CHI - BOS

$64 Find Cheap Flights from Chicago 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 Chicago to Boston departing on 2/18. 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
$131
Overall average: $252
Multiple Airlines
Tue 2/17Fri 2/27
ORD - BOS • 1 stop
Cheapest non-stop
$133
Typical prices: $192-$359
JetBlue
Fri 2/6Mon 2/9
ORD - BOS • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
JetBlue's Wi-Fi and live TV enhance in-flight comfort.
The Silver Line bus from BOS is free to South Station.
Expert advice
Expert advice
Expert advice
Expert advice
Video guide: How to find cheap flights to Boston
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Top airlines
JetBlue
Cheapest • from $133 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
ORD
-
BOS
Cheapest • 8% average savings
ORD
-
BOS
Most popular
Insights
Insights
Insights
Insights
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 38% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 9% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to Boston!
Flight Deals
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Expert advice
Flight Deals

Cheap Flights from Chicago to Boston (CHI-BOS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago 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 Chicago to Boston

Tue, Feb 17 - Fri, Feb 27
Multiple Airlines Logo
7:00 am - 5:15 pm
ORD
-
BOS
9h 15m
1 stop
Multiple Airlines Logo
6:00 am - 10:51 am
BOS
-
ORD
29h 51m
1 stop
$131Multiple Airlines
Wed, Feb 25 - Sat, Feb 28
Multiple Airlines Logo
6:02 pm - 1:13 am
ORD
-
BOS
6h 11m
1 stop
Multiple Airlines Logo
7:00 am - 9:10 am
BOS
-
ORD
3h 10mnonstop
$132Multiple Airlines
Sat, Feb 14 - Sat, Feb 21
Southwest Logo
6:10 pm - 9:25 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
2:10 pm - 7:25 pm
BOS
-
MDW
6h 15m
1 stop
$133Southwest
Fri, Feb 6 - Mon, Feb 9
JetBlue Logo
7:40 am - 11:05 am
ORD
-
BOS
2h 25mnonstop
JetBlue Logo
3:35 pm - 5:43 pm
BOS
-
ORD
3h 08mnonstop
$133JetBlue
Wed, Feb 25 - Sat, Feb 28
Delta Logo
10:11 am - 1:35 pm
ORD
-
BOS
2h 24mnonstop
Delta Logo
5:15 pm - 7:23 pm
BOS
-
ORD
3h 08mnonstop
$135Delta
Sat, Feb 7 - Sat, Feb 21
Southwest Logo
5:40 pm - 8:55 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:45 pm - 7:35 pm
BOS
-
MDW
2h 50mnonstop
$135Southwest
Sun, Feb 15 - Tue, Mar 3
Delta Logo
7:05 am - 10:37 am
ORD
-
BOS
2h 32mnonstop
Delta Logo
3:50 pm - 5:53 pm
BOS
-
ORD
3h 03mnonstop
$136Delta
Thu, Feb 26 - Wed, Mar 4
Frontier Logo
4:42 pm - 1:13 am
ORD
-
BOS
7h 31m
1 stop
Frontier Logo
6:00 am - 4:52 pm
BOS
-
ORD
11h 52m
1 stop
$138Frontier
Thu, Mar 12 - Thu, Mar 19
JetBlue Logo
11:00 am - 2:24 pm
ORD
-
BOS
2h 24mnonstop
JetBlue Logo
6:00 pm - 10:56 pm
BOS
-
ORD
5h 56m
1 stop
$141JetBlue
Thu, Feb 26 - Sun, Mar 1
Frontier Logo
4:42 pm - 1:13 am
ORD
-
BOS
7h 31m
1 stop
Frontier Logo
6:00 am - 10:51 am
BOS
-
ORD
29h 51m
1 stop
$142Frontier
Booking Insights

KAYAK's insights & trends for Chicago to Boston flights

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

Find cheap flights to Boston
Find cheap flights to Boston

Planning a trip from Chicago to Boston? 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.

What is the cheapest Chicago to Boston flight route?

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

The cheapest return flight from Chicago to Boston costs $116 on the route between Chicago O'Hare Intl Airport (ORD) and Boston (BOS). Over the past month, this route was, on average, 8% cheaper than other Chicago-Boston routes. It is also the most popular route.

