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Salem

$101+ Cheap flights from Chicago (CHI) to Salem, OR

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 10/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Oct 23 — Oct 301
Thu 10/23
Thu 10/30
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Salem are usually found in January or September, booked 60 days in advance, depart on a Wednesday or Tuesday and return on a Friday

Cheap flight deals from Chicago to Salem

Keep the following information in mind while searching for Chicago to Salem flight deals. Data was last updated September 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$203
(Trip.com)

One-way from

$101
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$278
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
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From Chicago (CHI) to Salem
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One-way flight from Chicago (CHI) to Salem
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Highest demand for flights based on searches. 2% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Chicago to Salem

Cheapest flights from Chicago to Salem
Explore the most affordable flight options available from Chicago to Salem. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 23, 2025.

This Trip.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/227:15 amORD - PDX
1 stop6h 33mMultiple Airlines
Wed 10/2911:00 pmPDX - ORD
Nonstop4h 01mMultiple Airlines
Deal found 9/22$203
This Booking.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/106:24 pmMDW - PDX
1 stop19h 24mFrontier
Sun 10/1212:43 pmPDX - MDW
1 stop18h 48mFrontier
Deal found 9/22$204
This Trip.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/166:00 amORD - PDX
1 stop7h 56mMultiple Airlines
Wed 11/197:00 amPDX - ORD
Nonstop4h 09mMultiple Airlines
Deal found 9/21$204
This Trip.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/147:15 amORD - PDX
1 stop6h 33mMultiple Airlines
Tue 10/217:00 amPDX - ORD
Nonstop4h 04mMultiple Airlines
Deal found 9/21$205
This Kissandfly.com deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:00 amORD - PDX
1 stop6h 48mAlaska Airlines
Fri 10/3111:00 pmPDX - ORD
Nonstop4h 01mAlaska Airlines
Deal found 9/23$206
This Orbitz deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/217:15 amORD - PDX
1 stop6h 33mMultiple Airlines
Wed 10/2911:00 pmPDX - ORD
Nonstop4h 01mMultiple Airlines
Deal found 9/21$207
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:00 amORD - PDX
1 stop8h 25mHawaiian Airlines
Fri 10/3111:00 pmPDX - ORD
Nonstop4h 01mHawaiian Airlines
Deal found 9/21$208
This Southwest deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/253:45 pmMDW - PDX
Nonstop4h 20mSouthwest
Fri 10/315:50 amPDX - MDW
Nonstop3h 55mSouthwest
Deal found 9/23$209
This Mytrip deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/236:24 pmMDW - PDX
1 stop19h 24mFrontier
Thu 10/3012:52 pmPDX - MDW
1 stop20h 38mFrontier
Deal found 9/22$211
This Frontier deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/236:50 amORD - PDX
1 stop6h 48mFrontier
Mon 10/2710:34 amPDX - ORD
2 stops12h 25mFrontier
Deal found 9/22$211
This Orbitz deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/82:05 pmORD - PDX
Nonstop4h 36mMultiple Airlines
Thu 11/1312:52 pmPDX - ORD
1 stop9h 23mMultiple Airlines
Deal found 9/21$212
This Frontier deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/166:50 amORD - PDX
1 stop6h 58mFrontier
Tue 10/2112:43 pmPDX - ORD
1 stop9h 10mFrontier
Deal found 9/21$213

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Salem 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 2,558,603 searches. Data last updated September 23, 2025.
Use the filters below to find and compare flights from Chicago to Salem that are best for you.

