HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Salem

$126+ 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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Apr 25 — May 21
Sat 4/25
Sat 5/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Salem with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.
Cheapflights Tip: The best prices from Chicago to Salem are usually found in January or May, booked 79 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

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 March 26, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Mon 4/133:21 pm
ORD
-
PDX
2 stops23h 41m
Multiple Airlines
Sun 4/1911:15 am
PDX
-
ORD
1 stop20h 35m
Multiple Airlines
Deal found 3/24$214
This Delta deal was found by Cheapflights users on 3/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/282:12 pm
MDW
-
PDX
1 stop7h 55m
Delta
Mon 5/412:30 am
PDX
-
MDW
1 stop6h 16m
Delta
Deal found 3/23$215
This Delta deal was found by Cheapflights users on 3/26. 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.
Wed 5/272:00 pm
ORD
-
PDX
1 stop10h 02m
Delta
Tue 6/23:30 pm
PDX
-
ORD
1 stop6h 25m
Delta
Deal found 3/26$215
This Super.com deal was found by Cheapflights users on 3/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/132:29 pm
ORD
-
PDX
1 stop24h 33m
Frontier
Wed 4/1512:28 pm
PDX
-
ORD
1 stop19h 22m
Frontier
Deal found 3/21$216
This United Airlines deal was found by Cheapflights users on 3/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:40 am
ORD
-
PDX
1 stop8h 50m
United Airlines
Wed 4/292:30 pm
PDX
-
ORD
Nonstop4h 04m
United Airlines
Deal found 3/23$217
This Booking.com deal was found by Cheapflights users on 3/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/68:56 pm
ORD
-
PDX
1 stop16h 54m
Frontier
Mon 5/115:31 pm
PDX
-
ORD
1 stop11h 08m
Frontier
Deal found 3/23$218
This Kiwi.com deal was found by Cheapflights users on 3/24. 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 6/59:42 pm
ORD
-
PDX
1 stop21h 04m
Frontier
Tue 6/95:42 pm
PDX
-
ORD
1 stop25h 11m
Frontier
Deal found 3/24$219
This Southwest deal was found by Cheapflights users on 3/24. 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 6/24:00 pm
MDW
-
PDX
2 stops9h 10m
Southwest
Tue 6/95:55 pm
PDX
-
MDW
1 stop9h 30m
Southwest
Deal found 3/24$220
This Southwest deal was found by Cheapflights users on 3/26. 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 5/274:50 pm
ORD
-
PDX
1 stop8h 20m
Southwest
Tue 6/211:45 am
PDX
-
ORD
2 stops9h 10m
Southwest
Deal found 3/26$220
This Southwest deal was found by Cheapflights users on 3/24. 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 4/143:40 pm
MDW
-
PDX
1 stop7h 05m
Southwest
Mon 4/2011:55 pm
PDX
-
MDW
Nonstop3h 55m
Southwest
Deal found 3/24$221
This Southwest deal was found by Cheapflights users on 3/23. 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.
Wed 4/224:50 pm
ORD
-
PDX
1 stop8h 20m
Southwest
Wed 4/296:00 am
PDX
-
ORD
2 stops10h 50m
Southwest
Deal found 3/23$221
This Southwest deal was found by Cheapflights users on 3/25. 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 5/96:05 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Tue 5/1911:55 pm
PDX
-
MDW
Nonstop3h 55m
Southwest
Deal found 3/25$223

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 March 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$214
(Kiwi.com)

One-way from

$126
(Southwest)

Popular in

March

Cheapest in

January

Average price

$435
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
Search Deals
From Chicago (CHI) to Salem
Search Deals
One-way flight from Chicago (CHI) to Salem
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

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 March 26, 2026.
Use the filters below to find and compare flights from Chicago to Salem that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 6/2

8:50 pm-11:10 pm

Nonstop4h 20m

Portland

Tue 6/9

11:30 pm-5:20 am

Nonstop3h 50m

$250

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 4/14

10:10 am-12:30 pm

Nonstop4h 20m

Portland

Wed 4/15

11:55 pm-5:50 am

Nonstop3h 55m

$251

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 5/6

8:50 am-4:49 pm

1 stop9h 59m

Portland

Sat 5/9

1:52 pm-11:59 pm

1 stop8h 07m

$255

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 5/30

5:19 pm-10:02 pm

1 stop6h 43m

Portland

Mon 6/1

3:30 pm-11:55 pm

1 stop6h 25m

$255

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 6/4

9:21 pm-11:53 pm

Nonstop4h 32m

Portland

Sat 6/13

11:40 pm-5:45 am

Nonstop4h 05m

$270

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 5/28

4:15 pm-6:47 pm

Nonstop4h 32m

Portland

Sun 5/31

11:40 pm-5:45 am

Nonstop4h 05m

$281

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 4/30

7:59 pm-9:48 am

1 stop15h 49m

Portland

Sun 5/3

7:55 am-2:08 pm

Nonstop4h 13m

$291

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 4/28

4:50 pm-11:10 pm

1 stop8h 20m

Portland

Mon 5/4

1:10 pm-11:55 pm

1 stop8h 45m

$309

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 4/28

6:00 am-10:56 am

1 stop6h 56m

Portland

Fri 5/8

8:45 am-7:52 pm

1 stop9h 07m

$309

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 5/19

8:50 pm-11:10 pm

Nonstop4h 20m

Portland

Tue 6/2

11:55 pm-5:50 am

Nonstop3h 55m

$313

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/21

Showing 1-10 of 45 resultsSorted by cheapest first
1
2
3
...
5

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 March 13, 2026.

Booking 79 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, January is the cheapest month in which you can book a flight from Chicago to Salem (average of $133). 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 March 26, 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 18% 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 March 23, 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 March 26, 2026.

The most flights from CHI to SA8 are scheduled on a Wednesday (19 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 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 March 26, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, andHawaiian 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.
Southwest
8.0
Very good
4,331 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,331 reviews
Southwest
8.0
Very good
4,331 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Alaska Airlines
7.9
Good
12,119 reviews
Southwest
8.0
Very good
4,331 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Hawaiian Airlines
7.8
Good
2,839 reviews
Southwest
8.0
Very good
4,331 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,489 reviews
Southwest
8.0
Very good
4,331 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,497 reviews
Southwest
8.0
Very good
4,331 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 5h 39m. 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 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 $98 one-way.

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

    Consider Alaska Airlines (89%), Hawaiian Airlines (78%) or Air Canada (69%) 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 $122. While the most popular route (Chicago O'Hare Intl - Portland) can be booked for $195 on average, our data indicates $665 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, January is the cheapest month in which you can book a flight from Chicago to Salem (average of $133). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 March 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$86Average$178FlexibilityNo cancel feeOn-time65%
Hawaiian AirlinesCheapest$124Average$351FlexibilityNo cancel feeOn-time85%
FrontierCheapest$150Average$232FlexibilityNo cancel feeOn-time62%
DeltaCheapest$192Average$449FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$192Average$391FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$193Average$358FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$200Average$313FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$227Average$383FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.