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.
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 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 | $42 |
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, +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, +20 more
ANA, Air New Zealand, +21 more
19
20
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, +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, +21 more
ANA, Air New Zealand, +22 more
20
21
Thursday
ANA, Air New Zealand, Alaska Airlines, +22 more
ANA, Air New Zealand, +23 more
21
22
Friday
ANA, Air New Zealand, Alaska Airlines, +20 more
ANA, Air New Zealand, +21 more
19
20
Saturday
ANA, Air New Zealand, Alaska Airlines, +20 more
ANA, Air New Zealand, +21 more
19
20
Sunday
ANA, Air New Zealand, Alaska Airlines, +22 more
ANA, Air New Zealand, +23 more
21
22
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.
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.
The best flight I’ve had in a while. The plane was like 25% capacity, if that. Smoothest boarding and deplaning process I’ve ever experienced. Wish all flights were this smooth.
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
As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.
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.
It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.
The flight from Buffalo to Chicago was on an older and smaller plane. Seating was tight. Looking closely at the interior of the aircraft there were definitely signs of aging and wear.
The flight encountered a delay exceeding 4 hours. The food voucher issued was valued at $12, insufficient to cover our meal expenses. Consequently, I was unable to take my medication, leading to a drop in blood sugar levels and exacerbating my anxiety.
Airplane was cold. Flight attendants were rude. Phone charger did not work. No food available.
3hour delay In the last 3 months i had 3 flights and 2 of these had a more than 2:40 hrs delayed
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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