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

The average price of all round-trip flights from Chicago 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 Thursday and more expensive on a Monday. On your return trip to Chicago, you should consider flying back on a Wednesday, and avoid Sundays for better deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago 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 to Boston is January, where tickets cost $207 (return) on average. On the other hand, the most expensive months are April and February, where the average cost of round-trip tickets is $265 and $235 respectively.

Can I save money by flying with a layover from Chicago 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 $210 on average.

How far in advance should I book a flight from Chicago 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 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 to Boston, you should book around 2 weeks before departure, which saves you about 38% 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 Chicago 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, ORD and MDW

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.

Blane Bachelor

Blane Bachelor

Expert on Southwest and 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.

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.

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

When planning a flight from Chicago to Boston, there are several strategies to consider for saving money. Generally, the cheapest day of the week to fly is Wednesday, and the most affordable month is September.

Booking Advance: Purchase tickets at least 90 days in advance for the best rates.

Airline Choice: Consider flying with Frontier, as it is generally the cheapest airline for this route.

Route Selection: Flights from Chicago Midway (MDW) to Boston Logan (BOS) tend to be the most affordable.

Direct or Layover: Direct flights are significantly more expensive, so consider flights with layovers to save money.

AI-powered; AI can make mistakes.

Good to know

Low seasonJanuary
Cheapest flight$64
Best time to beat the crowds with an average 10% 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 Chicago to Boston

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

  • Does Logan International Airport have pet relief areas?

    If you are traveling with a pet or service animal, make sure to stop by one of the pet relief areas in Logan International Airport after your flight has landed. There is a designated area conveniently located outside of the Arrivals doors for every terminal, and complimentary waste bags are provided for pet owners.

  • What are good hotels near Logan International Airport?

    The Hilton Boston Logan Airport is a chic, 4-star hotel that is directly connected to Logan International Airport via a skybridge and is less than a 7-minute drive from the Boston Common Park. The Hyatt Regency Boston Harbor is a standard option that is only a mile from the airport and a 5-minute drive from the famous Faneuil Hall.

  • What dining options are there in Chicago Midway International Airport?

    The Go Go White Sox Bar and Grill is located in the Central Market of Chicago Midway International Airport and serves classic American meals, while the Midway Pour House is in Concourse A and is known for having a variety of craft beers. Dunkin’ Donuts and Cafe Espresso are good options for travelers with little time that would like to purchase some to-go items.

  • Does Logan International Airport have a prayer room?

    Logan International Airport has the Our Lady of the Airways Chapel that is located in Terminal C of the Arrivals level. It is open during standard business hours and is available to all travelers, no matter what their spiritual affiliation is.

  • How can I get to the Freedom Trail from Boston Logan International Airport (BOS)?

    The distance between the Freedom Trail and Boston Logan International Airport (BOS) is around 3.7 miles, and various transportation options run between the two points. Line 88 bus and the subway provide the best opportunity to travel between the two points, taking about 26min to cover the distance. However, a taxi is a quicker option, taking about 6min to get there.

  • Where are spas located at Boston Logan International Airport (BOS)?

    Travelers arriving in BOS from Chicago while weary can seek some therapy in one of the spas on this property. XpresSpa at Terminal B provides ideal services to help you relax and self-indulge. They include manicures, pedicures, facials, and deep-tissue massages.

  • Where can I withdraw money at Boston Logan International Airport (BOS)?

    If your wallet is depleted and you want to recharge it, you’ll find several ATMs at BOS run by numerous banks and credit unions. These ATMs are located throughout the airport terminals, pre-and post-security. For instance, Bank of America has its ATMs at the Arrivals Level, East End by Taxi Stand, Pre-Security.

  • What family-friendly amenities are at Boston Logan International Airport (BOS)?

    BOS caters to the needs of moms and the littlest family members through the provision of Mamava suites where lactating mothers can pump and breastfeed in privacy. You can locate one of them in Terminal E post-security in the Women's Restroom lobby.

  • What is the cheapest flight from Chicago to Boston?

    In the last 3 days, the lowest price for a flight from Chicago to Boston was $64 for a one-way ticket and $131 for a round-trip.

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

    A passport is not required to fly from Chicago to Boston.

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

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

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

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

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

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

  • Which airline alliances offer flights from Chicago to Boston?

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

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

    There are nonstop flights from Chicago 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 $231 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 $230 and an overall rating of 7.9.

