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BOS - ORD

$23 Find cheap flights from Boston to Chicago O'Hare Airport

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 O'Hare Intl departing on 8/27. 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
0 bags
Sun 8/25
Sun 9/1

Search hundreds of travel sites at once for deals on flights to Chicago O'Hare Airport

 
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.
In the last 7 days travelers have searched 50,552,696 times on KAYAK, and here is why:

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Cheap flight deals from Boston to O'Hare Intl (BOS-ORD)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Boston to O'Hare Intl 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 and deals for you by selecting your travel dates.
Choose your dates
11:35 am - 1:27 pmBOS-ORD
2h 52mnonstop
2:17 pm - 5:42 pmORD-BOS
2h 25mnonstop
$47Spirit Airlines
Find Deal
Sat, Sep 7 - Sat, Sep 14
8:00 am - 9:53 amBOS-ORD
2h 53mnonstop
8:59 pm - 12:27 amORD-BOS
2h 28mnonstop
$48Spirit Airlines
Find Deal
Wed, Aug 28 - Tue, Sep 3
11:35 am - 1:27 pmBOS-ORD
2h 52mnonstop
4:17 pm - 12:29 amORD-BOS
7h 12m1 stop
Sat, Sep 7 - Thu, Sep 12
4:59 pm - 12:59 amBOS-ORD
9h 00m1 stop
4:17 pm - 12:29 amORD-BOS
7h 12m1 stop
Sat, Sep 7 - Thu, Sep 12
6:00 am - 11:00 amBOS-ORD
6h 00m1 stop
2:06 pm - 12:29 amORD-BOS
9h 23m1 stop
$116Frontier
Find Deal
Mon, Sep 16 - Thu, Sep 19
6:00 am - 11:59 amBOS-ORD
6h 59m1 stop
10:34 pm - 11:14 amORD-BOS
11h 40m1 stop
$142Frontier
Find Deal
Tue, Aug 13 - Thu, Aug 15
5:10 am - 8:40 amBOS-ORD
4h 30m1 stop
8:20 pm - 11:52 pmORD-BOS
2h 32mnonstop
$147JetBlue
Find Deal
Thu, Sep 5 - Mon, Sep 9
5:50 pm - 7:47 pmBOS-ORD
2h 57mnonstop
9:05 am - 12:35 pmORD-BOS
2h 30mnonstop
$159JetBlue
Find Deal
Tue, Aug 13 - Tue, Aug 20
7:30 am - 9:30 amBOS-ORD
3h 00mnonstop
1:59 pm - 5:41 pmORD-BOS
2h 42mnonstop
$184Delta
Find Deal
Thu, Aug 8 - Mon, Aug 19
11:05 am - 12:59 pmBOS-ORD
2h 54mnonstop
6:39 am - 10:05 amORD-BOS
2h 26mnonstop
$187Delta
Find Deal
Fri, Aug 16 - Sun, Aug 18

Flights from Boston to O'Hare Intl - Travel Insights & Trends

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

What’s the cheapest day of the week to fly from Boston to Chicago O'Hare Airport?

The average price of all flights from Boston to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from Boston to Chicago O'Hare Airport, look for departures on Wednesdays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Chicago O'Hare Airport, Wednesday is the cheapest day to fly and Sunday is the most expensive.

What is the cheapest month to fly from Boston to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Boston to Chicago O'Hare Intl Airport, 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 O'Hare Intl Airport is January, where tickets cost $196 on average. On the other hand, the most expensive months are October and November, where the average cost of tickets is $303 and $303 respectively.

How far in advance should I book a flight from Boston to Chicago O'Hare Intl Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Boston to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Boston to Chicago O'Hare Intl Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 151 days before departure.

Which airlines provide the cheapest flights from Boston to Chicago O'Hare Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the cheapest one-way ticket from Boston to Chicago O'Hare Airport found on KAYAK was with Spirit Airlines for $23. Spirit Airlines proposed a round-trip connection from $47 and Frontier from $116.

Which airlines fly most frequently between Boston and Chicago O'Hare Airport?

Boston and Chicago O'Hare Airport are connected by different airlines. The airlines that fly that route the most regularly are American Airlines (55 flights per week), United Airlines (52 flights per week), and Delta (26 flights per week).

Which airlines fly non-stop between Boston and Chicago O'Hare Intl Airport?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Boston to Chicago O'Hare Intl Airport.
There are 5 airlines that fly nonstop from Boston to Chicago O'Hare Intl Airport. They are: American Airlines, Delta, JetBlue, Spirit Airlines and United Airlines. The cheapest price of all airlines flying this route was found with Spirit Airlines at $39 for a one-way flight. On average, the best prices for this route can be found at Spirit Airlines.

How many flights are there between Boston and Chicago O'Hare Intl Airport per day?

