CHI - BOS

$63 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 12/17. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$124
Overall average: $299
Frontier
Fri 12/5Wed 12/10
MDW - BOS • 1 stop
Cheapest non-stop
$127
Typical prices: $149-$381
Delta
Thu 11/6Sat 11/8
ORD - BOS • Non-stop
Our travelers' advice
AI-generated summary based on content written by travel experts
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
Watch video
Watch video
Watch video
Watch video
Top airlines
Frontier
Cheapest • from $124 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
MDW-BOS
Cheapest
ORD-BOS
Most popular
Insights
Insights
Insights
Insights
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 42% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 12% price drop
October
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Boston!
Flight Deals
Booking Insights
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

Fri, Dec 5 - Wed, Dec 10
Frontier Logo
8:42 pm - 12:44 amMDW-BOS
27h 02m1 stop
Frontier Logo
6:00 am - 9:32 pmBOS-MDW
16h 32m1 stop
$124Frontier
Find Deal
Wed, Dec 3 - Mon, Dec 8
Frontier Logo
8:00 am - 12:01 amMDW-BOS
15h 01m1 stop
Frontier Logo
6:00 am - 11:05 pmBOS-MDW
18h 05m1 stop
$126Frontier
Find Deal
Thu, Nov 6 - Sat, Nov 8
Delta Logo
7:05 am - 10:29 amORD-BOS
2h 24mnonstop
Delta Logo
4:10 pm - 6:07 pmBOS-ORD
2h 57mnonstop
$127Delta
Find Deal
Fri, Oct 24 - Sat, Nov 1
Southwest Logo
9:20 pm - 12:40 amMDW-BOS
2h 20mnonstop
Southwest Logo
11:00 am - 3:05 pmBOS-MDW
5h 05m1 stop
$127Southwest
Find Deal
Thu, Dec 4 - Tue, Dec 9
Frontier Logo
7:47 pm - 12:44 amMDW-BOS
27h 57m1 stop
Frontier Logo
6:00 am - 9:32 pmBOS-MDW
16h 32m1 stop
$129Frontier
Find Deal
Tue, Oct 21 - Thu, Oct 23
Southwest Logo
2:30 pm - 10:40 pmMDW-BOS
7h 10m2 stops
Southwest Logo
5:15 am - 6:55 amBOS-MDW
2h 40mnonstop
$132Southwest
Find Deal
Wed, Oct 22 - Sat, Oct 25
United Airlines Logo
6:14 pm - 9:45 pmORD-BOS
2h 31mnonstop
United Airlines Logo
9:53 am - 11:43 amBOS-ORD
2h 50mnonstop
$133United Airlines
Find Deal
Thu, Oct 23 - Fri, Nov 7
United Airlines Logo
6:30 am - 9:56 amORD-BOS
2h 26mnonstop
United Airlines Logo
6:00 am - 8:00 amBOS-ORD
3h 00mnonstop
$134United Airlines
Find Deal
Wed, Oct 22 - Thu, Oct 23
Delta Logo
7:05 am - 10:29 amORD-BOS
2h 24mnonstop
Delta Logo
7:20 am - 9:22 amBOS-ORD
3h 02mnonstop
$137Delta
Find Deal
Sat, Nov 22 - Sun, Nov 23
American Airlines Logo
8:08 pm - 11:41 pmORD-BOS
2h 33mnonstop
American Airlines Logo
6:45 am - 8:52 amBOS-ORD
3h 07mnonstop
$179American Airlines
Find Deal
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 $117 on the route between Chicago Midway Airport (MDW) and Boston (BOS). This 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 September, where tickets cost $207 (return) on average. On the other hand, the most expensive months are April and December, where the average cost of round-trip tickets is $272 and $252 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 $214 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 3 weeks before departure, which saves you about 42% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Expert advice

Expert advice for your flight from Chicago to Boston

 
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

Basic Economy offers carry-on only travel with late boarding and no seat assignment until check-in.


Main Cabin Extra provides early boarding and complimentary drinks, ideal for longer flights.

United Airlines

Economy Plus offers 6 inches more legroom than standard economy seats, enhancing comfort.


Priority Boarding places you in Zone 2, ensuring overhead bin space for your carry-on.

Delta

Comfort Plus offers 3 inches extra legroom and is located in the front section of economy.


SkyMiles members enjoy free Wi-Fi on domestic flights, enhancing connectivity.

Read more about Deltaby Stefanie Waldek
Southwest

Southwest's new seating offers 34 inches of legroom in extra legroom seats, with early boarding benefits.


Southwest's free carry-on policy remains, despite changes to checked baggage allowances.

Read more about Southwestby Blane Bachelor
JetBlue

Even More Space seats provide 7 inches extra legroom and early boarding.


Free gate-to-gate Wi-Fi and live TV enhance in-flight entertainment.

Read more about JetBlueby Harriet Baskas
Spirit Airlines

Big Front Seat offers 11 inches more legroom than standard seats, enhancing comfort.


Wi-Fi packages include gate-to-gate connectivity, ensuring online access throughout the flight.

Airports
ORD

ORD offers a 24-hour Dunkin' in Terminal 3, perfect for early morning flights to BOS.

Read more about ORDby Stefanie Waldek
MDW

MDW's compact layout makes it easy to navigate, ideal for quick departures to BOS.

Read more about MDWby Stefanie Waldek
BOS

The Silver Line bus from BOS is free to South Station, offering a budget-friendly city transfer.

Read more about BOSby Blane Bachelor
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines and JetBlue

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
 AI-powered savings tips

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.

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 seasonFebruary
Cheapest flight$63
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Chicago Midway 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 $63 for a one-way ticket and $124 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, Finnair, British Airways, 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, Star Alliance, and oneworld 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 $238 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 $234 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 $109 or less one-way and $164 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 4237 reviews
8.6Crew
7.0Food
7.5Entertainment
8.1Boarding
8.0Comfort
Airline reviews

mandatory demand customer to check their carry on because not enough people check bags.

6.0 GoodHung, Oct 2025PHX - ABQ
Read more Southwest reviews

mandatory demand customer to check their carry on because not enough people check bags.

Connecting flight is on time and boarding was a breeze!

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

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.

The flight was great. The gate location was way to far away!!!

This was our second flight using the Delta One class of service. Overall, it’s a good product but for me the POD configuration is a bit constrictive. I am an average size male at 5’ 10” height weighing 190 lbs so it’s not a size thing for me. I’d rather have extra wide seats without the POD walls to be honest.

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

Gate agent rushed to fill hot jetway with crowd so it took over 12 minutes to go from gate to plane. Just like a discount airline Pooly prepared cabin and third time that claim of rough air prevented any cabin service. Friends on a Southwest flight at similar time had service.

Cramped seating for me. Luckily it wasn’t a long flight

Lounge in Lagos is terrible, food on board from Lagos to Atlanta was horrible. Only bright spot the cabin crew were awesome.

The staff and the boarding procedure were all amazing . The one flight was not equipped with WIFI which now adays seems odd. All in all the experience was good

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

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.

Ring in first class for an overnight flight, there was no blankets nor pillows for first class customers.

Flight was delayed. Staff at the gate effectively and proactively communicated about the delay.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

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.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

They have the most inexperienced / rude flight staff I’ve encountered

very difficult boarding process - aggressive passengers not the friendliest crew

WiFi was not eorkig (again) And the plane was from 1990 with the screens which were.not touch and most didn’t even work and if lucky could tune in tv

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.

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.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.