$94 Find Cheap Flights from Chicago to Salem

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Salem departing on 7/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$176
Typical prices: $192-$315
JetBlue
Tue 7/21Tue 7/28
ORD - BOS • 1 stop
Cheapest non-stop
$176
Typical prices: $180-$339
American Airlines
Thu 8/13Sun 8/16
ORD - BOS • Non-stop
Arrival airport
You can't fly directly to Salem. It is served by Boston (BOS), located 12.1 miles from Salem.
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Chicago to Salem (CHI-BOS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Salem that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Salem

Tue, Jul 21 - Tue, Jul 28
JetBlue Logo
9:40 am - 5:17 pm
ORD
-
BOS
6h 37m
1 stop
JetBlue Logo
5:01 am - 8:50 am
BOS
-
ORD
4h 49m
1 stop
$176JetBlue
Sat, Aug 15 - Mon, Aug 17
JetBlue Logo
9:40 am - 6:59 pm
ORD
-
BOS
8h 19m
1 stop
JetBlue Logo
4:55 pm - 9:58 pm
BOS
-
ORD
6h 03m
1 stop
$177JetBlue
Wed, Jul 8 - Fri, Jul 10
United Airlines Logo
9:41 pm - 1:14 am
ORD
-
BOS
2h 33mnonstop
United Airlines Logo
6:43 pm - 8:40 pm
BOS
-
ORD
2h 57mnonstop
$178United Airlines
Tue, Jul 28 - Fri, Jul 31
Southwest Logo
6:05 pm - 9:25 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
5:25 am - 7:00 am
BOS
-
MDW
2h 35mnonstop
$178Southwest
Fri, Jul 10 - Wed, Jul 15
Delta Logo
7:25 pm - 11:00 pm
ORD
-
BOS
2h 35mnonstop
Delta Logo
8:45 pm - 10:39 pm
BOS
-
ORD
2h 54mnonstop
$179Delta
Fri, Jul 10 - Tue, Jul 21
Southwest Logo
7:35 pm - 10:55 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
$179Southwest
Thu, Aug 6 - Thu, Aug 20
United Airlines Logo
6:05 am - 9:29 am
ORD
-
BOS
2h 24mnonstop
United Airlines Logo
5:45 am - 9:38 am
BOS
-
ORD
4h 53m
1 stop
$180United Airlines
Tue, Jul 21 - Wed, Jul 22
Southwest Logo
5:30 pm - 11:25 pm
MDW
-
BOS
4h 55m
1 stop
Southwest Logo
7:30 am - 9:10 am
BOS
-
MDW
2h 40mnonstop
$180Southwest
Fri, Jul 10 - Mon, Jul 13
United Airlines Logo
6:12 pm - 11:59 pm
ORD
-
BOS
4h 47m
1 stop
United Airlines Logo
3:13 pm - 5:05 pm
BOS
-
ORD
2h 52mnonstop
$181United Airlines
Tue, Jul 21 - Fri, Jul 24
Delta Logo
7:25 pm - 11:00 pm
ORD
-
BOS
2h 35mnonstop
Delta Logo
8:45 pm - 10:39 pm
BOS
-
ORD
2h 54mnonstop
$183Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$94
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Chicago O'Hare Airport to Boston

When to book flights from Chicago to Salem

Are your dates flexible? Find out the best times to travel from Chicago to Salem based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Salem

  • Which airports will I be using when flying from Chicago to Salem?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Salem does not have its own airport so you’ll be flying into nearby Boston Logan Intl airport, which is 12.1 mi away.

  • How long does a flight from Chicago to Salem take?

    Direct flights cover the 850 miles separating Chicago and Salem in about 2h 10m.

  • How many flights are there between Chicago and Salem?

    85 direct flights run between Chicago and Salem on a daily basis. On average, there are about 598 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Salem?

    Consider leaving on a Friday and avoid Sundays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Fridays and the most expensive ones on Saturdays.

