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$101+ Cheap flights from Orlando (ORL) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — CHI
Aug 17 — Aug 241
Mon 8/17
Mon 8/24
1 adult, Economy
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Find cheap flights from Orlando to Chicago with Cheapflights

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 Orlando to Chicago are usually found in September or February, booked 13 days in advance, depart on a Friday or Thursday and return on a Friday

Cheap flight deals from Orlando to Chicago

Cheapest flights from Orlando to Chicago
Explore the most affordable flight options available from Orlando to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 18, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/15. 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.
Mon 8/35:24 pm
MCO
-
ORD
1 stop15h 29m
Frontier
Thu 8/61:50 pm
ORD
-
MCO
1 stop7h 25m
Frontier
Deal found 7/15$190
This Kiwi.com deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:15 pm
MCO
-
ORD
1 stop7h 24m
Frontier
Mon 9/79:10 pm
ORD
-
MCO
Nonstop3h 08m
Frontier
Deal found 7/14$191
This Kiwi.com deal was found by Cheapflights users on 7/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2410:32 am
MCO
-
ORD
1 stop10h 12m
Frontier
Fri 10/29:26 am
ORD
-
MCO
Nonstop2h 49m
Frontier
Deal found 7/16$192
This Kiwi.com deal was found by Cheapflights users on 7/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:10 am
SFB
-
RFD
Nonstop2h 42m
Allegiant Air
Mon 9/1410:22 am
RFD
-
SFB
Nonstop2h 34m
Allegiant Air
Deal found 7/13$193
This WAYA deal was found by Cheapflights users on 7/14. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:15 pm
MCO
-
ORD
1 stop7h 24m
Frontier
Tue 9/87:44 pm
ORD
-
MCO
Nonstop2h 45m
Frontier
Deal found 7/14$193
This Super.com deal was found by Cheapflights users on 7/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/39:00 pm
MCO
-
ORD
Nonstop3h 08m
Frontier
Wed 9/94:49 pm
ORD
-
MCO
Nonstop2h 53m
Frontier
Deal found 7/15$194
This Kiwi.com deal was found by Cheapflights users on 7/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/189:47 pm
MCO
-
ORD
Nonstop3h 08m
Frontier
Mon 10/54:49 pm
ORD
-
MCO
Nonstop2h 53m
Frontier
Deal found 7/16$195
This Super.com deal was found by Cheapflights users on 7/13. 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 9/411:08 am
MCO
-
ORD
Nonstop3h 12m
Frontier
Mon 9/79:10 pm
ORD
-
MCO
Nonstop3h 08m
Frontier
Deal found 7/13$196
This Cheapflightsfares deal was found by Cheapflights users on 7/13. 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.
Tue 8/259:00 pm
MCO
-
ORD
Nonstop3h 08m
Frontier
Sun 8/307:44 pm
ORD
-
MCO
Nonstop2h 45m
Frontier
Deal found 7/13$197
This Kiwi.com deal was found by Cheapflights users on 7/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:10 am
SFB
-
RFD
Nonstop2h 42m
Allegiant Air
Fri 10/28:49 am
RFD
-
SFB
Nonstop2h 30m
Allegiant Air
Deal found 7/16$198
This Travelocity deal was found by Cheapflights users on 7/13. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:05 am
MCO
-
ORD
Nonstop3h 16m
Frontier
Mon 9/284:49 pm
ORD
-
MCO
Nonstop2h 53m
Frontier
Deal found 7/13$199
This Kiwi.com deal was found by Cheapflights users on 7/14. 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 10/147:00 am
SFB
-
RFD
Nonstop2h 44m
Allegiant Air
Sun 10/181:12 pm
RFD
-
SFB
1 stop21h 52m
Allegiant Air
Deal found 7/14$200

Find flight deals from Orlando to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Orlando (ORL) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$190
(Kiwi.com)

One-way from

$101
(CheapOair)

