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Cheap flights from Portland (PDX) to Chicago (CHI) from $54

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/22. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
PDX — CHI
Apr 28 — May 51
From?
To?
Sun 4/28
Sun 5/5
1 adult, Economy
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The best prices from Portland to Chicago are usually found in January or February, booked 81 days in advance, depart on a Saturday or Tuesday and return on a Wednesday

Cheap flight deals from Portland to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 23, 2024.

Popular in

June

Cheapest in

January

Round-trip from

$222

One-way from

$92
High demand for flights, 26% potential price rise
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Best time to find cheap flights, 21% potential price drop
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From Portland to Chicago (CHI)
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One-way flight from Portland to Chicago (CHI)
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What is the cheapest day to fly round-trip from Portland to Chicago?

Friday is generally a great day to depart. Flying on this day could help you save up to 16%.

How far in advance should I book a flight from Portland to Chicago?

Travelers have found it’s best to book a flight 16 days in advance to save up to 124% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 16 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Portland to Chicago 1-2 weeks in advance for as low as $528, or $743 for flights within the next 24 hours.

What is the cheapest month to fly from Portland to Chicago?

Due to multiple factors, expect to potentially pay more when booking in June. For low rates, January can be a great choice for travel to Chicago. Flights to Chicago from Portland in January are about $377 on average during January, but can be found for as low as $149.

When is the cheapest time to fly from Portland to Chicago (PDX - CHI)?

A simple way to save on the total cost of your ticket is to fly from Portland to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 24% on your trip compared to booking a flight in the morning.

Cheap Frontier flights from Portland to Chicago

Explore cheap flight options specifically provided by Frontier for the route between Portland and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 3,086,534 searches. Data last updated April 23, 2024.
Peruse some of the lowest-priced Frontier flights we've found from Portland to Chicago. Come back soon if you're not finding the exact deal you're looking for.
Sat 5/116:06 pmPDX - MDW
1 stop12h 25mFrontier
Sat 5/1810:01 pmMDW - PDX
1 stop13h 10mFrontier
Deal found 4/22$115
Sat 5/184:00 pmPDX - MDW
2 stops11h 50mFrontier
Mon 5/209:10 pmMDW - PDX
1 stop17h 11mFrontier
Deal found 4/22$125
Fri 5/1012:49 amPDX - ORD
1 stop22h 07mFrontier
Sat 5/185:56 pmORD - PDX
1 stop17h 15mFrontier
Deal found 4/22$136
Tue 5/1412:59 amPDX - ORD
1 stop21h 57mFrontier
Mon 5/207:59 pmORD - PDX
1 stop18h 22mFrontier
Deal found 4/22$138
Sat 5/46:06 pmPDX - MDW
1 stop12h 25mFrontier
Sat 5/1810:01 pmMDW - PDX
1 stop13h 10mFrontier
Deal found 4/22$139
Fri 5/1712:48 amPDX - MDW
1 stop8h 25mFrontier
Mon 5/209:10 pmMDW - PDX
1 stop17h 11mFrontier
Deal found 4/22$140
Mon 4/2910:16 pmPDX - ORD
1 stop11h 13mFrontier
Tue 5/76:27 pmORD - PDX
1 stop7h 32mFrontier
Deal found 4/22$141
Tue 5/146:05 pmPDX - MDW
1 stop13h 17mFrontier
Thu 5/167:35 amMDW - PDX
1 stop11h 07mFrontier
Deal found 4/22$142
Fri 5/177:54 pmPDX - ORD
2 stops31h 06mFrontier
Tue 5/217:59 pmORD - PDX
2 stops25h 21mFrontier
Deal found 4/22$148

  • One of the most popular airlines traveling from Portland to Chicago is Frontier. Flights from Frontier traveling this route typically cost $351.21 RT. This price is typically 33% cheaper than other airlines that offer Portland to Chicago flights. When booking this route, the cheapest RT price found was $149. Portland Airport is the most common Portland airport to take off from when flying to Chicago. Chicago O'Hare Intl Airport is the most popular arrival airport in Chicago. When flying from Portland to Chicago, Frontier flights are 11% more popular than any other airline flying that same route.

