Basic Economy offers carry-on only travel with late boarding and no seat assignment until check-in.
Main Cabin Extra provides early boarding and complimentary drinks, ideal for longer flights.
Planning a trip from Chicago to Boston? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.
When planning a flight from Chicago to Boston, there are several strategies to consider for saving money. Generally, the cheapest day of the week to fly is Wednesday, and the most affordable month is September.
Booking Advance: Purchase tickets at least 90 days in advance for the best rates.
Airline Choice: Consider flying with Frontier, as it is generally the cheapest airline for this route.
Route Selection: Flights from Chicago Midway (MDW) to Boston Logan (BOS) tend to be the most affordable.
Direct or Layover: Direct flights are significantly more expensive, so consider flights with layovers to save money.
This feature is powered by ChatGPT: an OpenAI-developed artificial intelligence model trained with KAYAK proprietary data and third-party data not verified by KAYAK.
Low season | February |
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High season | October |
Cheapest flight | $69 |
Direct departures
Chicago to Boston Logan Intl
Monday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Tuesday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Wednesday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Thursday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Friday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Saturday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Sunday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Direct returns
Boston Logan Intl to Chicago
Monday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Tuesday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Wednesday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Thursday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Friday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Saturday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
Sunday
American Airlines, Delta, JetBlue, +2 more
American Airlines, Delta, +3 more
1
2
AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.
AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.
Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.
Southwest's seats are the least comfortable I have ever sat in.
The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.
Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.
My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.
Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.
If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.
Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.
southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.
This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one
Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate
Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.
Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.
The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,
On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.
The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!
I believe that a four-hour trip should have a meal. Delta had none.
Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!
I was uncomfortably cold on the plane. Other than that it was uneventful and therefore as enjoyable as a plane ride can be.
Once we got in the air the pilot made up some of the time of the delay. So that was really nice.
Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.
It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.
It was great, I’m very grateful for the pilots and crew flight attendants for everything.
Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick
Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.
I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.
The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!
Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.
A bit rush for transit. Food and entertainment are not available
Ring in first class for an overnight flight, there was no blankets nor pillows for first class customers.
Flight was delayed. Staff at the gate effectively and proactively communicated about the delay.
3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!
After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"
After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.
Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan
I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.
I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude
Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!
Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.
I paid extra for a seat closer to the front. The TV didn’t work at all for the entire flight. Would have been nice to know before I purchased an “upgraded “ seat
It was great. I had never flown on JetBlue before, but would be very happy to fly with them in the future.
Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.
The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.
Too many long delays with JetBlue. Worst major airline that serves JFK but unfortunately I keep going back because of the prices.
My JetBlue experience was nice. The flights ran on time, the aircraft was clean and comfortable, and the flight attendants were attentive. My only issue, which is isolated to the low-cost (budget) option at JetBlue, is that the check in process makes the user feel that they have to buy their seats. The seats offered for purchase are upgrades from the budget seats you get (which are essentially the last seats remaining). The interface should not make it feel like you must purchase a seat.
The plane was late to leave.. Internet was lousy. TV was not working. when we arrived, We stayed on the plane for a long time before we got to the gate. It took us a long time to retrieve our luggage because they didn’t know what carousel to send them to. It was a bad experience.
I especially liked the lead crew officer. His boarding and safety announcements were made with a bit of novelty and humor. The flight also left the gate 10 minutes early and we landed about 20 minutes early… It was a delightful flight…
There were mutliple delays. There was inconsistent, delayed, and poor communication regarding the delays.
Spend hours delayed with no food, water anything sitting on the aieplane with no ability to eat or use the restroom. My entire experience was the absolute worst. I will never fly jet Blue again.
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