ORD - BOS

$83 Find Cheap Flights from Chicago O'Hare Airport to Boston

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 6/17. 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
1 adult, Economy, 0 bags

KAYAK searches 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.
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Everything you should know

Cheapest round-trip
$162
Typical prices: $334-$178
JetBlue
Wed 5/27Wed 6/3
ORD - BOS • Non-stop
Cheapest non-stop
$166
Typical prices: $343-$173
JetBlue
Wed 6/24Tue 6/30
ORD - BOS • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
JetBlue's Even More Space offers 7” extra legroom.
Expect 30-minute security lines at Chicago O'Hare.
Expert advice
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Top airlines
Cheapest • from $162 (round-trip)
Best reviews • 8.0 score
Airline reviews
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Nonstop flights
You can fly direct with American Airlines, Delta and others. Average duration is 2h 32m
Direct flights
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Direct flights
Direct flights
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Avoid delays
Most punctual • 79% on-time
Best time • Fewest delays
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Top layover airports
Cheapest • Avg $114 (round-trip)
Shortest trip • 4h 35m (one-way)
Insights
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When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 32% compared to booking last minute.
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When to travel
Cheapest • 17% price drop
Most popular
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Flight Deals

Cheap Flights from O'Hare Intl to Boston (ORD-BOS)

 
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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from O'Hare Intl to Boston

Wed, May 27 - Wed, Jun 3
JetBlue Logo
8:30 pm - 11:59 pm
ORD
-
BOS
2h 29mnonstop
JetBlue Logo
6:00 am - 8:00 am
BOS
-
ORD
3h 00mnonstop
$162JetBlue
Wed, Jun 24 - Tue, Jun 30
JetBlue Logo
10:56 am - 2:24 pm
ORD
-
BOS
2h 28mnonstop
JetBlue Logo
8:10 am - 10:06 am
BOS
-
ORD
2h 56mnonstop
$166JetBlue
Sat, May 30 - Sat, May 30
Delta Logo
7:00 am - 10:35 am
ORD
-
BOS
2h 35mnonstop
Delta Logo
5:30 pm - 7:33 pm
BOS
-
ORD
3h 03mnonstop
$167Delta
Sat, May 30 - Sun, May 31
JetBlue Logo
1:56 pm - 5:27 pm
ORD
-
BOS
2h 31mnonstop
JetBlue Logo
6:00 am - 8:00 am
BOS
-
ORD
3h 00mnonstop
$168JetBlue
Sat, May 30 - Sun, May 31
Delta Logo
4:30 pm - 8:06 pm
ORD
-
BOS
2h 36mnonstop
Delta Logo
7:35 am - 9:27 am
BOS
-
ORD
2h 52mnonstop
$172Delta
Sat, May 30 - Sun, May 31
Delta Logo
7:00 am - 10:35 am
ORD
-
BOS
2h 35mnonstop
Delta Logo
7:35 am - 9:27 am
BOS
-
ORD
2h 52mnonstop
$174Delta
Sun, May 31 - Fri, Jun 5
American Airlines Logo
6:00 am - 9:27 am
ORD
-
BOS
2h 27mnonstop
American Airlines Logo
5:00 am - 6:58 am
BOS
-
ORD
2h 58mnonstop
$176American Airlines
Thu, Jun 4 - Thu, Jun 11
United Airlines Logo
9:41 pm - 1:14 am
ORD
-
BOS
2h 33mnonstop
United Airlines Logo
6:40 pm - 8:40 pm
BOS
-
ORD
3h 00mnonstop
$177United Airlines
Wed, May 27 - Wed, Jun 3
Multiple Airlines Logo
8:30 pm - 11:59 pm
ORD
-
BOS
2h 29mnonstop
Multiple Airlines Logo
12:01 pm - 7:29 pm
BOS
-
ORD
8h 28m
1 stop
$179Multiple Airlines
Wed, Jun 3 - Thu, Jun 4
Frontier Logo
1:29 pm - 1:24 am
ORD
-
BOS
10h 55m
1 stop
Frontier Logo
9:12 am - 7:29 pm
BOS
-
ORD
11h 17m
1 stop
$180Frontier
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Boston flights

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.

How much is a round-trip flight from Chicago O'Hare Intl Airport to Boston?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to Boston departing in May.

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

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Boston clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Boston on a Wednesday and more expensive on a Monday. On your return trip to Chicago O'Hare Airport, you should consider flying back on a Friday, and avoid Sundays for better deals.