Cheap American Airlines flights from Portland to Chicago

Explore cheap flight options specifically provided by American Airlines for the route between Portland and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 3,086,534 searches. Data last updated April 23, 2024.
Have a look at some of the cheapest available American Airlines flights departing from Portland and landing in Chicago. Make sure to examine the flight information before completing your reservation.
Tue 6/1111:55 pmPDX - ORD
Nonstop4h 05mAmerican Airlines
Tue 7/98:24 pmORD - PDX
Nonstop4h 25mAmerican Airlines
Deal found 4/22$184
Fri 5/3111:54 pmPDX - ORD
Nonstop4h 06mAmerican Airlines
Tue 6/48:25 pmORD - PDX
Nonstop4h 28mAmerican Airlines
Deal found 4/21$197
Thu 6/611:55 pmPDX - ORD
Nonstop4h 05mAmerican Airlines
Tue 6/118:30 pmORD - PDX
Nonstop4h 28mAmerican Airlines
Deal found 4/22$199
Tue 6/116:24 pmPDX - ORD
1 stop9h 00mAmerican Airlines
Tue 7/98:24 pmORD - PDX
Nonstop4h 25mAmerican Airlines
Deal found 4/22$215
Thu 5/21:32 pmPDX - ORD
Nonstop3h 58mAmerican Airlines
Sun 5/510:06 amORD - PDX
Nonstop4h 31mAmerican Airlines
Deal found 4/22$821
Sun 4/281:32 pmPDX - ORD
Nonstop3h 58mAmerican Airlines
Sun 5/510:06 amORD - PDX
Nonstop4h 31mAmerican Airlines
Deal found 4/22$833

  • If you’re traveling from Portland to Chicago, one of the more common airlines traveling that route is American Airlines. Flights from American Airlines traveling this route typically cost $421.71 RT. This price is typically 44% more expensive than other airlines that offer Portland to Chicago flights. When booking this route, the cheapest RT price found was $198. The most popular departure airport in Portland when flying to Chicago is Portland Airport. The most popular airport to fly into when visiting Chicago is Chicago O'Hare Intl Airport. When flying from Portland to Chicago, American Airlines flights are 3% more popular than any other airline flying that same route.

Cheap Portland to Chicago flights in April & May 2024

Find cheap flight options from Portland to Chicago specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,086,534 searches. Prices were last updated on April 23, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. Check back soon for alternative fares.
Wed 5/811:30 pmPDX - ORD
Nonstop3h 50mSpirit Airlines
Wed 5/158:00 pmORD - PDX
Nonstop4h 30mSpirit Airlines
Deal found 4/21$107
Sat 5/1811:30 pmPDX - ORD
Nonstop3h 50mSpirit Airlines
Sat 5/258:00 pmORD - PDX
Nonstop4h 30mSpirit Airlines
Deal found 4/22$109
Wed 5/2911:30 pmPDX - ORD
Nonstop3h 50mSpirit Airlines
Wed 6/58:26 pmORD - PDX
Nonstop4h 27mSpirit Airlines
Deal found 4/22$113
Wed 5/2911:30 pmPDX - ORD
Nonstop3h 50mSpirit Airlines
Sat 6/18:00 pmORD - PDX
Nonstop4h 30mSpirit Airlines
Deal found 4/22$115
Sat 5/116:06 pmPDX - MDW
1 stop12h 25mFrontier
Sat 5/1810:01 pmMDW - PDX
1 stop13h 10mFrontier
Deal found 4/22$115
Sat 5/1811:30 pmPDX - ORD
Nonstop3h 50mSpirit Airlines
Sun 5/198:00 pmORD - PDX
Nonstop4h 30mSpirit Airlines
Deal found 4/22$124
Wed 5/811:30 pmPDX - ORD
Nonstop3h 50mMultiple Airlines
Sat 5/185:56 pmORD - PDX
1 stop17h 15mMultiple Airlines
Deal found 4/22$125
Sat 5/184:00 pmPDX - MDW
2 stops11h 50mFrontier
Mon 5/209:10 pmMDW - PDX
1 stop17h 11mFrontier
Deal found 4/22$125
Sat 5/1811:30 pmPDX - ORD
Nonstop3h 50mSpirit Airlines
Sun 5/268:00 pmORD - PDX
Nonstop4h 30mSpirit Airlines
Deal found 4/22$126

