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 | $45 |
Find which airlines fly direct from Boston Logan Intl Airport to Chicago O'Hare Intl Airport, which days they fly and book direct flights.
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, +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, +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, +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
Chicago O'Hare Intl to Boston Logan Intl
Monday
ANA, Air New Zealand, Alaska Airlines, +22 more
ANA, Air New Zealand, +23 more
21
22
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, +22 more
ANA, Air New Zealand, +23 more
21
22
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
This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.
This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.
Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.
The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.
A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.
Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.
The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.
The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.
Terrible and im avoiding them in the future. My initial flight was delayed causing me to rebook my flight and when speaking with the representative to rebook I explained this is the second time my flights were delayed and they did nothing to help me. I wasn't booked to comfort plus or given a voucher or anything. I was almost late for my meeting that I needed to attend on Monday because of the games delta played delaying my flights even more and putting me in the very back of the plane next to an extremely intoxicated passenger
Flights on time. .Ride was as comfortable as can be expected in steerage. Luggage arrived at destination. Attendants were fairly friendly.
Great staff. Wifi is terrible. Signing up for skylines is a painstaking process. Had to call customer service just to get my flight itinerary and confirmation sent to me. Consistent delays. A well staffed company that is run so poorly. Upper management needs to be renewed.
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 crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks
The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.
Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago
The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.
They canceled our flight and left us stranded to figure it out
Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done
Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA
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
The flight was delayed for 4 hours. Once onboard the crew was wonderful.
Overall was excellent. Will definitely us JetBlue in the future.
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.
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
The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.
Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?
Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.
Delayed due to no crew. On a major holiday travel day.
Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.
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.
Very difficult. Flew out on Dec 24th and it was a mess. They know it is going to be the busiest time of the year and they had no organization. Finally they called for people going on certiam flights so they could get them thru thw line then we had to rush to our gate to get in li e to board.We missed our flight do to being stuck at the border of Mexico. They would not work with us to make an affordable price so we had to wait a day with no where to go and pay 280 more for our flights. I would think that a complimentary drink would be nice. But we had to pay 4.49 for a coke. Not an overall good experience
I very late and supose be in home at 12 pm from yesterday but I stiill in detroi airport
I’ve now flown Spirit a few times and while the general perception of Spirit I feel is poor, I’ve had a great experience each time. They do charge extra for everything but you should know that going in
Horrible. Take off was delayed by an hour. They were letting people board d the plane right before takeoff. I was delayed an hour when I arrived and late for my meeting. Spirit is NEVER on time.
The MOST uncomfortable seat I've EVER experienced on ANY airlines. My wife & I were in agony at the end of the flight. NEVER AGAIN!
The flight landed with a delay and we had to wait almost an hour to be off boarded. So typical of spirit.
The gate employees and the flight crew were friendly and professional. Afterboarding we waited 20 minutes for another flight; a complimentary beverage would have ben appreciated for the inconvenience.
Spirit literally broke parts of two of our suitcases and call it “normal wear and tear.” Not worth the low price if we have to replace bags.
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