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$73+ Cheap flights from Washington, D.C. (WAS) 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 7/2. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Washington, D.C. to Chicago are usually found in September or January, booked 90 days in advance, depart on a Friday or Thursday and return on a Friday

Cheap flight deals from Washington, D.C. to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Washington, D.C. (WAS) 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 June 12, 2025.

Round-trip from

$118
(Kiwi.com)

One-way from

$73
(FlightHub)

Popular in

April

Cheapest in

September

Average price

$267

Good round-trip deal

$154 or less

Good one-way deal

$79 or less
From Washington, D.C. (WAS) to Chicago (CHI)
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One-way flight from Washington, D.C. (WAS) to Chicago (CHI)
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Highest demand for flights based on searches. 6% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Washington, D.C. (WAS) to Chicago (CHI).
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Price to beat on a one-way flight from Washington, D.C. (WAS) to Chicago (CHI).
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Find flight deals from Washington, D.C. to Chicago

Cheapest flights from Washington, D.C. to Chicago
Explore the most affordable flight options available from Washington, D.C. to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Wed 7/28:25 amBWI - ORD
1 stop11h 19mSpirit Airlines
Thu 7/104:37 pmORD - BWI
Nonstop1h 54mSpirit Airlines
Deal found 6/11$118
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Thu 8/147:38 amBWI - ORD
Nonstop2h 00mMultiple Airlines
Mon 8/187:45 amORD - BWI
Nonstop2h 06mMultiple Airlines
Deal found 6/10$120
This Cheapflightsfares deal was found by Cheapflights users on 6/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/66:31 pmBWI - MDW
Nonstop2h 05mFrontier
Mon 8/1112:50 pmMDW - BWI
Nonstop1h 56mFrontier
Deal found 6/12$122
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1910:58 pmBWI - ORD
Nonstop2h 16mFrontier
Mon 9/227:10 pmORD - BWI
Nonstop2h 03mFrontier
Deal found 6/11$125
This Southwest deal was found by Cheapflights users on 6/10. 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.
Wed 8/136:40 amBWI - MDW
Nonstop2h 00mSouthwest
Wed 8/1311:45 amMDW - BWI
Nonstop1h 50mSouthwest
Deal found 6/10$139
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2310:35 amBWI - ORD
Nonstop2h 15mSouthwest
Sat 8/231:30 pmORD - BWI
Nonstop2h 00mSouthwest
Deal found 6/11$139
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/146:15 amBWI - ORD
Nonstop2h 15mUnited Airlines
Tue 8/1910:45 amORD - BWI
Nonstop2h 03mUnited Airlines
Deal found 6/11$148
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/276:00 amDCA - MDW
Nonstop2h 00mSouthwest
Tue 10/287:40 amMDW - DCA
1 stop4h 10mSouthwest
Deal found 6/11$163
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/146:25 amDCA - ORD
Nonstop2h 14mUnited Airlines
Tue 8/198:50 amORD - DCA
1 stop4h 32mUnited Airlines
Deal found 6/11$167
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/272:15 pmDCA - ORD
Nonstop2h 13mAmerican Airlines
Sun 8/316:06 amORD - DCA
Nonstop1h 54mAmerican Airlines
Deal found 6/10$168
This United Airlines deal was found by Cheapflights users on 6/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/285:10 pmIAD - ORD
Nonstop2h 15mUnited Airlines
Sun 8/3110:43 amORD - IAD
Nonstop2h 06mUnited Airlines
Deal found 6/12$168
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/132:10 pmDCA - ORD
1 stop8h 20mSouthwest
Wed 8/203:10 pmORD - DCA
1 stop6h 50mSouthwest
Deal found 6/11$177

Cheapflights Fare Finder

Customize your flight search to find flights from Washington, D.C. 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 June 12, 2025.
Use the filters below to find and compare flights from Washington, D.C. to Chicago that are best for you.

Fly from

Washington, D.C.

Fly to

Chicago

Route

Depart

Return

Price

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 7/2

8:25 am-6:44 pm

1 stop11h 19m

Chicago O'Hare Intl

Thu 7/10

4:37 pm-7:31 pm

Nonstop1h 54m

$118

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Thu 8/14

7:38 am-8:38 am

Nonstop2h 00m

Chicago O'Hare Intl

Mon 8/18

7:45 am-10:51 am

Nonstop2h 06m

$120

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 8/6

6:31 pm-7:36 pm

Nonstop2h 05m

Chicago Midway

Mon 8/11

12:50 pm-3:46 pm

Nonstop1h 56m

$122

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Mon 8/11

11:36 am-12:58 pm

Nonstop2h 22m

Chicago O'Hare Intl

Sun 8/17

7:45 am-10:51 am

Nonstop2h 06m

$125

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Wed 8/13

6:40 am-7:40 am

Nonstop2h 00m

Chicago Midway

Wed 8/13

11:45 am-2:35 pm

Nonstop1h 50m

$139

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sat 8/23

6:15 am-7:30 am

Nonstop2h 15m

Chicago O'Hare Intl

Sat 8/30

7:00 am-9:55 am

Nonstop1h 55m

$139

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Thu 8/14

6:25 am-7:39 am

Nonstop2h 14m

Chicago O'Hare Intl

Tue 8/19

8:50 am-2:22 pm

1 stop4h 32m

$167

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 8/14

9:00 pm-10:00 pm

Nonstop2h 00m

Chicago Midway

Tue 8/19

9:55 am-2:25 pm

1 stop3h 30m

$167

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Wed 8/27

2:15 pm-3:28 pm

Nonstop2h 13m

Chicago O'Hare Intl

Sun 8/31

6:06 am-9:00 am

Nonstop1h 54m

$168

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 8/28

5:10 pm-6:25 pm

Nonstop2h 15m

Chicago O'Hare Intl

Sun 8/31

10:43 am-1:49 pm

Nonstop2h 06m

$168

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

Showing 1-10 of 59 results
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The best insider tips for Washington, D.C. 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 Washington, D.C. to Chicago trip
Airlines
United Airlines

United's Economy Plus offers extra legroom and priority boarding, ideal for frequent business travelers.