Fly from

Chicago

Fly to

Salem

Route

Depart

Return

Price

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 10/25

3:45 pm-6:05 pm

Nonstop4h 20m

Portland

Fri 10/31

5:50 am-11:45 am

Nonstop3h 55m

$209

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 10/31

7:00 am-9:39 am

Nonstop4h 39m

Portland

Mon 11/3

7:00 am-1:09 pm

Nonstop4h 09m

$228

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 10/25

7:37 am-12:49 pm

1 stop7h 12m

Portland

Fri 10/31

1:30 pm-11:50 pm

1 stop8h 20m

$228

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 11/21

7:00 am-9:39 am

Nonstop4h 39m

Portland

Mon 11/24

11:00 pm-5:01 am

Nonstop4h 01m

$228

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 10/21

7:50 pm-10:25 pm

Nonstop4h 35m

Portland

Wed 10/29

11:59 pm-5:54 am

Nonstop3h 55m

$231

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 10/21

8:25 pm-10:50 pm

Nonstop4h 25m

Portland

Wed 10/29

6:00 am-11:55 am

Nonstop3h 55m

$231

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 10/22

4:35 pm-9:15 pm

1 stop6h 40m

Portland

Wed 10/29

6:00 am-11:55 am

Nonstop3h 55m

$241

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 10/28

8:00 am-12:38 pm

1 stop6h 38m

Portland

Sat 11/1

11:59 pm-6:00 am

Nonstop4h 01m

$244

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 10/22

2:04 pm-4:37 pm

Nonstop4h 33m

Portland

Wed 10/29

11:00 pm-5:01 am

Nonstop4h 01m

$250

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 10/21

10:35 am-7:06 pm

1 stop10h 31m

Portland

Wed 10/29

6:00 am-4:09 pm

1 stop8h 09m

$251

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/21

Showing 1-10 of 39 results
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Best time to book a flight from Chicago to Salem

Have a flexible travel schedule? Discover the best time to fly to Salem from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Salem

How far ahead should I book a flight from Chicago to Salem?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Salem. Price data was last updated on September 19, 2025.

Booking 60 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Salem. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to Salem?

Currently, November is the cheapest month in which you can book a flight from Chicago to Salem (average of $277). Flying from Chicago to Salem in March is currently the most expensive (average of $368). 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.

What is the cheapest time of day to fly from CHI to SA8?

Find hourly flight availability from Chicago to Salem. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 23, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Salem as you normally would.

What is the cheapest day to fly from Chicago to Salem?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Salem. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Salem flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Salem

Explore weekly flight availability from Chicago to Salem. 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 September 23, 2025.

The most flights from CHI to SA8 are scheduled on a Monday (28 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (7 on average).

Reviews of airlines servicing Salem

Get insights into the airlines that provide service to Salem. 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 Salem. Reviews last updated September 23, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Hawaiian Airlines from Chicago to Salem by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Crew

8.5

Overall

8.0

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Crew

8.5

Overall

8.0

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Southwest
8.0
Very good
4,244 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Crew

8.5

Overall

8.0

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Hawaiian Airlines
7.8
Good
2,744 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Crew

8.5

Overall

8.0

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
8,928 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Crew

8.5

Overall

8.0

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Food

7.1

Crew

8.5

Overall

8.0

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

Related info for your journey

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

  • How long is the flight from Chicago to Salem?

    Southwest, Alaska Airlines, and Delta can get you from Chicago to Salem in just under 4h 20m. Your travel time can differ by up to 2h 52m. There are 1746 mi between Chicago and Salem. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $116. Alaska Airlines flights start at $116 while deals on United Airlines start at $116 one-way.

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

    Consider United Airlines (79%), Alaska Airlines (78%) or Hawaiian Airlines (78%) when booking your flight. These represent the most reliable airlines when flying from Chicago to Salem.

  • What are the cheapest flights from Chicago to Salem?

    Looking at all options, your cheapest flight can be booked for $108. While the most popular route (Chicago O'Hare Intl - Portland) can be booked for $182 on average, our data indicates $834 when flying from Chicago to Salem.

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

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

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

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

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

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

  • What is the cheapest month to book a flight from Chicago to Salem?

    Currently, November is the cheapest month in which you can book a flight from Chicago to Salem (average of $277). Flying from Chicago to Salem in March is currently the most expensive (average of $368). 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.

See more FAQs

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Top 8 airlines flying from Chicago to Salem

Discover the top 8 airlines that operate flights from Chicago to Salem. 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 2,558,603 searches. Data last updated September 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$86Average$186FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$166FlexibilityNo cancel feeOn-time62%
DeltaCheapest$123Average$402FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$134Average$364FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$183Average$401FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$210Average$318FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$225Average$474FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$238Average$447FlexibilityNo cancel feeOn-time63%

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