Book Cheap American Airlines flight from Boston (BOS) to Chicago (ORD) from CA $94

Find The Best Day to Book a Cheap American Airlines Flights From Boston to Chicago

Cheapest American Airlines Flights from Boston (BOS) to Chicago (ORD)

The cheapest flights to O'Hare Intl. found within the past 7 days were CA $276 round trip and CA $94 one way. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I catch a flight from Logan Intl. Airport (BOS) to O'Hare Airport right now?
For info on any current ORD quarantine requirements and travel advice, visit our Covid-19 Travel Advisor. Look before you book your flight, so you don’t get caught out.
What terminal is American Airlines at Logan Intl. Airport?
At BOS, American Airlines flights to O’Hare Airport normally set off from terminal B. Want to know exactly which terminal you’ll be disembarking at? It’s most likely to be terminal 3.
Are there American Airlines non-stop flights from BOS to ORD?
Yes. Lock in a nonstop flight with American Airlines from Logan Intl. Airport to ORD, and you won’t have to worry about lengthy stopovers or trying to run for your connecting flight.
How long is an American Airlines flight from BOS to ORD?
No horrid jet lag, no sore legs — there’s a great deal to love about short-haul flights. If you’re traveling aboard American Airlines from BOS to O’Hare Airport, the trip will zoom by in around 3 hours and 37 minutes.
What type of aircraft does American Airlines fly from BOS to ORD?
Reserved a seat with American Airlines between BOS and ORD? The Boeing 737-800 and the Embraer 175 are the two airplane models that often operate on this flight path.
How many direct and indirect flights does American Airlines fly from BOS to ORD?
You’ll have a lot of options if you choose to fly with American Airlines between BOS and ORD. It offers at least 8 flights each day.
If I am not able to travel due to COVID-19, can I change my booking to a later date?
For more info about changing your flight to O’Hare Airport, please visit our Customer Service Portal.
What is the best day to buy a plane ticket?
This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that is when prices are generally at their highest.
What are the cheapest days to fly?
Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2021, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.
How far in advance can you book a flight?
Trying to figure out how early you should book your flight? It’s possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Grab a great American Airlines flight from BOS to ORD 

To find a great deal on American Airlines flights with Travelocity, simply enter your origin and destination airports, pick your travel dates, and hit search. From here, you can sort by price, flight duration, and arrival/departure time. You can also filter to find nonstop flights. 

Flying American Airlines Boston to Chicago gives you 7 fights to choose from. With that direct flight time of 54, you’ll be touching down before you know it.  

 

Find cheap flights with American Airlines between Boston and Chicago 

American Airlines has a range of great fares on stacks of flights, and to find the most affordable for you, there are a few tricks you can try. Booking in advance, for example, is a great way to grab a fantastic deal. Also, choose the cheapest month, if you can. One-way flights from Boston to Chicago with American Airlines are September.  

The more flexible you are, the more affordable flights you’re likely to find. Consider one-way flights and connecting flights, as well as standard roundtrip and direct options. Even if you’re flying today, cheap last-minute flights are easy to find by entering your travel dates and hitting search.  

 

Reasons to book your American Airlines flights with Travelocity 

Travelocity makes it easy to book a seat, anywhere in the world. The vast inventory, fast search, and advanced filters put some of the best deals on the planet in one place. Whether you’re traveling on business, with friends, family, or on your own, take your pick from some fantastic options. And with free cancellation and pay later options, you can travel more and worry less.  

American Airlines Airports
Hop on a(n) American Airlines flight today by flying to many destinations out of these domestic and international airports:
Airport code
Country
Airport name
Number of flights
DFWUSADallas-Fort Worth Intl.599
CLTUSACharlotte-Douglas Intl.536
ORDUSAO'Hare Intl.317
PHLUSAPhiladelphia Intl.247
MIAUSAMiami Intl.193
DCAUSARonald Reagan Washington National152
PHXUSASky Harbor Intl.141
LAXUSALos Angeles Intl.81
LGAUSALaGuardia72
BOSUSALogan Intl.57

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Hilton Chicago O'Hare Airport
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Holiday Inn Chicago O'Hare - Rosemont
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.