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 | January |
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High season | October |
Cheapest flight | $42 |
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
It was one and half hour late... Not sure if any other experience matters.
It was one and half hour late... Not sure if any other experience matters.
Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.
For my birthday trip this was my second time ever flying, this trip was the best.
after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though
No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.
Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch
Sat on tarmac for 2 hours and then missed my connecting flight
First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.
Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.
Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.
Everything was fine except the entertainment was not working for half of the flight.
Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.
At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.
No one fussed at me about my pap machine as a 3rd pice on the plane. Boarding was pleasant and smooth. The boarding agent in Anchorage was a fun character- he could be in a movie. :~) The on-board crew were downright pleasant. No militant attitudes on Delta. Like all planes these days the seats are too narrow for standard Americans and at 5’2” there is barely enough leg room. I don’t know how tall people fold themselves into the seats. But that’s nothing specific to Delta
My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.
My flight was extremely cold. I had a jacket and a cover was left in each seat. The cover was extremely thin and I have a disability, fibromyalgia and arthrithis and AC air is the worst. I closed my vent and my husbands vent and it still was frigid. I asked the attendant if I could get another cover and she quickly almost dismissively and totally unconcerned stating, (I quote) (one per chair) and walked off so quickly that I didn't get a chance to explain to her that I literally have adisability. I didnt want to make a seen so I set on that flight for over 5 hours in pain, joints locking up and extremely uncomfortable. When my fibromyalgia flares up my joints not only ache but they will lock up also and it takes me days to get back to my regular self even though I take medication for it. I felt like it would not have hurt anyone at all for her to just give me an extra cover because I'm sure they have all types of medical issues in people that fly every day.
After all the weather issues at least they got me to my destination the next day
My flight was canceled after being rescheduled for four days canceling my trip. Kayak and everyone affiliated with it I.e the airlines, and just fly have been excruciating to deal with. My trip to visit family had to be canceled as there was no way to make it. I am furious at all of you.
They delayed our flight because of bad weather in NY which was completely understandable. Then they cancelled our flight and a later flight that evening. The earliest we could fly was the next morning. We ended up buying last minute tickets on another airline and made it home slightly delayed but safely that evening. Delta kept saying it was weather related but if that was the case how did we make it back on another airline? The weather in NY was cloudy but not bad.
From Atlanta to Savannah - flight connection was way to short (we weren't even late landing ) and flight was already boarding when we landed - we were told we were the last on board and so we had to gate check our bags. Once we got on the plane, there were at least seven open bag spots so that was unnecessary delay. There should be better communication between the gate agent and the crew.
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
Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.
My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.
Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours
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.
It would have been nice if they had offered more than one set of snacks
Seats were not too comfortable; it was impossible to locate the underseat power outlet.
You get what you pay for with JetBlue. Every little thing costs more, you are nickel and dimed until the end. Entertainment doesn’t function. Flight attendants do the bare minimum.
The check in and boarding process was a bit of a cluster. Two people at the counter to check in, three random lines that nobody knew which was for what, and people kept getting shuffled from one line to another for no apparent reason because then they’d get shuffled back and end up getting out further back in the line than they were originally. I only had to hand my already checked bag over and it took 45 minutes. I was never assigned a seat so when I tried to board I was pulled out of line again while someone had to try to manually assign me a seat. During the flight I got up to go to the bathroom, and there was an attendant in the aisle offering pillows etc and it was a 30 min wait unbuckled standing by the bathrooms because she said I couldn’t go past her. First and last time flying jet blue to be honest.
Communication since no reason or explanation was given for 3 hrs delay
Flight was delayed several 3 hours - no reason was given and no communication what so ever.
No overhead baggage room even though I was seated in row 2. Consequently had to check in my carry on bag. Baggage carousel was jammed. Took 45 min to get my bag.
Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.
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.
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.
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