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 | $55 |
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
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
Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.
Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.
We sat on the plane on the tarmac for 4 hours.
I'm not a fan of Southwest's model. I don't like the herding style of boarding.
Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.
Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.
Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.
It is southwest seat was ok. Not the most comfortable seat
I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight
The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.
Plz don't take away free bags and free seating
Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗
5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.
Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market
It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane
My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.
The entertainment and wifi mostly didn't work on this flight.
Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.
The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.
I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us
I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.
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
Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service
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.
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.
Great flight. Departed early, arrived early. However they were out of meals for sale. Also, we arrived early and the gate was not available so we sat on the taxiway for quite a while (not JetBlue’s fault).
Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.
It was too hot in the cabin. The AC did not help.
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
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.
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.
Transportation mode | Average price | Average duration |
---|---|---|
Flights | $288 | 2h 15m |
Trains | $342 | 22h 03m |
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