Popular in

June

Cheapest in

September

Average price

$239

Good round-trip deal

$138 or less

Good one-way deal

$134 or less
Provider with most accurate pricing for Orlando (ORL)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Orlando (ORL)-Chicago (CHI) flights.
Search Deals
From Orlando (ORL) to Chicago (CHI)
Search Deals
One-way flight from Orlando (ORL) to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 26% potential increase in price ($70 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Orlando (ORL) to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Orlando (ORL) to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Orlando to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 18, 2026.
Use the filters below to find and compare flights from Orlando to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Mon 9/21

7:50 am-9:32 am

Nonstop2h 42m

Chicago Greater Rockford

Fri 10/2

8:49 am-12:19 pm

Nonstop2h 30m

$193

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Fri 9/11

7:10 am-8:52 am

Nonstop2h 42m

Chicago Greater Rockford

Mon 9/14

10:22 am-1:56 pm

Nonstop2h 34m

$193

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Mon 11/9

8:00 am-9:48 am

Nonstop2h 48m

Chicago Greater Rockford

Wed 11/11

3:34 pm-7:10 pm

Nonstop2h 36m

$202

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Fri 8/14

3:45 pm-5:36 pm

Nonstop2h 51m

Chicago Greater Rockford

Mon 8/17

6:26 pm-10:05 pm

Nonstop2h 39m

$206

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Wed 11/25

6:15 am-8:06 am

Nonstop2h 51m

Chicago Greater Rockford

Fri 11/27

6:04 pm-9:36 pm

Nonstop2h 32m

$208

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Wed 7/29

7:30 am-9:13 am

Nonstop2h 43m

Chicago Greater Rockford

Fri 7/31

7:50 pm-11:29 pm

Nonstop2h 39m

$213

OrlandoChicago

MCO - RFD

MCORFD

Orlando

Thu 9/24

9:00 am-3:03 pm

1 stop7h 03m

Chicago Greater Rockford

Sun 10/4

10:08 am-11:47 am

2 stops24h 39m

$226

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Fri 8/7

3:45 pm-5:36 pm

Nonstop2h 51m

Chicago Greater Rockford

Mon 8/10

6:26 pm-10:05 pm

Nonstop2h 39m

$227

OrlandoChicago

MCO - RFD

MCORFD

Orlando

Thu 8/27

9:05 am-3:09 pm

1 stop7h 04m

Chicago Greater Rockford

Sun 8/30

3:59 pm-2:25 pm

1 stop21h 26m

$228

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 8/11

7:40 pm-9:54 pm

Nonstop3h 14m

Chicago O'Hare Intl

Tue 8/18

11:01 am-2:58 pm

Nonstop2h 57m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/13

Showing 1-10 of 60 resultsSorted by cheapest first
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Compare providers for flights from Orlando 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 Orlando to Chicago in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
CheapfaremartPrice Accuracy-Trust Score*1 star
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy2 starsTrust Score*3 stars
Super.comPrice Accuracy-Trust 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 Orlando-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Orlando-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Orlando-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Orlando-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 Orlando-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 Orlando to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Orlando 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 Orlando to Chicago

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

Currently, February is the cheapest month in which you can book a flight from Orlando to Chicago (average of $168). Flying from Orlando to Chicago in June is currently the most expensive (average of $358). 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 ORL to CHI?

Find hourly flight availability from Orlando to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 18, 2026.

One of the essential ways to save on airfare from Orlando to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 53% on airfare.

Weekly flight availability from Orlando to Chicago

Explore weekly flight availability from Orlando to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 18, 2026.

The most flights from ORL to CHI are scheduled on a Saturday (83 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (53 on average).

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

How often are flights from Orlando to Chicago delayed?

About 18% of weekly flights between Orlando and Chicago have experienced delays in the past year, with the average delay time being 150 minutes.

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

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

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

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

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

Over the last year, United Airlines have had the lowest number of delays on this route, with just 9% of flights being delayed.

