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$72+ 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 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
PHL — CHI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheapflights Tip: The best prices from Philadelphia to Chicago are usually found in September or October, booked 69 days in advance, depart on a Friday or Thursday and return on a Thursday

Cheap 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 September 17, 2025.

Round-trip from

$111
(Kiwi.com)

One-way from

$72
(Priceline)

Popular in

March

Cheapest in

September

Average price

$177

Good round-trip deal

$171 or less

Good one-way deal

$132 or less
From Philadelphia to Chicago (CHI)
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One-way flight from Philadelphia to Chicago (CHI)
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Highest demand for flights based on searches. 17% potential increase in price ($55 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Philadelphia to Chicago (CHI).
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Price to beat on a one-way flight from Philadelphia to Chicago (CHI).
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Find 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 September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/204:13 pmPHL - MDW
Nonstop2h 14mFrontier
Sun 11/28:32 amMDW - PHL
Nonstop2h 02mFrontier
Deal found 9/17$111
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/234:10 pmPHL - ORD
Nonstop2h 30mFrontier
Sat 10/252:45 pmORD - PHL
Nonstop2h 15mFrontier
Deal found 9/15$112
This CheapOair deal was found by Cheapflights users on 9/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/126:10 amPHL - MDW
Nonstop2h 15mFrontier
Sun 10/268:25 amMDW - PHL
Nonstop2h 02mFrontier
Deal found 9/17$112
This Priceline deal was found by Cheapflights users on 9/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/236:37 pmPHL - MDW
1 stop6h 09mFrontier
Fri 10/319:15 amMDW - PHL
Nonstop2h 04mFrontier
Deal found 9/17$113
This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/117:10 pmPHL - ORD
Nonstop2h 38mFrontier
Fri 10/178:44 amORD - PHL
1 stop15h 23mFrontier
Deal found 9/15$114
This Flightnetwork deal was found by Cheapflights users on 9/16. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/311:19 pmPHL - MDW
Nonstop2h 14mFrontier
Fri 11/712:14 pmMDW - PHL
Nonstop2h 00mFrontier
Deal found 9/16$114
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/89:14 pmPHL - ORD
1 stop12h 00mFrontier
Thu 10/96:50 pmORD - PHL
Nonstop2h 20mFrontier
Deal found 9/15$115
This Priceline deal was found by Cheapflights users on 9/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/164:10 pmPHL - ORD
Nonstop2h 30mFrontier
Fri 10/1711:50 amORD - PHL
Nonstop2h 09mFrontier
Deal found 9/16$116
This CheapOair deal was found by Cheapflights users on 9/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/166:10 amPHL - MDW
Nonstop2h 15mFrontier
Mon 10/2012:13 pmMDW - PHL
Nonstop2h 00mFrontier
Deal found 9/16$116
This Priceline deal was found by Cheapflights users on 9/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/166:10 amPHL - MDW
Nonstop2h 15mFrontier
Fri 10/175:28 pmMDW - PHL
1 stop6h 39mFrontier
Deal found 9/16$117
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2510:21 amPHL - ORD
Nonstop2h 37mFrontier
Thu 9/258:49 pmORD - PHL
1 stop9h 46mFrontier
Deal found 9/15$118
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/56:00 amPHL - MDW
Nonstop2h 11mFrontier
Thu 10/168:25 amMDW - PHL
Nonstop2h 02mFrontier
Deal found 9/16$119

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 September 17, 2025.
Use the filters below to find and compare flights from Philadelphia to Chicago that are best for you.

Fly from

Philadelphia

Fly to

Chicago

Route

Depart

Return

Price

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Sat 10/18

1:05 pm-2:27 pm

Nonstop2h 22m

Chicago O'Hare Intl

Tue 10/21

8:45 am-11:56 am

Nonstop2h 11m

$139

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Sat 11/1

5:10 pm-6:15 pm

Nonstop2h 05m

Chicago Midway

Tue 11/4

11:05 am-2:00 pm

Nonstop1h 55m

$139

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Tue 10/28

12:22 pm-1:43 pm

Nonstop2h 21m

Chicago O'Hare Intl

Wed 10/29

9:15 pm-12:15 am

Nonstop2h 00m

$139

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Fri 10/10

4:19 pm-3:45 pm

1 stop24h 26m

Chicago O'Hare Intl

Sat 10/18

8:40 am-5:35 pm

1 stop7h 55m

$144

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Mon 10/20

8:35 pm-9:45 pm

Nonstop2h 10m

Chicago Midway

Wed 10/22

2:50 pm-5:45 pm

Nonstop1h 55m

$158

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Fri 10/31

6:00 am-7:25 am

Nonstop2h 25m

Chicago O'Hare Intl

Sat 11/1

6:13 pm-9:21 pm

Nonstop2h 08m

$158

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Wed 10/8

10:05 am-11:27 am

Nonstop2h 22m

Chicago O'Hare Intl

Sat 10/11

6:17 pm-9:28 pm

Nonstop2h 11m

$159

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Thu 11/27

10:05 am-11:25 am

Nonstop2h 20m

Chicago O'Hare Intl

Tue 12/2

9:00 am-12:07 pm

Nonstop2h 07m

$169

PhiladelphiaChicago

PHL - MDW

PHLMDW

Philadelphia

Mon 11/10

12:35 pm-1:45 pm

Nonstop2h 10m

Chicago Midway

Thu 11/13

11:45 am-2:40 pm

Nonstop1h 55m

$177

PhiladelphiaChicago

PHL - ORD

PHLORD

Philadelphia

Fri 10/31

6:00 am-7:25 am

Nonstop2h 25m

Chicago O'Hare Intl

Sun 11/2

7:25 am-10:24 am

Nonstop1h 59m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 58 results
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The best insider tips for Philadelphia to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Philadelphia to Chicago trip
Airlines
Frontier

Frontier's UpFront Plus seats guarantee an empty middle seat for added comfort.


