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ORD - BOS

Find cheap flights from Chicago O'Hare Airport to Boston from $70

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to Boston departing on 5/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sat 4/27
Sat 5/4

Search hundreds of travel sites at once for deals on flights to Boston

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Boston.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Boston.
In the last 7 days travelers have searched 47,584,047 times on KAYAK, and here is why:

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Cheap flight deals from O'Hare Intl to Boston

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to Boston that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
5:51 pm - 8:08 amORD-BOS
13h 17m1 stop
8:21 am - 10:47 amBOS-ORD
27h 26m1 stop
$101Frontier
Find Deal
Thu, May 2 - Wed, May 8
5:51 pm - 8:08 amORD-BOS
13h 17m1 stop
8:21 am - 10:47 amBOS-ORD
27h 26m1 stop
$118Frontier
Find Deal
Sun, May 5 - Wed, May 8
7:15 pm - 10:41 pmORD-BOS
2h 26mnonstop
6:10 am - 8:04 amBOS-ORD
2h 54mnonstop
$127JetBlue
Find Deal
Wed, May 8 - Tue, May 14
6:38 pm - 10:04 pmORD-BOS
2h 26mnonstop
6:10 am - 8:04 amBOS-ORD
2h 54mnonstop
$133JetBlue
Find Deal
Wed, May 1 - Tue, May 7
8:10 pm - 11:46 pmORD-BOS
2h 36mnonstop
4:43 pm - 6:45 pmBOS-ORD
3h 02mnonstop
$158Delta
Find Deal
Fri, May 10 - Tue, May 14
6:30 am - 12:14 pmORD-BOS
4h 44m1 stop
5:25 am - 7:21 amBOS-ORD
2h 56mnonstop
$165American Airlines
Find Deal
Wed, May 8 - Tue, May 28
5:15 pm - 8:44 pmORD-BOS
2h 29mnonstop
4:43 pm - 6:45 pmBOS-ORD
3h 02mnonstop
$168Delta
Find Deal
Sat, May 25 - Tue, May 28
6:25 pm - 12:52 amORD-BOS
5h 27m1 stop
8:30 am - 10:28 amBOS-ORD
2h 58mnonstop
$172American Airlines
Find Deal
Wed, Apr 24 - Tue, Apr 30
7:10 am - 2:37 pmORD-BOS
6h 27m1 stop
6:01 am - 7:54 amBOS-ORD
2h 53mnonstop
$238United Airlines
Find Deal
Wed, Apr 24 - Wed, May 1
6:00 am - 12:41 pmORD-BOS
5h 41m1 stop
8:00 am - 9:52 amBOS-ORD
2h 52mnonstop
$258United Airlines
Find Deal
Sun, Apr 14 - Sun, Apr 21

Flights from O'Hare Intl to Boston - Travel Insights & Trends

Get data-powered insights and trends into flights from O'Hare Intl to Boston to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Boston?

The average price of all flights from Chicago O'Hare Intl Airport to Boston clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from Chicago O'Hare Airport to Boston, look for departures on Wednesdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Boston, Wednesday is the cheapest day to fly and Friday is the most expensive.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Boston?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago O'Hare Intl Airport to Boston, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago O'Hare Intl Airport to Boston is February, where tickets cost $158 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is $336 and $324 respectively.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Boston?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago O'Hare Intl Airport to Boston, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago O'Hare Intl Airport to Boston, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 84 days before departure.

Which airlines provide the cheapest flights from Chicago O'Hare Airport to Boston?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the cheapest one-way ticket from Chicago O'Hare Airport to Boston found on KAYAK was with JetBlue for $70. Frontier proposed a round-trip connection from $101 and Spirit Airlines from $120.

Which airlines fly most frequently between Chicago O'Hare Airport and Boston?

Delta connects Chicago O'Hare Airport to Boston with up to 8 flights per day. American Airlines also offers 5 flights per day, while United Airlines follows with 5 flights per day.

Which airlines fly non-stop between Chicago O'Hare Intl Airport and Boston?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Chicago O'Hare Intl Airport to Boston.
There are 4 airlines that fly nonstop from Chicago O'Hare Intl Airport to Boston. They are: American Airlines, Delta, JetBlue and United Airlines. The cheapest price of all airlines flying this route was found with JetBlue at $66 for a one-way flight. On average, the best prices for this route can be found at JetBlue.

