Cheap flights to Chicago from Boston

Flights to Chicago from Boston

Price	To/From	Dates	Supplier
1
$279 RTIncludes tax	From: Boston, MA (BOS) To: Chicago, IL (ORD) Depart: 28 Aug 2008 Return: 04 Sep 2008 Deal Details Get our lowest price or an automatic cash refund!		Orbitz Book online
$243 RTIncludes tax	From: Boston, MA (BOS) To: Chicago, IL (MDW) Depart: 27 Aug 2008 Return: 03 Sep 2008 Deal Details Cheap air tickets, hotels, travel deals, and more.		CheapTickets Book online
$267 RTIncludes tax	From: Boston, MA (BOS) To: Chicago, IL (ORD) Travel valid from: 01 Oct 2008 Travel valid until: 15 Oct 2008 Deal Details Save $10 instantly. CheapOair. The Only Way to Go		CheapOAir.com Book online
$242 RTIncludes tax	From: Boston, MA (BOS) To: Chicago, IL (CHI) Travel valid from: 02 Jul 2008 Travel valid until: 31 Aug 2008 Deal Details Student Airfares - Travel more. Spend less		Student Universe Book online
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$243 RTIncludes tax	From: Boston, MA (BOS) To: Chicago, IL (ORD) Depart: 27 Aug 2008 Return: 03 Sep 2008 Deal Details Cheap air tickets, hotels, travel deals, and more.		CheapTickets Book online
$256 RTIncludes tax	From: Boston, MA (BOS) To: Chicago, IL (CHI) Depart: 19 Aug 2008 Return: 22 Aug 2008 Deal Details Other dates & prices offered		Kayak Book online
$256 RTIncludes tax	From: Boston, MA (BOS) To: Chicago, IL (ORD) Depart: 20 Aug 2008 Return: 23 Aug 2008 Deal Details Other dates & prices offered		Kayak Book online
$256 RTIncludes tax	From: Boston, MA (BOS) To: Chicago, IL (CHI) Depart: 27 Aug 2008 Return: 01 Sep 2008 Deal Details Other dates & prices offered		Kayak Book online
$256 RTIncludes tax	From: Boston, MA (BOS) To: Chicago, IL (CHI) Depart: 29 Aug 2008 Return: 02 Sep 2008 Deal Details Other dates & prices offered		Kayak Book online
$256 RTIncludes tax	From: Boston, MA (BOS) To: Chicago, IL (ORD) Depart: 12 Sep 2008 Return: 15 Sep 2008 Deal Details Other dates & prices offered		Kayak Book online
$267 RTIncludes tax	From: Boston, MA (BOS) To: Chicago, IL (MDW) Travel valid from: 01 Oct 2008 Travel valid until: 15 Oct 2008 Deal Details Save $10 instantly. CheapOair. The Only Way to Go		CheapOAir.com Book online
$277 RTIncludes tax	From: Boston, MA (BOS) To: Chicago, IL (MDW) Depart: 26 Sep 2008 Return: 30 Sep 2008 Deal Details Other dates & prices offered		Kayak Book online
$277 RTIncludes tax	From: Boston, MA (BOS) To: Chicago, IL (MDW) Depart: 22 Oct 2008 Return: 25 Oct 2008 Deal Details Other dates & prices offered		Kayak Book online
$277 RTIncludes tax	From: Boston, MA (BOS) To: Chicago, IL (ORD) Travel valid from: 16 Oct 2008 Travel valid until: 30 Oct 2008 Deal Details Save $10 instantly. CheapOair. The Only Way to Go		CheapOAir.com Book online
$281 RTIncludes tax	From: Boston, MA (BOS) To: Chicago, IL (ORD) Travel valid from: 31 Oct 2008 Travel valid until: 14 Nov 2008 Deal Details Save $10 instantly. CheapOair. The Only Way to Go		CheapOAir.com Book online
$283 RTIncludes tax	From: Boston, MA (BOS) To: Chicago, IL (MDW) Depart: 04 Aug 2008 Return: 07 Aug 2008 Deal Details Other dates & prices offered		Kayak Book online
$284 RTIncludes tax	From: Boston, MA (BOS) To: Chicago, IL (MDW) Travel valid from: 15 Nov 2008 Travel valid until: 01 Dec 2008 Deal Details Save $10 instantly. CheapOair. The Only Way to Go		CheapOAir.com Book online
$290 RTIncludes tax	From: Boston, MA (BOS) To: Chicago, IL (MDW) Depart: 28 Aug 2008 Return: 04 Sep 2008 Deal Details Get our lowest price or an automatic cash refund!		Orbitz Book online
$294 RTIncludes tax	From: Boston, MA (BOS) To: Chicago, IL (MDW) Depart: 25 Sep 2008 Return: 29 Sep 2008 Deal Details Other dates & prices offered		Kayak Book online
$300 RTIncludes tax	From: Boston, MA (BOS) To: Chicago, IL (MDW) Depart: 10 Aug 2008 Return: 17 Aug 2008 Deal Details Get our lowest price or an automatic cash refund!		Orbitz Book online
$313 RTIncludes tax	From: Boston, MA (BOS) To: Chicago, IL (ORD) Depart: 09 Aug 2008 Return: 16 Aug 2008 Deal Details Cheap air tickets, hotels, travel deals, and more.		CheapTickets Book online
$318 RTIncludes tax	From: Boston, MA (BOS) To: Chicago, IL (MDW)	Travel valid from: 16 Aug 2008 Travel valid until: 30 Aug 2008 Deal Details	BookAirlineTickets.com Book online
$326 RTIncludes tax	From: Boston, MA (BOS) To: Chicago, IL (ORD)	Travel valid from: 15 Aug 2008 Travel valid until: 22 Aug 2008 Deal Details	BookAirlineTickets.com Book online
$360 RTExcludes tax	From: Boston, MA (BOS) To: Chicago, IL (ORD)	Depart: 05 Aug 2008 Return: 12 Aug 2008 Deal Details	CheapOAir.com Book online
$393 RTExcludes tax	From: Boston, MA (BOS) To: Chicago, IL (ORD)	Depart: 14 Aug 2008 Return: 21 Aug 2008 Deal Details	CheapOAir.com Book online
$509 RTExcludes tax	From: Boston, MA (BOS) To: Chicago, IL (ORD)	Depart: 30 Jul 2008 Return: 07 Aug 2008 Deal Details	CheapOAir.com Book online
From $13.95 per day	Find Rental Cars from $13.95 a Day at Hotwire Rental car brands you trust with low Hotwire Hot Rates!		Hotwire Book online
Save up to 60%	4 Star Hotels at 2 Star Prices! Hotels for less with low Hotwire Hot-Rates!		Hotwire Book online

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Boston

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Chicago

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Avg. Flight Duration2 hr 41 mins

Flight guide to Chicago

Overview of Chicago

As Frank Sinatra crooned, “Chicago is my kind of town,” and many tourists agree. Book a flight to Chicago and shop the Miracle Mile, step back in time at the National History Museum, tour the artist’s lofts in the heart of the city, and enjoy some cool...