Each day, there are between 19 and 23 nonstop flights that take off from Boston and land in Chicago O'Hare Intl Airport, with an average flight time of 2h 53m. The most common departure time is 5:00 pm and most flights take off in the morning. Each week, there are 154 flights. The most frequent day of departure is Monday, when 15% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between Boston and Chicago O'Hare Intl Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Boston to Chicago O'Hare Airport take?

The duration of a nonstop flight to Chicago O'Hare Airport from Boston is typically 2h 43m. The journey crosses a distance of 864 miles.

What’s the earliest departure time from Boston to Chicago O'Hare Airport?

Early birds can take the earliest flight from Boston at 5:15 am and will be landing in Chicago O'Hare Intl Airport at 7:10 am.

What’s the latest departure time from Boston to Chicago O'Hare Airport?

If you prefer to fly at night, the latest flight from Boston to Chicago O'Hare Intl Airport jets off at 10:06 pm and lands at 11:59 pm.

Good to know

Low season

January

High season

August

Cheapest flight

$23
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Boston to Chicago O'Hare Airport

When to book flights from Boston to O'Hare Intl

Are your dates flexible? Find out the best times to travel from Boston to O'Hare Intl 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 Boston to Chicago O'Hare Airport flights

  • What can I do while waiting on my plane to leave the Chicago O'Hare Airport (ORD)?

    There is a public art exhibit at the Chicago O'Hare Airport (ORD). Throughout the airport, there are sculptures, paintings, murals, and photography that you can appreciate. There is also a yoga room where you can relax, a business center where you can catch up on e-mails, and many different airline lounges where members can enjoy a variety of benefits.

  • Where can I eat at the Boston Logan International Airport (BOS)?

    There are several places to eat while you're waiting on your plane to leave Boston. You can dine at Friendly's Restaurant, Sbarro, Potbelly Sandwich Shop, or WPizza by Wolfgang Puck. If you want something light to eat or a little java before you board, there is a Dunkin's Donut and several Starbucks around the airport.

  • How can I get to my hotel from the Chicago O'Hare International Airport (ORD)?

    Public transit is easily accessible from the airport. This includes a commuter train that goes from the airport into many areas of the city and its outlining communities. Known as the Metra Train, you'll catch it by taking the airport shuttle bus to the Multi-Modal Facility. The train station is a short walk from this building.

  • Is it easy to get around the Boston Logan International Airport (BOS)?

    The Boston Logan International Airport (BOS) has four terminals and 94 gates. There is a complimentary shuttle that takes passengers from one terminal to another. You can also take this shuttle to other parts of the airport including the rental car center and the airport train station.

  • What is the cheapest flight from Boston to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Boston to Chicago O'Hare Intl Airport was $23 for a one-way ticket and $47 for a round-trip.

  • Do I need a passport to fly between Boston and Chicago O'Hare Airport?

    A passport is not required to fly from Boston to Chicago O'Hare Airport.

  • Which airlines offer Wi-Fi service onboard planes from Boston to Chicago O'Hare Airport?

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

  • Which aircraft models fly most regularly from Boston to Chicago O'Hare Airport?

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

  • Which airline alliances offer flights from Boston to Chicago O'Hare Airport?

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

  • On which days can I fly direct from Boston to Chicago O'Hare Airport?

    There are nonstop flights from Boston to Chicago O'Hare Airport on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from Boston to Chicago are Delta and Alaska Airlines. With an average price for the route of $263 and an overall rating of 8.0, Delta is the most popular choice. Alaska Airlines is also a great choice for the route, with an average price of $94 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from Boston to Chicago O'Hare Airport?

    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 O'Hare Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport 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 O'Hare Airport?

    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 O'Hare Airport with an airline and back to Boston with another airline. Booking your flights between Boston and ORD can sometimes prove cheaper using this method.

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

    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 O'Hare Airport from Boston up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

KAYAK’s top tips for finding a cheap flight from Boston to Chicago O'Hare Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $108 or less one-way and $184 or less round-trip.
  • You'll easily find a nonstop flight going from Boston Logan International (BOS) to Chicago O-Hare International Airport (ORD). If you have a layover, you'll probably change planes in either Philadelphia, Detroit, or Washington, D.C. On average, these are short layovers of less than 2h.
  • If you drive yourself to Boston Logan International (BOS) for your trip, you'll have the option of parking in a garage or an uncovered parking lot. You can save money by parking in the economy garage which is just a few minutes from the airport. A complimentary shuttle will take you to the airport from the garage.
  • Withdraw money for your trip to Chicago at one of the ATM machines at the Boston Logan International Airport (BOS). There is an ATM machine in Terminal A, Terminal B, Terminal C, and Terminal E.
  • Amenities and services at the Boston Logan International Airport (BOS) include baggage trolleys, a shoe shine, hydration stations, a beauty salon where you can get a pedicure or manicure, a spa where you can relax with a massage, and several airport lounges with benefits like complimentary beverages, television, and comfortable seating.
  • Passengers who are delayed or have a late flight to Chicago will benefit from its on-site hotel. There is a Hilton Chicago O'Hare Hotel across from Terminals 1, 2, and 3. Along with sleeping rooms, the hotel has a variety of amenities such as a fitness center and sports bar.
See more tips

Prefer to fly non-stop from Boston to Chicago O'Hare Airport?