How many flights are there between Chicago O'Hare Intl Airport and Boston per day?

Each day, there are between 19 and 25 nonstop flights that take off from Chicago O'Hare Intl Airport and land in Boston, with an average flight time of 2h 24m. The most common departure time is 5:00 pm and most flights take off in the morning. Each week, there are 161 flights. The most frequent day of departure is Friday, when 16% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between Chicago O'Hare Intl Airport and Boston?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Chicago O'Hare Airport to Boston take?

The duration of a nonstop flight to Boston from Chicago O'Hare Airport is typically 2h 17m. The journey crosses a distance of 864 miles.

What’s the earliest departure time from Chicago O'Hare Airport to Boston?

Early birds can take the earliest flight from Chicago O'Hare Intl Airport at 5:45 am and will be landing in Boston at 9:08 am.

What’s the latest departure time from Chicago O'Hare Airport to Boston?

If you prefer to fly at night, the latest flight from Chicago O'Hare Intl Airport to Boston jets off at 9:45 pm and lands at 1:06 am.

Good to know

Low season

January

High season

October

Cheapest flight

$70
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Chicago O'Hare Airport to Boston

When to book flights from O'Hare Intl to Boston

Are your dates flexible? Find out the best times to travel from O'Hare Intl to Boston based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago O'Hare Airport to Boston flights

  • If you arrive at ORD airport early, what activities can you do to pass the time?

    There is a yoga room with mats where passengers can practice yoga, relax, and meditate as they wait for their flights. It is located on the mezzanine level of terminal 3. For those interested in the arts, there is a public art program with sculptures and paintings where you can browse art pieces before flying.

  • If you have an early morning flight, where can you spend the night in ORD?

    You can spend your night at the Hilton Chicago O'Hare airport hotel found within the airport grounds. It is located near terminals 1, 2, and 3, and you can walk from the airport to the hotel. The hotel has a fitness center, showers, restaurant, and elegant rooms.

  • Which family services are offered at ORD airport?

    ORD has a family lounge near gate F1 in terminal 2. The lounge has space where kids can play and stroller parking for passengers traveling with infants. Nursing rooms are also available in every terminal. They provide a clean and safe space for nursing parents to pump and breastfeed their babies. The rooms have changing tables, comfortable seats, and soft lighting, making them comfortable for lactating parents. Most restrooms in the terminals have changing stations for young children.

  • Are there child-friendly restaurants in ORD?

    Many restaurants offer high chairs and a children's menu. Some restaurants in ORD provide a fantastic view of the airplanes landing and taking off. These restaurants include Berghoff Café and the Food Court seating area found at terminal 1 near Gate C. Other restaurants like Tuscany at gate B18 in Terminal 1 have a view of the airplanes on the ground.

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Boston?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Boston was $70 for a one-way ticket and $101 for a round-trip.

  • Do I need a passport to fly between Chicago O'Hare Airport and Boston?

    A passport is not required to fly from Chicago O'Hare Airport to Boston.

  • Which airlines offer Wi-Fi service onboard planes from Chicago O'Hare Airport to Boston?

    All the following airlines offer inflight Wi-Fi service on the Chicago O'Hare Airport to Boston flight route: American Airlines, Delta, JetBlue, Finnair, British Airways, and Iberia.

  • Which aircraft models fly most regularly from Chicago O'Hare Airport to Boston?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago O'Hare Airport to Boston flight route.

  • Which airline alliances offer flights from Chicago O'Hare Airport to Boston?

    oneworld, SkyTeam, and Star Alliance are the airline alliances operating flights between Chicago O'Hare Airport and Boston, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Chicago O'Hare Airport to Boston?

    There are nonstop flights from Chicago O'Hare Airport to Boston on a daily basis.

  • Which is the best airline for flights from Chicago to Boston, Delta or JetBlue?

    The two airlines most popular with KAYAK users for flights from Chicago to Boston are Delta and JetBlue. With an average price for the route of $251 and an overall rating of 8.0, Delta is the most popular choice. JetBlue is also a great choice for the route, with an average price of $213 and an overall rating of 7.7.