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

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

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

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

  • Looking for a cheap flight? 25% of our users found flights on this route for $84 or less one-way and $181 or less round-trip.
  • If you’re looking at flights from Chicago to Boston, there are two different airports that you can fly out of. O'Hare International Airport is the largest airport in the region and harbors a high concentration of flights, while Chicago Midway International Airport is a smaller choice that is located only several miles from the city’s downtown.
  • Hoping to have a direct flight from Chicago to Boston? There are several major airlines that you can choose from. Southwest Airlines is popular amongst travelers with a large amount of luggage, as they allow you to check up to two bags for free, while Delta Airlines offers many upgrade options for those who would prefer more comfortable chairs or extra legroom.
  • For those that are traveling with kids, make sure to stop by one of the several children’s play areas located in Logan International Airport. These play areas are free for all travelers and feature a variety of toys, games, and activities that will help kids (and their parents) unwind after a long day of traveling.
  • To help pass the time before your flight takes off from O'Hare International Airport, see if you can access one of the airport’s private lounges. American, United, and Delta Airlines all have lounges in Chicago, and they often provide complimentary or reduced price access passes for their customers.
  • Flying can sometimes be stressful, so make sure you’re taking the time to unwind before boarding your plane. O'Hare International Airport has both a fitness club and a yoga room, both of which are perfect ways to let off some steam and relax before embarking on a day of traveling.
  • Travelers flying American Airlines from Chicago to Boston should remember that the airline’s hub is at Boston Logan International Airport (BOS). You’ll arrive through Terminal B, and the airline’s Admirals Club is located at the same terminal. Members and holders and registered cards enjoy unrestricted access to this amenity. However, Economy Class travelers can access it at a reduced cost.
  • If you’re departing to BOS via Chicago Midway International Airport (MDW), you’ll find a road system between the terminal and the secure area. Inter-terminal movement between the two buildings is through a pedestrian bridge. However, every traveler must be cleared at the security checkpoint in the terminal building on the way out to the concourse.
  • Suppose you’re flying aboard Delta Airlines from Chicago O’Hare International Airport (ORD) to Boston Logan International Airport (BOS). In that case, you’ll be glad to note that the carrier allows pets such as cats and dogs in the cabin. Nevertheless, your four-legged friends must bear certified vaccination certificates and relevant health licenses. Still, it would help if you confined them in their cages to prevent them from disturbing other passengers.
  • Chicago Midway International Airport (MDW) sits about 10.7 miles from Downtown Chicago, and several public transportation options travel between the two destinations. The most convenient commute from downtown Chicago to MDW is via the Orange Line train. The train regularly plies between the two points, covering the distance in approximately 20-25min.
  • Before your trip from Chicago to BOS, you might wish to have a private session with the Almighty. Those departing through ORD will be glad to know that this prayer suite is tucked away from the noisy terminals. The airport’s chapel lies on the Mezzanine level of Terminal 2, atop the Delta Air Lines ticket desk.

Prefer to fly direct from Chicago to Boston?

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

Direct departures

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

Direct returns

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

Reviews of the top 5 airlines serving from Chicago 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 Chicago 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 4267 reviews
8.6Crew
7.0Food
7.5Entertainment
8.1Boarding
8.0Comfort
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

I like flying first class, and United has a nice one

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

United airlines has the best customer experience from booking to arrival. I always fly United airlines. The mileage program is excellent

I liked the snacks and the flight attendants were friendly.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

No enough space plus only allowing one laggage instead of two like other airlines.

Qatar airways ,boarding arrangements at Hamid international airport could been better

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

AA should improve their in air internet & entertainment options. Seems unreasonable to charge $20/hr and should have some form of free connections. The entertainment options are also pretty limited, movies are outdated and the series only show 3-5 episodes.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

Horribly rude check in at airport, worst in 25 years of flying. All over a simple issue they could have googled to resolve.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

It was good. I prefer JB over other airlines.I just wish we had headphones for the films, but other than that - good.

we were delayed because of some safety check that wasn't done or available

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

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

Other airlines flying from Chicago to Boston

Flights from the other most popular airlines that fly from Chicago to Boston 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 Chicago to Boston

Transportation modeAverage priceAverage duration
Flights$5632h 15m
Trains$26521h 58m