CHI - BOS

$94 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 7/7. 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, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Boston, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$176
Typical prices: $192-$315
JetBlue
Thu 7/16Wed 7/22
ORD - BOS • 1 stop
Cheapest non-stop
$178
Typical prices: $195-$320
United Airlines
Wed 7/15Sun 7/19
ORD - BOS • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
American Basic Economy is carry-on only; JetBlue adds Wi-Fi and live TV.
For more comfort, JetBlue Even More Space beats Delta and United on legroom.
Expert advice
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Cheapest • from $176 (round-trip)
Best reviews • 7.9 score
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Nonstop flights
You can fly direct with American Airlines, Delta and others. Average duration is 2h 30m
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Top routes
Cheapest • 10% average savings
Most popular
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Avoid delays
Most punctual • 80% on-time
Best time • Fewest delays
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When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 26% compared to booking last minute.
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Cheapest • 22% price drop
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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

Thu, Jul 16 - Wed, Jul 22
JetBlue Logo
9:40 am - 5:07 pm
ORD
-
BOS
6h 27m
1 stop
JetBlue Logo
5:01 am - 8:50 am
BOS
-
ORD
4h 49m
1 stop
$176JetBlue
Thu, Aug 20 - Tue, Aug 25
JetBlue Logo
9:35 am - 5:07 pm
ORD
-
BOS
6h 32m
1 stop
JetBlue Logo
2:45 pm - 9:58 pm
BOS
-
ORD
8h 13m
1 stop
$177JetBlue
Wed, Jul 15 - Sun, Jul 19
United Airlines Logo
6:05 am - 9:29 am
ORD
-
BOS
2h 24mnonstop
United Airlines Logo
6:00 am - 7:58 am
BOS
-
ORD
2h 58mnonstop
$178United Airlines
Tue, Jul 14 - Fri, Jul 17
Southwest Logo
9:00 am - 12:15 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:25 am - 7:00 am
BOS
-
MDW
2h 35mnonstop
$178Southwest
Fri, Jul 10 - Wed, Jul 15
Delta Logo
7:25 pm - 11:00 pm
ORD
-
BOS
2h 35mnonstop
Delta Logo
8:45 pm - 10:39 pm
BOS
-
ORD
2h 54mnonstop
$179Delta
Mon, Jul 20 - Wed, Jul 22
Southwest Logo
7:35 pm - 10:55 pm
MDW
-
BOS
2h 20mnonstop
Southwest Logo
5:35 am - 7:10 am
BOS
-
MDW
2h 35mnonstop
$179Southwest
Tue, Aug 25 - Wed, Aug 26
JetBlue Logo
6:00 am - 2:43 pm
ORD
-
BOS
7h 43m
1 stop
JetBlue Logo
8:15 am - 10:11 am
BOS
-
ORD
2h 56mnonstop
$180JetBlue
Tue, Aug 25 - Tue, Aug 25
Southwest Logo
6:40 am - 9:55 am
MDW
-
BOS
2h 15mnonstop
Southwest Logo
4:55 pm - 8:45 pm
BOS
-
MDW
4h 50m
1 stop
$180Southwest
Wed, Aug 5 - Sat, Aug 8
Delta Logo
7:30 pm - 11:00 pm
ORD
-
BOS
2h 30mnonstop
Delta Logo
7:30 am - 9:26 am
BOS
-
ORD
2h 56mnonstop
$183Delta
Mon, Jul 27 - Tue, Jul 28
United Airlines Logo
6:05 am - 9:29 am
ORD
-
BOS
2h 24mnonstop
United Airlines Logo
7:27 pm - 11:31 pm
BOS
-
ORD
5h 04m
1 stop
$184United Airlines
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.

How much is a round-trip flight from Chicago 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 to Boston departing in July.

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 $157 on the route between Chicago O'Hare Intl Airport (ORD) and Boston (BOS). Over the past month, this route was, on average, 10% 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 Friday, 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 November, where tickets cost $183 (return) on average. On the other hand, the most expensive months are June and October, where the average cost of round-trip tickets is $316 and $296 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 $252 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 26% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 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.

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$94
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 3% 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 5 days, the lowest price for a flight from Chicago to Boston was $94 for a one-way ticket and $176 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, Iberia, Finnair, and British Airways.

  • 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 $233 and an overall rating of 7.9, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $241 and an overall rating of 7.8.