Find which airlines fly direct from Boston Logan Intl Airport to Chicago O'Hare Intl Airport, which days they fly and book direct flights.

Nonstop departures

Boston Logan Intl to Chicago O'Hare Intl

Monday

ANA, Air New Zealand, Alaska Airlines, +20 more

ANA, Air New Zealand, +21 more

Tuesday

ANA, Air New Zealand, Alaska Airlines, +19 more

ANA, Air New Zealand, +20 more

Wednesday

ANA, Air New Zealand, Alaska Airlines, +20 more

ANA, Air New Zealand, +21 more

Thursday

ANA, Air New Zealand, Alaska Airlines, +21 more

ANA, Air New Zealand, +22 more

Friday

ANA, Air New Zealand, Alaska Airlines, +20 more

ANA, Air New Zealand, +21 more

Saturday

ANA, Air New Zealand, Alaska Airlines, +20 more

ANA, Air New Zealand, +21 more

Sunday

ANA, Air New Zealand, Alaska Airlines, +21 more

ANA, Air New Zealand, +22 more

See more direct flights

Nonstop returns

Chicago O'Hare Intl to Boston Logan Intl

Monday

ANA, Air New Zealand, Alaska Airlines, +20 more

ANA, Air New Zealand, +21 more

Tuesday

ANA, Air New Zealand, Alaska Airlines, +19 more

ANA, Air New Zealand, +20 more

Wednesday

ANA, Air New Zealand, Alaska Airlines, +21 more

ANA, Air New Zealand, +22 more

Thursday

ANA, Air New Zealand, Alaska Airlines, +20 more

ANA, Air New Zealand, +21 more

Friday

ANA, Air New Zealand, Alaska Airlines, +21 more

ANA, Air New Zealand, +22 more

Saturday

ANA, Air New Zealand, Alaska Airlines, +19 more

ANA, Air New Zealand, +20 more

Sunday

ANA, Air New Zealand, Alaska Airlines, +22 more

ANA, Air New Zealand, +23 more

See more direct flights
See more direct flights

Top 5 airlines serving from Boston to O'Hare Intl

 
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 O'Hare Intl? 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
DeltaOverall score based on 9630 reviews
8.6Crew
7.4Food
8.2Boarding
7.9Comfort
8.0Entertainment
Airline reviews

The boarding was great. With all the delays I was grateful to get on the plane and headed for home. There was no in flight entertainment. Seats were very uncomfortable! Unfortunately we were seated next to an exit row so there was no recline in our seat. Other than that it was a smooth ride.

6.0 GoodKathy, Jul 2024ANC - SLC
Read more about Delta reviews

The boarding was great. With all the delays I was grateful to get on the plane and headed for home. There was no in flight entertainment. Seats were very uncomfortable! Unfortunately we were seated next to an exit row so there was no recline in our seat. Other than that it was a smooth ride.

My flight was cancelled twice and the third time I tried to rebook it online I cancelled the flight because it looked like I would get a refund to my credit card. Instead I now have a credit. I was also on hold for three hours waiting for a representative and then disconnected. I will never fly delta again.

Flight for canceled. Horrible experience.. had to rent a car to drive myself up here.

Flights were terribly delayed. I was at At,anta Airport for over 4 hours waiting for my connection.

My flight consistently said it was on time and the plane didn’t arrive until after 30 minutes after take off and nothing was announced to passengers

The flight was canceled two hours before departure, it took over five hours to rebook us on another flight.

First, the flight was schedule to leave at 12:08. Delayed to 12:38. It is 12:58 and I am sitting at the gate. The staff are not communicating with us (just tell me it’s gonna be five hours if that’s the case, quit hufflepuffing around like you’re trying to board us when the plane isn’t even here and you don’t know where your crew are. I’m still waiting for any communication about the further delay. This is a rebooked flight from a cancelled flight yesterday, when the airline failed to fulfill its fiduciary responsibility to hotel and cover transport for overnight cancelations. Asking about the food on the flight? What food?!? Delta doesn’t serve meals unless you pay for them and you really want me to give delta a high rating for passing out processed snacks (fun size!)? Can we be for real. Delta is cementing itself in history as one of the cheap, stingy, outdated, glory days are over airlines, and it shows. I took this flight knowing delta was going to provide below level service but this is beyond burgers!! I can’t believe a multi billion or dollar company looked straight in my eyes yesterday and I told me this wasn’t their fault and there for the extra cost in hotel and hundreds of dollars in Ubers are MY RESPONSIBILITY. The only thing I am at fault for is believing delta is reputable company worthy of my dollars. I’m not even sure I want to be compensated unless it is cash because I would rather die never traveling again than to put money in their pockets.

