Salem

$113+ 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 3/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Mar 3 — Mar 101
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Find cheap flights from Chicago to Salem with Cheapflights

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Cheapflights Tip: The best prices from Chicago to Salem are usually found in September or May, booked 60 days in advance, depart on a Wednesday or Tuesday and return on a Friday

Cheap 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 February 1, 2026.

This CheapOair deal was found by Cheapflights users on 1/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/229:18 pm
ORD
-
PDX
1 stop13h 41m
Frontier
Mon 4/2712:52 pm
PDX
-
ORD
1 stop15h 55m
Frontier
Deal found 1/31$201
This Southwest deal was found by Cheapflights users on 1/31. 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 5/306:05 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Sat 6/611:30 pm
PDX
-
MDW
Nonstop3h 50m
Southwest
Deal found 1/31$202
This United Airlines deal was found by Cheapflights users on 1/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:15 pm
ORD
-
PDX
Nonstop4h 41m
United Airlines
Sat 3/71:00 pm
PDX
-
ORD
1 stop6h 29m
United Airlines
Deal found 1/31$203
This American Airlines deal was found by Cheapflights users on 1/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:20 am
ORD
-
PDX
Nonstop4h 25m
American Airlines
Wed 6/311:30 pm
PDX
-
ORD
Nonstop4h 01m
American Airlines
Deal found 1/30$204
This Southwest deal was found by Cheapflights users on 1/31. 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.
Tue 3/105:45 am
MDW
-
PDX
2 stops10h 45m
Southwest
Sat 3/146:20 pm
PDX
-
MDW
1 stop9h 35m
Southwest
Deal found 1/31$206
This Southwest deal was found by Cheapflights users on 1/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2012:05 pm
MDW
-
PDX
Nonstop4h 25m
Southwest
Tue 2/246:30 am
PDX
-
MDW
Nonstop3h 55m
Southwest
Deal found 1/29$207
This Alaska Airlines deal was found by Cheapflights users on 1/30. 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.
Wed 3/42:07 pm
ORD
-
PDX
Nonstop4h 43m
Alaska Airlines
Sun 3/87:00 am
PDX
-
ORD
Nonstop4h 11m
Alaska Airlines
Deal found 1/30$207
This Southwest deal was found by Cheapflights users on 1/31. 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 2/288:30 pm
MDW
-
PDX
Nonstop4h 30m
Southwest
Sun 3/89:25 pm
PDX
-
MDW
1 stop6h 30m
Southwest
Deal found 1/31$208
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/68:42 pm
ORD
-
PDX
2 stops39h 27m
Multiple Airlines
Mon 3/912:04 pm
PDX
-
ORD
1 stop10h 53m
Multiple Airlines
Deal found 1/31$208
This Orbitz deal was found by Cheapflights users on 1/29. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:21 pm
ORD
-
PDX
1 stop18h 36m
Multiple Airlines
Sun 4/267:55 am
PDX
-
ORD
Nonstop4h 13m
Multiple Airlines
Deal found 1/29$209
This Southwest deal was found by Cheapflights users on 1/31. 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.
Wed 3/116:30 am
MDW
-
PDX
1 stop8h 05m
Southwest
Sat 3/146:20 pm
PDX
-
MDW
1 stop9h 35m
Southwest
Deal found 1/31$210
This Alaska Airlines deal was found by Cheapflights users on 2/1. 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.
Wed 3/113:54 pm
ORD
-
PDX
1 stop8h 47m
Alaska Airlines
Sat 3/143:52 pm
PDX
-
ORD
1 stop6h 04m
Alaska Airlines
Deal found 2/1$210

Find flight deals from Chicago to Salem

Keep the following information in mind while searching for Chicago to Salem flight deals. Data was last updated February 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$201
(CheapOair)

One-way from

$113
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$309
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
From Chicago (CHI) to Salem
One-way flight from Chicago (CHI) to Salem
Highest demand for flights based on searches. 5% potential increase in price ($19 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Average for round-trip flights in February 2026

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 February 1, 2026.
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

Tue 3/10

5:45 am-2:30 pm

2 stops10h 45m

Portland

Sat 3/14

6:20 pm-5:55 am

1 stop9h 35m

$206

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 2/24

9:10 am-11:55 am

Nonstop4h 45m

Portland

Thu 2/26

11:59 pm-5:53 am

Nonstop3h 54m

$207

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 2/20

12:05 pm-2:30 pm

Nonstop4h 25m

Portland

Wed 2/25

6:30 am-12:25 pm

Nonstop3h 55m

$207

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 4/28

8:50 pm-11:10 pm

Nonstop4h 20m

Portland

Mon 5/4

11:55 pm-5:50 am

Nonstop3h 55m

$207

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 4/29

8:50 pm-11:10 pm

Nonstop4h 20m

Portland

Mon 5/4

11:55 pm-5:50 am

Nonstop3h 55m

$207

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 2/20

12:05 pm-2:30 pm

Nonstop4h 25m

Portland

Tue 2/24

6:30 am-12:25 pm

Nonstop3h 55m

$207

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 3/5

10:20 pm-12:45 am

Nonstop4h 25m

Portland

Wed 3/11

11:55 pm-5:45 am

Nonstop3h 50m

$207

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 4/29

5:30 pm-10:00 pm

1 stop6h 30m

Portland

Tue 5/5

11:55 pm-5:50 am

Nonstop3h 55m

$207

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 2/14

9:10 am-11:55 am

Nonstop4h 45m

Portland

Sat 2/21

11:59 pm-5:53 am

Nonstop3h 54m

$214

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 3/11

2:05 pm-8:25 pm

1 stop8h 20m

Portland

Fri 3/13

12:30 am-8:50 am

1 stop6h 20m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

Showing 1-10 of 41 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 January 30, 2026.

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, March is the cheapest month in which you can book a flight from Chicago to Salem (average of $122). Flying from Chicago to Salem in December is currently the most expensive (average of $207). 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 February 1, 2026.

One of the essential ways to save on airfare from Chicago to Salem is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 25% on airfare.

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 January 31, 2026.

Travelers seeking maximum savings on their Chicago to Salem flight should consider departing on Saturday mornings 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 February 1, 2026.

The most flights from CHI to SA8 are scheduled on a Friday (19 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 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 February 1, 2026.
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.

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

Overall

8.0

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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, United Airlines, and Delta can get you from Chicago to Salem in just under 4h 45m. Your travel time can differ by up to 6h. There are 1733 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 Spirit Airlines, which is currently one of the cheapest options available, starting at $90. Hawaiian Airlines flights start at $90 while deals on Frontier start at $96 one-way.

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

    Consider Malaysia Airlines (80%), British Airways (75%) or Air Canada (74%) 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 $197 on average, our data indicates $662 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, March is the cheapest month in which you can book a flight from Chicago to Salem (average of $122). Flying from Chicago to Salem in December is currently the most expensive (average of $207). 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

Browse thousands of different options on Cheapflights for your next trip

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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 February 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$86Average$178FlexibilityNo cancel feeOn-time65%
DeltaCheapest$88Average$430FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$128Average$358FlexibilityNo cancel feeOn-time85%
FrontierCheapest$150Average$227FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$194Average$379FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$202Average$404FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$204Average$312FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$234Average$413FlexibilityNo cancel feeOn-time63%

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