  • 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 $143 or less one-way and $224 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.
7.9
SouthwestOverall score based on 4246 reviews
7.5Entertainment
8.1Boarding
8.0Comfort
7.0Food
8.6Crew
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

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

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

My flight was delayed by 4 hours in 30 minute increments. The gate agents were amazing but the communication was not. We were told that there was a maintenance issue but they didn't know what it was. That didn't inspire confidence. Then they said they found it and it was fixed and the pilot just needed to sign off. Then the pilot needed to talk to the other pilot from the arriving flight and we'd be fine. Then we were waiting for the pilot to call back. Then the maintenance issue wasn't fixed. Then they decided we were getting a new plane (why didn't they decide this earlier??). Fine. But then they announced we were changing gates AND terminals. And we were boarding in 20 minutes. So we all had to run to the new terminal gate. We could have taken off at that time, but we then had to wait for all the people who rebooked on a different flight to book this flight again. That took 30+ minutes because there was only one gate agent. When everyone ditched this flight, I saw it as an opportunity to upgrade to comfort. Delta, the greedy jerks they are, charged me $121. After their delay, their fault, their issues, couldn't even discount an upgrade. They only handed out $12 meal vouchers for the delay. I can't even get a snack from starbucks for that.

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.

My flight yesterday evening was delayed 3.5 hours with no water or food service. Poor experience

The tray table was broken and the food was terrible.

Flight delayed. Air broken. Cabin was hot enough to pass out. Delta shuttle’s becoming worse and worse.

The first class flight attendant was awful to everyone. Very rude; no customer service. She should not be working in first class.

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

It was Delta, but the flight attendants were stressful and disrespectful. I am a diamond member a travel weekly. I have not had a negative thing to share in quite some time. But this was noticeable.

Advertised fruit trays with cheese, but only snacks handed out!

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

My service dog and I were asked to deplane just before they closed the door - clearly very last minute they couldn’t find the documentation that I have filled out many many times before that is for flying service animals. I purposely purchase 3seats (a whole row) since he is large and not all passengers want to sit next to a dog on a cross country flight. The plane departed with my husband on it!!! They made me fill out a hard copy of the same form and had to reschedule me on a later flight where they could find 3 seats together!! I’ve done this so many times before - clearly the error was on their part in a technology glitch - but really people - do better!! Very traumatic - and my husband had to wait for us when he landed ….so bad. Poor pup was confused and tired.

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

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

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

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Plenty of room for me and the cat in Premium Economy. Seat was comfortable. Boarding was a breeze. The lady at the special check-in desk was great, super helpful and professional.

It’s been awhile since I have traveled on United. I, along with my family who were on the flight noted how smoothly everything went . Boarding, flight crew and service was excellent.

I was forced to check my carry-on backpack despite there being space - but it came out on the baggage carousel so fast it didn't even delay my pickup. Otherwise a good flight. Boarding began early (which was disadvantageous for me) but fine.

Excellent staff helping my 96 year old senior promptly with her oxygen needs

Good even though flight was delayed, the crew was prompt and efficient.

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 —

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.

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.

We had a male flight attendant who was super attentive and wonderful! Very professional. I have both gluten and dairy intolerance, and was only able to get a gluten free part, and not the dairy free part of the meal. Easy to order ahead of time and I appreciate being able to do that.

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

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.

They only offered water for Group 6. Awful announcements from the Crew. Couldn't understand a single word. Barely came by for the trash afterwards. Man, I love water for a premium flight. Wow. Water in a cup.

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

The plane was freezing cold. Normally I’m fine on planes but I needed to toss a sweatshirt on this time.

A nightmare. Scheduled flight delayed 2 hours then cancelled because pilot timed out . Unable to find another pilot. Really?! Weather certainly a factor, but JetBlue seemed totally unprepared for the chaos that ensued when flight routes were cancelled. More cancelled flights, finally many of us who had been bumped from other flights were allowed to board a Boston bound plane around 3:00am, delay after delay, sat on tarmac for another half hour while pilot dealt with weight distribution issues (?), arrived in Boston 4:30. Crew were wonderful- same attendants all day and night and they were exhausted. Fortunately for me and my son that Boston was our final destination, not so lucky for many who missed connecting flights.

The flight was delayed 14 hours and communication was very poor. No one seemed to know what was happening and the gate agent was trying to help people for several flights. She was by herself trying to help 100s of people.

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

This was the first flight I've taken since pre-pandemic. I was pleased with how orderly the boarding and disembarking went. The seats were comfortable. I loved that there was no "first class'. The attendants and passengers I met were all very friendly and welcoming.

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

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$5662h 15m
Trains$30021h 54m