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport to Boston?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago O'Hare Airport to Boston.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport to Boston?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Chicago O'Hare Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago O'Hare Airport to Boston?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Boston with an airline and back to Chicago O'Hare Airport with another airline. Booking your flights between Chicago O'Hare Airport and BOS can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago O'Hare Airport to Boston?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Boston from Chicago O'Hare Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding a cheap flight from ORD to Boston

  • Looking for a cheap flight? 25% of our users found flights on this route for $139 or less one-way and $211 or less round-trip.
  • If you are in Chicago O'Hare International Airport (ORD) and you lose items at the security lines or checkpoints, you can ask the security guards to help you locate them. If things get lost on the flight, contact your airline for assistance.
  • Passengers transiting throughinORD can stay connected while waiting for their flight. Every terminal has free Wi-Fi access. Changing stations are available in the seating areas to ensure your device's battery stays full.
  • If you want a place to pray and relax while waiting for your flight in ORD, there is a multi-faith chapel found at terminal 2 on the mezzanine level. Boston Logan International Airport (BOS) also has a place where you can pray. In the terminal C pre-security area, there is a chapel known as Our Lady of the Airways Chapel.
  • If you are traveling with your pet, ORD has six animal relief areas- four outdoor areas and two after airport security. ORD pet policy states that when traveling with a pet, they should be carried inside a crate or carrier at the airport.
  • If you want to travel from BOS to downtown Boston, you can take the MBTA into Boston. It is the most efficient and cost-effective way to reach the city from BOS. The air shuttle offers free shuttle services from the airport station to the rental car center, water taxi, and airline terminals.
See more tips

Prefer to fly non-stop from Chicago O'Hare Airport to Boston?

Find which airlines fly direct from O'Hare Intl to Logan Intl, which days they fly and book direct flights.

Nonstop departures

Chicago O'Hare Intl to Boston Logan Intl

Monday

ANA, Air New Zealand, Alaska Airlines, +19 more

ANA, Air New Zealand, +20 more

Tuesday

ANA, Air New Zealand, Alaska Airlines, +18 more

ANA, Air New Zealand, +19 more

Wednesday

ANA, Air New Zealand, Alaska Airlines, +18 more

ANA, Air New Zealand, +19 more

Thursday

ANA, Air New Zealand, Alaska Airlines, +20 more

ANA, Air New Zealand, +21 more

Friday

ANA, Air New Zealand, Alaska Airlines, +20 more

ANA, Air New Zealand, +21 more

Saturday

ANA, Air New Zealand, Alaska Airlines, +19 more

ANA, Air New Zealand, +20 more

Sunday

ANA, Air New Zealand, Alaska Airlines, +21 more

ANA, Air New Zealand, +22 more

See more direct flights

Nonstop returns

Boston Logan Intl to Chicago O'Hare Intl

Monday

ANA, Air New Zealand, Alaska Airlines, +20 more

ANA, Air New Zealand, +21 more

Tuesday

ANA, Air New Zealand, Alaska Airlines, +19 more

ANA, Air New Zealand, +20 more

Wednesday

ANA, Air New Zealand, Alaska Airlines, +18 more

ANA, Air New Zealand, +19 more

Thursday

ANA, Air New Zealand, Alaska Airlines, +21 more

ANA, Air New Zealand, +22 more

Friday

ANA, Air New Zealand, Alaska Airlines, +21 more

ANA, Air New Zealand, +22 more

Saturday

ANA, Air New Zealand, Alaska Airlines, +20 more

ANA, Air New Zealand, +21 more

Sunday

ANA, Air New Zealand, Alaska Airlines, +21 more

ANA, Air New Zealand, +22 more

See more direct flights
See more direct flights

Top 5 airlines serving from O'Hare Intl to Boston

Need help choosing which airline to fly with from O'Hare Intl to Boston? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to KAYAK reviews.
8.0
DeltaOverall score based on 11418 reviews
82boarding
81overall
79comfort
86crew
80entertainment
75food
Airline reviews

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

Read more about Delta

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

Terrible. Delta delays caused us to miss our flight and they did nothing to fix it.

