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 53mDirectORD 07:53Portland - Chicago | Fri, Jun 6 | United Airlines
ORD 11:052h 26mDirectPWM 14:31Chicago - Portland | Mon, Jun 9 | United AirlinesNZD 395 NZD 45713% OFF13% OFFNZD 457 NZD 395 -
PWM 06:002h 53mDirectORD 07:53Portland - Chicago | Fri, May 23 | United Airlines
ORD 09:482h 30mDirectPWM 13:18Chicago - Portland | Sun, May 25 | American AirlinesNZD 407 NZD 45711% OFF11% OFFNZD 457 NZD 407
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PWM 05:307h 23m1 stopsMDW 11:53Portland - Chicago | Sat, May 31 | Delta Air Lines
MDW 16:156h 44m1 stopsPWM 23:59Chicago - Portland | Sat, May 31 | Delta Air LinesNZD 350 NZD 45723% OFF23% OFFNZD 457 NZD 350 -
PWM 06:055h 7m1 stopsORD 10:12Portland - Chicago | Sun, May 25 | Delta Air Lines
ORD 06:005h 35m1 stopsPWM 12:35Chicago - Portland | Thu, May 29 | Delta Air LinesNZD 35023% OFFNZD 457 NZD 350
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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 36021% OFFNZD 457 NZD 360
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PWM 17:004h 21m1 stopsORD 20:21Portland - Chicago | Thu, May 29 | Delta Air Lines
ORD 09:006h 3m1 stopsPWM 16:03Chicago - Portland | Sun, Jun 1 | Delta Air LinesNZD 36121% OFFNZD 457 NZD 361
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PWM 18:566h 3m1 stopsORD 23:59Portland - Chicago | Wed, Jul 2 | Delta Air Lines
ORD 11:004h 11m1 stopsPWM 16:11Chicago - Portland | Mon, Jul 7 | Delta Air LinesNZD 36321% OFFNZD 457 NZD 363
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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 36620% OFFNZD 457 NZD 366
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PWM 13:075h 55m1 stopsMDW 18:02Portland - Chicago | Thu, Jul 10 | Delta Air Lines
ORD 09:255h 46m1 stopsPWM 16:11Chicago - Portland | Mon, Jul 14 | Delta Air LinesNZD 37019% OFFNZD 457 NZD 370
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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 37119% OFFNZD 457 NZD 371
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PWM 12:496h 14m1 stopsORD 18:03Portland - Chicago | Mon, Jun 16 | Delta Air Lines
ORD 07:053h 59m1 stopsPWM 12:04Chicago - Portland | Mon, Jun 23 | Delta Air LinesNZD 37119% OFFNZD 457 NZD 371
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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 37119% OFFNZD 457 NZD 371
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PWM 13:0017h 25m1 stopsCHI Invalid DatePortland - Chicago | Fri, May 16 | Normal Airline
CHI 15:006hDirectPWM 16:00Chicago - Portland | Sun, May 18 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstop
PWM 11:403h 3mDirectORD 13:43Portland - Chicago | Sat, May 24 | United AirlinesNZD 203 NZD 35743% OFF43% OFFNZD 357 NZD 203
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PWM 11:433h 3mDirectORD 13:46Portland - Chicago | Wed, May 28 | United AirlinesNZD 206 NZD 35742% OFF42% OFFNZD 357 NZD 206
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PWM 05:307h 23m1 stopsMDW 11:53Portland - Chicago | Wed, May 21 | Delta Air LinesNZD 169 NZD 35753% OFF53% OFFNZD 357 NZD 169
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PWM 06:006h 56m1 stopsMDW 11:56Portland - Chicago | Tue, Jul 1 | Delta Air LinesNZD 17451% OFFNZD 357 NZD 174
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PWM 05:307h 23m1 stopsMDW 11:53Portland - Chicago | Sat, May 31 | Delta Air LinesNZD 17551% OFFNZD 357 NZD 175
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PWM 13:308h 50m1 stopsORD 21:20Portland - Chicago | Fri, May 30 | Delta Air LinesNZD 17551% OFFNZD 357 NZD 175
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PWM 16:578h 7m1 stopsORD 00:04Portland - Chicago | Sat, May 31 | Frontier AirlinesNZD 17551% OFFNZD 357 NZD 175 -
PWM 05:307h 23m1 stopsMDW 11:53Portland - Chicago | Sun, Jun 1 | Delta Air LinesNZD 18050% OFFNZD 357 NZD 180
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PWM 13:156h 26m1 stopsMDW 18:41Portland - Chicago | Sat, Jun 21 | Delta Air LinesNZD 18548% OFFNZD 357 NZD 185
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PWM 18:566h 3m1 stopsORD 23:59Portland - Chicago | Fri, Jun 13 | Delta Air LinesNZD 18648% OFFNZD 357 NZD 186
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PWM 13:536h 15m1 stopsORD 19:08Portland - Chicago | Tue, Jun 24 | Delta Air LinesNZD 18748% OFFNZD 357 NZD 187
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PWM 21:2927h 3m1 stopsORD 23:32Portland - Chicago | Thu, May 15 | Frontier AirlinesNZD 31811% OFFNZD 357 NZD 318
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PWM 13:0017h 25m1 stopsCHI Invalid DatePortland - Chicago | Fri, May 16 | 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 168 |
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| Cheapest round-trip ticket price | NZD 386 |
| Off-season for travel | March |
| Peak season for travel | February |
| Flight distance | 1,425.81 km |
| Average flight time | 2 hours 55 minutes |
| 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 633. -
How long does it take to fly from Portland (PWM) to Chicago (CHI) and what is the distance?
It takes around 2 hours 55 minutes 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): United Airlines, Emirates, Qatar Airways, Air New Zealand and American Airlines.
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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