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$68+ 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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
WAS — CHI
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheapflights Tip: The best prices from Washington, D.C. to Chicago are usually found in September or February, booked 83 days in advance, depart on a Friday or Thursday and return on a Friday

Cheap 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 December 23, 2025.

This Frontier deal was found by Cheapflights users on 12/21. 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.
Wed 12/3111:55 amBWI - ORD
1 stop7h 38mFrontier
Thu 1/84:20 pmORD - BWI
Nonstop2h 02mFrontier
Deal found 12/21$172
This Delta deal was found by Cheapflights users on 12/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/314:49 pmBWI - MDW
1 stop6h 33mDelta
Thu 1/16:08 pmMDW - BWI
1 stop4h 23mDelta
Deal found 12/21$177
This Delta deal was found by Cheapflights users on 12/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:00 amBWI - ORD
1 stop4h 01mDelta
Thu 1/16:35 amORD - BWI
1 stop6h 16mDelta
Deal found 12/22$177
This Frontier deal was found by Cheapflights users on 12/21. 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.
Tue 12/309:37 amBWI - ORD
Nonstop2h 18mFrontier
Thu 1/84:20 pmORD - BWI
Nonstop2h 02mFrontier
Deal found 12/21$180
This Frontier deal was found by Cheapflights users on 12/21. 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.
Mon 12/2910:00 pmBWI - ORD
1 stop12h 02mFrontier
Thu 1/84:20 pmORD - BWI
Nonstop2h 02mFrontier
Deal found 12/21$191
This Frontier deal was found by Cheapflights users on 12/21. 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.
Wed 12/315:30 amBWI - MDW
1 stop8h 51mFrontier
Thu 1/812:41 pmMDW - BWI
1 stop10h 48mFrontier
Deal found 12/21$209
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:40 amBWI - ORD
1 stop9h 22mMultiple Airlines
Mon 1/512:39 pmORD - BWI
1 stop11h 01mMultiple Airlines
Deal found 12/21$211
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:55 amBWI - ORD
1 stop7h 38mFrontier
Wed 1/74:49 pmORD - BWI
1 stop6h 40mFrontier
Deal found 12/21$212
This Delta deal was found by Cheapflights users on 12/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:00 amBWI - MDW
1 stop3h 49mDelta
Tue 1/65:31 pmMDW - BWI
1 stop5h 06mDelta
Deal found 12/21$213
This Delta deal was found by Cheapflights users on 12/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:00 amBWI - ORD
1 stop4h 01mDelta
Tue 1/611:05 amORD - BWI
1 stop4h 33mDelta
Deal found 12/21$213
This American Airlines deal was found by Cheapflights users on 12/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:00 amBWI - ORD
Nonstop2h 22mAmerican Airlines
Thu 1/15:00 amORD - BWI
1 stop7h 07mAmerican Airlines
Deal found 12/20$219
This Frontier deal was found by Cheapflights users on 12/21. 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.
Tue 12/309:37 amBWI - ORD
Nonstop2h 18mFrontier
Wed 1/74:49 pmORD - BWI
1 stop6h 40mFrontier
Deal found 12/21$221

Find 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 December 23, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$82
(Kiwi.com)

One-way from

$68
(Kiwi.com)

Popular in

November

Cheapest in

September

Average price

$278

Good round-trip deal

$167 or less

Good one-way deal

$127 or less
Provider with most accurate pricing for Washington, D.C. (WAS)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Washington, D.C. (WAS)-Chicago (CHI) flights.
Search Deals
From Washington, D.C. (WAS) to Chicago (CHI)
Search Deals
One-way flight from Washington, D.C. (WAS) to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Washington, D.C. (WAS) to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Washington, D.C. (WAS) to Chicago (CHI).
Search Deals

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 December 23, 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 1/7

