Cheap flights from Boston to Chicago

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Travel tip: Visit Chicago on your holidays!

Price evolution for flights from Boston to Chicago:

Price overview for flights from Boston to Chicago
Today's pick From $36.53/day
travelgrove.com Details

After booking your flight from Boston to Chicago why not drive away with a rental car bargain?

Cheap Chicago car rental at $36.53 / day is provided by Travelgrove. Discount available from top car rental supliers all over the U.S., including Alamo, National and Budget. Simply choose your airport and dates - Travelgrove does the searching for you! Date posted: 20 Nov 2009

Recent Deals on Flights from Boston to Chicago:Roundtrip / Oneway

$171 RT
United Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (CHI) 
Departure:
12/02/2009 
Return:
12/12/2009
Airline:United Airlines    
jetcombo.com
Check price
$184 RT
United Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (ORD) 
Departure:
12/16/2009 
Return:
12/22/2009
Airline:United Airlines    
jetcombo.com
Check price
$191 RT
Delta Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (CHI) 
Departure:
12/02/2009 
Return:
12/12/2009
Airline:Delta Airlines    
cfares.com
Check price
$194 RT
American Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (CHI) 
Departure:
11/22/2009 
Return:
12/04/2009
Airline:American Airlines    
jetcombo.com
Check price
$199 RT
Delta Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (ORD) 
Departure:
12/16/2009 
Return:
12/22/2009
Airline:Delta Airlines    
cfares.com
Check price
$200 RT
Northwest Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (CHI) 
Departure:
11/22/2009 
Return:
12/04/2009
Airline:Northwest Airlines    
cfares.com
Check price
$210 RT
United Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (CHI) 
Departure:
12/02/2009 
Return:
12/12/2009
Airline:United Airlines    
airfare.com
Check price
$229 RT
United Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (ORD) 
Departure:
12/16/2009 
Return:
12/22/2009
Airline:United Airlines    
airfare.com
Check price
$229 RT
United Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (ORD) 
Departure:
12/19/2009 
Return:
12/29/2009
Airline:United Airlines    
jetcombo.com
Check price
$235 RT
Delta Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (MDW) 
Departure:
11/26/2009 
Return:
12/06/2009
Airline:Delta Airlines    
cfares.com
Check price
$259 RT
Continental Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (CHI) 
Departure:
11/22/2009 
Return:
12/04/2009
Airline:Continental Airlines    
airfare.com
Check price
$259 RT
United Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (CHI) 
Departure:
12/27/2009 
Return:
01/10/2010
Airline:United Airlines    
jetcombo.com
Check price
$292 RT
United Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (ORD) 
Departure:
12/19/2009 
Return:
12/29/2009
Airline:United Airlines    
cfares.com
Check price
$299 RT
Jetblue Airways flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (CHI) 
Departure:
12/27/2009 
Return:
01/10/2010
Airline:Jetblue Airways    
airfare.com
Check price
$300 RT
United Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (ORD) 
Departure:
11/25/2009 
Return:
11/30/2009
Airline:United Airlines    
jetcombo.com
Check price
$300 RT
Northwest Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (CHI) 
Departure:
12/27/2009 
Return:
01/10/2010
Airline:Northwest Airlines    
cfares.com
Check price
$305 RT
Delta Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (MDW) 
Departure:
11/26/2009 
Return:
12/06/2009
Airline:Delta Airlines    
jetcombo.com
Check price
$314 RT
Continental Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (ORD) 
Departure:
12/19/2009 
Return:
12/29/2009
Airline:Continental Airlines    
airfare.com
Check price
$328 RT
American Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (ORD) 
Departure:
11/25/2009 
Return:
11/30/2009
Airline:American Airlines    
cfares.com
Check price
$344 RT
American Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (ORD) 
Departure:
11/25/2009 
Return:
11/30/2009
Airline:American Airlines    
jetcombo.com
Check price
$356 RT
United Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (ORD) 
Departure:
12/23/2009 
Return:
01/03/2010
Airline:United Airlines    
jetcombo.com
Check price
$426 RT
United Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (ORD) 
Departure:
11/25/2009 
Return:
11/30/2009
Airline:United Airlines    
airfare.com
Check price
$429 RT
American Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (ORD) 
Departure:
11/25/2009 
Return:
11/30/2009
Airline:American Airlines    
cfares.com
Check price
$434 RT
Jetblue Airways flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (ORD) 
Departure:
12/23/2009 
Return:
01/03/2010
