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.
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
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 | January |
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High season | October |
Cheapest flight | $42 |
Find which airlines fly direct from Chicago to Boston Logan Intl Airport, which days they fly and book direct flights.
Direct departures
Chicago to Boston Logan Intl
Monday
ANA, Air New Zealand, Alaska Airlines, +23 more
ANA, Air New Zealand, +24 more
22
23
Tuesday
ANA, Air New Zealand, Alaska Airlines, +22 more
ANA, Air New Zealand, +23 more
21
22
Wednesday
ANA, Air New Zealand, Alaska Airlines, +22 more
ANA, Air New Zealand, +23 more
21
22
Thursday
ANA, Air New Zealand, Alaska Airlines, +23 more
ANA, Air New Zealand, +24 more
22
23
Friday
ANA, Air New Zealand, Alaska Airlines, +21 more
ANA, Air New Zealand, +22 more
20
21
Saturday
ANA, Air New Zealand, Alaska Airlines, +21 more
ANA, Air New Zealand, +22 more
20
21
Sunday
ANA, Air New Zealand, Alaska Airlines, +23 more
ANA, Air New Zealand, +24 more
22
23
Direct returns
Boston Logan Intl to Chicago
Monday
ANA, Air New Zealand, Alaska Airlines, +24 more
ANA, Air New Zealand, +25 more
23
24
Tuesday
ANA, Air New Zealand, Alaska Airlines, +22 more
ANA, Air New Zealand, +23 more
21
22
Wednesday
ANA, Air New Zealand, Alaska Airlines, +22 more
ANA, Air New Zealand, +23 more
21
22
Thursday
ANA, Air New Zealand, Alaska Airlines, +24 more
ANA, Air New Zealand, +25 more
23
24
Friday
ANA, Air New Zealand, Alaska Airlines, +21 more
ANA, Air New Zealand, +22 more
20
21
Saturday
ANA, Air New Zealand, Alaska Airlines, +21 more
ANA, Air New Zealand, +22 more
20
21
Sunday
ANA, Air New Zealand, Alaska Airlines, +24 more
ANA, Air New Zealand, +25 more
23
24
Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons
Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons
I loved having a most black flight crew during Black History Month; rather by design or accident I appreciated the representation. ❤️
This was the second flight this week with flight attendant Marcus I’m not sure if his last name is Lane or Lang but this guy is awesome. He funny, attentive and his service is 5 stars. Marcus makes business travel more enjoyable !
Although the flight left late, we arrived early. It was one of the quickest boarding and off boarding experiences I’ve had. It was kind of annoying the only drinks they had were water, coffee, and tea. The flight was very smooth, temperature was just right, and flight attendants were friendly.
Lower number on this flight so spaced out passengers. Able to enjoy more room to relax during flight. It was lovely.
Kind staff. Snacks are small but that’s the new normal.
The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.
Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.
Flight left early and arrived early. the whole trip was excellent.
Seats were really tight and the seat belts did not give enough slack.
Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.
Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking
It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable
The flight was delayed for 4 hours. Once onboard the crew was wonderful.
Overall was excellent. Will definitely us JetBlue in the future.
Love the mosaic program, being able to move to an extra space seat for free is awesome
I rate it is good we had a 4-hour travel delay at one point but JetBlue gave out food vouchers and travel points credits for another flight so they try to make up for it
Smooth boarding and friendly crew. Unfortunately as soon as we boarded the unit that provides air circulation failed. The pilot informed us and requested maintenance technicians to check it out. The plane became uncomfortably warm without any fresh air coming in. Plus the repair delayed our departure. I am glad the maintenance crew were able to fix the problem. I also was without use of my tv monitor for the first 1/3rd of the trip.
Communication with the customer and stay is important. Staff off with a minor inconvenience but it worked out of course. Also this was a very old Mint Class plane. They snuck this one in on us. The updated aircraft are much better.
The flight itself was fine, but the boarding process was extremely frustrating. There is no one scanning boarding passes - passengers just scan themselves and enter the jetway. By the time my husband and I got on the plane and were halfway to our seats they determined there were too many bags on the plane and everything at that point needed to be checked. This created a lot of unnecessary chaos. They should have alerted people before getting on the plane that they would need to start checking bags instead of waiting until people were already on the plane.
