BOS - CHI

$64 Find Cheap Flights from Boston to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Chicago departing on 3/25. 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 Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Chicago.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Chicago.
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
$128
Overall average: $259
Southwest
sáb 5/9ter 5/12
BOS - ORD • 1 stop
Cheapest non-stop
$129
Typical prices: $170-$343
American Airlines
sáb 5/9seg 5/11
BOS - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Delta's free Wi-Fi benefits SkyMiles members on flights.
Download the FlyLogan app for updates at Boston Logan.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Southwest
Cheapest • from $128 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with American Airlines, Delta and others. Average duration is 3h 05m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
BOS
-
ORD
Cheapest • 4% average savings
BOS
-
ORD
Most popular
Insights
Insights
Insights
Insights
Avoid delays
United Airlines
Most punctual • 89% on-time
Morning flights
Best time • Fewest delays
Insights
Insights
Insights
Insights
Top layover airports
St. Louis (STL)
Cheapest • Avg $116 (round-trip)
Detroit (DTW)
Shortest trip • 4h 27m (one-way)
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 36% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 19% price drop
May
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 Chicago!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Boston to Chicago (BOS-CHI)

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

sáb, mai 9 - ter, mai 12
Southwest Logo
9:00 am - 3:30 pm
BOS
-
ORD
7h 30m
1 stop
Southwest Logo
2:40 pm - 10:30 pm
ORD
-
BOS
6h 50m
1 stop
$128Southwest
ter, abr 14 - qui, abr 16
Multiple Airlines Logo
7:35 pm - 9:39 pm
BOS
-
ORD
3h 04mnonstop
Multiple Airlines Logo
4:28 pm - 1:31 am
ORD
-
BOS
8h 03m
1 stop
$129Multiple Airlines
sáb, abr 11 - qua, abr 15
Multiple Airlines Logo
6:05 am - 8:08 am
BOS
-
ORD
3h 03mnonstop
Multiple Airlines Logo
6:08 pm - 1:31 am
ORD
-
BOS
6h 23m
1 stop
$130Multiple Airlines
qua, mar 18 - qua, abr 29
Delta Logo
8:20 pm - 10:16 pm
BOS
-
ORD
2h 56mnonstop
Delta Logo
8:50 am - 5:04 pm
ORD
-
BOS
7h 14m
1 stop
$131Delta
dom, abr 12 - qua, abr 15
American Airlines Logo
8:03 am - 10:12 am
BOS
-
ORD
3h 09mnonstop
American Airlines Logo
3:16 pm - 6:50 pm
ORD
-
BOS
2h 34mnonstop
$132American Airlines
ter, abr 14 - ter, abr 21
Southwest Logo
5:35 am - 4:35 pm
BOS
-
MDW
12h 00m
2 stops
Southwest Logo
7:45 am - 11:00 am
MDW
-
BOS
2h 15mnonstop
$132Southwest
sex, mai 1 - seg, mai 4
United Airlines Logo
8:10 pm - 10:05 pm
BOS
-
ORD
2h 55mnonstop
United Airlines Logo
6:00 am - 9:25 am
ORD
-
BOS
2h 25mnonstop
$133United Airlines
sáb, abr 11 - seg, abr 13
Southwest Logo
7:15 am - 9:05 am
BOS
-
MDW
2h 50mnonstop
Southwest Logo
7:00 pm - 10:20 pm
MDW
-
BOS
2h 20mnonstop
$133Southwest
sáb, abr 11 - qui, abr 16
JetBlue Logo
6:05 am - 8:08 am
BOS
-
ORD
3h 03mnonstop
JetBlue Logo
6:00 am - 9:13 am
ORD
-
BOS
2h 13mnonstop
$135JetBlue
ter, mar 17 - ter, mar 24
Delta Logo
4:25 pm - 6:31 pm
BOS
-
ORD
3h 06mnonstop
Delta Logo
7:00 am - 10:25 am
ORD
-
BOS
2h 25mnonstop
$136Delta
Booking Insights

KAYAK's insights & trends for Boston to Chicago flights

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

What is the cheapest Boston to Chicago flight route?

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

The cheapest return flight from Boston to Chicago costs $134 on the route between Boston (BOS) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 4% cheaper than other Boston-Chicago routes. It is also the most popular route.

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

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Boston to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Boston to Chicago is September, where tickets cost $187 (return) on average. On the other hand, the most expensive months are March and April, where the average cost of round-trip tickets is $259 and $253 respectively.