Portland to Chicago 2024 flight deals

Discover exclusive flight deals for travel between Portland and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,086,534 searches. Data last updated April 23, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. Check back soon for alternative fares.
Wed 5/811:30 pmPDX - ORD
Nonstop3h 50mSpirit Airlines
Wed 5/158:00 pmORD - PDX
Nonstop4h 30mSpirit Airlines
Deal found 4/21$107
Sat 5/1811:30 pmPDX - ORD
Nonstop3h 50mSpirit Airlines
Sat 5/258:00 pmORD - PDX
Nonstop4h 30mSpirit Airlines
Deal found 4/22$109
Wed 5/2911:30 pmPDX - ORD
Nonstop3h 50mSpirit Airlines
Wed 6/58:26 pmORD - PDX
Nonstop4h 27mSpirit Airlines
Deal found 4/22$113
Wed 5/2911:30 pmPDX - ORD
Nonstop3h 50mSpirit Airlines
Sat 6/18:00 pmORD - PDX
Nonstop4h 30mSpirit Airlines
Deal found 4/22$115
Sat 5/116:06 pmPDX - MDW
1 stop12h 25mFrontier
Sat 5/1810:01 pmMDW - PDX
1 stop13h 10mFrontier
Deal found 4/22$115
Sat 5/1811:30 pmPDX - ORD
Nonstop3h 50mSpirit Airlines
Sun 5/198:00 pmORD - PDX
Nonstop4h 30mSpirit Airlines
Deal found 4/22$124
Wed 5/811:30 pmPDX - ORD
Nonstop3h 50mMultiple Airlines
Sat 5/185:56 pmORD - PDX
1 stop17h 15mMultiple Airlines
Deal found 4/22$125
Sat 5/184:00 pmPDX - MDW
2 stops11h 50mFrontier
Mon 5/209:10 pmMDW - PDX
1 stop17h 11mFrontier
Deal found 4/22$125
Sat 5/1811:30 pmPDX - ORD
Nonstop3h 50mSpirit Airlines
Sun 5/268:00 pmORD - PDX
Nonstop4h 30mSpirit Airlines
Deal found 4/22$126

Non-stop flights to Chicago from Portland

Discover non-stop flight options from Portland to Chicago. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 3,086,534 searches. Data last updated April 23, 2024.
Consider booking one of these non-stop flights heading from Portland to Chicago. Search for alternative flights from Portland to Chicago by utilizing the search form above.
Wed 5/811:30 pmPDX - ORD
Nonstop3h 50mSpirit Airlines
Wed 5/158:00 pmORD - PDX
Nonstop4h 30mSpirit Airlines
Deal found 4/21$107
Sat 5/1811:30 pmPDX - ORD
Nonstop3h 50mSpirit Airlines
Sat 5/258:00 pmORD - PDX
Nonstop4h 30mSpirit Airlines
Deal found 4/22$109
Wed 5/2911:30 pmPDX - ORD
Nonstop3h 50mSpirit Airlines
Wed 6/58:26 pmORD - PDX
Nonstop4h 27mSpirit Airlines
Deal found 4/22$113
Wed 5/2911:30 pmPDX - ORD
Nonstop3h 50mSpirit Airlines
Sat 6/18:00 pmORD - PDX
Nonstop4h 30mSpirit Airlines
Deal found 4/22$115
Wed 5/811:30 pmPDX - ORD
Nonstop3h 50mSpirit Airlines
Fri 5/108:00 pmORD - PDX
Nonstop4h 30mSpirit Airlines
Deal found 4/22$124
Sat 5/1811:30 pmPDX - ORD
Nonstop3h 50mSpirit Airlines
Sun 5/268:00 pmORD - PDX
Nonstop4h 30mSpirit Airlines
Deal found 4/22$126
Wed 5/2911:30 pmPDX - ORD
Nonstop3h 50mSpirit Airlines
Thu 6/68:26 pmORD - PDX
Nonstop4h 27mSpirit Airlines
Deal found 4/22$131
Fri 5/3111:30 pmPDX - ORD
Nonstop3h 50mSpirit Airlines
Sat 6/18:00 pmORD - PDX
Nonstop4h 30mSpirit Airlines
Deal found 4/22$133
Fri 5/1711:30 pmPDX - ORD
Nonstop3h 50mSpirit Airlines
Sun 5/198:00 pmORD - PDX
Nonstop4h 30mSpirit Airlines
Deal found 4/21$140