Plenty of room for me and the cat in Premium Economy. Seat was comfortable. Boarding was a breeze. The lady at the special check-in desk was great, super helpful and professional.
Our seats were all the way in back of the plane,
It’s been awhile since I have traveled on United. I, along with my family who were on the flight noted how smoothly everything went . Boarding, flight crew and service was excellent.
The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.
The seats on this flight were almost roomy enough to be the basic amount needed for human existence.
The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.
Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.
We arrived early and finally made it to our gate almost an hour after.
Was a pain having to leave the plane and reboard but glad the plane was fixed
I was forced to check my carry-on backpack despite there being space - but it came out on the baggage carousel so fast it didn't even delay my pickup. Otherwise a good flight. Boarding began early (which was disadvantageous for me) but fine.
Good crew and a great experience. Only good things to say.
Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.
I had a horrible experience from the time I dropped off my bags until the time I landed. The staff taking the bags at the check-in counter prior to security, forced me to check my baby stroller, even though it weighed less than 20 pounds. their excuse was that the wheels were too big. I have never had an issue gate checking this exact same stroller in the past either on American or on any other airline. when I asked for the agent to show me the rule about the size of the wheels on strollers, they told me to look it up on the AA website. I did so, and did not find any indication that wheel size was a problem for gate checking strollers. The only limitation would be the weight of the stroller which mine was below. I was left with a one-year-old child and all of my carry-on luggage, diaper bag, and the like to walk around the airport without the assistance of a stroller and had the same issue when I exited the plane and had to go all the way to baggage claim without a stroller. In addition, while on the airplane, I was told I can only get one bag of cookies as a snack, even though I was with a child. Apparently my child and I were supposed to share a cookie. While this latter issue is a minor one, it is just another example of the absolutely horrible customer service that American Airlines provides. In addition, the 737 aircraft that I was on was extremely hot and the air vents above the seat were so far away from the aisle and middle seats that it was comical. I could barely reach the air vent to adjust it. I had to ask the person in the window seat to do it for me. The whole experience was just a nightmare.
You were more on time than United. I'm so over united delays.
Flight was late and TSA had shut down so (almost) no passengers could get to the gate. American failed to inform TSA to stay open! Needed to get back home so we had to rent a car & drive 13 hours all through the night. It was bad.
The flight was on time and everything went very smoothly.
The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.
I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.
I was in a wheelchair and went from international to domestic. I was transferred to several different modes of transport and expected to give a tip at each transfer. I was, although, grateful to get to the gate in time for my flight.
My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks
The flight took an extra 30 min to take off because we were waiting for crew to board then it took another 30 min to get off the plane because there was no parking. Just overall ridiculous also please add a head rest my neck was gonna snap off thanks.
Your employees need to learn how to talk to people as creations of Yah. We are not their children nor are we lower than them.
Helpful attendants at check-in is very good. The $70 charge for a checked bags I didn't care for.and the constant charges for picking a seat and faster check-in are too much. Please cut the prices by at least 50% would be fantastic!
Absolutely the MOST uncomfortable seat I've EVER had on ANY airline. It should be a criminal act (cruel & unusual punishment). NEVER AGAIN will I travel your airline.
The flight was delayed over an hour and we had to sit on the plane. Crew does not apologize due to the delay. Spirit will NEVER do anything to give a customer a better experience. A child next to me was kicking me the whole time. I don't ever enjoy flying with Spirit.
Easy! As long as you don’t mind no frills, our flight was enjoyable and on time
Fantastic. Had handicapped traveler and they helped us through security, helped with boarding, helped put wheelchair together, and were all very patient. A pleasant change from previous spirit flights I’ve taken. Highly recommend.
No frills, cheap price & flight was on time, I'm happy.
Flight delayed. Seat assignment doesn’t get assign until last minute. Seats don’t recline and very stiff
The flight was delayed, and we waited for more than an hour on the plane.
Average price | Average duration | |
---|---|---|
Flights | $453 | 2h 15m |
Trains | $291 | 22h 01m |
Buses | $249 | 31h 13m |
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