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 round-trip 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 September, where tickets cost $197 (return) on average. On the other hand, the most expensive months are April and March, where the average cost of round-trip tickets is $266 and $257 respectively.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Boston?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $218 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip 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 week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to Boston, you should book around 2 weeks before departure, which saves you about 32% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Expert advice

Expert advice for your flight from O'Hare Intl to Boston

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, Delta and ORD

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Harriet Baskas

Harriet Baskas

Expert on American Airlines and JetBlue

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Joe Cortez

Joe Cortez

Expert on Spirit Airlines

Joe Cortez is a seasoned managing editor in aviation with over a decade of industry experience. His work has been featured on prominent platforms such as FlyerTalk and TripSavvy, establishing him as a respected voice in aviation journalism.

Blane Bachelor

Blane Bachelor

Expert on BOS

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Good to know

Low seasonJanuary
Cheapest flight$83
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 4% lower on average.
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 $83 for a one-way ticket and $162 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, JetBlue, Delta, 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?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between Chicago O'Hare Airport and Boston, with SkyTeam 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, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Boston are Southwest and Delta. With an average price for the route of $206 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $236 and an overall rating of 7.9.

  • 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.

KAYAK’s top tips for finding a cheap flight from Chicago O'Hare Intl Airport to Boston

  • Looking for a cheap flight? 25% of our users found flights on this route for $116 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.

Prefer to fly direct from Chicago O'Hare Airport to Boston?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago O'Hare Intl to Boston Logan Intl.
Find which airlines fly direct from Chicago O'Hare Intl Airport to Boston Logan Intl Airport, which days they fly and book direct flights.

Direct departures

Chicago O'Hare Intl to Boston Logan Intl

Monday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Tuesday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Wednesday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Thursday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Friday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Saturday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Sunday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

See more direct flights

Direct returns

Boston Logan Intl to Chicago O'Hare Intl

Monday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Tuesday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Wednesday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Thursday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Friday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Saturday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Sunday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

See more direct flights

Reviews of the top 5 airlines serving from O'Hare Intl to Boston

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Boston. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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 verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4298 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

I'm glad it wasn't only 75% full because I could get a good seat

8.0 ExcellentBobby, May 2026
BNA - GSP
Read more Southwest reviews

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

It was a pleasant surprise to have complimentary Wi-Fi on the flight

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

The space between seat rows seemed to be larger than other airlines. I didn’t check their food or entertainment since I slept most of the way. They do seem to have a lot of options for purchase though.

Boarding was extremely slow and disorganized. Onboard crew was unfriendly.

Kayak sucked. You gave me a confirmation number that was not useable by the jet blue system. Nor did you send any check in emails. I’ll not be using your site again. Nice work.

Given us a free miles or free flight for waiting for 9 hours I didn’t get home till 5am in the morning and I was supposed to be home at 9:30 touch down.

Excellent price. Everything on time. two bad parts. Kayak said I couldn't sign in for the flight online, but I got an email at the same time from Jet Blue and they let me sign in online. Second bad part was that, although I had provided my known traveler number, neither of my boarding passes, for this flight and the previous one, had TSA pre-check showing.

There was a screen but no earphones that could use the older input so I could listen to anything.

Jet blue just had great service overall! Only a little turbulence heading out of Austin, otherwise the jet stream helped the speed of the trip!

Boarding was quick and efficient. The flight crew were friendly. There were limited food options available on the flight. The pocket guide said there would be salad and sandwich sections available on flights over 3.5 hours. The only food available were snack boxes. And those were limited as well. My flight was over 5 hours. The entertainment system worked well. I had both extra legroom seats and regular coach seats. The seats were not very comfortable. The entertainment controls in the armrest made it difficult to rest my arm without changing the channel on my neighbors TV. Overall, my experience was mediocre.

Boarding was fast, easy, and we landed early. The entertainment system was very buggy and kept resetting throughout the flight.

I purchased ticket so our daughter ( a minor) can sit next to her mother. No help at gate after kayak insisted that this could be done. She ended sitting by herself

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Same plane as RDU to LGA — internet not working. Pilot issue of some sort at end of prior flight - I was on same plane for my connection. Late/delayed —

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

Half of the TSA checkpoints at PHL are closed. Also, there is no standby for first class passengers. You can only standby for coach. Very dated policy and inconsistent with peers.

The gate got changed several times and the flight was delayed over an hour. Awful experience

Everything you need to know for your flight from O'Hare Intl to Boston

Information on your arrival and departure airports