$66+ 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 2/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Feb 28 — Mar 71
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 September, 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 SalemExplore 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 January 29, 2026.
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 January 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Tue 2/177:00 am
ORD
- BOS
1 stop9h 15m
Multiple Airlines
Fri 2/276:00 am
BOS
- ORD
1 stop29h 51m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$131
This Priceline deal was found by Cheapflights users on 1/28. 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 2/256:02 pm
ORD
- BOS
1 stop6h 11m
Multiple Airlines
Sat 2/287:00 am
BOS
- ORD
Nonstop3h 10m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Tue 2/247:23 pm
ORD
- BOS
1 stop20h 22m
Multiple Airlines
Tue 3/36:00 am
BOS
- ORD
1 stop11h 52m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/55:01 pm
MDW
- BOS
1 stop7h 12m
Frontier
Mon 2/96:00 am
BOS
- MDW
1 stop6h 45m
Frontier
Deal found 1/26![Frontier logo]()
$133
This Cheapflightsfares deal was found by Cheapflights users on 1/28. 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.
Sat 1/317:40 am
ORD
- BOS
Nonstop2h 25m
JetBlue
Mon 2/23:35 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Deal found 1/28![JetBlue logo]()
$134
This United Airlines deal was found by Cheapflights users on 1/28. 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 2/1811:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Sat 2/214:25 pm
BOS
- ORD
Nonstop3h 05m
United Airlines
Deal found 1/28![United Airlines logo]()
$135
This Southwest deal was found by Cheapflights users on 1/27. 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 1/305:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 2/15:20 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 1/27![Southwest logo]()
$135
This Delta deal was found by Cheapflights users on 1/27. 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.
Sun 2/157:05 am
ORD
- BOS
Nonstop2h 32m
Delta
Tue 3/33:50 pm
BOS
- ORD
Nonstop3h 03m
Delta
Deal found 1/27![Delta logo]()
$136
This Delta deal was found by Cheapflights users on 1/27. 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.
Sun 2/157:05 am
ORD
- BOS
Nonstop2h 32m
Delta
Wed 2/257:45 pm
BOS
- ORD
Nonstop3h 03m
Delta
Deal found 1/27![Delta logo]()
$137
This Delta deal was found by Cheapflights users on 1/28. 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 2/256:40 pm
ORD
- BOS
Nonstop2h 29m
Delta
Sat 2/289:05 am
BOS
- ORD
1 stop8h 49m
Delta
Deal found 1/28![Delta logo]()
$138
This Kissandfly.com deal was found by Cheapflights users on 1/27. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/307:40 am
ORD
- BOS
Nonstop2h 25m
JetBlue
Sun 2/16:10 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 1/27![JetBlue logo]()
$139
This Delta deal was found by Cheapflights users on 1/28. 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 2/2811:45 am
MDW
- BOS
1 stop6h 30m
Delta
Tue 3/36:55 am
BOS
- MDW
1 stop6h 04m
Delta
Deal found 1/28![Delta logo]()
$139
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 January 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $131 (Kiwi.com) |
One-way from | $66 (Kiwi.com) |
Popular in | April |
Cheapest in | January |
Average price | $207 |
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 January 29, 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
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 4/29
9:41 am-1:09 pm
Nonstop2h 28m
Boston Logan Intl
Sat 5/2
7:35 pm-9:36 pm
Nonstop3h 01m
$135
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 2/28
7:05 am-10:37 am
Nonstop2h 32m
Boston Logan Intl
Tue 3/3
3:50 pm-5:53 pm
Nonstop3h 03m
$135
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 6/3
6:15 am-9:39 am
Nonstop2h 24m
Boston Logan Intl
Sat 6/6
6:00 am-7:58 am
Nonstop2h 58m
$135
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 5/27
7:00 am-10:28 am
Nonstop2h 28m
Boston Logan Intl
Sat 5/30
7:00 am-8:58 am
Nonstop2h 58m
$135
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 4/21
9:41 am-1:09 pm
Nonstop2h 28m
Boston Logan Intl
Wed 5/13
6:52 am-8:51 am
Nonstop2h 59m
$135
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 2/28
11:45 am-7:15 pm
1 stop6h 30m
Boston Logan Intl
Sat 3/7
5:29 am-8:54 am
1 stop4h 25m
$139
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 2/25
10:00 am-1:20 pm
Nonstop2h 20m
Boston Logan Intl
Wed 3/4
7:07 am-12:04 pm
1 stop5h 57m
$151
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 4/22
8:31 am-2:16 pm
1 stop4h 45m
Boston Logan Intl
Tue 4/28
7:35 pm-9:36 pm
Nonstop3h 01m
$151
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Wed 2/25
10:49 am-5:32 pm
1 stop5h 43m
Boston Logan Intl
Sat 2/28
5:29 am-8:54 am
1 stop4h 25m
$152
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 2/28
1:02 pm-7:08 pm
1 stop5h 06m
Boston Logan Intl
Mon 3/2
6:28 pm-8:30 pm
Nonstop3h 02m
$153
Showing 1-10 of 45 results
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 23, 2026.
Booking 86 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, September is the cheapest month in which you can book a flight from Chicago to Salem (average of $91). Flying from Chicago to Salem in February is currently the most expensive (average of $117). 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 January 29, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 8% 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 January 24, 2026.
Travelers seeking maximum savings on their Chicago to Salem flight should consider departing on Saturday afternoons 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 January 29, 2026.
The most flights from CHI to SA9 are scheduled on a Thursday (56 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (19 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 January 29, 2026.
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.
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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.
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.
Alternative routes for Chicago to Salem
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from Chicago to Salem
Discover the top 6 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 January 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$61 | Average$157 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$79 | Average$158 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$94 | Average$217 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$254 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$117 | Average$324 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$136 | Average$286 | FlexibilityNo cancel fee | On-time63% |