$82 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 5/27. 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
$161
Typical prices: $318-$168
JetBlue
Wed 5/27Wed 6/3
ORD - BOS • Non-stop
Cheapest one-way
$82
Typical prices: $108-$256
JetBlue
Wed 5/27
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

Wed, May 27 - Wed, Jun 3
JetBlue Logo
8:30 pm - 11:59 pm
ORD
-
BOS
2h 29mnonstop
JetBlue Logo
6:00 am - 8:00 am
BOS
-
ORD
3h 00mnonstop
$161JetBlue
Tue, Jul 7 - Wed, Jul 8
JetBlue Logo
8:20 pm - 11:51 pm
ORD
-
BOS
2h 31mnonstop
JetBlue Logo
5:20 pm - 7:25 pm
BOS
-
ORD
3h 05mnonstop
$162JetBlue
Wed, May 20 - Mon, May 25
Multiple Airlines Logo
1:59 pm - 1:24 am
ORD
-
BOS
10h 25m
1 stop
Multiple Airlines Logo
6:00 am - 8:00 am
BOS
-
ORD
3h 00mnonstop
$164Multiple Airlines
Wed, May 20 - Tue, May 26
Frontier Logo
1:59 pm - 1:24 am
ORD
-
BOS
10h 25m
1 stop
Frontier Logo
9:12 am - 7:41 pm
BOS
-
ORD
11h 29m
1 stop
$165Frontier
Sat, May 30 - Wed, Jun 3
United Airlines Logo
3:55 pm - 7:30 pm
ORD
-
BOS
2h 35mnonstop
United Airlines Logo
7:19 am - 9:17 am
BOS
-
ORD
2h 58mnonstop
$167United Airlines
Tue, Jun 16 - Tue, Jun 23
Southwest Logo
6:05 pm - 9:20 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
$167Southwest
Sat, May 30 - Sat, Jun 6
American Airlines Logo
6:00 am - 9:27 am
ORD
-
BOS
2h 27mnonstop
American Airlines Logo
7:46 pm - 10:00 pm
BOS
-
ORD
3h 14mnonstop
$168American Airlines
Wed, May 20 - Sat, May 23
Multiple Airlines Logo
1:59 pm - 1:24 am
ORD
-
BOS
10h 25m
1 stop
Multiple Airlines Logo
11:00 am - 1:01 pm
BOS
-
ORD
3h 01mnonstop
$169Multiple Airlines
Tue, Jun 30 - Tue, Jun 30
American Airlines Logo
6:04 am - 9:30 am
ORD
-
BOS
2h 26mnonstop
American Airlines Logo
7:46 pm - 10:00 pm
BOS
-
ORD
3h 14mnonstop
$171American Airlines
Mon, Jun 29 - Tue, Jun 30
Southwest Logo
7:35 pm - 10:50 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
$172Southwest
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$82
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 3% increase in price.
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?

    107 direct flights run between Chicago and Salem on a daily basis. On average, there are about 751 departures each week.

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

    Consider leaving on a Monday and avoid Saturdays 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 Sundays.

  • 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 72 hours, the cheapest one-way ticket between Chicago and Salem found on KAYAK was with JetBlue for $60. JetBlue offered a round-trip connection from $67 and Spirit Airlines from $79.

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 86 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 4307 reviews
7.5Entertainment
8.1Boarding
7.0Food
8.0Comfort
8.6Crew
Airline reviews

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

2.0 MediocreAnonymous, May 2026
SEA - SMF
Read more Southwest reviews

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

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.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

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.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

Excellent price. Everything on time. two bad parts. Kayak said I couldn't sign in for the flight online, but I got an email at the same time from Jet Blue and they let me sign in online. Second bad part was that, although I had provided my known traveler number, neither of my boarding passes, for this flight and the previous one, had TSA pre-check showing.

Jet blue was great But the Jayak system Wasa pure nightmare and wasted so much of my time and energy by not giving me a way to access jet blue to check in the flight back I didn’t even get the number confirmation code 24 hours before. Because I didn’t receive the email with the confirmation code I could NoT CHECk IN. I spoke to a kayak third party and they informed me I could not carry a carry on, on the flight which caused me so much extra stress it was just too much. You can be sure I will not be using it recommending your site. Again.

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

My experience with JetBlue was fine BUT I am very upset with Kayak! JetBlue had delayed our scheduled departure by an hour and you NEVER notified me of the change. I did not hear directly from JetBlue because the trip was booked through Kayak, a mistake I will not repeat. Your reminder of the our trip last week still had the WRONG departure time. Our return trip has also changed, and again no notice from you.

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.

Purchased through 3rd party vendor which made everything difficult. Unable to check in online. Unable to get flight updates easily, tsa precheck information didn’t carry through, longer time to check in in person. Entertainment looked good but had to purchase conventional headphones to view.

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

Not having an assigned seat until boarding and then having to check my bag.

Flight emergency landed in Chicago due to “Odor” in back of plane . Had to buy ANOTHER TICKET to get to Boston cash out of my own pocket . Then they would notchange my return flight time without a 400. Charge!!!! Insulting.

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