United's Polaris Lounges in Chicago offer showers, napping areas, and dining for premium passengers.

Read more about United Airlinesby Harriet Baskas
Southwest

Southwest's Wanna Get Away fare includes two free checked bags, perfect for budget-conscious travelers.


Southwest offers free in-flight entertainment streamed to your device, enhancing the travel experience.

Read more about Southwestby Marisa Garcia
Airports
DCA

DCA offers easy Metro access with a dedicated stop on the Yellow and Blue lines, making it a convenient choice for travelers from D.C. and nearby areas.

Read more about DCAby Emily Zemler
IAD

IAD's Aerotrain connects the main terminal to concourses, but be prepared for long walks, especially to United Express gates.

Read more about IADby Ramsey Qubein
ORD

At ORD, expect long walks between terminals. Use the free shuttle train for easier navigation, especially if arriving internationally at Terminal 5.

Read more about ORDby Ramsey Qubein
MDW

MDW is closer to downtown Chicago than ORD, with the Orange Line offering a quick, affordable ride to the city center in under 30 minutes.

Read more about MDWby Ramsey Qubein
Our travel experts
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
Marisa Garcia

Marisa Garcia

Expert on 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
Ramsey Qubein

Ramsey Qubein

Expert on ORD, MDW and IAD

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
Emily Zemler

Emily Zemler

Expert on DCA

Emily Zemler

Emily Zemler

Emily is a freelance writer and book author based in London covering entertainment and travel. Her work has appeared in Los Angeles Times, Observer, and Conde Nast Traveler She has ventured to more than 40 countries and all seven continents, always in search of a great art museum. She has written extensively about hotels, luxury travel, and aviation.

Read more

Best time to book a flight from Washington, D.C. to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Washington, D.C. 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 Washington, D.C. to Chicago

How far ahead should I book a flight from Washington, D.C. to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Washington, D.C. to Chicago. Price data was last updated on June 9, 2025.

To ensure you get the cheapest price possible for a flight from Washington, D.C. to Chicago, you should look to book at least 90 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.

What is the cheapest month to book a flight from Washington, D.C. to Chicago?

Currently, August is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of $245). Flying from Washington, D.C. 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 WAS to CHI?

Find hourly flight availability from Washington, D.C. 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 June 12, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 25% on flights from Washington, D.C. to Chicago by exploring options for tickets in the evening.

What is the cheapest day to fly from Washington, D.C. to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Washington, D.C. to Chicago. Price data was last updated on June 8, 2025.

Travelers seeking maximum savings on their Washington, D.C. to Chicago flight should consider departing on Tuesday 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.

Weekly flight availability from Washington, D.C. to Chicago

Explore weekly flight availability from Washington, D.C. 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 June 12, 2025.

The most flights from WAS to CHI are scheduled on a Thursday (88 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (40 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
Read through reviews of airlines operating flights from Washington, D.C. to Chicago, such as Alaska Airlines, Southwest and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,925 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Related info for your journey

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

  • What are the cheapest airlines flying from Washington, D.C. to Chicago round-trip?

    Cheapflights users have booked flights from Washington, D.C. to Chicago round-trip from $118. Other airlines that can offer you cheap pricing are Frontier, from $122, and Southwest, from $139. Spirit Airlines is 53% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Washington, D.C. to Chicago one-way?

    One-way options have recently been found by users for as low as $73 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $73 and Southwest from $79 one-way.

  • What are the most popular routes from Washington, D.C. to Chicago?

    The most popular route from Washington, D.C. to Chicago is Baltimore/Washington - Chicago O'Hare Intl. You may also consider Washington, D.C. Reagan-National - Chicago O'Hare Intl or Washington, D.C. Dulles Intl - Chicago O'Hare Intl.

  • What are the most reliable airlines from Washington, D.C. to Chicago?

    The top 3 most reliable airlines when flying from Washington, D.C. to Chicago are ANA (96%), Cathay Pacific (88%) and Spirit Airlines (88%).

  • What are the cheapest flights from Washington, D.C. to Chicago?

    Looking at all options, your cheapest flight can be booked for $72. While the most popular route (Baltimore/Washington - Chicago O'Hare Intl) can be booked for $98 on average our data indicates $977 when flying from Washington, D.C. to Chicago.

  • Can I find deals for flights from Washington, D.C. to Chicago that include hotel bookings?

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

  • How can I find direct flights from Washington, D.C. to Chicago?

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

  • Can I find deals for business class flights from Washington, D.C. to Chicago?

    Yes. Cheapflights offers flight deals from Washington, D.C. 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 Washington, D.C. to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of $245). Flying from Washington, D.C. 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 Washington, D.C.?

Book flights to Washington, D.C. if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Washington, D.C. to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Washington, D.C. to Chicago

Discover the top 6 airlines that operate flights from Washington, D.C. 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$55Average$158FlexibilityNo cancel feeOn-time65%
FrontierCheapest$58Average$176FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$272FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$145Average$328FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$155Average$326FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$166Average$298FlexibilityNo cancel feeOn-time63%

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