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$102+ Cheap flights from Reagan-National (DCA) 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
DCA — CHI
Apr 23 — Apr 301
Thu 4/23
Thu 4/30
1 adult, Economy
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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”

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Cheapflights Tip: The best prices from Washington, D.C. Reagan-National to Chicago are usually found in September or July, booked 57 days in advance, depart on a Wednesday or Friday and return on a Thursday

Cheap flight deals from Reagan-National to Chicago

Cheapest flights from Reagan-National to Chicago
Explore the most affordable flight options available from Reagan-National to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 24, 2026.

This Super.com deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:00 pm
DCA
-
ORD
1 stop27h 37m
Frontier
Mon 5/119:42 pm
ORD
-
DCA
1 stop23h 16m
Frontier
Deal found 3/22$212
This Mytrip deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/91:00 pm
DCA
-
ORD
1 stop25h 19m
Frontier
Thu 4/1610:55 am
ORD
-
DCA
1 stop10h 04m
Frontier
Deal found 3/22$215
This Southwest deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/219:55 am
DCA
-
MDW
Nonstop2h 00m
Southwest
Wed 4/221:55 pm
MDW
-
DCA
1 stop3h 45m
Southwest
Deal found 3/20$215
This Super.com deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/127:00 am
DCA
-
ORD
1 stop14h 37m
Frontier
Thu 5/219:42 pm
ORD
-
DCA
1 stop18h 17m
Frontier
Deal found 3/22$216
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/912:15 pm
DCA
-
MDW
1 stop3h 30m
Southwest
Tue 5/121:55 pm
MDW
-
DCA
1 stop3h 45m
Southwest
Deal found 3/23$216
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1411:45 am
DCA
-
MDW
Nonstop2h 00m
Southwest
Sat 4/187:45 am
MDW
-
DCA
2 stops9h 40m
Southwest
Deal found 3/24$219
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:15 pm
DCA
-
MDW
1 stop4h 45m
Southwest
Tue 6/21:55 pm
MDW
-
DCA
1 stop3h 45m
Southwest
Deal found 3/23$220
This American Airlines deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/311:35 am
DCA
-
ORD
Nonstop2h 20m
American Airlines
Mon 6/88:57 pm
ORD
-
DCA
Nonstop2h 02m
American Airlines
Deal found 3/23$221
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/229:05 am
DCA
-
MDW
2 stops7h 40m
Southwest
Sat 4/256:35 pm
MDW
-
DCA
Nonstop1h 55m
Southwest
Deal found 3/23$221
This Frontier deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/161:59 pm
DCA
-
ORD
1 stop7h 38m
Frontier
Wed 5/209:42 pm
ORD
-
DCA
1 stop14h 17m
Frontier
Deal found 3/21$222
This United Airlines deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:30 am
DCA
-
ORD
Nonstop2h 16m
United Airlines
Thu 4/304:00 pm
ORD
-
DCA
Nonstop2h 05m
United Airlines
Deal found 3/24$223
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/289:35 pm
DCA
-
MDW
Nonstop2h 00m
Southwest
Mon 6/18:05 pm
MDW
-
DCA
Nonstop1h 50m
Southwest
Deal found 3/24$223

Find flight deals from Reagan-National to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Reagan-National (DCA) 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 March 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$212
(Super.com)

One-way from

$102
(CheapOair)

Popular in

March

Cheapest in

September

Average price

$385

Good round-trip deal

$305 or less

Good one-way deal

$198 or less
Provider with most accurate pricing for Washington, D.C. Reagan-National-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Washington, D.C. Reagan-National-Chicago (CHI) flights.
Search Deals
From Washington, D.C. Reagan-National to Chicago (CHI)
Search Deals
One-way flight from Washington, D.C. Reagan-National to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals
Price to beat on a round-trip flight from Washington, D.C. Reagan-National to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Washington, D.C. Reagan-National to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Reagan-National 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 March 24, 2026.
Use the filters below to find and compare flights from Washington, D.C. Reagan-National Airport to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Mon 4/27

5:45 pm-10:15 pm

1 stop5h 30m

Chicago O'Hare Intl

Wed 4/29

1:36 pm-6:59 pm

1 stop4h 23m

$224

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 5/9

6:10 am-2:35 pm

2 stops9h 25m

Chicago Midway

Tue 5/12

1:55 pm-6:40 pm

1 stop3h 45m

$225

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 5/30

6:40 am-7:45 am

Nonstop2h 05m

Chicago Midway

Mon 6/1

5:40 pm-10:40 pm

1 stop4h 00m

$235

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Sat 5/9

1:00 pm-2:20 pm

Nonstop2h 20m

Chicago O'Hare Intl

Mon 5/11

7:45 pm-10:47 pm

Nonstop2h 02m

$239

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 4/9

9:35 pm-10:35 pm

Nonstop2h 00m

Chicago Midway

Mon 4/13

5:00 pm-7:55 pm

Nonstop1h 55m

$239

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Tue 4/14

1:40 pm-6:35 pm

1 stop5h 55m

Chicago O'Hare Intl

Mon 4/20

5:53 pm-11:41 pm

1 stop4h 48m

$244

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Fri 5/15

9:35 pm-10:35 pm

Nonstop2h 00m

Chicago Midway

Tue 5/19

11:30 am-2:20 pm

Nonstop1h 50m

$248

Washington, D.C.Chicago

DCA - ORD

DCAORD

Washington, D.C. Reagan-National

Mon 4/13

6:05 am-12:50 pm

1 stop7h 45m

Chicago O'Hare Intl

Tue 4/14

11:55 am-8:45 pm

2 stops7h 50m

$249

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 4/23

7:25 am-12:20 pm

1 stop5h 55m

Chicago Midway

Sat 4/25

9:15 am-8:55 pm

2 stops10h 40m

$250

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 5/14

9:35 pm-10:35 pm

Nonstop2h 00m

Chicago Midway

Fri 5/15

5:00 pm-7:55 pm

Nonstop1h 55m

$253

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

Showing 1-10 of 54 resultsSorted by cheapest first
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Compare providers for flights from Reagan-National 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 Reagan-National to Chicago in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust 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 Washington, D.C. Reagan-National Airport-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Washington, D.C. Reagan-National Airport-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Washington, D.C. Reagan-National Airport-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Washington, D.C. Reagan-National Airport-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 Washington, D.C. Reagan-National Airport-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 Reagan-National to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Reagan-National 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. Reagan-National Airport to Chicago

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

Use this chart to determine the optimal time to book a round-trip flight from Reagan-National to Chicago. Price data was last updated on March 13, 2026.

The best time to book flights from Washington, D.C. Reagan-National Airport to Chicago is 57 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, November is the cheapest month in which you can book a flight from Washington, D.C. Reagan-National Airport to Chicago (average of $98). Flying from Washington, D.C. Reagan-National Airport to Chicago in December is currently the most expensive (average of $237). 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 DCA to CHI?

Find hourly flight availability from Reagan-National 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 March 24, 2026.

It’s typically best to fly out from Washington, D.C. Reagan-National Airport to Chicago in the evening. Doing so could potentially save you 9% on the flight price compared to flying in the afternoon, which is usually more expensive.

What is the cheapest day to fly from Washington, D.C. Reagan-National Airport to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Reagan-National to Chicago. Price data was last updated on March 23, 2026.

Travelers seeking maximum savings on their Washington, D.C. Reagan-National Airport 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 Washington, D.C. Reagan-National Airport to Chicago

Explore weekly flight availability from Reagan-National 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 March 24, 2026.

The most flights from DCA to CHI are scheduled on a Monday (57 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (10 on average).

The best insider tips for Washington, D.C. Reagan-National Airport 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 Washington, D.C. Reagan-National Airport to Chicago trip
Our travel experts
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
Emily Zemler

Emily Zemler

Expert on DCA

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

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 March 24, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Washington, D.C. Reagan-National Airport to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,331 reviews

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,331 reviews
Southwest
8.0
Very good
4,331 reviews

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,470 reviews
Southwest
8.0
Very good
4,331 reviews

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,491 reviews
Southwest
8.0
Very good
4,331 reviews

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
3,018 reviews
Southwest
8.0
Very good
4,331 reviews

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

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

  • How long is the flight from Washington, D.C. Reagan-National Airport to Chicago?

    Departing from Washington, D.C. Reagan-National Airport to Chicago will take you 2h 20m. Airlines will cover a distance of 610 mi. This flight may include one or multiple stops.

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

    Flying on Frontier is currently your cheapest option to Chicago, with prices starting at $29. Additional round-trip tickets that might be worth considering are offered by American Airlines and Southwest, with the lowest prices starting at $166 and $187, respectively. Frontier is 90% 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. Reagan-National Airport to Chicago one-way?

    The cheapest airlines for a one-way flight from Washington, D.C. Reagan-National Airport to Chicago are Frontier ($89), American Airlines ($89), and Southwest ($98).

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

    The most popular flight routes from Washington, D.C. Reagan-National Airport to Chicago are Washington, D.C. Reagan-National - Chicago O'Hare Intl, Washington, D.C. Reagan-National - Chicago Midway and Washington, D.C. Reagan-National - Chicago Greater Rockford.

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

    Before booking your flight to Chicago from Washington, D.C. Reagan-National Airport, check out the most reliable airlines to get you to your destination on time: Qatar Airways (79%), ANA (76%), Air New Zealand( 72%).

  • What are the cheapest flights from Washington, D.C. Reagan-National Airport to Chicago?

    While on average a flight from Washington, D.C. Reagan-National Airport to Chicago is generally $901, our data shows the cheapest flight currently is $122. When looking at the most popular route, (Washington, D.C. Reagan-National - Chicago O'Hare Intl), you can expect to pay $185 for that flight.

  • Can I find deals for flights from Reagan-National to Chicago that include hotel bookings?

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

  • How can I find direct flights from Reagan-National to Chicago?

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

  • Can I find deals for business class flights from Reagan-National to Chicago?

    Yes. Cheapflights offers flight deals from Reagan-National 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. Reagan-National Airport to Chicago?

    Currently, November is the cheapest month in which you can book a flight from Washington, D.C. Reagan-National Airport to Chicago (average of $98). Flying from Washington, D.C. Reagan-National Airport to Chicago in December is currently the most expensive (average of $237). 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

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Top 4 airlines flying from Reagan-National to Chicago

Discover the top 4 airlines that operate flights from Reagan-National 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 March 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$29Average$130FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$166Average$309FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$187Average$309FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$209Average$343FlexibilityNo cancel feeOn-time69%

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