Flights to Chicago from Portland Intl (PDX)

Price	To/From	Dates	Supplier
1
$265 RTIncludes tax	From: Portland (PDX) To: Chicago (ORD) Depart: 21 Jul 2009 Return: 28 Jul 2009 Deal Details Take the Easy Way Out. Book with CheapAir.com.		CheapAir.com Book Online
$283 RTIncludes tax	From: Portland (PDX) To: Chicago (CHI) Travel valid from: 01 Jul 2009 Travel valid until: 31 Jul 2009 Deal Details Student Airfares - Travel more. Spend less		Student Universe Book Online
$358 RTIncludes tax	From: Portland (PDX) To: Chicago (ORD)	Depart: 29 Jul 2009 Return: 05 Aug 2009 Deal Details	Travelocity Book Online
$300 RTIncludes tax	From: Portland (PDX) To: Chicago (MDW)	Depart: 15 Jul 2009 Return: 21 Jul 2009 Deal Details	Expedia Book Online
$331 RTIncludes tax	From: Portland (PDX) To: Chicago (MDW) Depart: 08 Jul 2009 Return: 15 Jul 2009 Deal Details OneTravel.com # 1 in Travel Deals		OneTravel.com Book Online
$328 RTIncludes tax	From: Portland (PDX) To: Chicago (MDW) Depart: 14 Jul 2009 Return: 21 Jul 2009 Deal Details Save $10 instantly. CheapOair. The Only Way to Go		CheapOair.com Book Online
Sort by:
$265 RTIncludes tax	From: Portland (PDX) To: Chicago (ORD) Depart: 29 Jul 2009 Return: 05 Aug 2009 Deal Details Take the Easy Way Out. Book with CheapAir.com.		CheapAir.com Book Online
$265 RTIncludes tax	From: Portland (PDX) To: Chicago (ORD) Depart: 08 Aug 2009 Return: 15 Aug 2009 Deal Details Take the Easy Way Out. Book with CheapAir.com.		CheapAir.com Book Online
$273 RTIncludes tax	From: Portland (PDX) To: Chicago (ORD) Travel valid from: 01 Sep 2009 Travel valid until: 30 Sep 2009 Deal Details Save up to 50% off last minute fares!		Hotwire Book Online
$273 RTIncludes tax	From: Portland (PDX) To: Chicago (ORD) Travel valid from: 30 Sep 2009 Travel valid until: 07 Oct 2009 Deal Details Save up to 50% off last minute fares!		Hotwire Book Online
$280 RTIncludes tax	From: Portland (PDX) To: Chicago (MDW) Travel valid from: 19 Aug 2009 Travel valid until: 22 Aug 2009 Deal Details Save up to 50% off last minute fares!		Hotwire Book Online
$286 RTIncludes tax	From: Portland (PDX) To: Chicago (CHI) Depart: 21 Jul 2009 Return: 28 Jul 2009 Deal Details Take the Easy Way Out. Book with CheapAir.com.		CheapAir.com Book Online
$323 RTIncludes tax	From: Portland (PDX) To: Chicago (ORD) Travel valid from: 02 Sep 2009 Travel valid until: 09 Sep 2009 Deal Details Save up to 50% off last minute fares!		Hotwire Book Online
$323 RTIncludes tax	From: Portland (PDX) To: Chicago (ORD) Travel valid from: 07 Sep 2009 Travel valid until: 15 Sep 2009 Deal Details Save up to 50% off last minute fares!		Hotwire Book Online
$328 RTIncludes tax	From: Portland (PDX) To: Chicago (ORD) Depart: 14 Jul 2009 Return: 21 Jul 2009 Deal Details Save $10 instantly. CheapOair. The Only Way to Go		CheapOair.com Book Online
$331 RTIncludes tax	From: Portland (PDX) To: Chicago (ORD) Depart: 08 Jul 2009 Return: 15 Jul 2009 Deal Details OneTravel.com # 1 in Travel Deals		OneTravel.com Book Online
$338 RTIncludes tax	From: Portland (PDX) To: Chicago (ORD) Depart: 22 Jul 2009 Return: 29 Jul 2009 Deal Details Save $10 instantly. CheapOair. The Only Way to Go		CheapOair.com Book Online
$410 RTIncludes tax	From: Portland (PDX) To: Chicago (ORD)	Depart: 17 Jul 2009 Return: 19 Jul 2009 Deal Details	Expedia Book Online
From $12 per day	Car Rentals from $12 per Day Hit the open road this weekend. Rent a car any day between Thursday and Sunday for the lowest rates. Choose from a variety of cars including economy, mid-size and SUVs.		Priceline.com Book online
Under $200 RT*	Flight Deals Under $200 RT this Summer with No Booking Fees! Book your round-trip flight today for under $200 RT. Hurry - sale ends soon! Book now at priceline.com.		Priceline.com Book online

Search by date - Step one

* Required

Flights only

Flights + Hotels

Hotel only

Car Rental only

Ticket Type One Way Round Trip

From

List all departures

List all destinations Recent searches

Select new route

Depart

Return

Adults Children

Step two

Enter your information and click 'Search recommended websites' to book your travel with one of our partners, including...

Cheap Flights to Chicago from Portland Intl (PDX)

Hide

Modify Search

From

List all departures

List all destinations Recent searches

Filter Deals

Filter by price

from $265 to

Show

Alternative airports

Departure airports

Portland Intl

Portland Intl

Destination airports

Chicago

Show

Top cities in Illinois

Fact Finder

Avg. Flight Duration3 hr 49 mins

Chicago Travel Guide

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...

Airport Guides

Departure:

Portland Intl(PDX)

Destination:

Chicago Midway(MDW)
Chicago-O'Hare Intl(ORD)

Useful Links

Useful links for Chicago

Frommer's guide: Read up on Chicago before your trip
Fodor’s guide: Get the most out of Chicago
Map: Get a Bird’s Eye View of "The Windy City"
Weather: Check out the local forecast for "The Windy City"
Events calendar: What’s on When: Include these Chicago Events in your Illinois Trip Itinerary

Travel Tips

Read expert tips on getting the most out of travel

Airline and Air Travel Information: Getting Bumped; Airline Upgrade Guide; Airport Security
Find the Best Airfare Deals: Last-minute Airfares 101; Alternate Airports; Booking Flights by Phone; Fat-Finger Fares
International Travel Tips: Embassies and Consulates Abroad
Trip Planning: Airport Amusements; Timing Your Trip

More travel tips

Flight News

Catch up on the latest flight news

Guides

Popular Flight Guides:

Find Cheap Flights to:

Supplementary navigation

Airline Tickets (USA)
Cheap flights (UK & Ireland)
Cheap flights (Canada)
Billigflüge (Deutschland)
Cheap flights (Australia & New Zealand)
More international sites

I am in USA

Accessibility options

Newsletter Pop up box

Email:
Zip Code: