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  4. Chicago - Boston

Book $52 Cheap American Airlines flights from Chicago (CHI) to Boston (BOS)

Flight deals from Chicago to Boston

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Prices shown below were available within the past 3 days for the period specified and should not be considered the final price offered. Please note that availability and prices are subject to change.

American Airlines flight deals from Chicago to Boston

Chicago Boston
BEST
DEAL
Sat, 11 Jan ORD - BOS
-20 %
$65 $52
Prime price per passenger
Chicago Boston Harbor SPB
BEST
DEAL
Wed, 15 Jan ORD - BDL
$130 $126
Prime price per passenger
Chicago Providence, RI
BEST
DEAL
Sat, 15 Feb ORD - PVD
$151 $142
Prime price per passenger
Chicago Boston Harbor SPB
BEST
DEAL
Tue, 24 Dec ORD - BDL
Wed, 25 Dec BDL - ORD
$254 $244
Prime price per passenger
Chicago Boston
BEST
DEAL
Fri, 20 Dec ORD - BOS
Mon, 23 Dec BOS - ORD
$281 $275
Prime price per passenger
Chicago Boston
BEST
DEAL
Sun, 22 Dec ORD - BOS
Tue, 24 Dec BOS - ORD
$319 $310
Prime price per passenger
Chicago Providence, RI
BEST
DEAL
Mon, 23 Dec ORD - PVD
Wed, 25 Dec PVD - ORD
$416 $407
Prime price per passenger
Chicago Worcester, MA
BEST
DEAL
Sat, 28 Dec ORD - ORH
$460 $452
Prime price per passenger
Chicago Boston Harbor SPB
BEST
DEAL
Sun, 22 Dec ORD - BDL
Wed, 25 Dec BDL - ORD
$463 $453
Prime price per passenger
Chicago Providence, RI
BEST
DEAL
Fri, 20 Dec ORD - PVD
Sun, 22 Dec PVD - ORD
-12 %
$787 $692
Prime price per passenger

Best flight offers from other airlines

Chicago Boston Harbor SPB
BEST
DEAL
Fri, 20 Dec MDW - BDL
Tue, 24 Dec BDL - MDW
$167 $155
Prime price per passenger
Chicago Boston Harbor SPB
BEST
DEAL
Fri, 20 Dec MDW - BDL
Wed, 25 Dec BDL - MDW
$204 $198
Prime price per passenger
Chicago Boston Harbor SPB
BEST
DEAL
Fri, 20 Dec MDW - BDL
Wed, 25 Dec BDL - MDW
$207 $201
Prime price per passenger
Chicago Boston
BEST
DEAL
Fri, 20 Dec ORD - BOS
Mon, 23 Dec BOS - ORD
$244 $237
Prime price per passenger
Chicago Boston Harbor SPB
BEST
DEAL
Fri, 20 Dec MDW - BDL
Tue, 24 Dec BDL - MDW
$280 $271
Prime price per passenger
Chicago Boston Harbor SPB
BEST
DEAL
Fri, 20 Dec MDW - BDL
Tue, 24 Dec BDL - MDW
$281 $272
Prime price per passenger

Get your flight with American Airlines to Boston from Chicago starting at $52

The Best Chicago to Boston Flight Deals with American Airlines

With eDreams, finding the best American Airlines deals for your trip from Chicago to Boston couldn’t be easier. Imagine this: exclusive discounts, intuitive booking tools, and plenty of helpful perks—all at your fingertips! Say goodbye to the hassle of planning and hello to the excitement of your upcoming adventure in Boston.

Whether you’re looking for unbeatable prices, a custom-fit itinerary, or some extra perks, eDreams is your all-in-one travel partner for every part of the Chicago (CHI) to Boston (BOS) journey. Stick around to find out why booking with eDreams is the best way to kick off your trip.

Flying from Chicago to Boston with American Airlines

Flying from Chicago (CHI) to Boston (BOS) with American Airlines (AA) is all about comfort and convenience. From check-in to touchdown, American Airlines ensures a smooth experience, so you can just sit back and relax. You’ll find fast check-ins, extra legroom, and attentive service designed for a stress-free trip.

Once onboard, the friendly crew will make sure you have everything you need. Many routes offer in-flight Wi-Fi, so you can stay connected, binge-watch shows, or catch up on work if you need to. Feeling hungry? American Airlines has a great selection of snacks and meals to keep you satisfied mid-flight. And if you want a bit more luxury, you can treat yourself to upgrades and priority boarding, adding a personal touch to your journey. With great service and a focus on a smooth, enjoyable flight, American Airlines makes your trip from Chicago to Boston easy and fun.

Book Your Flight with eDreams and Enjoy the Perks

Booking affordable flights from Chicago (CHI) to Boston (BOS) with eDreams isn’t just about getting a great deal—it’s about making travel planning effortless. With eDreams, you get awesome perks that make your journey easier and more enjoyable:

Your Journey from Chicago to Boston with American Airlines

The journey from Chicago (CHI) to Boston (BOS) is all about getting you to your destination comfortably and quickly, so your adventure can start as soon as you land. This direct route offers plenty of options, whether you prefer a quick non-stop flight or more flexibility with layovers. Whatever your style, there’s a schedule that fits.

Departing from Chicago and Arriving at Boston: What to Expect

When departing from Chicago, enjoy easy airport access, clear signage, and quick check-ins for a stress-free start. You’ll breeze through security, leaving plenty of time to relax before takeoff.

When you land in Boston, you’ll be greeted by a modern terminal with plenty of transportation options like taxis, buses, and shuttles to get you on your way. Whether heading to your hotel or diving into sightseeing, everything you need is right there.

Best Time to Book Your Chicago — Boston Trip with American Airlines

For the best American Airlines flight deals from Chicago to Boston, timing is everything! Booking in advance often means lower fares, especially during off-peak seasons when Boston is quieter and flights are more budget-friendly. Check the climate to plan for the ideal weather to suit your trip—whether for mild outdoor adventures or cultural explorations. With a bit of planning, you’re set for an unforgettable getaway!

American Airlines Chicago-Boston flights FAQ's

Which airports does American Airlines fly between Chicago and Boston?
For flights between Chicago and Boston, American Airlines operates the following airport routes: For flights between Chicago and Boston, American Airlines operates from the following airport routes: O hare International Airport (ORD) to Logan International Airport (BOS)
What do American Airlines flights from Chicago to Boston cost?
One of American Airlines cheapest prices for a Chicago to Boston flight we have right now is $52. On average though, flights with American Airlines cost $332.53 for the route Chicago to Boston, but it mostly depends on the season and how far in advance you book your tickets.
Cheapest Ticket Price $52 The most affordable rate found in the last 72 hours for flights operated by American Airlines leaving from Chicago and going to Boston, according to our customers' bookings.
Flight Time 2 h and 27 m The American Airlines flight duration between Chicago and Boston is around 2 h and 27 m, however it could be affected by other circumstances.
Departure Airport O'hare International Airport Your departure will be from O'hare International Airport, when flying with American Airlines from Chicago to Boston.
Arrival Airport Logan International Airport When flying with American Airlines from Chicago to Boston, your arrival airport will be O'hare International Airport.

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