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  4. Boston - Chicago

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

Flight deals from Boston to Chicago

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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 Boston to Chicago

Boston Chicago
BEST
DEAL
Tue, 07 Jan BOS - ORD
-23 %
$68 $52
Prime price per passenger
Boston Harbor SPB Chicago
BEST
DEAL
Tue, 14 Jan BDL - ORD
$130 $126
Prime price per passenger
Providence, RI Chicago
BEST
DEAL
Sat, 11 Jan PVD - ORD
$171 $166
Prime price per passenger
Worcester, MA Chicago
BEST
DEAL
Sat, 28 Dec ORH - ORD
$239 $234
Prime price per passenger
Boston Chicago
BEST
DEAL
Sun, 22 Dec BOS - ORD
Tue, 24 Dec ORD - BOS
$371 $364
Prime price per passenger
Boston Chicago
BEST
DEAL
Fri, 20 Dec BOS - ORD
Tue, 24 Dec ORD - BOS
$384 $375
Prime price per passenger
Providence, RI Chicago
BEST
DEAL
Fri, 20 Dec PVD - ORD
Mon, 23 Dec ORD - PVD
$443 $439
Prime price per passenger
Providence, RI Chicago
BEST
DEAL
Fri, 20 Dec PVD - ORD
Fri, 20 Dec ORD - PVD
$453 $448
Prime price per passenger
Boston Harbor SPB Chicago
BEST
DEAL
Fri, 20 Dec BDL - ORD
Tue, 24 Dec ORD - BDL
$572 $564
Prime price per passenger
Boston Harbor SPB Chicago
BEST
DEAL
Fri, 20 Dec BDL - ORD
Sun, 22 Dec ORD - BDL
$791 $783
Prime price per passenger
Worcester, MA Chicago
BEST
DEAL
Fri, 20 Dec ORH - ORD
Sun, 22 Dec ORD - ORH
$894 $890
Prime price per passenger

Best flight offers from other airlines

Boston Chicago
BEST
DEAL
Fri, 20 Dec BOS - MDW
Tue, 24 Dec MDW - BOS
$262 $254
Prime price per passenger
Boston Harbor SPB Chicago
BEST
DEAL
Sat, 21 Dec BDL - MDW
Wed, 25 Dec MDW - BDL
$272 $264
Prime price per passenger
Boston Harbor SPB Chicago
BEST
DEAL
Sat, 21 Dec BDL - MDW
Wed, 25 Dec MDW - BDL
$272 $264
Prime price per passenger
Boston Harbor SPB Chicago
BEST
DEAL
Sat, 21 Dec BDL - MDW
Wed, 25 Dec MDW - BDL
$273 $265
Prime price per passenger
Boston Harbor SPB Chicago
BEST
DEAL
Sat, 21 Dec BDL - MDW
Wed, 25 Dec MDW - BDL
$273 $265
Prime price per passenger
Boston Harbor SPB Chicago
BEST
DEAL
Sat, 21 Dec BDL - MDW
Wed, 25 Dec MDW - BDL
$274 $265
Prime price per passenger

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

The Best Boston to Chicago Flight Deals with American Airlines

With eDreams, finding the best American Airlines deals for your trip from Boston to Chicago 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 Chicago.

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 Boston (BOS) to Chicago (CHI) journey. Stick around to find out why booking with eDreams is the best way to kick off your trip.

Flying from Boston to Chicago with American Airlines

Flying from Boston (BOS) to Chicago (CHI) 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 Boston to Chicago easy and fun.

Book Your Flight with eDreams and Enjoy the Perks

Booking affordable flights from Boston (BOS) to Chicago (CHI) 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 Boston to Chicago with American Airlines

The journey from Boston (BOS) to Chicago (CHI) 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 Boston and Arriving at Chicago: What to Expect

When departing from Boston, 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 Chicago, 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 Boston — Chicago Trip with American Airlines

For the best American Airlines flight deals from Boston to Chicago, timing is everything! Booking in advance often means lower fares, especially during off-peak seasons when Chicago 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 Boston-Chicago flights FAQ's

Which airports does American Airlines fly between Boston and Chicago?
For flights between Boston and Chicago, American Airlines operates the following airport routes: For flights between Boston and Chicago, American Airlines operates from the following airport routes: Logan International Airport (BOS) to O hare International Airport (ORD)
What do American Airlines flights from Boston to Chicago cost?
One of American Airlines cheapest prices for a Boston to Chicago flight we have right now is $52. On average though, flights with American Airlines cost $410.52 for the route Boston to Chicago, 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 Boston and going to Chicago, according to our customers' bookings.
Flight Time 2 h and 54 m The American Airlines flight duration between Boston and Chicago is around 2 h and 54 m, however it could be affected by other circumstances.
Departure Airport Logan International Airport Your departure will be from Logan International Airport, when flying with American Airlines from Boston to Chicago.
Arrival Airport O'hare International Airport When flying with American Airlines from Boston to Chicago, your arrival airport will be Logan International Airport.

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