Cheap flights to Chicago from Portland Intl Jetport (PWM)

Flights to Chicago from Portland Intl Jetport (PWM)

Price	To/From	Supplier
1
$264 RTIncludes tax	From: Portland, ME (PWM) To: Chicago, IL (CHI) Travel valid from: 26 Jul 2008 Travel valid until: 25 Jun 2009 Deal Details Take the Easy Way Out. Book with CheapAir.com.	CheapAir.com Book online
$298 RTIncludes tax	From: Portland, ME (PWM) 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
$274 RTIncludes tax	From: Portland, ME (PWM) 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
$385 RTIncludes tax	From: Portland, ME (PWM) 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
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$261 RTIncludes tax	From: Portland, ME (PWM) To: Chicago, IL (ORD) Depart: 28 Aug 2008 Return: 03 Sep 2008 Deal Details Other dates & prices offered	Kayak Book online
$264 RTIncludes tax	From: Portland, ME (PWM) To: Chicago, IL (CHI) Travel valid from: 26 Jul 2008 Travel valid until: 10 Aug 2008 Deal Details Take the Easy Way Out. Book with CheapAir.com.	CheapAir.com Book online
$275 RTIncludes tax	From: Portland, ME (PWM) To: Chicago, IL (ORD) Depart: 08 Aug 2008 Return: 12 Aug 2008 Deal Details Other dates & prices offered	Kayak Book online
$290 RTIncludes tax	From: Portland, ME (PWM) To: Chicago, IL (ORD) Depart: 04 Aug 2008 Return: 12 Aug 2008 Deal Details Other dates & prices offered	Kayak Book online
$315 RTIncludes tax	From: Portland, ME (PWM) To: Chicago, IL (CHI) Depart: 13 Aug 2008 Return: 31 Aug 2008 Deal Details Other dates & prices offered	Kayak Book online
$316 RTIncludes tax	From: Portland, ME (PWM) To: Chicago, IL (ORD) Depart: 06 Aug 2008 Return: 12 Aug 2008 Deal Details Other dates & prices offered	Kayak Book online
$316 RTIncludes tax	From: Portland, ME (PWM) To: Chicago, IL (ORD) Depart: 07 Aug 2008 Return: 12 Aug 2008 Deal Details Other dates & prices offered	Kayak Book online
$327 RTIncludes tax	From: Portland, ME (PWM) 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
$351 RTIncludes tax	From: Portland, ME (PWM) To: Chicago, IL (CHI) Depart: 12 Aug 2008 Return: 31 Aug 2008 Deal Details Other dates & prices offered	Kayak Book online
$351 RTIncludes tax	From: Portland, ME (PWM) To: Chicago, IL (CHI) Depart: 21 Aug 2008 Return: 24 Aug 2008 Deal Details Other dates & prices offered	Kayak Book online
$387 RTIncludes tax	From: Portland, ME (PWM) 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
$395 RTIncludes tax	From: Portland, ME (PWM) To: Chicago, IL (MDW) 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
$399 RTIncludes tax	From: Portland, ME (PWM) To: Chicago, IL (MDW) 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
$401 RTIncludes tax	From: Portland, ME (PWM) To: Chicago, IL (CHI) Depart: 11 Aug 2008 Return: 31 Aug 2008 Deal Details Other dates & prices offered	Kayak Book online
$402 RTIncludes tax	From: Portland, ME (PWM) 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
$453 RTIncludes tax	From: Portland, ME (PWM) To: Chicago, IL (ORD) Depart: 10 Aug 2008 Return: 17 Aug 2008 Deal Details Get our lowest price or an automatic cash refund!	Orbitz Book online
$458 RTIncludes tax	From: Portland, ME (PWM) To: Chicago, IL (MDW) Depart: 20 Aug 2008 Return: 27 Aug 2008 Deal Details Cheap air tickets, hotels, travel deals, and more.	CheapTickets 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
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Avg. Flight Duration2 hr 39 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...