pm
MDW
-
PHL
Nonstop2h 00m
Southwest
Deal found 7/10$216
This Kiwi.com deal was found by Cheapflights users on 7/12. 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.
Thu 9/32:45 pm
PHL
-
ORD
1 stop6h 14m
Frontier
Wed 9/92:03 pm
ORD
-
PHL
1 stop8h 08m
Frontier
Deal found 7/12$217
This Kiwi.com deal was found by Cheapflights users on 7/12. 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.
Thu 9/32:45 pm
PHL
-
MDW
1 stop9h 02m
Frontier
Sat 9/511:45 am
MDW
-
PHL
1 stop7h 43m
Frontier
Deal found 7/12$217
This Kiwi.com deal was found by Cheapflights users on 7/12. 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 9/42:45 pm
PHL
-
ORD
1 stop6h 14m
Frontier
Sat 9/51:59 pm
ORD
-
PHL
1 stop7h 34m
Frontier
Deal found 7/12$218
This American Airlines deal was found by Cheapflights users on 7/9. 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.
Sat 8/293:25 pm
PHL
-
ORD
1 stop4h 29m
American Airlines
Mon 8/314:00 pm
ORD
-
PHL
Nonstop2h 19m
American Airlines
Deal found 7/9$219

Find flight deals from Philadelphia to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Philadelphia (PHL) 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 July 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$213
(Frontier)

One-way from

$102
(Delta)

Popular in

June

Cheapest in

January

Average price

$302

Good round-trip deal

$326 or less

Good one-way deal

$159 or less
Provider with most accurate pricing for Philadelphia-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Philadelphia-Chicago (CHI) flights.
Search Deals
From Philadelphia to Chicago (CHI)
Search Deals
One-way flight from Philadelphia to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Philadelphia to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Philadelphia to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Philadelphia 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 2,558,603 searches. Data last updated July 12, 2026.
Use the filters below to find and compare flights from Philadelphia to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Thu 10/1

6:30 am-12:40 pm

1 stop7h 10m

Chicago O'Hare Intl

Thu 10/1

6:25 pm-12:41 am

1 stop5h 16m

$229

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 11/6

3:40 pm-10:25 pm

1 stop7h 45m

Chicago Midway

Mon 11/9

5:25 pm-12:51 am

1 stop6h 26m

$229

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 8/14

4:05 pm-11:45 pm

1 stop8h 40m

Chicago Midway

Tue 8/18

12:35 pm-9:50 pm

2 stops8h 15m

$235

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Wed 8/5

1:45 pm-2:50 pm

Nonstop2h 05m

Chicago Midway

Sat 8/8

8:10 am-11:15 am

Nonstop2h 05m

$235
Quickest round-trip

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 8/6

10:20 am-11:25 am

Nonstop2h 05m

Chicago Midway

Mon 8/10

9:30 am-12:25 pm

Nonstop1h 55m

$257

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Sat 9/19

8:05 am-9:10 am

Nonstop2h 05m

Chicago Midway

Mon 9/21

9:30 am-12:25 pm

Nonstop1h 55m

$257

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 8/14

12:45 pm-1:45 pm

Nonstop2h 00m

Chicago Midway

Thu 8/20

1:00 pm-4:00 pm

Nonstop2h 00m

$258

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Thu 9/3

2:05 pm-3:10 pm

Nonstop2h 05m

Chicago Midway

Sat 9/5

8:05 am-1:30 pm

1 stop4h 25m

$267

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Fri 8/28

7:10 am-1:45 pm

2 stops7h 35m

Chicago Midway

Sat 8/29

7:40 am-4:10 pm

2 stops7h 30m

$271

PhiladelphiaChicago

PHL - RFD

PHLRFD

Philadelphia

Wed 8/5

4:30 pm-10:47 am

2 stops19h 17m

Chicago Greater Rockford

Sun 8/9

11:37 am-12:43 am

1 stop12h 06m

$285

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/8

Showing 1-10 of 60 resultsSorted by cheapest first
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6

Compare providers for flights from Philadelphia to Chicago

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 Philadelphia to Chicago in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars
Super.comPrice Accuracy-Trust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
BudgetAirPrice Accuracy2 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Philadelphia-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Philadelphia-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Philadelphia-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Philadelphia-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 Philadelphia-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 Philadelphia to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Philadelphia with our price prediction graph.
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 Philadelphia to Chicago

What is the cheapest month to book a flight from Philadelphia to Chicago?

Currently, February is the cheapest month in which you can book a flight from Philadelphia to Chicago (average of $40). Flying from Philadelphia to Chicago in January is currently the most expensive (average of $899). 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 PHL to CHI?

Find hourly flight availability from Philadelphia 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 July 12, 2026.