Airline:Jetblue Airways    
airfare.com
Check price
$434 RT
Jetblue Airways flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (ORD) 
Departure:
11/25/2009 
Return:
11/30/2009
Airline:Jetblue Airways    
airfare.com
Check price
$464 RT
Delta Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (MDW) 
Departure:
11/26/2009 
Return:
12/06/2009
Airline:Delta Airlines    
airfare.com
Check price
$480 RT
American Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (ORD) 
Departure:
12/23/2009 
Return:
01/03/2010
Airline:American Airlines    
cfares.com
Check price
$1006 RT
Delta Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (MDW) 
Departure:
11/25/2009 
Return:
11/29/2009
Airline:Delta Airlines    
cfares.com
Check price
$1263 RT
Delta Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (MDW) 
Departure:
11/25/2009 
Return:
11/29/2009
Airline:Delta Airlines    
jetcombo.com
Check price
$1403 RT
Delta Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (MDW) 
Departure:
11/25/2009 
Return:
11/29/2009
Airline:Delta Airlines    
airfare.com
Check price
$105 OW
United Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (CHI) 
Departure:
11/27/2009 
Return:
-
Airline:United Airlines    
jetcombo.com
Check price
$115 OW
Continental Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (CHI) 
Departure:
11/24/2009 
Return:
-
Airline:Continental Airlines    
jetcombo.com
Check price
$155 OW
Northwest Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (CHI) 
Departure:
11/27/2009 
Return:
-
Airline:Northwest Airlines    
cfares.com
Check price
$197 OW
Delta Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (CHI) 
Departure:
11/24/2009 
Return:
-
Airline:Delta Airlines    
cfares.com
Check price
$225 OW
Delta Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (MDW) 
Departure:
12/22/2009 
Return:
-
Airline:Delta Airlines    
cfares.com
Check price
$229 OW
United Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (CHI) 
Departure:
11/27/2009 
Return:
-
Airline:United Airlines    
airfare.com
Check price
$256 OW
American Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (CHI) 
Departure:
11/29/2009 
Return:
-
Airline:American Airlines    
jetcombo.com
Check price
$296 OW
United Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (CHI) 
Departure:
11/29/2009 
Return:
-
Airline:United Airlines    
cfares.com
Check price
$344 OW
Continental Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (CHI) 
Departure:
11/24/2009 
Return:
-
Airline:Continental Airlines    
airfare.com
Check price
$404 OW
American Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (CHI) 
Departure:
11/29/2009 
Return:
-
Airline:American Airlines    
airfare.com
Check price
$455 OW
Delta Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (MDW) 
Departure:
12/22/2009 
Return:
-
Airline:Delta Airlines    
jetcombo.com
Check price
$577 OW
Delta Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (MDW) 
Departure:
11/29/2009 
Return:
-
Airline:Delta Airlines    
cfares.com
Check price
$714 OW
Delta Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (MDW) 
Departure:
12/22/2009 
Return:
-
Airline:Delta Airlines    
airfare.com
Check price
$777 OW
Delta Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (MDW) 
Departure:
11/29/2009 
Return:
-
Airline:Delta Airlines    
jetcombo.com
Check price
$866 OW
Delta Airlines flight
From:
Boston, MA (BOS) 
To:
Chicago, IL (MDW) 
Departure:
11/29/2009 
Return:
-
Airline:Delta Airlines    
airfare.com
Check price
 

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Know what to do when flying to Chicago?

Chicago Travel Guide Founded in the early 1800s, Chicago is positioned between civilization and wilderness and many aspects of modern life had their start here. Chicago really does have it all, with less infrastructural problems than its coastal rivals. Though [...]

Chicago History The site where Chicago stands had long been considered as an important portage point on the water route linking the Great Lakes with the Mississippi river.  Aside from this important fact, there are a lot of interesting things you need to know [...]

Chicago Sightseeing The rich cultural heritage of Chicago is depicted in its famous sights.  Other tourist attractions in the city can be seen in zoos and parks as well.  If you are thinking about visiting, it will help if you take a look at some of the travel [...]

Chicago Nightlife Chicago is one of the cities blessed with a variety of nightlife options.  Discos, clubs, bars - name it and the place will certainly give you the pleasure you are looking for. You will surely dance the night away as you listen to the music [...]

Chicago PicturesBean - ChicagoCity Reflections - Chicagocool site - Chicago
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