Cheap Flights from Portland to Chicago
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Airlines Flying from Portland to Chicago
Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
Flight deals from Portland to Chicago
We've found these cheap flights for you. You can book one-way or return flight tickets.
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Round-trip
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One way
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Cheapest nonstop
PWM 06:002h 56mDirectORD 07:56Portland - Chicago | Wed, Jul 30 | American Airlines
ORD 19:182h 34mDirectPWM 22:52Chicago - Portland | Sun, Aug 3 | American AirlinesNZD 390 NZD 49721% OFF21% OFFNZD 497 NZD 390 -
PWM 06:102h 55mDirectORD 08:05Portland - Chicago | Thu, Jul 31 | United Airlines
ORD 19:182h 34mDirectPWM 22:52Chicago - Portland | Mon, Aug 4 | American AirlinesNZD 403 NZD 49719% OFF19% OFFNZD 497 NZD 403 -
PWM 11:446h 56m1 stopsMDW 17:40Portland - Chicago | Wed, Jul 2 | Delta Air Lines
ORD 18:275h 19m1 stopsPWM 00:46Chicago - Portland | Fri, Jul 4 | Delta Air LinesNZD 346 NZD 49730% OFF30% OFFNZD 497 NZD 346 -
PWM 18:536h 16m1 stopsORD 00:09Portland - Chicago | Thu, Jul 31 | Delta Air Lines
ORD 09:255h 46m1 stopsPWM 16:11Chicago - Portland | Tue, Aug 5 | Delta Air LinesNZD 35728% OFFNZD 497 NZD 357
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PWM 17:355h 46m1 stopsORD 22:21Portland - Chicago | Wed, Jun 25 | Delta Air Lines
ORD 17:595h 27m1 stopsPWM 00:26Chicago - Portland | Wed, Jul 2 | Delta Air LinesNZD 35728% OFFNZD 497 NZD 357
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PWM 18:536h 16m1 stopsORD 00:09Portland - Chicago | Wed, Jul 30 | Delta Air Lines
ORD 09:006h 11m1 stopsPWM 16:11Chicago - Portland | Mon, Aug 4 | Delta Air LinesNZD 35728% OFFNZD 497 NZD 357
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PWM 18:566h 2m1 stopsORD 23:58Portland - Chicago | Mon, Jun 9 | Delta Air Lines
ORD 05:355h 15m1 stopsPWM 11:50Chicago - Portland | Wed, Jun 11 | Delta Air LinesNZD 36227% OFFNZD 497 NZD 362
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PWM 06:006h 59m1 stopsMDW 11:59Portland - Chicago | Tue, Jul 1 | Delta Air Lines
ORD 05:355h 15m1 stopsPWM 11:50Chicago - Portland | Fri, Jul 4 | Delta Air LinesNZD 36626% OFFNZD 497 NZD 366
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PWM 12:556h 54m1 stopsORD 18:49Portland - Chicago | Tue, Jun 10 | Delta Air Lines
ORD 15:407h 46m1 stopsPWM 00:26Chicago - Portland | Tue, Jun 17 | Delta Air LinesNZD 36626% OFFNZD 497 NZD 366
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PWM 06:007h 29m1 stopsORD 12:29Portland - Chicago | Sat, Jun 21 | Delta Air Lines
MDW 10:266h 35m1 stopsPWM 18:01Chicago - Portland | Tue, Jun 24 | Delta Air LinesNZD 36726% OFFNZD 497 NZD 367
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PWM 06:307h 17m1 stopsORD 12:47Portland - Chicago | Tue, Jun 17 | Delta Air Lines
ORD 18:275h 19m1 stopsPWM 00:46Chicago - Portland | Tue, Jun 17 | Delta Air LinesNZD 36726% OFFNZD 497 NZD 367
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PWM 18:536h 16m1 stopsORD 00:09Portland - Chicago | Fri, Jul 25 | Delta Air Lines
ORD 09:255h 46m1 stopsPWM 16:11Chicago - Portland | Mon, Jul 28 | Delta Air LinesNZD 36726% OFFNZD 497 NZD 367
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PWM 13:0017h 25m1 stopsCHI Invalid DatePortland - Chicago | Mon, Jun 9 | Normal Airline
CHI 15:006hDirectPWM 16:00Chicago - Portland | Wed, Jun 11 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstop
PWM 07:002h 57mDirectORD 08:57Portland - Chicago | Fri, Jul 4 | American AirlinesNZD 151 NZD 23034% OFF34% OFFNZD 230 NZD 151
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PWM 12:496h 52m1 stopsMDW 18:41Portland - Chicago | Fri, Jul 4 | Delta Air LinesNZD 171 NZD 23026% OFF26% OFFNZD 230 NZD 171
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PWM 18:566h 3m1 stopsORD 23:59Portland - Chicago | Mon, Jun 30 | Delta Air LinesNZD 171 NZD 23026% OFF26% OFFNZD 230 NZD 171
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PWM 11:446h 2m1 stopsORD 16:46Portland - Chicago | Wed, Jul 2 | Delta Air LinesNZD 17225% OFFNZD 230 NZD 172
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PWM 06:006h 56m1 stopsMDW 11:56Portland - Chicago | Tue, Jul 1 | Delta Air LinesNZD 17325% OFFNZD 230 NZD 173
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PWM 18:566h 1m1 stopsORD 23:57Portland - Chicago | Wed, Jun 18 | Delta Air LinesNZD 18122% OFFNZD 230 NZD 181
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PWM 06:007h 16m1 stopsORD 12:16Portland - Chicago | Tue, Jul 15 | Delta Air LinesNZD 18520% OFFNZD 230 NZD 185
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PWM 13:536h 15m1 stopsORD 19:08Portland - Chicago | Tue, Jun 24 | Delta Air LinesNZD 18520% OFFNZD 230 NZD 185
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PWM 12:496h 52m1 stopsMDW 18:41Portland - Chicago | Thu, Jun 26 | Delta Air LinesNZD 18519% OFFNZD 230 NZD 185
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PWM 06:007h 9m1 stopsORD 12:09Portland - Chicago | Sat, Jul 19 | Delta Air LinesNZD 18619% OFFNZD 230 NZD 186
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PWM 13:0017h 25m1 stopsCHI Invalid DatePortland - Chicago | Mon, Jun 9 | Normal AirlineFind More FlightsFind More Flights
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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
Flight Information from Portland to Chicago
| Cheapest one-way flight price | NZD 150 |
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| Cheapest round-trip ticket price | NZD 331 |
| Off-season for travel | April |
| Peak season for travel | June |
| Flight distance | 1,425.81 km |
| Average flight time | 3 hours 1 minute |
| Popular airline | Delta Air Lines |
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Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
FAQ
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When are flight tickets from Portland (PWM) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from Portland to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays. -
How much do flights from Portland (PWM) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around NZD 626. -
How long does it take to fly from Portland (PWM) to Chicago (CHI) and what is the distance?
It takes around 3 hours 1 minute to fly from Portland (PWM) to Chicago (CHI). -
What are the most popular airlines that fly from Portland (PWM) to Chicago (CHI)?
Airlines with flights from Portland (PWM) to Chicago (CHI): Qatar Airways, United Airlines, Southwest Airlines, American Airlines and Air New Zealand.
How to find a cheap flight from Portland to Chicago
Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Portland to Chicago. Book your flights at the right time and save more.
Book Early
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Compare Flight Prices
Compare prices on travel agency and airline websites.
Look Out for Deals
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Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
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