8:38 pm-9:48 pm

Nonstop2h 10m

Chicago O'Hare Intl

Sun 1/11

4:20 pm-7:22 pm

Nonstop2h 02m

$120

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Wed 1/7

8:38 pm-9:48 pm

Nonstop2h 10m

Chicago O'Hare Intl

Sun 1/11

12:44 pm-11:47 pm

1 stop10h 03m

$134

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Sat 2/21

5:40 pm-6:50 pm

Nonstop2h 10m

Chicago Midway

Mon 2/23

7:05 pm-9:55 pm

Nonstop1h 50m

$139

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Sat 1/17

5:18 pm-6:38 pm

Nonstop2h 20m

Chicago O'Hare Intl

Sun 1/18

11:05 am-2:11 pm

Nonstop2h 06m

$139

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Thu 2/12

7:35 am-8:50 am

Nonstop2h 15m

Chicago Midway

Sat 2/14

2:10 pm-4:55 pm

Nonstop1h 45m

$139

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Mon 1/19

1:54 pm-3:21 pm

Nonstop2h 27m

Chicago O'Hare Intl

Tue 1/20

2:18 pm-10:27 am

1 stop19h 09m

$154

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Fri 1/30

5:50 pm-7:00 pm

Nonstop2h 10m

Chicago Midway

Mon 2/2

5:15 pm-8:10 pm

Nonstop1h 55m

$158

Washington, D.C.Chicago

IAD - ORD

IADORD

Washington, D.C. Dulles Intl

Thu 1/8

6:00 am-11:35 am

1 stop6h 35m

Chicago O'Hare Intl

Mon 1/12

5:50 am-3:27 pm

1 stop8h 37m

$162

BaltimoreChicago

BWI - MDW

BWIMDW

Baltimore/Washington

Mon 1/26

6:00 am-11:45 am

1 stop6h 45m

Chicago Midway

Thu 1/29

5:01 pm-12:36 am

1 stop6h 35m

$162

BaltimoreChicago

BWI - ORD

BWIORD

Baltimore/Washington

Mon 1/19

5:18 pm-6:38 pm

Nonstop2h 20m

Chicago O'Hare Intl

Tue 1/20

11:05 am-2:11 pm

Nonstop2h 06m

$166

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 60 results
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Compare providers for flights from Washington, D.C. 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 Washington, D.C. to Chicago in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
OvagoPrice Accuracy2 starsTrust Score*2 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
Trip.comPrice Accuracy2 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*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.-Chicago flights, users find the pricing of Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on Washington, D.C.-Chicago flight deals on Cheapflights vs. Mytrip >95% of the time. Price accuracy is based on data collected from Washington, D.C.-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Washington, D.C.-Chicago flights, Cheapflights users trust Mytrip the most. Mytrip 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.-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 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 December 19, 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 67 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, March is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of $50). Flying from Washington, D.C. to Chicago in June is currently the most expensive (average of $133). 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 December 23, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 36% 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 December 20, 2025.

Travelers seeking maximum savings on their Washington, D.C. to Chicago flight should consider departing on Saturday evenings when fares are most often at their lowest. Monday mornings 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 December 23, 2025.

The most flights from WAS to CHI are scheduled on a Monday (77 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (40 on average).

How much does it cost to fly round-trip from Washington, D.C. to Chicago?

The best insider tips for Washington, D.C. 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. to Chicago trip
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
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

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 December 23, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, and American Airlines from Washington, D.C. 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
4,253 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,105 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,054 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,196 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,075 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • How long is the flight from Washington, D.C. to Chicago?

    Airlines like Spirit Airlines, Southwest, and United Airlines fly from Washington, D.C. to Chicago in about 2h 10m. The time it takes to get you to your destination is usually consistent. The distance from Washington, D.C. to Chicago is about 620 mi. Most flights are nonstop.

  • 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 $98. Other airlines that can offer you cheap pricing are American Airlines, from $168, and Southwest, from $178. Frontier is 60% 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 $16 on Frontier. Other airlines that offer cheap prices include Southwest from $88 and American Airlines from $89 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 Egyptair (85%), Air China (84%) and ANA (82%).

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

    Looking at all options, your cheapest flight can be booked for $115. While the most popular route (Baltimore/Washington - Chicago O'Hare Intl) can be booked for $85 on average, our data indicates $1,046 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, March is the cheapest month in which you can book a flight from Washington, D.C. to Chicago (average of $50). Flying from Washington, D.C. to Chicago in June is currently the most expensive (average of $133). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$52Average$120FlexibilityNo cancel feeOn-time65%
FrontierCheapest$58Average$179FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$148Average$294FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$158Average$322FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$167Average$311FlexibilityNo cancel feeOn-time71%
DeltaCheapest$234Average$327FlexibilityNo cancel feeOn-timeN/A

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