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 $29.08/day

Details

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

$171 RT	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	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	From: Boston, MA (BOS) To: Chicago, IL (CHI) Departure: 12/02/2009 Return: 12/12/2009 Airline:Delta Airlines	cfares.com Check price
$199 RT	From: Boston, MA (BOS) To: Chicago, IL (ORD) Departure: 12/16/2009 Return: 12/22/2009 Airline:Delta Airlines	cfares.com Check price
$203 RT	From: Boston, MA (BOS) To: Chicago, IL (ORD) Departure: 11/13/2009 Return: 11/20/2009 Airline:American Airlines	jetcombo.com Check price
$210 RT	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	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	From: Boston, MA (BOS) To: Chicago, IL (ORD) Departure: 12/19/2009 Return: 12/29/2009 Airline:United Airlines	jetcombo.com Check price
$234 RT	From: Boston, MA (BOS) To: Chicago, IL (ORD) Departure: 11/13/2009 Return: 11/20/2009 Airline:Delta Airlines	cfares.com Check price
$235 RT	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	From: Boston, MA (BOS) To: Chicago, IL (CHI) Departure: 12/27/2009 Return: 01/10/2010 Airline:United Airlines	jetcombo.com Check price
$265 RT	From: Boston, MA (BOS) To: Chicago, IL (MDW) Departure: 11/19/2009 Return: 11/28/2009 Airline:Delta Airlines	jetcombo.com Check price
$289 RT	From: Boston, MA (BOS) To: Chicago, IL (ORD) Departure: 11/13/2009 Return: 11/20/2009 Airline:Continental Airlines	airfare.com Check price
$292 RT	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	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	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	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	From: Boston, MA (BOS) To: Chicago, IL (ORD) Departure: 12/19/2009 Return: 12/29/2009 Airline:Continental Airlines	airfare.com Check price
$344 RT	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	From: Boston, MA (BOS) To: Chicago, IL (ORD) Departure: 12/23/2009 Return: 01/03/2010 Airline:United Airlines	jetcombo.com Check price
$363 RT	From: Boston, MA (BOS) To: Chicago, IL (MDW) Departure: 11/19/2009 Return: 11/28/2009 Airline:Delta Airlines	airfare.com Check price
$429 RT	From: Boston, MA (BOS) To: Chicago, IL (ORD) Departure: 11/25/2009 Return: 11/30/2009 Airline:American Airlines	cfares.com Check price
$429 RT	From: Boston, MA (BOS) To: Chicago, IL (MDW) Departure: 11/19/2009 Return: 11/28/2009 Airline:Northwest Airlines	cfares.com Check price
$434 RT	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	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	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	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	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	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	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	From: Boston, MA (BOS) To: Chicago, IL (CHI) Departure: 11/27/2009 Return: - Airline:United Airlines	jetcombo.com Check price
$109 OW	From: Boston, MA (BOS) To: Chicago, IL (CHI) Departure: 11/18/2009 Return: - Airline:Delta Airlines	cfares.com Check price
$109 OW	From: Boston, MA (BOS) To: Chicago, IL (ORD) Departure: 11/10/2009 Return: - Airline:Delta Airlines	cfares.com Check price
$115 OW	From: Boston, MA (BOS) To: Chicago, IL (CHI) Departure: 11/24/2009 Return: - Airline:Continental Airlines	jetcombo.com Check price
$155 OW	From: Boston, MA (BOS) To: Chicago, IL (CHI) Departure: 11/27/2009 Return: - Airline:Northwest Airlines	cfares.com Check price
$197 OW	From: Boston, MA (BOS) To: Chicago, IL (CHI) Departure: 11/24/2009 Return: - Airline:Delta Airlines	cfares.com Check price
$225 OW	From: Boston, MA (BOS) To: Chicago, IL (MDW) Departure: 12/22/2009 Return: - Airline:Delta Airlines	cfares.com Check price
$229 OW	From: Boston, MA (BOS) To: Chicago, IL (CHI) Departure: 11/27/2009 Return: - Airline:United Airlines	airfare.com Check price
$256 OW	From: Boston, MA (BOS) To: Chicago, IL (CHI) Departure: 11/29/2009 Return: - Airline:American Airlines	jetcombo.com Check price
$259 OW	From: Boston, MA (BOS) To: Chicago, IL (CHI) Departure: 11/18/2009 Return: - Airline:Us Airways	airfare.com Check price
$296 OW	From: Boston, MA (BOS) To: Chicago, IL (CHI) Departure: 11/29/2009 Return: - Airline:United Airlines	cfares.com Check price
$344 OW	From: Boston, MA (BOS) To: Chicago, IL (CHI) Departure: 11/24/2009 Return: - Airline:Continental Airlines	airfare.com Check price
$404 OW	From: Boston, MA (BOS) To: Chicago, IL (CHI) Departure: 11/29/2009 Return: - Airline:American Airlines	airfare.com Check price
$455 OW	From: Boston, MA (BOS) To: Chicago, IL (MDW) Departure: 12/22/2009 Return: - Airline:Delta Airlines	jetcombo.com Check price
$577 OW	From: Boston, MA (BOS) To: Chicago, IL (MDW) Departure: 11/29/2009 Return: - Airline:Delta Airlines	cfares.com Check price
$714 OW	From: Boston, MA (BOS) To: Chicago, IL (MDW) Departure: 12/22/2009 Return: - Airline:Delta Airlines	airfare.com Check price
$777 OW	From: Boston, MA (BOS) To: Chicago, IL (MDW) Departure: 11/29/2009 Return: - Airline:Delta Airlines	jetcombo.com Check price
$866 OW	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?

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Chicago Pictures

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