It’s optimal to fly from Philadelphia to Chicago in the evening. By choosing this option you can save up to 15% on the cost of your flight, compared to a flight in the morning.

Weekly flight availability from Philadelphia to Chicago

Explore weekly flight availability from Philadelphia 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 July 12, 2026.

The most flights from PHL to CHI are scheduled on a Friday (61 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (40 on average).

How much does it cost to fly round-trip from Philadelphia to Chicago?

How often are flights from Philadelphia to Chicago delayed?

About 18% of weekly flights between Philadelphia and Chicago have experienced delays in the past year, with the average delay time being 144 minutes.

What is the most punctual flight time for Philadelphia to Chicago flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Saturday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Philadelphia to Chicago flights?

Over the last year, United Airlines have had the lowest number of delays on this route, with just 10% of flights being delayed.

How far ahead should I book a flight from Philadelphia to Chicago?

The price you pay for your flight from Philadelphia to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 64 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest day to fly from Philadelphia to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Philadelphia to Chicago. Price data was last updated on July 4, 2026.

Travelers seeking maximum savings on their Philadelphia to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

The best insider tips for Philadelphia to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Philadelphia to Chicago trip
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Frontier and Southwest

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Mark Chesnut

Mark Chesnut

Expert on PHL

Mark Chesnut is a travel writer and public speaker with more than 30 years of experience. The 2019 winner of the NLGJA Excellence in Travel Writing Award, Mark is the author of the book “Prepare for Departure” and has covered air travel for multiple top consumer and trade media outlets.

Read more

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 July 12, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines from Philadelphia to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,251 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
7.9
Good
4,251 reviews
Southwest
7.9
Good
4,251 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Delta
7.8
Good
8,458 reviews
Southwest
7.9
Good
4,251 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
9,980 reviews
Southwest
7.9
Good
4,251 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,804 reviews
Southwest
7.9
Good
4,251 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Frontier
5.6
Fair
2,824 reviews
Southwest
7.9
Good
4,251 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

Related info for your journey

Find useful and relevant information for your journey from Philadelphia to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Philadelphia to Chicago?

    Most people fly from Philadelphia (PHL) if they book a flight from Philadelphia to Chicago. On average, Philadelphia has 49 outbound flights to Chicago per day from 5 airlines. Philadelphia is conveniently located just 7.0 mi from Philadelphia’s city center.

  • How long is the flight from Philadelphia to Chicago?

    Departing from Philadelphia to Chicago will take you 2h 30m. There are 676 mi between Philadelphia and Chicago. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Philadelphia to Chicago round-trip?

    Our cheapest airline available from Philadelphia to Chicago is Frontier. Our recent data shows that you can find tickets from as low as $77 on this airline. Additional options worth looking into are Delta and Southwest, starting at $133 and $158 round-trip. You may be able to fly from Philadelphia to Chicago for 72% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Philadelphia to Chicago one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $39. However, be on the lookout for offers from American Airlines and United Airlines, as they are both options that can get you from Philadelphia to Chicago for a low price.

  • What are the most popular routes from Philadelphia to Chicago?

    Most travelers choose Philadelphia - Chicago O'Hare Intl, Philadelphia - Chicago Midway or Philadelphia - Chicago Greater Rockford when deciding on the best route from Philadelphia to Chicago.

  • What are the most reliable airlines from Philadelphia to Chicago?

    The top 3 most reliable airlines when flying from Philadelphia to Chicago are Republic Airways (100%), SWISS (90%) and ANA (88%).

  • What are the cheapest flights from Philadelphia to Chicago?

    The cheapest flight price from Philadelphia to Chicago is $96. On average you can expect to pay $817. The most popular route, (Philadelphia - Chicago O'Hare Intl), can usually be booked for $91.

  • Can I find deals for flights from Philadelphia to Chicago that include hotel bookings?

    Yes. In addition to deals on Philadelphia to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Philadelphia to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Philadelphia to Chicago.

  • Can I find deals for business class flights from Philadelphia to Chicago?

    Yes. Cheapflights offers flight deals from Philadelphia to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Philadelphia to Chicago?

    Currently, February is the cheapest month in which you can book a flight from Philadelphia to Chicago (average of $40). Flying from Philadelphia to Chicago in January is currently the most expensive (average of $899). 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.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Hammond
Lansing
Merrillville
Valparaiso
Porter

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Top 5 airlines flying from Philadelphia to Chicago

Discover the top 5 airlines that operate flights from Philadelphia 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 2,558,603 searches. Data last updated July 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$77Average$175FlexibilityNo cancel feeOn-time62%
DeltaCheapest$133Average$266FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$158Average$352FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$162Average$325FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$164Average$345FlexibilityNo cancel feeOn-time69%

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