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

Find The Best Day To Fly from Boston to Chicago

Amazing American Airlines BOS to ORD Flight Deals

The cheapest flights to O'Hare Intl. found within the past 7 days were $137 round trip and $69 one way. Prices and availability subject to change. Additional terms may apply.

Sat, Sep 13 - Sun, Sep 14
BOS
Boston
ORD
Chicago
$137 Roundtrip, found 2 hours ago
$137
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Sat, Sep 13 from Boston to Chicago, returning Sun, Sep 14, priced at $137 found 2 hours ago
Wed, Jul 23 - Wed, Aug 20
BOS
Boston
ORD
Chicago
$139 Roundtrip, found 1 day ago
$139
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Jul 23 from Boston to Chicago, returning Wed, Aug 20, priced at $139 found 1 day ago

ORD From BOS Economy Coach Packages on Similar Airlines

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 3
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
per person
Oct 4 - Oct 11
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Don't see what you're looking for?
See all available trips from Logan Intl. to O'Hare Intl.
View all trips

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.

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

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

 

Return flights from Boston BOS to Chicago ORD 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 $137 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 Boston BOS to Chicago ORD 

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 Boston to Chicago costs from $69. Prices and availability subject to change. Additional terms may apply. 

 

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

To find a cheap American Airlines flight from Boston BOS to Chicago ORD, 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 Boston BOS to Chicago ORD 

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 September, or if you book a flight with a stopover. 

 

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

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

 

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

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 Chicago ORD from  Boston BOS 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

Travelers ❤️ these 🏨 after their flight to Chicago

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport, Chicago, IL
This hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, ...
8/10 Very Good! (2,084 reviews)
"Great location for quick access to ORD travel. Rather pricey. Room was nice except way too cold on arrival (about 60 deg per thermostat) and couldn't get the temp to increase by setting thermostat higher."

Reviewed on Jul 15, 2025

Hilton Chicago O'Hare Airport
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and ...
8.6/10 Excellent! (1,743 reviews)
"Generally a very nice hotel. Escalators to lower level with not working all weekend making it difficult for people with mobility issues."

Reviewed on Jul 15, 2025

Hyatt Regency O'Hare Chicago
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
5440 N River Rd, Rosemont, IL
This hotel features 3 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and free ...
8.6/10 Excellent! (2,290 reviews)
"My husband and I stayed in mid-June for the 1st Annual Midwest Convention (held onsite), and while the event was great, the hotel’s accessibility and amenities were seriously lacking. There was insufficient parking for wheelchair users, which created immediate challenges. My husband is in a wheelchair, ..."

Reviewed on Jul 13, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
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.