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

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

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $208 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Boston to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Boston to Chicago, you should book around 2 weeks before departure, which saves you about 36% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Expert advice

Expert advice for your flight from Boston to Chicago

 
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
Harriet Baskas

Harriet Baskas

Expert on American Airlines

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.

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.

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 Boston to Chicago flight

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

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

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

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

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

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

AI-powered; AI can make mistakes.

Good to know

Low seasonJanuary
Cheapest flight$64
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 8% increase in price.
Flight from Boston to Chicago Midway Airport

When to book flights from Boston to Chicago

Are your dates flexible? Find out the best times to travel from Boston to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Boston to Chicago

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

  • What is the cheapest flight from Boston to Chicago?

    In the last 3 days, the lowest price for a flight from Boston to Chicago was $64 for a one-way ticket and $128 for a round-trip.

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

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

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

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

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

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

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

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

  • Which airline alliances offer flights from Boston to Chicago?

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Boston to Chicago are Southwest and Delta. With an average price for the route of $210 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 $249 and an overall rating of 7.9.

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

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Boston to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Boston is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Boston to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Boston with another airline.

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

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Boston up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Boston to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $136 or less one-way and $252 or less round-trip.
  • Before your flight from Boston to Chicago, be sure to get a taste of some excellent seafood at Legal Sea Foods. This restaurant features an all-day menu, but its specialties are its seafood-inspired dishes like shrimp cocktail and a variety of clam chowders. Located in Terminal A of Boston Logan International Airport (BOS), this is a perfect spot to get that last New England-style seafood meal before your flight to the Midwest.
  • There may be nothing that says Boston better than Wahlburgers. Founded and operated by the iconic Wahlberg family, this burger joint is known for its oversized burgers and outrageous onion rings. They are located in Terminal C of Boston Logan International Airport, and they make a great spot to grab a burger and beer before your flight from Boston to Chicago.
  • Flights from Boston to Chicago can be stressful. Why not slow down for a few minutes before your flight with a chair massage or a manicure at Classique Hair Salon? Located in Terminal C near Gare C-25 at Boston Logan International Airport, Classique Hair Salon also offers waxing and facial care to give you your best look and most relaxed self before your flight.
  • Travelers on flights from Boston to Chicago looking for a convenient hotel need look no further than the Hilton Chicago O'Hare Airport. This on-site property is excellent for business travelers who do not want to bother with the hassle of downtown hotels. The hotel features an indoor pool, an excellent restaurant for steaks and seafood, and a lively sports bar.
  • When looking for a hotel that is conveniently located close to Chicago Midway airport, the Chicago Marriott Midway is an excellent choice. They offer a 24-hour airport shuttle, tasteful decor, an indoor pool, tons of meeting space, a fitness center, wireless internet access and even a Starbucks coffee shop.
  • Consider booking flights with at least a single stop en route if you want to fly more affordably from Boston to Chicago. These flights have different stopover options depending on your airline and arrival airport. Spirit Airlines, American Airlines and Delta have common stops in Philadelphia, Detroit, Myrtle Beach, Washington and LaGuardia Airport (LGA).
  • Flights from Boston to Chicago arrive at either O’Hare International Airport (ORD) or Chicago Midway International Airport (MDW). Of the two, ORD stands out as the best airport to fly into. It serves most of the direct flights from Boston and also has good connections to various modes of transportation.
  • Passengers flying to Chicago O’Hare International Airport (ORD) are welcome to use the charging stations at the airport. You can find the charging stations by Gates B19, B15, B14, B11 and B4 in Terminal 1. In Terminal 2, you will find the charging ports by Gates C28, C21, C15, C7, E7 and F2B.
  • If you need cash before flying out from Boston Logan International Airport (BOS), visit the ATMs at the airport. Citizens Bank, Chase and Bank of America operate ATMs in the Departures area in Terminal A. ATMs are also available in various locations in Terminals B, C and E.
  • Travelers with kids will be glad to learn that Boston Logan International Airport (BOS) has Kidports where their kids can let off steam before catching their flight. They are near Gate 18 in Terminal A, and by Gate 25 in Terminal C. In Terminal B, they are between Gates B30 and B36.

Prefer to fly direct from Boston to Chicago?

