BOS - CHI

$66 Find Cheap Flights from Boston to Chicago

1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Chicago.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Chicago.
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Expert advice
Booking Insights
Expert advice

Expert advice for your flight from Boston to Chicago

 
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.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
American Airlines

American's Main Cabin Extra offers early boarding and complimentary drinks for a fee.


American Airlines provides high-speed Wi-Fi for purchase on most flights, enhancing connectivity.

United Airlines

United's Economy Plus offers up to six inches more legroom than standard economy seats.


United's Premier Access provides priority check-in and boarding for premium cabin passengers.

Southwest

Southwest offers two free checked bags, saving costs for travelers with more luggage.


Southwest's EarlyBird Check-In improves boarding position for a fee, avoiding middle seats.

Read more about Southwestby Blane Bachelor
Delta

Delta offers free Wi-Fi for SkyMiles members on domestic flights, enhancing onboard connectivity.


Delta's Sky Priority check-in offers faster service for elite status and premium cabin passengers.

Read more about Deltaby Stefanie Waldek
Spirit Airlines

Spirit's Big Front Seat offers 20-inch width and 11-inch extra legroom for a nominal fee.


Spirit's Browsing Wi-Fi package allows basic online activities like email and social media.

Airports
BOS

Download the FlyLogan app for gate info, flight status, and order ahead options at BOS restaurants.

Read more about BOSby Blane Bachelor
ORD

Take the CTA Blue Line from ORD to downtown Chicago for a 45-minute, traffic-free ride.

Read more about ORDby Stefanie Waldek
MDW

Use the CTA Orange Line from MDW to reach downtown Chicago in about 25 minutes.

Read more about MDWby Stefanie Waldek
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

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.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, Delta, ORD and MDW

Stefanie Waldek

Stefanie Waldek

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.

Read more
Blane Bachelor

Blane Bachelor

Expert on Southwest and BOS

Blane Bachelor

Blane Bachelor

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.

Read more
Joe Cortez

Joe Cortez

Expert on Spirit Airlines

Joe Cortez

Joe Cortez

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.

Read more
Booking Insights

KAYAK's insights & trends for Boston to Chicago flights

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

Find cheap flights to Chicago
Find cheap flights to Chicago

Planning a trip from Boston to Chicago? 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.

How much is a round-trip flight from Boston to Chicago?

What is the cheapest Boston to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Boston to Chicago costs $95 on the route between Boston (BOS) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 12% cheaper than other Boston-Chicago routes. The most popular route is between Boston (BOS) and Chicago O'Hare Intl Airport (ORD).

What’s the cheapest day of the week to fly from Boston to Chicago?

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

If your flying dates are flexible, you should consider flying to Chicago on a Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Boston to Chicago. For your return ticket, we recommend flying on a Thursday and avoiding Sundays for the best deals.

What is the cheapest month to fly from Boston to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Boston to Chicago, 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 Boston to Chicago is September, where tickets cost $184 (return) on average. On the other hand, the most expensive months are March and April, where the average cost of round-trip tickets is $265 and $263 respectively.

Can I save money by flying with a layover from Boston to Chicago?

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 $358 on average.

How far in advance should I book a flight from Boston to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Boston to Chicago, 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 Boston to Chicago, you should book around 2 weeks before departure, which saves you about 34% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

 AI-powered savings tips

KAYAK's tips to save more on a Boston to Chicago flight

When planning a flight from Boston to Chicago, it's important to consider a few factors to ensure you're getting the best deal. Generally, Tuesdays are the cheapest day of the week to fly, while January tends to be the cheapest month.

Day Selection: Choose to fly on a Tuesday for the best rates.

Advance Booking: Book your flight at least 23 days in advance to secure the best prices.

Airline Choice: Spirit Airlines typically offers the cheapest fares for this route.

Route Selection: The route from Boston Logan Intl to Chicago O'Hare Intl is usually the cheapest.

Flight Type: Direct flights are significantly more expensive, consider flights with layovers to save money.

This feature is powered by ChatGPT: an OpenAI-developed artificial intelligence model trained with KAYAK proprietary data and third-party data not verified by KAYAK. 

Good to know

Low seasonJanuary
Cheapest flight$66
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Boston to Chicago O'Hare Airport

When to book flights from Boston to Chicago

Are your dates flexible? Find out the best times to travel from Boston to Chicago 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 flights from Boston to Chicago

  • If I want to use mass transit to get to Boston Logan International Airport (BOS), what is my best choice?

    The Blue Line Subway is an excellent choice for quick and reliable transportation to the airport. Save the headaches of traffic by taking the MBTA Blue Line to the station at the airport and then simply board one of the free shuttle buses to all of the airport terminal buildings.

  • Are there pet relief areas at Boston Logan International Airport (BOS)?