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

To ensure you get the cheapest price possible for a flight from Orlando to Chicago, you should look to book at least 81 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 day to fly from Orlando to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Orlando to Chicago. Price data was last updated on July 11, 2026.

Travelers seeking maximum savings on their Orlando to Chicago flight should consider departing on Saturday at noon 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.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated July 18, 2026.
Read through reviews of airlines operating flights from Orlando to Chicago, such as Southwest,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,243 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
10,006 reviews
Southwest
8.0
Very good
4,243 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,829 reviews
Southwest
8.0
Very good
4,243 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
JetBlue
7.1
Good
3,012 reviews
Southwest
8.0
Very good
4,243 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Frontier
5.6
Fair
2,794 reviews
Southwest
8.0
Very good
4,243 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

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

Related info for your journey

Find useful and relevant information for your journey from Orlando 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 Orlando to Chicago?

    Departing from Orlando to Chicago will take you 2h 42m. Orlando and Chicago are separated by a distance of 1025 mi. Generally, flights for this route are nonstop.

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

    Frontier, at $68, was found to be the cheapest airline from Orlando to Chicago.Alternate airlines to your destination round-trip include Allegiant Air and Southwest. Frontier is 64% cheaper than the average price of flights available within the next 90 days to this destination.

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

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $41. Users have also found prices from $48 and $78 on Allegiant Air and Southwest, respectively.

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

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

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

    Before booking your flight to Chicago from Orlando, check out the most reliable airlines to get you to your destination on time: ITA Airways (97%), Cathay Pacific (89%), Japan Airlines( 87%).

  • What are the cheapest flights from Orlando to Chicago?

    Looking at all options, your cheapest flight can be booked for $105. While the most popular route (Orlando - Chicago O'Hare Intl) can be booked for $146 on average, our data indicates $1,478 when flying from Orlando to Chicago.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Orlando 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 Orlando to Chicago?

    Currently, February is the cheapest month in which you can book a flight from Orlando to Chicago (average of $168). Flying from Orlando to Chicago in June is currently the most expensive (average of $358). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

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

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Alternative routes for Orlando to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Orlando to O'Hare Intl flights
Tampa to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Miami to O'Hare Intl flights
Orlando to Midway flights
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Tampa to Midway flights
Miami to Midway flights
Fort Lauderdale to Midway flights
Fort Myers to O'Hare Intl flights
West Palm Beach to O'Hare Intl flights
Sarasota to O'Hare Intl flights
Orlando to St. Louis flights
Pensacola to O'Hare Intl flights
West Palm Beach to Midway flights
Jacksonville to Midway flights
Tampa to St. Louis flights
Panama City to O'Hare Intl flights
Fort Myers to Midway flights
Tallahassee to O'Hare Intl flights
Miami to St. Louis flights
Fort Lauderdale to St. Louis flights
Jacksonville to St. Louis flights
Fort Lauderdale to Rockford flights
Orlando Sanford Intl to Rockford flights
Pensacola to Midway flights
St Petersburg to Rockford flights
Sarasota to Midway flights
Daytona Beach to O'Hare Intl flights
Gainesville to O'Hare Intl flights
Fort Myers to St. Louis flights
Sarasota to St. Louis flights
Valparaiso to O'Hare Intl flights
Pensacola to St. Louis flights
West Palm Beach to St. Louis flights
Tampa to Peoria flights
Panama City to Midway flights
Gainesville to Midway flights
Daytona Beach to St. Louis flights
Panama City to St. Louis flights
Melbourne to O'Hare Intl flights
Orlando to Bloomington flights
Daytona Beach to Midway flights
Fort Lauderdale to Peoria flights
Key West to O'Hare Intl flights
Valparaiso to Midway flights
Orlando to Evansville flights
Key West to Midway flights

Top 5 airlines flying from Orlando to Chicago

Discover the top 5 airlines that operate flights from Orlando to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$68Average$171FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$82Average$181FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$157Average$273FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$157Average$329FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$295FlexibilityNo cancel feeOn-time71%

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