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$59+ Cheap flights from Chicago (CHI) to Salem, MA, MA

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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Salem are usually found in September or August, booked 52 days in advance, depart on a Wednesday or Saturday and return on a Wednesday

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 May 1, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$113
(Cheapflightsfares)

One-way from

$59
(United Airlines)

Popular in

April

Cheapest in

September

Average price

$266
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl 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. 10% potential increase in price ($28 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1610:48 amORD - BOS
Nonstop2h 26mSpirit Airlines
Tue 10/216:10 amBOS - ORD
1 stop9h 24mSpirit Airlines
Deal found 4/30$113
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/89:20 pmORD - BOS
Nonstop2h 25mUnited Airlines
Tue 5/136:00 amBOS - ORD
Nonstop2h 57mUnited Airlines
Deal found 4/30$117
This Southwest deal was found by Cheapflights users on 4/30. 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 5/106:30 pmMDW - BOS
Nonstop2h 15mSouthwest
Sun 5/117:40 amBOS - MDW
Nonstop2h 35mSouthwest
Deal found 4/30$117
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/44:40 pmORD - BOS
Nonstop2h 21mAmerican Airlines
Mon 6/95:00 amBOS - ORD
Nonstop2h 54mAmerican Airlines
Deal found 5/1$118
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/87:00 amORD - BOS
Nonstop2h 25mDelta
Sun 6/86:15 amBOS - ORD
Nonstop2h 57mDelta
Deal found 4/29$137
This JetBlue deal was found by Cheapflights users on 4/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/216:15 amORD - BOS
1 stop4h 27mJetBlue
Sun 5/256:00 amBOS - ORD
Nonstop3h 00mJetBlue
Deal found 4/30$140
This Southwest deal was found by Cheapflights users on 4/30. 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.
Fri 6/61:50 pmORD - BOS
1 stop9h 35mSouthwest
Tue 6/108:30 amBOS - ORD
1 stop8h 55mSouthwest
Deal found 4/30$142
This CheapOair deal was found by Cheapflights users on 5/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/174:15 pmORD - BOS
1 stop7h 29mMultiple Airlines
Sat 5/244:49 pmBOS - ORD
1 stop8h 16mMultiple Airlines
Deal found 5/1$191
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/139:12 amMDW - BOS
1 stop25h 49mAllegiant Air
Sun 6/1511:31 amBOS - MDW
1 stop20h 44mAllegiant Air
Deal found 4/30$206
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/104:15 pmORD - BOS
1 stop7h 29mFrontier
Sun 5/116:00 amBOS - ORD
1 stop18h 32mFrontier
Deal found 4/30$210
This CheapOair deal was found by Cheapflights users on 5/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/121:19 pmMDW - BOS
1 stop10h 25mFrontier
Wed 5/148:00 amBOS - MDW
1 stop29h 24mFrontier
Deal found 5/1$211
This Delta deal was found by Cheapflights users on 5/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/245:55 pmMDW - BOS
1 stop4h 01mDelta
Tue 5/275:20 amBOS - MDW
1 stop4h 20mDelta
Deal found 5/1$316

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 May 1, 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

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 10/16

10:48 am-2:14 pm

Nonstop2h 26m

Boston Logan Intl

Tue 10/21

6:10 am-2:34 pm

1 stop9h 24m

$113

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/31

7:00 am-10:25 am

Nonstop2h 25m

Boston Logan Intl

Mon 6/2

7:15 am-9:09 am

Nonstop2h 54m

$117

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 5/30

7:20 pm-10:35 pm

Nonstop2h 15m

Boston Logan Intl

Mon 6/2

4:40 pm-6:20 pm

Nonstop2h 40m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 6/4

4:40 pm-8:01 pm

Nonstop2h 21m

Boston Logan Intl

Mon 6/9

5:00 am-6:54 am

Nonstop2h 54m

$118

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 6/3

7:53 pm-11:20 pm

Nonstop2h 27m

Boston Logan Intl

Tue 8/12

6:59 pm-11:37 pm

1 stop5h 38m

$123

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 5/21

6:15 am-11:42 am

1 stop4h 27m

Boston Logan Intl

Sun 5/25

6:00 am-8:00 am

Nonstop3h 00m

$140

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 6/6

1:50 pm-12:25 am

1 stop9h 35m

Boston Logan Intl

Tue 6/10

8:30 am-4:25 pm

1 stop8h 55m

$142

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/17

4:15 pm-12:44 am

1 stop7h 29m

Boston Logan Intl

Sat 5/24

4:49 pm-12:05 am

1 stop8h 16m

$191

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 6/13

9:12 am-12:01 pm

1 stop25h 49m

Boston Logan Intl

Sun 6/15

11:31 am-7:15 am

1 stop20h 44m

$206

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 5/12

1:19 pm-12:44 am

1 stop10h 25m

Boston Logan Intl

Wed 5/14

8:00 am-12:24 pm

1 stop29h 24m

$211

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 27 results
1
2
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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 April 25, 2025.

Booking 52 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 $218). Flying from Chicago to Salem in July is currently the most expensive (average of $310). 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 SA9?

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 May 1, 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 March 30, 2025.

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 afternoons 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 May 1, 2025.

The most flights from CHI to SA9 are scheduled on a Thursday (72 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 on average).

Rainfall in Salem by month

Plan your trip to Salem by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Salem ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Salem when rainfall is around 3.1 in.

Temperature in Salem by month

Plan your trip to Salem by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Salem, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

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 May 1, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta from Chicago to Salem. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,293 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,923 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 United Airlines, which is currently one of the cheapest options available, starting at $59. Southwest flights start at $59 while deals on Spirit Airlines start at $61 one-way.

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

    Consider Air France (100%), Iberia (91%) or Virgin Atlantic (88%) 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?

    The cheapest flight price from Chicago to Salem is $50. On average you can expect to pay $616. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $113.

  • 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 $218). Flying from Chicago to Salem in July is currently the most expensive (average of $310). 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 7 airlines flying from Chicago to Salem

Discover the top 7 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$94FlexibilityNo cancel feeOn-time65%
DeltaCheapest$63Average$298FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$69Average$118FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$79Average$205FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$137Average$331FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$138Average$293FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$157Average$338FlexibilityNo cancel feeOn-time63%

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