The A330-200 was showing its age but otherwise this was a pleasant flight with friendly crew. The meals/snack provided were pretty good.

The most unprofessional and disorganized experience I’ve ever had with an airlines. After the flight was diverted on the runway and we returned to the gate, there was no communication about the plans and it took an additional 5 hours to get set up with a hotel and a new flight, information that was not readily given to the passengers and mostly gotten second hand from what other passengers heard from each other. Based on this experience I cannot recommend flying delta again

The boarding process was terrible especially with an indirect flight Chicago to Seattle to San Diego was terrible talking about we overbooked a flight idk if I’d take this airline ever again we got off our flight from Chicago to Seattle and we traveled for business and they told us our connecting flight was over booked and their was no seats asking people to take a delayed next flight and they don’t tell anyone coughing to wear masks seats 30A-B were terrible during the flight no one wants to sit next to people coughing all around I don’t want to be sick traveling for work or get sick anytime it’s very upsetting the staff doesn’t take this stuff serious to tell them to wear masks when they see people coughing and sneezing

I was traveling with my 85 years old grandma and 60 years old mother. Which I requested to get a wheelchair. I went to the Delta Kiosk and asked for a wheelchair.  They brought a wheelchair and 2 minutes (without exaggerating, time is important for me as I am well disciplined with a military background) later they said that the wheelchair belongs to American Airlines, so we need to switch it.  We were like where is the other one so my grandma can use it? They are like, "it's on its way, she has to wait for the other one" I asked them why does she have to wait? Is it ok for her to sit on this one when the other one arrives. Answer was "NO". I guess lack of common sense was the issue. I started to explain to the agent that she can not stand still or wait. Finally, someone said that in spanish "she can not stand, let's wait for the other one" . Delta's wheelchair came, without an attendant or helper. They brought that wheelchair and left it in the middle of the airport. Nobody seemed to care. I had to push her to the gate. Then they finally realized that "wait a minute, there is something wrong with that". So they send someone, who later started harassing us, to tell us how he works for cash tips. Then a "Private Security Interviewer" approached us. I think his name was Carlos (His descriptions - tall for an average worker, ginger curly hair, wears glasses, overweight). He did not represent himself. All he did was show his badge for two seconds and when (later on) I asked him what his name was, he said "I already told you at the beginning". At that point we were waiting to be called at the Delta Kiosk (this is prior to the Customs first check in point). So, Delta Airlines hired "Private security interviewers" to make sure that nobody brings anything illegally to the US. Which is great, makes me feel safe and secure. But, it does not serve the purpose. Let me explain to you why. These interviewers do not know what they are doing or saying and you can clearly see that. They think that they are CBP or Immigration officers. They will get angry If you ask them any questions. Then they will put all these stickers on the back of your passport like they caught "Pablo Escobar". At one point I was sarcastic and told the interviewer that "I like those stickers, It's my hobby and I am collecting them. Can I have more of those?"  and interviewers eyes and brain goes like "error 404". He did not know how to react or respond to that. Then he flags my itinerary on his iPad. Trying to give me a hard time since I asked him about his name, so I can call him by his name. But of course that did not change the fact that his lack of english made everything even harder. After 45 mins of wait and clearing the "Private Security Interviewer" you would think that we are going to be all set to depart. I was wrong. We waited in line to go through the security line, just like other citizens. No wheelchair, disability, seniority etc were important for her. They treat us like she is in her twenties.  On several occasions they forced her to stand up. She was like "I swear to God that I can not walk, my son I wish I could walk, but I can not". They did not seem like they cared. Then finally they realized that she is legit disabled. They let her pass on a wheelchair. At the gate, Carlos showed up to make sure that I am going through the secondary check. They pulled me to the secondary check. And started asking me about my luggage. My response was "I only have one carry-on bag, to make everyone's (including my life) life easier". They asked the same question over again "Sir, do you just have only one bag?" I replied saying "Yes". She did not believe me and said "Just only one". So, I thought she did not believe me and I said "Yes, Si, Si, solo uno". She looked at me and then turned to the agent (Carlos) and stared at him like "did you not ask him about his bags, did you not know that he only had one carry on?". I am sorry to say that but they just looked like a bunch of idiots who do not know what they are doing. Finally they released me after a minute of secondary check. Meanwhile everyone is boarding and my grandma is waiting on her wheelchair. Then we approached the gate agent and I asked her if I could sit next to my family, if they had any seats available. She replied that "I can not change any seat at the gate, I do not have any authority". I replied "I understood". We got on the plane last and I asked our flight attendant if I could change my seat to be next to my family. FYI, their seats were 10 B and C, mine was the 35 D. Meanwhile there were empty seats on 10 D and F. Even flight attendants surprisingly said that "why did she put you all the way back, while we had 1/2 full flight. I will go and ask her". Our flight attendant was great and he made sure that I am next to my family. He went above and beyond and he gave the closest seat to the. Flight was good. Delta Airlines failed to bring the wheelchair when we arrived. Excuse was "Gate changed, that is why". I walked outside and grabbed an empty wheelchair. I put my grandma and brought her to the Customs. Then a Delta Airline worker approaches me and says that you can not move this wheelchair, it belongs to the gate. We will bring you a new one. A CBP officer heard our conversation and jumped in and said, "wait a minute you want her (pointed my grandma) to wait here while you bring her wheelchair?". He (delta worker) responded "yes sir". But when he talks to me, no sir, nothing. The CBP officer goes "Nope, she is not waiting here and I will make sure to pull her wheelchair". If that officer was not there we probably would have had to wait and be forced to change the wheelchair. The CBP officer, again the CBP officer, not the Delta employee, pushed our wheelchairs to the gate. Sincerely,