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

Direct departures

Boston Logan Intl to Chicago

Monday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Tuesday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Wednesday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Thursday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Friday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Saturday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Sunday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

See more direct flights

Direct returns

Chicago to Boston Logan Intl

Monday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Tuesday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Wednesday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Thursday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Friday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Saturday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

Sunday

American Airlines, Delta, JetBlue, +2 more

American Airlines, Delta, +3 more

See more direct flights

Reviews of the top 5 airlines serving from Boston to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Boston to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Boston to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4306 reviews
7.5Entertainment
8.0Comfort
8.1Boarding
7.0Food
8.6Crew
Airline reviews

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

2.0 MediocreAnonymous, Feb 2026
BWI - PBI
Read more Southwest reviews

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

I have not flown Southwest in awhile and had a very pleasant experience. From ticketing to boarding to the flight. The flight left on time and landed ahead of schedule. It won't be so long next time!!

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The charges were ridiculous for an hour flight and the turbulence was very scary.

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

There’s not much to say about a one hour flight. This is a connection from LA to RNO that I missed the previous night due to a mechanical check delay on my originating flight from JFK to LAX. The short flight itself was fine. Instructions from the pilot and crew were per usual. The coffee was barely lukewarm, which possibly was purposeful so we would down it quickly. Bags were already on carousel upon reaching baggage claim, which was excellent.

Flight was warm for first few hours and quite rough

Seat was extremely hard which made even a short 1 hour 20 minute flight fairly uncomfortable.

Everything was good except wifi and a leaking drink chiller. The floor was all wet and my bag was soaked. Did not notice until debarking. Have not heard back from Delta. Even though this was leg one of an international flight in first class, they denied access to their Sky Club - very disappointing!

The staff was fine. The plane was extremely tight, and I paid for the wifi and it did not work at all. I was actually going to ask for a refund.

two hour delay and the Delta representative on the PA system was unable to understand

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Very old flight - time to retire it for newer airplanes

2+ hours delayed Outlet in row 12 did not work Tv monitors did not work Lights kept off the entire flight for at 5pm-7pm flight

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

We were made to wait in the airport for six hours for a flight that was ultimately canceled.

Both flights were significantly delayed. The flight experience itself was great.

My flight got delayed and eventually canceled, then rescheduled. I and several others had a connection from Boston to Paris and asked several times if we would make it. They assured us we would and then rebooked us mid flight without our consent and closed doors early even though they said they communicated we were a bit delayed. We got stranded in Boston and I opted with being rebooked for a different connection to France since they refused to pay for a Hotel. I've now been in Europe for 5 days and still haven't recieved my bags. There was absolutely no urgency for the fact that I'm in a foreign country with absolutely no change of clothes or any of my medication. Such an overwhelming and frustrating experience.

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

The crew for the flight was A+ top notch. They were friendly and professional and made the flight a very relaxing and enjoable.

Rude crew member. She seemed annoyed at me without me saying a single word. Also loudly admonished me for having my bag next to my seat instead of tucked away before landing. Just telling me to put it away and guiding me without giving me a lecture would have been enough.

No included food for a 5 hour flight and the entertainment was only accessible if you had wired headphones (not provided). Otherwise though, great and smooth flying and customer service.

Crew were fantastic and so catering and wonderful! Full score for the entire crew!

Because of weather and mechanical issues our flight was 4 hours late. The only compensation offered to us was a meal voucher to be used only at Boston Airport and only on the day issued. But by the time it was offered to us all the restaurants were closed, so there was no way to use that offer.

Friendly crew, efficient boarding and flight arrived early. Couldn’t ask for a better experience

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

Worst experience ever. Flight could not land in Charlotte for what we were told was a ground stop. Had to be diverted to Raleigh to refuel. Strangely during ground stop, our connecting flight had no issue taking off on time causing us to miss our flight. We were told there were no other flights that day to our final destination and that two days out was the next one. The only flights to get us there were from Chicago the next morning. Completely opposite direction but it was a direct flight. So we get flown to Chicago and have to find a hotel in our own dime. The flight in the morning was also delayed. Thankfully only a short time. The non too of all this, our luggage did not arrive by the time we were there. Communication was terrible, through the entire trip. Complete incompetence. Will never fly American again.

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

The flight was fine, once we got underway. It was more than hour delayed

Waited for oxygen tanks for 30 minutes after boarding was complete.

The flight was significantly delayed for 6.5 hours because of snow. There was no communication once the plane returned to the gate regarding when the flight would resume. Other flights were departing while our flight was being unloaded for reasons unknown. Our flight also seemed out of the queue regarding further deicing, refueling, and waiting to Taxi to the runway.

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

Other airlines flying from Boston to Chicago

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

Compare transportation modes for Boston to Chicago

Transportation modeAverage priceAverage duration
Flights$7232h 50m
Trains$51922h 20m
Buses$21829h 45m