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Book 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
Fri, 06 Dec BOS - ORD
$82 $77
Prime price per passenger
Providence, RI Chicago
BEST
DEAL
Tue, 17 Dec PVD - ORD
$160 $155
Prime price per passenger
Boston Harbor SPB Chicago
BEST
DEAL
Wed, 27 Nov BDL - ORD
$266 $260
Prime price per passenger
Worcester, MA Chicago
BEST
DEAL
Thu, 28 Nov ORH - ORD
$320 $314
Prime price per passenger
Boston Harbor SPB Chicago
BEST
DEAL
Sat, 23 Nov BDL - ORD
Sun, 24 Nov ORD - BDL
$333 $326
Prime price per passenger
Boston Harbor SPB Chicago
BEST
DEAL
Sun, 24 Nov BDL - ORD
Wed, 27 Nov ORD - BDL
$432 $424
Prime price per passenger

Best flight offers from other airlines

Boston Chicago
BEST
DEAL
Fri, 22 Nov BOS - ORD
Sun, 24 Nov ORD - BOS
$109 $102
Prime price per passenger
Boston Chicago
BEST
DEAL
Fri, 22 Nov BOS - ORD
Sun, 24 Nov ORD - BOS
$110 $103
Prime price per passenger
Boston Chicago
BEST
DEAL
Fri, 22 Nov BOS - ORD
Mon, 25 Nov ORD - BOS
$124 $117
Prime price per passenger
Boston Chicago
BEST
DEAL
Sat, 23 Nov BOS - ORD
Tue, 26 Nov ORD - BOS
$124 $117
Prime price per passenger
Boston Chicago
BEST
DEAL
Fri, 22 Nov BOS - ORD
Tue, 26 Nov ORD - BOS
$125 $118
Prime price per passenger
Boston Chicago
BEST
DEAL
Sat, 23 Nov BOS - ORD
Thu, 28 Nov ORD - BOS
$126 $118
Prime price per passenger

Get your flight with American Airlines to Chicago starting at $77

Flying with American Airlines

Looking for a great deal on American Airlines flights from Boston to Chicago? eDreams US has an amazing search engine for you to check the last minute American Airlines airfares if you are in hurry to see a loved one or for a last minute business trip. No need to worry for a smart choice! You can also look for the cheapest prices and save some money to enjoy more in Chicago. We quickly compare and display the cheapest flight combinations in seconds and bring you the best ones! Adjust your travel dates now and explore the dozens of American Airlines offers from Boston at great prices, as you have all the privilege to access the top airline carriers and their best offers. Already chose American Airlines's best suited deal? DonĀ“t forget to enhance your Chicago holiday by booking a hotel and renting a car! Convenience will take on a completely new meaning after your experience with eDreams!.

Fly with eDreams

At eDreams, your online travel portal, you can easily find cheap flights with American Airlines from Boston to Chicago. Our fast search engine compares thousands of flights in just a few seconds and only shows you the really suitable flight connections.

Find the best deals on American Airlines flights from Boston to Chicago!

Easy online travel

You can easily choose from various options, such as price, departure times, airport, flight duration, flight connections (direct flight or with a stopover) and many more, thereby filtering the most suitable American Airlines flight from Boston after Chicago. Book your trip and save a lot of time with the simple and clear flight search from eDreams!

Book now

It is also worth downloading the eDreams app and subscribing to our newsletter - here you will also receive exclusive discounts and offers with which you can save a lot of money on your next travel booking. You can also easily book a hotel or rental car in Chicago with your trip at eDreams. With our combination offers you save even more! Book your American Airlines flights from Boston to Chicago quickly, easily and conveniently now with eDreams.

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 $77. On average though, flights with American Airlines cost $265.47 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 $77 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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