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Salem

$63+ 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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Salem are usually found in September or January, booked 89 days in advance, depart on a Wednesday or Thursday 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 December 18, 2025.

This United Airlines deal was found by Cheapflights users on 12/17. 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 12/246:11 pmORD - BOS
Nonstop2h 33mUnited Airlines
Thu 1/14:15 pmBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 12/17$127
This United Airlines deal was found by Cheapflights users on 12/17. 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 12/246:11 pmORD - BOS
Nonstop2h 33mUnited Airlines
Mon 1/56:23 pmBOS - ORD
Nonstop2h 59mUnited Airlines
Deal found 12/17$132
This JetBlue deal was found by Cheapflights users on 12/17. 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.
Sat 12/278:15 pmORD - BOS
Nonstop2h 29mJetBlue
Sun 12/284:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 12/17$137
This JetBlue deal was found by Cheapflights users on 12/17. 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.
Sun 12/287:41 pmORD - BOS
Nonstop2h 29mJetBlue
Tue 12/304:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 12/17$147
This Southwest deal was found by Cheapflights users on 12/17. 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 12/248:25 amMDW - BOS
1 stop7h 55mSouthwest
Thu 1/15:30 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 12/17$153
This Priceline deal was found by Cheapflights users on 12/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:41 pmORD - BOS
Nonstop2h 29mJetBlue
Thu 1/14:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 12/17$157
This United Airlines deal was found by Cheapflights users on 12/15. 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.
Sun 12/219:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Thu 1/86:21 pmBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 12/15$158
This United Airlines deal was found by Cheapflights users on 12/17. 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 12/316:21 pmORD - BOS
1 stop4h 33mUnited Airlines
Thu 1/16:29 pmBOS - ORD
Nonstop3h 06mUnited Airlines
Deal found 12/17$162
This United Airlines deal was found by Cheapflights users on 12/17. 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 12/316:21 pmORD - BOS
1 stop4h 33mUnited Airlines
Mon 1/56:23 pmBOS - ORD
Nonstop2h 59mUnited Airlines
Deal found 12/17$167
This Delta deal was found by Cheapflights users on 12/16. 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.
Fri 12/197:10 amORD - BOS
Nonstop2h 26mDelta
Tue 1/137:55 pmBOS - ORD
Nonstop3h 06mDelta
Deal found 12/16$177
This United Airlines deal was found by Cheapflights users on 12/16. 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 12/246:11 pmORD - BOS
Nonstop2h 33mUnited Airlines
Wed 12/3112:20 pmBOS - ORD
Nonstop3h 03mUnited Airlines
Deal found 12/16$179
This JetBlue deal was found by Cheapflights users on 12/17. 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.
Sat 12/278:15 pmORD - BOS
Nonstop2h 29mJetBlue
Wed 12/315:05 pmBOS - ORD
1 stop5h 59mJetBlue
Deal found 12/17$181

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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$124
(Kiwi.com)

One-way from

$63
(Super.com)

Popular in

April

Cheapest in

September

Average price

$266
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl 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 ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 18, 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

Sat 1/17

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

Tue 1/20

3:35 pm-5:43 pm

Nonstop3h 08m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 1/20

5:35 pm-8:50 pm

Nonstop2h 15m

Boston Logan Intl

Thu 1/22

5:30 am-7:20 am

Nonstop2h 50m

$132

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/17

5:15 am-4:28 pm

1 stop10h 13m

Boston Logan Intl

Tue 1/20

3:35 pm-5:43 pm

Nonstop3h 08m

$136

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 1/7

5:00 pm-8:21 pm

Nonstop2h 21m

Boston Logan Intl

Sun 1/11

7:55 pm-10:01 pm

Nonstop3h 06m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 1/9

7:30 am-10:52 am

Nonstop2h 22m

Boston Logan Intl

Sun 1/11

10:30 am-12:34 pm

Nonstop3h 04m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 4/18

6:26 pm-9:51 pm

Nonstop2h 25m

Boston Logan Intl

Wed 4/22

3:39 pm-5:31 pm

Nonstop2h 52m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/10

2:00 pm-5:29 pm

Nonstop2h 29m

Boston Logan Intl

Sun 1/11

7:55 pm-10:01 pm

Nonstop3h 06m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 1/12

7:30 am-10:52 am

Nonstop2h 22m

Boston Logan Intl

Wed 1/14

4:16 pm-6:16 pm

Nonstop3h 00m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 1/7

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

Wed 1/14

3:35 pm-5:43 pm

Nonstop3h 08m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/24

7:05 am-10:40 am

Nonstop2h 35m

Boston Logan Intl

Sun 1/25

7:30 am-9:41 am

Nonstop3h 11m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 42 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 December 12, 2025.

Booking 89 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 $88). Flying from Chicago to Salem in February is currently the most expensive (average of $137). 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 December 18, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 36% on flights from Chicago to Salem by exploring options for tickets in the evening.

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 13, 2025.

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

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 December 18, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Chicago to Salem to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,005 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,092 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,055 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
JetBlue
7.2
Good
2,897 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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?

    JetBlue, Southwest, and Delta can get you from Chicago to Salem in just under 2h 15m. Your travel time will be generally consistent. There are 857 mi between Chicago and Salem. Most flights are nonstop.

  • 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 $55. JetBlue flights start at $58 while deals on United Airlines start at $64 one-way.

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

    Consider Etihad Airways (79%), Envoy Air (78%) or Avianca (73%) 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 $63. On average you can expect to pay $729. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $127.

  • 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 $88). Flying from Chicago to Salem in February is currently the most expensive (average of $137). 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 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$78Average$177FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$83Average$166FlexibilityNo cancel feeOn-time65%
DeltaCheapest$104Average$226FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$104Average$115FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$117Average$325FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$117Average$261FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$135Average$295FlexibilityNo cancel feeOn-time63%

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