    The pet relief areas at Boston Logan International Airport (BOS) are located on the arrivals level of every terminal building. In addition, there is a pet relief area located in Terminal E near gate E7. Keep in mind that this is the only pet relief area that is past security.

  • If I am being picked up at Chicago O'Hare International Airport (ORD), where is the best place to meet my ride?

    For most requests, you'll meet your rideshare driver on the Departures level of Terminal 2. As a reminder, there is no parking at the terminal building at any time. It is advisable to use the cell phone lot that is provided at the airport to wait for arriving passengers rather than just circling the airport.

  • Where can I rent a car at Chicago O'Hare International Airport (ORD)?

    The airport offers a complimentary shuttle to the airport's Multi-Modal Facility, where all on-site car rental companies are located. Travelers can find the shuttle by exiting the Lower Level Baggage Claim and boarding the shuttle bus at the curb front. Each terminal has a designated pickup area outside the building.

  • What are the most sustainable airlines with Boston to Chicago flights?

    Porter Airlines, United Airlines and American Airlines offer some of the most environmental-friendly flights to Chicago from Boston. Their flights emit about 48%, 46% and 42% less carbon respectively than their competitors. Those looking to fly more sustainably from Boston to Chicago should prioritize nonstop flights, embrace the use of recycled plastics and pack light for the trip.

  • What are the parking options at Boston Logan International Airport (BOS)?

    If you’ll be driving to the airport, you’ll be happy to know that Boston Logan International Airport (BOS) offers convenient onsite parking options. Parking is available in Central Parking Garage, Economy Garage, and the Terminal B Garage. All the parking garages are easily accessible from the terminals by the moving sidewalks and walkways. Additionally, the airport partners with other agencies to offer multiple secure offsite parking options.

  • What accessible services are offered at Boston Logan International Airport (BOS)?

    Boston Logan International Airport (BOS) provides Braille and Emergency Call keys in elevators. All restrooms within the airport are accessible, and it also provides restrooms for the companions. To enhance transit for passengers with reduced mobility, BOS provides Massport Shuttles. These buses are free, are equipped with wheelchair lifts and use visual and audio assistance systems to announce the bus stops. All airlines flying through BOS also run wheelchair assistance services.

  • Are there nursing rooms at Chicago O’Hare International Airport (ORD)?

    Yes, Chicago O’Hare International Airport (ORD) provides Mother's Rooms in every terminal. The rooms offer a space for traveling mothers to breastfeed or pump and are equipped with a sink, comfortable seats, power outlets and diaper changing tables. The rooms are available near Gate B10 on Concourse B in Terminal 1. In Terminal 2, they are by Gates E5 and F9. Others are also near Gate L6 in Terminal 3 and also at Gate M8​, Gate M20​, Gate M32 and Gate M37 in Terminal 5. There are also others at Multi-Modal Facility on Level 1, North and South Side.

  • What is the cheapest flight from Boston to Chicago?

    In the last 3 days, the lowest price for a flight from Boston to Chicago was $66 for a one-way ticket and $129 for a round-trip.

  • Do I need a passport to fly between Boston and Chicago?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Boston to Chicago?

    When flying out of Boston you will be using Boston Logan Intl. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Boston to Chicago?

    American Airlines, JetBlue, Delta, and Alaska Airlines offer inflight Wi-Fi service on the Boston to Chicago flight route.

  • Which aircraft models fly most regularly from Boston to Chicago?

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

  • Which airline alliances offer flights from Boston to Chicago?

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

  • On which days can I fly direct from Boston to Chicago?

    There are nonstop flights from Boston to Chicago on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from Boston to Chicago are Southwest and Delta. With an average price for the route of $222 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 $244 and an overall rating of 7.9.

  • How does KAYAK find such low prices on flights from Boston to Chicago?

    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 Boston to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Boston 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 Boston to Chicago?

    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 Chicago with an airline and back to Boston with another airline.