Frontier offers Zone 1 boarding with a carry-on purchase or special fare bundle.

Read more about Frontierby Marisa Garcia
Southwest

Southwest offers free snacks and non-alcoholic beverages during flights.


Southwest's open seating policy allows you to choose any available seat upon boarding.

Read more about Southwestby Marisa Garcia
United Airlines

Basic Economy on United allows a personal item only; no carry-on bags permitted.


United Economy Plus offers extra legroom seats towards the front of the economy cabin.

Read more about United Airlinesby Harriet Baskas
Airports
PHL

For quick access to Center City, use SEPTA's Airport Line. It's efficient and operates from 5:00 a.m. to midnight.

Read more about PHLby Mark Chesnut
ORD

Use the 'L' train for a reliable trip from ORD to downtown Chicago, avoiding traffic delays.

Read more about ORDby Ramsey Qubein
MDW

The Orange Line train from MDW takes less than 30 minutes to reach downtown Chicago.

Read more about MDWby Ramsey Qubein
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Frontier and Southwest

Marisa Garcia

Marisa Garcia

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 Baskas

Harriet Baskas

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

Ramsey Qubein

Ramsey Qubein

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

Mark Chesnut

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

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

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

Use this chart to determine the optimal time to book a round-trip flight from Philadelphia to Chicago. Price data was last updated on September 12, 2025.

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 69 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, August is the cheapest month in which you can book a flight from Philadelphia to Chicago (average of $245). Flying from Philadelphia to Chicago in March is currently the most expensive (average of $321). 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 September 17, 2025.

It’s optimal to fly from Philadelphia to Chicago in the evening. By choosing this option you can save up to 38% on the cost of your flight, compared to a flight in the morning.

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 September 14, 2025.

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

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 September 17, 2025.

The most flights from PHL to CHI are scheduled on a Monday (56 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 on average).

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

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 September 17, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, and American 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
8.0
Very good
4,242 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,173 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 48 outbound flights to Chicago per day from 6 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 05m. There are 666 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 $61 on this airline. Additional options worth looking into are Spirit Airlines and Delta, starting at $83 and $118 round-trip. You may be able to fly from Philadelphia to Chicago for 75% 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 $75. However, be on the lookout for offers from Southwest and Delta, 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 SWISS (90%), ANA (87%) and Air Canada (74%).

  • What are the cheapest flights from Philadelphia to Chicago?

    The cheapest flight price from Philadelphia to Chicago is $79. On average you can expect to pay $843. The most popular route, (Philadelphia - Chicago O'Hare Intl), can usually be booked for $129.

  • 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, August is the cheapest month in which you can book a flight from Philadelphia to Chicago (average of $245). Flying from Philadelphia to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Philadelphia to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
LaGuardia to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Philadelphia to O'Hare Intl flights
Newark to Midway flights
LaGuardia to Midway flights
Dulles Intl to Midway flights
Philadelphia to Midway flights
Reagan-National to Midway flights
LaGuardia to St. Louis flights
Newark to St. Louis flights
John F Kennedy Intl to St. Louis flights
Dulles Intl to St. Louis flights
Reagan-National to St. Louis flights
Pittsburgh to O'Hare Intl flights
Philadelphia to St. Louis flights
Scranton to O'Hare Intl flights
Allentown to O'Hare Intl flights
Harrisburg to O'Hare Intl flights
Pittsburgh to Midway flights
Allentown to Midway flights
State College to O'Hare Intl flights
Harrisburg to Midway flights
Harrisburg to St. Louis flights
Pittsburgh to St. Louis flights
Newark to Rockford flights
LaGuardia to Moline flights
Elmira to O'Hare Intl flights
John F Kennedy Intl to Moline flights
Newark to Moline flights
Reagan-National to Peoria flights
Dulles Intl to Moline flights
Dulles Intl to Peoria flights
Elmira to Midway flights
Reagan-National to Moline flights
LaGuardia to Evansville flights
Philadelphia to Moline flights
LaGuardia to Peoria flights
State College to St. Louis flights
Scranton to St. Louis flights
John F Kennedy Intl to Evansville flights
Newark to Evansville flights
Newark to Bloomington flights
John F Kennedy Intl to Bloomington flights
Newark to Peoria flights
LaGuardia to Bloomington flights
Elmira to St. Louis flights

Top 6 airlines flying from Philadelphia to Chicago

Discover the top 6 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$61Average$166FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$83Average$185FlexibilityNo cancel feeOn-time65%
DeltaCheapest$118Average$277FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$157Average$367FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$163Average$307FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$167Average$301FlexibilityNo cancel feeOn-time63%

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