$69 Cheap American Airlines flights from Chicago to Boston (ORD to BOS)

Find The Best Day To Fly from Chicago to Boston

Amazing American Airlines ORD to BOS Flight Deals

The cheapest flights to Logan Intl. found within the past 7 days were $129 round trip and $69 one way. Prices and availability subject to change. Additional terms may apply.

Tue, Aug 19 - Tue, Sep 2
ORD
Chicago
BOS
Boston
$129 Roundtrip, found 6 hours ago
$129
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Tue, Aug 19 from Chicago to Boston, returning Tue, Sep 2, priced at $129 found 6 hours ago
Fri, Sep 19 - Sun, Sep 21
ORD
Chicago
BOS
Boston
$139 Roundtrip, just found
$139
Roundtrip
just found
Select American Airlines flight, departing Fri, Sep 19 from Chicago to Boston, returning Sun, Sep 21, priced at $139 just found

BOS From ORD Economy Coach Packages on Similar Airlines

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Boston Seaport District

Hampton Inn Boston Seaport District

3 out of 5
Save 100% on your flight
per person
Oct 1 - Oct 6
found 9 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
per person
Oct 4 - Oct 10
found 23 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
Homewood Suites by Hilton Boston Seaport District

Homewood Suites by Hilton Boston Seaport District

3 out of 5
Save 100% on your flight
per person
Oct 4 - Oct 10
found 23 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
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Frequently asked questions

Can I catch a flight from O'Hare Airport to Logan Intl. Airport (BOS) right now?
For info on any current Logan Intl. Airport travel advice and quarantine requirements, go to our Covid-19 Travel Advisor. Check before you arrange your flight, so you don't get caught up en route.
What terminal is American Airlines at O'Hare Airport?
At O'Hare Airport, American Airlines flights to Logan Intl. Airport typically head off from terminal 3. Wondering exactly which terminal you'll be exiting the plane at? It'll likely be terminal B.
Are there American Airlines non-stop flights from ORD to BOS?
Yes, you can go straight from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS) with American Airlines and avoid time-consuming stopovers. The less time you spend waiting around for your next flight, the more time you'll have for adventuring.
How long is an American Airlines flight from ORD to BOS?
No horrid jet lag, no sore legs --- there's plenty to love about short flights. If you've reserved a seat with American Airlines from O'Hare Intl. Airport (ORD) to Logan Intl. Airport (BOS), the trip will zoom by in about 3 hours and 2 minutes.
What type of aircraft does American Airlines fly from ORD to BOS?
The Boeing 737-800 and the Embraer 175 are the types of aircraft generally operated by American Airlines between ORD and Logan Intl. Airport (BOS).
How many direct and indirect flights does American Airlines fly from ORD to BOS?
When journeying from ORD to BOS, there are approximately 8 American Airlines daily flights to choose from.
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 BOS, 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.

Discover our best American Airlines flight from Chicago ORD to Boston BOS 

To find the best deals on flights to Chicago from Boston with American Airlines, just enter your travel dates, filter by American Airlines, and hit search. You’ll find 9 flights to choose from and can sort by price, flight duration, and arrival or departure time.  

 

Return flights from Chicago ORD to Boston BOS with American Airlines 

If you’re planning a round trip, booking return flights with American Airlines is usually the most cost-effective option. With airfares ranging from $129 to $139, it’s easy to find a flight that suits your budget. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way American Airlines flights from Chicago ORD to Boston BOS 

A one-way ticket gives you much greater flexibility—allowing you to choose your return date, destination, and time whenever you’re ready. By booking in advance you can find great deals on one-way tickets too. Right now, a one-way American Airlines flight from Chicago to Boston costs from $69. Prices and availability subject to change. Additional terms may apply. 

 

The easy way to find cheap flights to Boston BOS from  Chicago ORD with American Airlines 

To find a cheap American Airlines flight from Chicago ORD to Boston BOS, sort your search results by price or filter by budget. Thanks to Travelocity’s Price Match Promise, if you find a better airfare deal anywhere else within 24 hours, we’ll credit or refund the difference. 

 

How to find our best airfare deals on American Airlines flights from Chicago ORD to Boston BOS 

If you’re looking for cheap flights, it helps to be flexible when it comes to your travel dates. You’ll usually find lower cost tickets when you travel during quieter months such as August, or if you book a flight with a stopover. 

 

Find nonstop flights from Chicago ORD to Boston BOS with American Airlines 

If you’re keen to be on Boston soil fast, don’t waste time with a stopover—filter your search results to show direct American Airlines flights only. The journey takes around 2 hour(s) 21 min(s) – so you’ll be there before you know it. 

 

Flexible airline tickets for American Airlines flights from Chicago ORD to Boston BOS 

Make sure you’re not out of pocket if plans change by choosing a flexible ticket with penalty-free amendment and cancellation options. Use our ‘no change fee’ filter to see which flights have this option.  

 

There are a lot of reasons to book your flights to Boston BOS from  Chicago ORD with American Airlines on Travelocity 

At Travelocity our vast and up-to-the-minute inventory puts all of our best flight deals in one place. So, whether you’re traveling on business or jetting off with friends and family, you can trust Travelocity to get you there.

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 Boston Logan Airport

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4 out of 5
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Omni Boston Hotel at the Seaport

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4 out of 5
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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.