The boarding agents appeared to do the minimum customer service. They did not appear to try to find solutions to problems.

The only real hiccups in the flight were things beyond Delta’s control - turbulence which delayed food service and a departure delay caused by some VIP plane which stopped all departures and landings for 30 minutes - and was never explained to us by the crew. Otherwise good flight. I would fly Delta again.

Checkin was easy, boarding was organized, employees friendly and nice. Was a lovely flight.

I understand why there was a 40 minute delay, but we should have been offered snacks during that time. We weren’t offered it until later.

Delayed by almost an hour - I also noticed that all JetBlue flights departing from PBI were delayed yet the weather was perfect.

I loved the wifi, much better than Delta. Seats were old. and bathrooms dingy.

There was no wheelchair or wheelchair escort at the gate..unacceptable

Delayed 4 hours because of maintenance issue they knew about all day. Get another plane. Time is precious!

I liked that boarding and take off were timely despite a 15 minute delay due to weather. The pilot communicated with us the entire flight keeping us informed re: turbulance and slight delays on the runway after we landed.

Has been always great except flight cancelation in the past at very last minute waiting till 2am and we when have to beg for overnight accommodation

There were weather issues and coding problems whatever those refer to, but JetBlue, for two days in a row was unbelievably late. Several hours late, resulting in almost no sleep for passengers like me.

The plane was very hot. There were delays . Generally, the flight was great.

If jet blue is going to offer tv at every seat, fix the headphone connection so you can hear. Haven’t had a usable headphone jack in years

Plane is old and seats are worn. Add to it the plane was dirty. No plugs for laptop.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

Unfortunately our flight was delayed by 45 minutes due to Kate arriving aircraft. Once we stated everything was great.

Flight canceled due to weather. Rescheduled flight canceled due to maintenance. I’m stuck!

You could have been ON TIME! And I was miffed because I spent an extra $82 to get my seat and the steward put a woman from the back in my aisle for nothing because her movies wouldn’t work. I’ll try that next time and save $82!

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

This plane is my favorite despite the very limited overhead space. Seats are comfortable!

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

3.5 hour delay!!! No plane for hours, mechanical issues and poor communication from airline. Horrible! Supposed to land at 8:54, landed at 12:32!

I had a phobia for Spirit and now is 100% confirmed. Flight delayed, missed connecting flight and staying overnight . Now not even able to get my boarding pass until I’ll get into the airport. It’s really really bad at this point

the landing was terrible. the plane touched down and had take off. the plane flew around and landed a second time.i understand the weather might of been the problem. It was a scary experience and no explanation from the captain.