Portland to Chicago flights leaving soon

Find last-minute flight options from Portland to Chicago for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,086,534 searches. Data last updated April 23, 2024.
Have a look at some of the last-minute flights available departing from Portland to Chicago. Users should be sure to double check the price, date, and time of their last-minute flight.
Mon 4/2910:16 pmPDX - ORD
1 stop11h 13mFrontier
Tue 5/76:27 pmORD - PDX
1 stop7h 32mFrontier
Deal found 4/22$141
Sun 4/2812:59 amPDX - ORD
1 stop21h 57mFrontier
Tue 5/76:27 pmORD - PDX
1 stop7h 32mFrontier
Deal found 4/22$152
Wed 5/110:09 pmPDX - ORD
1 stop11h 36mFrontier
Sat 5/46:27 pmORD - PDX
1 stop7h 32mFrontier
Deal found 4/22$160
Sat 4/276:06 pmPDX - MDW
1 stop12h 25mFrontier
Tue 4/305:01 amMDW - PDX
1 stop14h 04mFrontier
Deal found 4/22$160
Sat 4/2710:17 pmPDX - ORD
1 stop11h 12mFrontier
Tue 5/76:27 pmORD - PDX
1 stop7h 32mFrontier
Deal found 4/22$168
Wed 5/110:09 pmPDX - ORD
1 stop11h 36mFrontier
Mon 5/66:27 pmORD - PDX
1 stop7h 32mFrontier
Deal found 4/22$172
Sat 4/276:06 pmPDX - MDW
1 stop12h 25mFrontier
Mon 5/65:30 amMDW - PDX
1 stop20h 29mFrontier
Deal found 4/22$173
Thu 5/210:16 pmPDX - ORD
1 stop12h 26mFrontier
Tue 5/76:27 pmORD - PDX
1 stop7h 32mFrontier
Deal found 4/22$179
Mon 4/2910:16 pmPDX - ORD
1 stop11h 13mFrontier
Mon 5/66:27 pmORD - PDX
1 stop7h 32mFrontier
Deal found 4/22$181

One-way flights to Chicago from Portland

Search for one-way flight options from Portland to Chicago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,086,534 searches. Data last updated April 23, 2024.
Take a look at some of the best available options we've come across on one-way flights from Portland to Chicago. For those needing a return trip from Portland, there is a search form available above.
Wed 5/2211:30 pmPDX - ORD
Nonstop3h 50mSpirit Airlines
Deal found 4/22$54
Sat 5/184:00 pmPDX - ORD
2 stops11h 00mFrontier
Deal found 4/22$64
Mon 5/1310:16 pmPDX - ORD
1 stop11h 13mFrontier
Deal found 4/22$65
Fri 5/3111:30 pmPDX - ORD
Nonstop3h 50mSpirit Airlines
Deal found 4/22$71
Tue 5/213:57 pmPDX - ORD
1 stop12h 33mSpirit Airlines
Deal found 4/22$79
Sat 5/188:54 amPDX - ORD
1 stop9h 04mFrontier
Deal found 4/22$80
Tue 5/712:59 amPDX - MDW
1 stop8h 39mFrontier
Deal found 4/22$80
Fri 5/177:54 pmPDX - ORD
2 stops31h 06mFrontier
Deal found 4/22$84
Fri 5/177:54 pmPDX - MDW
2 stops31h 56mFrontier
Deal found 4/22$84

Find flights from Portland to Chicago within your budget

Customize your flight search to find flights from Portland to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 3,086,534 searches. Data last updated April 23, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$107 - $219

