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$69+ 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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
out 23 — out 301
qui 10/23
qui 10/30
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 Thursday or Wednesday 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 setembro 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$127
(United Airlines)

One-way from

$69
(United Airlines)

Popular in

April

Cheapest in

September

Average price

$207
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. 6% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 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 setembro 23, 2025.

This United Airlines deal was found by Cheapflights users on 9/22. 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.
sáb 10/46:30 amORD - BOS
Nonstop2h 26mUnited Airlines
ter 10/73:17 pmBOS - ORD
Nonstop2h 50mUnited Airlines
Deal found 9/22$127
This Southwest deal was found by Cheapflights users on 9/23. 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.
qua 10/2212:30 pmMDW - BOS
1 stop4h 15mSouthwest
sáb 10/255:20 amBOS - MDW
Nonstop2h 40mSouthwest
Deal found 9/23$127
This United Airlines deal was found by Cheapflights users on 9/23. 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.
sex 11/79:25 pmORD - BOS
Nonstop2h 20mUnited Airlines
dom 11/96:00 amBOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 9/23$131
This JetBlue deal was found by Cheapflights users on 9/21. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 10/19:51 amORD - BOS
Nonstop2h 29mJetBlue
qua 10/14:40 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 9/21$132
This Southwest deal was found by Cheapflights users on 9/22. 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.
sex 11/71:50 pmMDW - BOS
1 stop8h 50mSouthwest
dom 11/95:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 9/22$133
This JetBlue deal was found by Cheapflights users on 9/23. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 10/207:13 pmORD - BOS
Nonstop2h 33mJetBlue
qua 10/224:05 pmBOS - ORD
Nonstop3h 13mJetBlue
Deal found 9/23$135
This United Airlines deal was found by Cheapflights users on 9/23. 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.
sex 10/249:20 pmORD - BOS
Nonstop2h 30mUnited Airlines
dom 10/266:00 amBOS - ORD
Nonstop3h 01mUnited Airlines
Deal found 9/23$136
This JetBlue deal was found by Cheapflights users on 9/22. 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.
qui 12/48:38 pmORD - BOS
Nonstop2h 28mJetBlue
seg 12/85:29 pmBOS - ORD
Nonstop3h 14mJetBlue
Deal found 9/22$137
This Southwest deal was found by Cheapflights users on 9/22. 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.
qui 12/46:15 pmMDW - BOS
Nonstop2h 20mSouthwest
dom 12/75:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 9/22$137
This Cheapflightsfares deal was found by Cheapflights users on 9/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 10/286:00 amORD - BOS
1 stop6h 20mSpirit Airlines
qua 10/293:00 pmBOS - ORD
1 stop11h 03mSpirit Airlines
Deal found 9/23$139
This Gotogate deal was found by Cheapflights users on 9/21. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 11/510:49 amORD - BOS
1 stop12h 51mSpirit Airlines
qua 11/126:15 amBOS - ORD
1 stop11h 49mSpirit Airlines
Deal found 9/21$140
This United Airlines deal was found by Cheapflights users on 9/22. 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.
sáb 10/49:20 pmORD - BOS
Nonstop2h 30mUnited Airlines
seg 10/68:00 amBOS - ORD
Nonstop2h 55mUnited Airlines
Deal found 9/22$141

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 setembro 23, 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

MDW - BOS

MDWBOS

Chicago Midway

qua 10/22

12:30 pm-5:45 pm

1 stop4h 15m

Boston Logan Intl

sáb 10/25

5:20 am-7:00 am

Nonstop2h 40m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

sex 11/7

1:50 pm-11:40 pm

1 stop8h 50m

Boston Logan Intl

sáb 11/8

12:35 pm-2:20 pm

Nonstop2h 45m

$133

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

qui 2/26

12:10 pm-3:36 pm

Nonstop2h 26m

Boston Logan Intl

dom 3/1

9:30 am-11:24 am

Nonstop2h 54m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

qui 11/27

10:35 am-2:03 pm

Nonstop2h 28m

Boston Logan Intl

sex 12/5

7:50 pm-9:46 pm

Nonstop2h 56m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

qui 11/27

12:28 pm-3:54 pm

Nonstop2h 26m

Boston Logan Intl

seg 12/1

1:34 pm-3:32 pm

Nonstop2h 58m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

ter 3/10

7:00 am-10:33 am

Nonstop2h 33m

Boston Logan Intl

qua 3/11

7:00 am-9:10 am

Nonstop3h 10m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

ter 10/21

1:50 pm-9:10 pm

1 stop6h 20m

Boston Logan Intl

sáb 10/25

8:15 am-11:50 am

1 stop4h 35m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

qua 10/8

7:05 am-10:29 am

Nonstop2h 24m

Boston Logan Intl

qua 10/15

7:20 am-9:22 am

Nonstop3h 02m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

sex 11/7

1:50 pm-11:40 pm

1 stop8h 50m

Boston Logan Intl

seg 11/10

5:55 pm-11:00 pm

1 stop6h 05m

$142

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sex 11/7

6:55 pm-10:27 pm

Nonstop2h 32m

Boston Logan Intl

seg 11/10

8:30 am-10:35 am

Nonstop3h 05m

$149

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/22

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 September 19, 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 $218). Flying from Chicago to Salem in July is currently the most expensive (average of $311). 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 setembro 23, 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 September 21, 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 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 setembro 23, 2025.

The most flights from CHI to SA9 are scheduled on a Tuesday (68 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (25 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 setembro 23, 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
8.0
Very good
4,244 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,973 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,928 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,912 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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, JetBlue, and Delta can get you from Chicago to Salem in just under 2h 26m. Your travel time can differ by up to 1h 49m. There are 864 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 Delta, which is currently one of the cheapest options available, starting at $69. United Airlines flights start at $69 while deals on Southwest start at $69 one-way.

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

    Consider Envoy Air (96%), Air France (78%) or Scandinavian Airlines (76%) 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 $68. On average you can expect to pay $451. 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 $311). 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 setembro 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$46Average$156FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$78Average$182FlexibilityNo cancel feeOn-time62%
DeltaCheapest$96Average$228FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$100Average$115FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$118Average$331FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$127Average$288FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$139Average$318FlexibilityNo cancel feeOn-time63%

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