The flight attendants were very personable, extremely friendly, and had a very good feeling of the energy around them not to mention they’re very funny and engaging. What made up for the discomfort of the seats and the fact that the plane sat for a long time on the Turmac. Not sure if the pilot was new, but the landing was very rough sort of like I was at a magic mountain theme park ride that was built in 1959

Flight was delayed 2+ hours missed a concert because of it…

Service was awesome 👍🙏 thank you Spirit Airlines...love the Big Seat...😎

Crew was very engaging and welcoming. Seat very uncomfortable and inadequate leg room made the trip a long 3 hours.

Plane two hours late. Missed flight to Boston. Spirit should have already reticketed us at the last jet blue flight. But no. No help, only confusion. Reticketing line a mile long. Agent couldn’t care less whether I lived or died. Offered flight two days later - unacceptable. Now going - hopefully - via Orlando to Boston with a 7 hour layover. Locator GJLSJG BTW, am a travel counselor at a large corporate agency.

The flight was delayed. The boarding process disorganized. Poor communication regarding the delays. We were sitting on the runway in Boston for over 1-hr. Again very poor communication regarding the status. Bags didn’t arrive after almost 2-hr wait. I gave up and went home without my bag and had to return to the airport to pick it up the next day. Very exhausting experience!

Would not change a thing, NA on food And entertainment for this flight. I will be Back to fly again with you.

Got great seats without paying for them and only 2 people in our row. Flight landed 45 minutes early.

Book cheap flights from Chicago to Boston

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Boston found on KAYAK in the last 72 hours.
5/1Wed
nonstopJetBlue
2h 26mORD-BOS
$70
4/13Sat
1 stopSpirit Airlines
10h 25mORD-BOS
$71
5/28Tue
1 stopFrontier
5h 24mORD-BOS
$78
4/30Tue
2 stopsFrontier
14h 04mORD-BOS
$84
5/3Fri
nonstopDelta
2h 33mORD-BOS
$90
4/26Fri
1 stopAmerican Airlines
6h 04mORD-BOS
$104
4/29Mon
nonstopUnited Airlines
2h 21mORD-BOS
$108
4/4Thu
nonstopAmerican Airlines
2h 26mORD-BOS
$115
6/23Sun
nonstopDelta
2h 31mORD-BOS
$124
4/7Sun
nonstopUnited Airlines
2h 23mORD-BOS
$140

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Last minute flights from O'Hare Intl to Boston

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Boston that are departing in the next 10 days.
4/2Tue
multi-stop
13h 24mORD-BOS
4/8Mon
multi-stop
14h 51mBOS-ORD
$182
4/2Tue
multi-stop
13h 47mORD-BOS
4/3Wed
multi-stop
10h 44mBOS-ORD
$198
4/2Tue
nonstopJetBlue
2h 23mORD-BOS
4/4Thu
nonstopJetBlue
2h 53mBOS-ORD
$219
4/2Tue
nonstopDelta
2h 20mORD-BOS
4/7Sun
multi-stopDelta
5h 06mBOS-ORD
$273
3/29Fri
nonstopAmerican Airlines
2h 16mORD-BOS
4/17Wed
multi-stopAmerican Airlines
6h 04mBOS-ORD
$283
4/1Mon
nonstopJetBlue
2h 26mORD-BOS
4/4Thu
nonstopJetBlue
2h 53mBOS-ORD
$284
3/30Sat
multi-stopAmerican Airlines
6h 47mORD-BOS
4/3Wed
nonstopAmerican Airlines
2h 59mBOS-ORD
$292
4/1Mon
multi-stopDelta
5h 14mORD-BOS
4/10Wed
nonstopDelta
2h 56mBOS-ORD
$293
3/29Fri
nonstopUnited Airlines
2h 16mORD-BOS
4/17Wed
nonstopUnited Airlines
2h 53mBOS-ORD
$299
4/1Mon
nonstopUnited Airlines
2h 21mORD-BOS
4/5Fri
nonstopUnited Airlines
2h 53mBOS-ORD
$369

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Chicago O'Hare Airport - Boston Flights

Departure:

Chicago O'Hare Airport (ORD)United States

Destination:

Boston (BOS)United States

Return flight deals:

Boston - Chicago O'Hare Airport

Cabin classes:

$298
$487
$402
$104