Route

Depart

Return

Price

PortlandChicago O'Hare Intl

PDX - ORD

PDXORD

Portland

Wed 5/8

Nonstop3h 50m

Chicago O'Hare Intl

Wed 5/15

Nonstop4h 30m

$107

PortlandChicago O'Hare Intl

PDX - ORD

PDXORD

Portland

Sat 5/18

Nonstop3h 50m

Chicago O'Hare Intl

Sat 5/25

Nonstop4h 30m

$109

PortlandChicago O'Hare Intl

PDX - ORD

PDXORD

Portland

Wed 5/29

Nonstop3h 50m

Chicago O'Hare Intl

Wed 6/5

Nonstop4h 27m

$113

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Sat 5/11

1 stop12h 25m

Chicago Midway

Sat 5/18

1 stop13h 10m

$115

PortlandChicago O'Hare Intl

PDX - ORD

PDXORD

Portland

Wed 5/8

Nonstop3h 50m

Chicago O'Hare Intl

Sat 5/18

1 stop17h 15m

$125

PortlandChicago Midway

PDX - MDW

PDXMDW

Portland

Sat 5/18

2 stops11h 50m

Chicago Midway

Mon 5/20

1 stop17h 11m

$125

PortlandChicago O'Hare Intl

PDX - ORD

PDXORD

Portland

Tue 6/11

Nonstop4h 05m

Chicago O'Hare Intl

Tue 7/9

Nonstop4h 25m

$184

PortlandChicago O'Hare Intl

PDX - ORD

PDXORD

Portland

Sat 6/1

1 stop6h 38m

Chicago O'Hare Intl

Tue 6/4

1 stop6h 12m

$216

PortlandChicago O'Hare Intl

PDX - ORD

PDXORD

Portland

Thu 8/15

Nonstop4h 04m

Chicago O'Hare Intl

Fri 8/30

Nonstop4h 30m

$219

Flights are sorted by cheapest first

Deals found on 4/21

When is the best time to book a flight from Portland to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Portland to Chicago. Price data was last updated on January 28, 2024.
Booking 81 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
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When is the cheapest time to fly from Portland to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Portland to Chicago. Price data was last updated on April 14, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Portland to Chicago flight should consider departing on Sunday afternoons when fares are most often at their lowest. Thursday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Average price of flights to Chicago by month

Plan your trip from Portland to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight from Portland to Chicago is currently $73 while a round-trip flight costs $146. Price data was last updated on April 21, 2024.

Currently, February is the cheapest month in which you can book a flight from Portland to Chicago (average of $245). Flying from Portland to Chicago in June is currently the most expensive (average of $356). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

January

$248

February

$245

March

$280

April

$273

May

$282

June

$356

July

$336

August

$276

September

$258

October

$248

November

$270

December

$248

Temperature and rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

23 - 73.4 °F

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated April 23, 2024.
See what other customers who have flown with Frontier, American Airlines and Delta from Portland to Chicago have to say. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.1
Very good
9,102 reviews
Check prices

Entertainment

7.3

Food

7.3

Comfort

7.9

Overall

8.1

Boarding

8.2

Crew

8.6

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

Alaska Airlines
8.1
Very good
9,102 reviews
Alaska Airlines
8.1
Very good
9,102 reviews
Check prices

Entertainment

7.3

Food

7.3

Comfort

7.9

Overall

8.1

Boarding

8.2

Crew

8.6

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

Delta
8.1
Very good
11,028 reviews
Alaska Airlines
8.1
Very good
9,102 reviews
Check prices

Entertainment

7.3

Food

7.3

Comfort

7.9

Overall

8.1

Boarding

8.2

Crew

8.6

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

Allegiant Air
7.5
Good
1,037 reviews
Alaska Airlines
8.1
Very good
9,102 reviews
Check prices

Entertainment

7.3

Food

7.3

Comfort

7.9

Overall

8.1

Boarding

8.2

Crew

8.6

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

United Airlines
7.4
Good
11,289 reviews
Alaska Airlines
8.1
Very good
9,102 reviews
Check prices

Entertainment

7.3

Food

7.3

Comfort

7.9

Overall

8.1

Boarding

8.2

Crew

8.6

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

American Airlines
7.3
Good
14,914 reviews
Alaska Airlines
8.1
Very good
9,102 reviews
Check prices

Entertainment

7.3

Food

7.3

Comfort

7.9

Overall

8.1

Boarding

8.2

Crew

8.6

Reviews

1 / 10

Paid a lot for our exit row seats and they weren’t that roomy.

Related info for your journey

Find useful and relevant information for your journey from Portland to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Portland to Chicago?

    For a flight from Portland to Chicago, you will be flying from Portland. Portland (PDX) is just 6.0 mi from the center of the city. Portland is the only Portland airport and it handles 14 outbound flights to Chicago per day. 6 airlines have flights to Chicago from Portland on a regular basis.

  • Can I find flights from Portland to Chicago for under $200 on Cheapflights?

    Yes, there are multiple flights from Portland to Chicago for under $200. The cheapest flight booked recently is on Spirit Airlines for just $107, but on average you can expect to pay $128.

  • Are there nonstop flights from Portland to Chicago for under $200 on Cheapflights?

    Cheapflights has at least 20 direct flights from Portland to Chicago under $200. A good price for a nonstop flight from Portland to Chicago is less than $139.

