Basic Economy offers low fares but includes late boarding and no free checked bags.
Main Cabin Extra provides early boarding and complimentary drinks for a small fee.
Planning a trip from Boston to O'Hare Intl? 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.
Low season | January |
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High season | August |
Cheapest flight | $55 |
Direct departures
Boston Logan Intl to Chicago O'Hare 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, +20 more
ANA, Air New Zealand, +21 more
19
20
Wednesday
ANA, Air New Zealand, Alaska Airlines, +21 more
ANA, Air New Zealand, +22 more
20
21
Thursday
ANA, Air New Zealand, Alaska Airlines, +23 more
ANA, Air New Zealand, +24 more
22
23
Friday
ANA, Air New Zealand, Alaska Airlines, +22 more
ANA, Air New Zealand, +23 more
21
22
Saturday
ANA, Air New Zealand, Alaska Airlines, +20 more
ANA, Air New Zealand, +21 more
19
20
Sunday
ANA, Air New Zealand, Alaska Airlines, +23 more
ANA, Air New Zealand, +24 more
22
23
Direct returns
Chicago O'Hare Intl to Boston Logan Intl
Monday
ANA, Air New Zealand, Alaska Airlines, +21 more
ANA, Air New Zealand, +22 more
20
21
Tuesday
ANA, Air New Zealand, Alaska Airlines, +21 more
ANA, Air New Zealand, +22 more
20
21
Wednesday
ANA, Air New Zealand, Alaska Airlines, +22 more
ANA, Air New Zealand, +23 more
21
22
Thursday
ANA, Air New Zealand, Alaska Airlines, +21 more
ANA, Air New Zealand, +22 more
20
21
Friday
ANA, Air New Zealand, Alaska Airlines, +21 more
ANA, Air New Zealand, +22 more
20
21
Saturday
ANA, Air New Zealand, Alaska Airlines, +22 more
ANA, Air New Zealand, +23 more
21
22
Sunday
ANA, Air New Zealand, Alaska Airlines, +22 more
ANA, Air New Zealand, +23 more
21
22
Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.
Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.
Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.
Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had
Food was surprisingly good but the WiFi was not great
this crew didn't care much. bumping carts into seats more times than i care to remember
Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.
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
Overall it was good. I missed my connection but I was put on another flight.
Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.
It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.
I liked that the flight was nonstop from ORD to CIU for $200 round trip.
While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.
The first flight was better in terms of the aircraft.
Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.
Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint
There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.
The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks
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.
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.
The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.
The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.
Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.
The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!
Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows
To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.
The plane was late and then sat on the runway for almost 45 minutes before taking off.
Crew professional. Easy bag drop off. On time. Good entertainment.
Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.
Per usual, flight status, staff courtesy and professionalism were excellent
I enjoyed my flight, it was pretty smooth and we landed earlier than eta.
Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.
Seats too hard, too much lumbar. Space between rows was extremely tight, so tight hard to place item under seat in front of me. No tv screens. Zero plugs for charging phones. Too many sales pitches
While on the flight we had a delay and had to sit on the plane while maintenance fixed it. It’s ended up taking an hour and a half longer to leave than expected. I had an unruly passenger sitting behind me that vaped during the flight and was rude and loud for the majority of the flight.
Spirit is by far the worst airline to travel with, period. Seats are cardboard, flight attendants need anger management and if you ask for water, you’re basically a criminal. I don’t care how much it costs but I will travel with an airline who actually cares about their customers. Oh and one more thing, the next time your gate agent puts his foot on someone’s baggage's scale, I hope they get what’s coming next, a viral video of your scams. You suck Spirit, do better.
I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.
Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.
terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money
Terrible-extreme delay with very little communication, plane was overfull, luggage was returned on baggage claim in filthy condition.
Lower cost is the reason to fly Spirit. Should give free baggage with credit card.
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