Cheap Flights 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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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 18:233hDirectORD 20:23Portland - Chicago | Tue, Aug 26 | United Airlines
ORD 08:052h 32mDirectPWM 11:37Chicago - Portland | Mon, Sep 1 | American AirlinesNZD 331 NZD 42622% OFF22% OFFNZD 426 NZD 331 -
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 345 NZD 42619% OFF19% OFFNZD 426 NZD 345 -
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 355 NZD 42617% OFF17% OFFNZD 426 NZD 355
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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 35517% OFFNZD 426 NZD 355
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PWM 18:566h 3m1 stopsORD 23:59Portland - Chicago | Tue, Jul 1 | Delta Air Lines
ORD 05:355h 15m1 stopsPWM 11:50Chicago - Portland | Fri, Jul 4 | Delta Air LinesNZD 36414% OFFNZD 426 NZD 364
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PWM 11:597h 4m1 stopsMDW 18:03Portland - Chicago | Tue, Jul 8 | Delta Air Lines
ORD 15:357h 24m1 stopsPWM 23:59Chicago - Portland | Tue, Jul 15 | Delta Air LinesNZD 37013% OFFNZD 426 NZD 370
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PWM 06:007h 16m1 stopsORD 12:16Portland - Chicago | Fri, Aug 1 | Delta Air Lines
ORD 17:595h 32m1 stopsPWM 00:31Chicago - Portland | Tue, Aug 5 | Delta Air LinesNZD 37811% OFFNZD 426 NZD 378
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PWM 18:536h 16m1 stopsORD 00:09Portland - Chicago | Thu, Jul 10 | Delta Air Lines
ORD 09:255h 46m1 stopsPWM 16:11Chicago - Portland | Mon, Jul 14 | Delta Air LinesNZD 38210% OFFNZD 426 NZD 382
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PWM 07:002h 57mDirectORD 08:57Portland - Chicago | Fri, Jul 4 | American Airlines
ORD 14:505h 7m1 stopsPWM 20:57Chicago - Portland | Fri, Jul 4 | American AirlinesNZD 3879% OFFNZD 426 NZD 387 -
PWM 12:536h 44m1 stopsMDW 18:37Portland - Chicago | Tue, Aug 26 | Delta Air Lines
ORD 06:005h 29m1 stopsPWM 12:29Chicago - Portland | Sun, Aug 31 | Delta Air LinesNZD 3879% OFFNZD 426 NZD 387
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PWM 13:0017h 25m1 stopsCHI Invalid DatePortland - Chicago | Wed, Jul 2 | Normal Airline
CHI 15:006hDirectPWM 16:00Chicago - Portland | Fri, Jul 4 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstop
PWM 06:142h 51mDirectORD 08:05Portland - Chicago | Tue, Aug 26 | United AirlinesNZD 172 NZD 46563% OFF63% OFFNZD 465 NZD 172
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PWM 06:102h 55mDirectORD 08:05Portland - Chicago | Tue, Jul 1 | United AirlinesNZD 205 NZD 46556% OFF56% OFFNZD 465 NZD 205
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PWM 07:002h 57mDirectORD 08:57Portland - Chicago | Fri, Jul 4 | American AirlinesNZD 418 NZD 46510% OFF10% OFFNZD 465 NZD 418
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PWM 06:102h 55mDirectORD 08:05Portland - Chicago | Fri, Jul 4 | United AirlinesNZD 4239% OFFNZD 465 NZD 423
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PWM 18:566h 3m1 stopsORD 23:59Portland - Chicago | Tue, Jul 1 | Delta Air LinesNZD 17263% OFFNZD 465 NZD 172
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PWM 06:007h 16m1 stopsORD 12:16Portland - Chicago | Tue, Jul 15 | Delta Air LinesNZD 18460% OFFNZD 465 NZD 184
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PWM 12:496h 52m1 stopsMDW 18:41Portland - Chicago | Wed, Jul 2 | Delta Air LinesNZD 18860% OFFNZD 465 NZD 188
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PWM 11:486h 49m1 stopsMDW 17:37Portland - Chicago | Tue, Aug 19 | Delta Air LinesNZD 19956% OFFNZD 465 NZD 199
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PWM 12:496h 52m1 stopsMDW 18:41Portland - Chicago | Fri, Jul 4 | Delta Air LinesNZD 37819% OFFNZD 465 NZD 378
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PWM 18:566h 3m1 stopsORD 23:59Portland - Chicago | Mon, Jun 30 | Delta Air LinesNZD 39216% OFFNZD 465 NZD 392
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PWM 13:0017h 25m1 stopsCHI Invalid DatePortland - Chicago | Wed, Jul 2 | 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 172 |
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| Cheapest round-trip ticket price | NZD 331 |
| Off-season for travel | March |
| Peak season for travel | June |
| Flight distance | 1,425.81 km |
| Average flight time | 3 hours |
| Popular airline | American Airlines |
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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 624. -
How long does it take to fly from Portland (PWM) to Chicago (CHI) and what is the distance?
It takes around 3 hours 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, American Airlines, Southwest 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
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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.
Use the Trip.com App
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