  • Are there last-minute flights available from Portland to Chicago for under $200?

    There are currently 20+ open flights from Portland to Chicago within the next 7 days for less than $200.

  • What days are nonstop flights available from Portland to Chicago?

    Days when nonstop flights are available for this flight are: Wednesday, Saturday.

  • How many flights depart from Portland to Chicago on average per day?

    Travelers can expect 3 flights from Portland to Chicago on average per day.
    Morning (6am - Noon) - 67% of flight departures
    Evening (6pm - Midnight) - 33% of flight departures

  • How long is the flight from Portland to Chicago?

    For as low as $107, Spirit Airlines can have you in Chicago from Portland in 3h 50m. Airlines will cover a distance of 1744 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Portland to Chicago round-trip?

    Spirit Airlines, at $107, was found to be the cheapest airline from Portland to Chicago. An alternate airline flying to your destination would be Frontier. You may be able to fly from Portland to Chicago for 71% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Portland to Chicago one-way?

    $54 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and Alaska Airlines, with prices starting from $64 and $99, respectively.

  • What are the most popular routes from Portland to Chicago?

    When deciding which route to take from Portland to Chicago consider Portland - Chicago O'Hare Intl, Portland - Chicago Midway or Portland - Chicago Greater Rockford as they are the most popular.

  • What are the most popular airlines that fly from Portland to Chicago?

    American Airlines, Alaska Airlines and Delta are the most popular airlines when flying from Portland to Chicago.

  • What are the most reliable airlines from Portland to Chicago?

    Consider Lufthansa (97%), Air Canada (96%) or Scandinavian Airlines (96%) when booking your flight. These represent the most reliable airlines when flying from Portland to Chicago.

  • What are the cheapest flights from Portland to Chicago?

    While on average a flight from Portland to Chicago is generally $987, our data shows the cheapest flight currently is $99. When looking at the most popular route, (Portland - Chicago O'Hare Intl), you can expect to pay $107 for that flight.

  • What does PDX to ORD mean?

    Portland Airport is PDX and Chicago O'Hare Intl Airport is ORD. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.

  • Can I find deals for flights from Portland to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Portland to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Portland to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Portland to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Portland to Chicago that include hotel bookings?

    Yes. In addition to deals on Portland to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Chicago.

  • Can I find deals for business class flights from Portland to Chicago?

    Yes. Cheapflights offers flight deals from Portland to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Portland to Chicago that allow pets onboard?

    Many airlines flying from Portland to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Portland to Chicago?

    Yes, you can often find last-minute deals on Portland to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Portland to Chicago flight deals updated?

    The Portland to Chicago flight deals you see on this page were last updated on 4/22.

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Alternative routes for Portland to Chicago
See prices for flight routes from nearby airports that may be better suited for you.

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Top 6 airlines flying from Portland to Chicago

Discover the top 6 airlines that operate flights from Portland to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 3,086,534 searches. Data last updated April 23, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$234FlexibilityNo cancel feeOn-time62%
Search Frontier flights
Spirit AirlinesCheapest$126Average$236FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines flights
Alaska AirlinesCheapest$149Average$351FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights
DeltaCheapest$152Average$500FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapest$198Average$422FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
American AirlinesCheapest$222Average$381FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
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Search flights from Portland to Chicago by cabin class

Find flights from Portland to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
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Hourly flight availability from Portland to Chicago

Find hourly flight availability from Portland to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 23, 2024.
4%of flight departuresEarly morningMidnight to 6 am
63%of flight departuresMorning6 am to noon
25%of flight departuresAfternoonNoon to 6 pm
8%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Portland to Chicago

Explore weekly flight availability from Portland to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 23, 2024.
Sunday14daily flights
Monday17daily flights
Tuesday16daily flights
Wednesday14daily flights
Thursday14daily flights
Friday15daily flights
Saturday12daily flights

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Fly with Cheapflights

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How does Cheapflights help users find flights from Portland to Chicago?

Deals for Portland to Chicago flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Portland to Chicago?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Portland to Chicago for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Portland to Chicago with no change fees?

Yes! Cheapflights helps users easily find flights from Portland to Chicago with no change fees.

Can Cheapflights notify me if prices for flights from Portland to Chicago become cheaper?

Of course! You can now track prices for flights from Portland to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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