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Salem

$98+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Salem are usually found in September or January, booked 69 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 July 31, 2025.

Round-trip from

$176
(Kiwi.com)

One-way from

$98
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$317
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. 4% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 31, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/30. 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 8/237:00 amORD - PDX
Nonstop4h 25mHawaiian Airlines
Sat 8/305:50 pmPDX - ORD
Nonstop4h 09mHawaiian Airlines
Deal found 7/30$176
This CheapOair deal was found by Cheapflights users on 7/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/16:00 amORD - PDX
1 stop7h 12mSpirit Airlines
Wed 10/298:04 pmPDX - ORD
1 stop6h 45mSpirit Airlines
Deal found 7/29$177
This Southwest deal was found by Cheapflights users on 7/30. 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 8/302:10 pmMDW - PDX
Nonstop4h 15mSouthwest
Sun 8/316:55 amPDX - MDW
Nonstop4h 00mSouthwest
Deal found 7/30$179
This Alaska Airlines deal was found by Cheapflights users on 7/30. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/307:00 amORD - PDX
Nonstop4h 25mAlaska Airlines
Sun 8/317:00 amPDX - ORD
Nonstop4h 09mAlaska Airlines
Deal found 7/30$179
This American Airlines deal was found by Cheapflights users on 7/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/17:25 amORD - PDX
Nonstop4h 22mAmerican Airlines
Sat 10/41:12 pmPDX - ORD
Nonstop4h 16mAmerican Airlines
Deal found 7/29$197
This Delta deal was found by Cheapflights users on 7/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:00 amMDW - PDX
1 stop8h 59mDelta
Thu 10/3012:50 amPDX - MDW
1 stop6h 05mDelta
Deal found 7/31$208
This CheapOair deal was found by Cheapflights users on 7/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/137:00 amORD - PDX
1 stop6h 30mMultiple Airlines
Mon 8/187:52 pmPDX - ORD
1 stop6h 58mMultiple Airlines
Deal found 7/28$212
This Southwest deal was found by Cheapflights users on 7/31. 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 8/301:30 pmORD - PDX
1 stop9h 05mSouthwest
Tue 9/29:05 pmPDX - ORD
1 stop12h 45mSouthwest
Deal found 7/31$213
This Frontier deal was found by Cheapflights users on 7/29. 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.
Sat 8/92:44 pmMDW - PDX
1 stop10h 40mFrontier
Sat 8/166:35 amPDX - MDW
1 stop12h 19mFrontier
Deal found 7/29$238

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 July 31, 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

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 8/23

7:00 am-9:25 am

Nonstop4h 25m

Portland

Sat 8/30

5:50 pm-11:59 pm

Nonstop4h 09m

$176

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 10/1

6:00 am-11:12 am

1 stop7h 12m

Portland

Tue 10/7

12:07 pm-9:01 pm

1 stop6h 54m

$177

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 8/30

2:10 pm-4:25 pm

Nonstop4h 15m

Portland

Sun 8/31

6:55 am-12:55 pm

Nonstop4h 00m

$179

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 8/30

7:00 am-9:25 am

Nonstop4h 25m

Portland

Sun 8/31

7:00 am-1:09 pm

Nonstop4h 09m

$179

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sun 8/31

1:05 pm-3:25 pm

Nonstop4h 20m

Portland

Wed 9/3

2:15 pm-8:25 pm

Nonstop4h 10m

$188

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 10/1

7:25 am-9:47 am

Nonstop4h 22m

Portland

Sat 10/4

1:12 pm-7:28 pm

Nonstop4h 16m

$197

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 10/25

6:00 am-12:59 pm

1 stop8h 59m

Portland

Fri 10/31

11:36 am-10:14 pm

1 stop8h 38m

$208

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 8/13

7:00 am-11:30 am

1 stop6h 30m

Portland

Mon 8/18

7:52 pm-4:50 am

1 stop6h 58m

$212

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 8/30

1:30 pm-8:35 pm

1 stop9h 05m

Portland

Tue 9/2

9:05 pm-11:50 am

1 stop12h 45m

$213

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 8/9

2:44 pm-11:24 pm

1 stop10h 40m

Portland

Sat 8/16

6:35 am-8:54 pm

1 stop12h 19m

$238

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 22 results
1
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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

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 July 31, 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 Tuesday evenings when fares are most often at their lowest. Monday 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 July 31, 2025.

The most flights from CHI to SA8 are scheduled on a Thursday (29 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (10 on average).

How much does it cost to fly round-trip from Chicago to Salem?

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 July 31, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest, and Delta 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

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Hawaiian Airlines
7.8
Good
2,611 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,900 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Overall

8.0

Boarding

8.1

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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.

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

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $98. Southwest flights start at $99 while deals on Alaska Airlines start at $99 one-way.

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

    Consider Brussels Airlines (90%), Air Canada (82%) or United Airlines (81%) 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 $96. While the most popular route (Chicago O'Hare Intl - Portland) can be booked for $174 on average our data indicates $760 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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Alternative routes for Chicago to Salem

See prices for flight routes from nearby airports that may be better suited for you.
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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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$81Average$179FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$179FlexibilityNo cancel feeOn-time62%
DeltaCheapest$123Average$371FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$134Average$366FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$181Average$407FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$226Average$483FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$227Average$422FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$238Average$475FlexibilityNo cancel feeOn-time63%

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