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

    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 Chicago from Boston 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 Boston to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $150 or less one-way and $200 or less round-trip.
  • Before your flight from Boston to Chicago, be sure to get a taste of some excellent seafood at Legal Sea Foods. This restaurant features an all-day menu, but its specialties are its seafood-inspired dishes like shrimp cocktail and a variety of clam chowders. Located in Terminal A of Boston Logan International Airport (BOS), this is a perfect spot to get that last New England-style seafood meal before your flight to the Midwest.
  • There may be nothing that says Boston better than Wahlburgers. Founded and operated by the iconic Wahlberg family, this burger joint is known for its oversized burgers and outrageous onion rings. They are located in Terminal C of Boston Logan International Airport, and they make a great spot to grab a burger and beer before your flight from Boston to Chicago.
  • Flights from Boston to Chicago can be stressful. Why not slow down for a few minutes before your flight with a chair massage or a manicure at Classique Hair Salon? Located in Terminal C near Gare C-25 at Boston Logan International Airport, Classique Hair Salon also offers waxing and facial care to give you your best look and most relaxed self before your flight.
  • Travelers on flights from Boston to Chicago looking for a convenient hotel need look no further than the Hilton Chicago O'Hare Airport. This on-site property is excellent for business travelers who do not want to bother with the hassle of downtown hotels. The hotel features an indoor pool, an excellent restaurant for steaks and seafood, and a lively sports bar.
  • When looking for a hotel that is conveniently located close to Chicago Midway airport, the Chicago Marriott Midway is an excellent choice. They offer a 24-hour airport shuttle, tasteful decor, an indoor pool, tons of meeting space, a fitness center, wireless internet access and even a Starbucks coffee shop.
  • Consider booking flights with at least a single stop en route if you want to fly more affordably from Boston to Chicago. These flights have different stopover options depending on your airline and arrival airport. Spirit Airlines, American Airlines and Delta have common stops in Philadelphia, Detroit, Myrtle Beach, Washington and LaGuardia Airport (LGA).
  • Flights from Boston to Chicago arrive at either O’Hare International Airport (ORD) or Chicago Midway International Airport (MDW). Of the two, ORD stands out as the best airport to fly into. It serves most of the direct flights from Boston and also has good connections to various modes of transportation.
  • Passengers flying to Chicago O’Hare International Airport (ORD) are welcome to use the charging stations at the airport. You can find the charging stations by Gates B19, B15, B14, B11 and B4 in Terminal 1. In Terminal 2, you will find the charging ports by Gates C28, C21, C15, C7, E7 and F2B.
  • If you need cash before flying out from Boston Logan International Airport (BOS), visit the ATMs at the airport. Citizens Bank, Chase and Bank of America operate ATMs in the Departures area in Terminal A. ATMs are also available in various locations in Terminals B, C and E.
  • Travelers with kids will be glad to learn that Boston Logan International Airport (BOS) has Kidports where their kids can let off steam before catching their flight. They are near Gate 18 in Terminal A, and by Gate 25 in Terminal C. In Terminal B, they are between Gates B30 and B36.

Prefer to fly direct from Boston to Chicago?

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

Direct departures

Boston Logan Intl to Chicago

Monday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Tuesday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Wednesday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Thursday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Friday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Saturday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Sunday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

See more direct flights

Direct returns

Chicago to Boston Logan Intl

Monday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Tuesday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Wednesday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Thursday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Friday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Saturday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Sunday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

See more direct flights

Reviews of the top 5 airlines serving from Boston to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Boston to Chicago. 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 Boston to Chicago? 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 4243 reviews
8.1Boarding
8.0Comfort
7.0Food
8.6Crew
7.5Entertainment
Airline reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

2.0 MediocreMike, Aug 2025AUS - BWI
Read more Southwest reviews

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

I believe that a four-hour trip should have a meal. Delta had none.

Great flight with Delta! Boarding was quick and easy, the amenities were solid, and the plane was in great shape. The flight attendants had a fun, lively energy while staying professional. All in all, a smooth trip — even managed to catch up on some rest. Thanks, Delta!

I was uncomfortably cold on the plane. Other than that it was uneventful and therefore as enjoyable as a plane ride can be.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

The service was good, the food could have been better.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

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.

Excellent service despite turbulence during the flight. Flight attendants were remarkable!

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.

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Flight was cancelled 3 hrs AFTER etd. Thetefore Missed connection from JFK to New Zealand . No accommodation provided… This cost ne aporox 1000 USD in extra expenses and turned whst should have been a 24 hr trip ftom Boston - New Zealand into a VERY expensive , late 70+ hr nightmare … Complete nonsense!!!

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.

I paid extra for a seat closer to the front. The TV didn’t work at all for the entire flight. Would have been nice to know before I purchased an “upgraded “ seat

It was great. I had never flown on JetBlue before, but would be very happy to fly with them in the future.

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.

Too many long delays with JetBlue. Worst major airline that serves JFK but unfortunately I keep going back because of the prices.

My JetBlue experience was nice. The flights ran on time, the aircraft was clean and comfortable, and the flight attendants were attentive. My only issue, which is isolated to the low-cost (budget) option at JetBlue, is that the check in process makes the user feel that they have to buy their seats. The seats offered for purchase are upgrades from the budget seats you get (which are essentially the last seats remaining). The interface should not make it feel like you must purchase a seat.

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.

Everything you need to know for your flight from Boston to Chicago

Other airlines flying from Boston to Chicago

Flights from the other most popular airlines that fly from Boston to Chicago according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.

Compare transportation modes for Boston to Chicago

Transportation modeAverage priceAverage duration
Flights$5292h 35m
Buses$21128h 20m

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