  • How does KAYAK find such low prices on flights from Chicago to Salem?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Salem.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Salem?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Salem from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Salem?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Salem with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Salem?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Salem from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Salem?

    In the last 5 days, the cheapest one-way ticket between Chicago and Salem found on KAYAK was with JetBlue for $67. JetBlue offered a round-trip connection from $68 and Delta from $82.

Top tips for finding cheap flights from Chicago to Salem

  • There is no airport in Salem. Instead, you’ll be flying into Boston Logan Airport when flying between Chicago and Salem.
  • The cheapest flight from Chicago to Salem was found 54 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be March, April and May. The cheapest month to fly is January.

Reviews of the top 5 airlines serving Chicago to Salem

 
Need help choosing which airline to fly with from Chicago to Salem? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4242 reviews
7.5Entertainment
7.0Food
8.6Crew
8.0Comfort
8.1Boarding
Airline reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

2.0 MediocreIrene, Jun 2026
DEN - SFO
Read more Southwest reviews

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

It was just okay, no frills, basic transportation with no luxury. No screens on the seats, no water or drinks on a short flight. Full flight but at least it was on time.

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

Over a 3 hour flight. The turbulence was almost imperceptible except for 2 short periods which were not bad and over quickly. The attendants claimed "Safety first" and sat looking at their phones for 3 hours with no drink or snack service. This isn't the first time with Southwest. I thinkit may be there new plan of operation. Oh, and it was June 18, Southwest's Birthday which offered free drinks. NOT.

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Very good flight. Crew was great. No issues and we even arrived early.

The flights are constantly late anymore, and they won't even give you a glass of water on the plane. For years, they were able to do a service on this flight from Atlanta to Knoxville and Knoxville Atlanta now they say it's too short of a flight. You can't even get a quick drink of water.

Flight got canceled 4 times, missed my connecting flight due to delays, have to wait to go home tomorrow

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Great experience nice pilot very soft and easy landing and take off

We sat on the runway for over an hour before departure. That was unwelcome.

Horrible. Faucet in sink not working, wifi not working. Didn’t bring food or snacks

Flight was delayed before take off and at landing. Baggage took 20 minutes. Flight crew would not serve full soft drink and had to ask multiple times before receiving water.

If you cant travel Delta One, Comfort Class is the next best thing!

Arrived early, comfortable seats (Comfort+). Mediocre food, poor wifi (intermittent).

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

For whatever reason, I could not check in online. Kept getting the "It's not you it's us" message. Even when we tried the kiosk at the airport - same results. The check-in person had a very difficult time getting our boarding passes together despite the fact that we could show confirmation on the jetblue website. After a very long time we finally got boarding passes. The only other issue is, my vegetarian meal featured chicken.

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

My bag was not loaded on my flight. it was not communicated to me until i was waiting for my bag at my destination. there was no confirmation of when my bag was arriving and no way to track it.

This was the first flight I've taken since pre-pandemic. I was pleased with how orderly the boarding and disembarking went. The seats were comfortable. I loved that there was no "first class'. The attendants and passengers I met were all very friendly and welcoming.

Boarding was extremely slow and disorganized. Onboard crew was unfriendly.

There was a screen but no earphones that could use the older input so I could listen to anything.

Jet blue just had great service overall! Only a little turbulence heading out of Austin, otherwise the jet stream helped the speed of the trip!

Boarding was quick and efficient. The flight crew were friendly. There were limited food options available on the flight. The pocket guide said there would be salad and sandwich sections available on flights over 3.5 hours. The only food available were snack boxes. And those were limited as well. My flight was over 5 hours. The entertainment system worked well. I had both extra legroom seats and regular coach seats. The seats were not very comfortable. The entertainment controls in the armrest made it difficult to rest my arm without changing the channel on my neighbors TV. Overall, my experience was mediocre.

Boarding was fast, easy, and we landed early. The entertainment system was very buggy and kept resetting throughout the flight.

Everything you need to know for your flight from Chicago to Salem

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