The flight was great. The crew were a little terse about the size of my bag. It fit fine.

I know it was not in Deltas fault. But numerous delays and cancelations. I requested a hotel voucher and was told they weren't available. The lady on my hotel shuttle did receive one from American. Why the difference?

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

I volunteered to let them put my carry on suitcase in the baggage storage area. But when we landed I was told it was being unloaded IN A DIFFERENT TERMINAL! I had to walk (painful for me) a long way to retrieve my bag and my ride had to move from the waiting area they were in to a totally different one. Not happy.

Overall fine but both ways for this trip was delayed.

I had back trouble prior to my flight and everyone was great about helping me.

My tv was broken on the flight which is disappointing when you pay for a seat and expect a service

Always delays from Boston to Salt lake but this time was very long. Don’t understand while they board the passengers and then make them sit in the plane

The boarding and flight were ok, but there were several painful issues. The flight was 3:20 in the air and almost four hours door to door, but they only had snack packs on the plane. They really need to have food on longer flights or make it clear to everyone that they won’t have food. They also advertise free WiFi, but it did not work for 90% of this flight. Again, almost four hours door to door. If I had known I was flying spirit for JetBlue prices then I would have planned differently.

Service for food to our seat was a bit slow. Snack choices were just pretzels or baked chips. My seat cushion was not attached. Other than Barbie, video choice were not very good or current.

After we landed, we were held on the plane for 30 minutes. There was no one at the gate once we landed and we forced to sit on a plan that had already over an hour delayed.

almost 4 hour delay as they over booked and had to wait for 8-10 volunteers to agree to travel next day.

Old plane. No outlets for laptop or phone. Seats worn out. Area around seat dirty.

At least the delays were short. Business class, even in the new planes is very crowded now with crappy tray tables

The new Airbus A231neo has neat tech but the economy seats are so tight together that I always had my shoulders against one passenger or the other. I was very miffed that Basic Economy REQUIRES check-in of bags other than your personal carry-on; if you want to offer low-cost airline prices and then add services for a fee, just let me carry on my duffel. Hell, I could have put my carry on IN the duffel and called it a day but the gate agent would not let me; I ended up paying $40 for the risk of losing my bag. Not the worst flight, but far from the best.

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

It was freezing in there. When I asked about it, the response is “we would have to tell them” and then she just walked away and continued to serve beverages. Everyone was cold and they didn’t care at all.

I did not enjoy continuously being lied to about the amount of time we would circle Chicago before deciding to redirect to Milwaukee. Then the amount of time we would sit on the ground in Milwaukee waiting for gas, or to take off again. Or the amount of time it would then take to get to Chicago again, or sit on the runway waiting for a gate. The whole time continuously hopefully we would make our connecting flight that kept getting delayed as well. Only to scramble and miss it. Enough with the BS. Tell me the truth. "Sorry, things are backed up and your probably not going to make your flight. You should rebook on the next flight now rather than wait." You'll never hear those words from an airline. Speaking of which. If the flight has been redirected and/or is seriously delayed, how about making the WiFi free for everyone so they get to rebooking and reserving hotel rooms while still in the air. You've inconvenienced me already and now you want me to pay $20 for Internet so I can try to make other plans. Absolutely disgusting!

Great flight. The captain did a great job of minimizing some minor turbulence and in general it was a smooth flight. Early departure and early arrival at destination. Great service.

Our flight left on time and we arrived a few minutes early. Great service!

Our 9:10 am scheduled flight continued to get delayed all day with no information given from the agents as to why. It wasn’t until I went to the customer service desk and got us switched to another flight at 2:44 pm (that wasn’t nonstop like our booked flight) that the agent finally was able to find out it was due to a fuel leak. I don’t know if our original flight ever took off but I don’t find it acceptable to leave people sitting in an airport all day with no explanation.

I am very disappointed with american. We have flown American airlines numerous times, as well as other airlines and never had such an experience. My son's flight for Sunday afternoon was cancelled around 11 am. We were told not to do anything bec AA would. After an hour of not seeing a change in his flight status. I called AA. I was on hold for half hour then opted for a call back. That call back never came. So I called again, in meantime I started looking online at my options. No flights were leaving that day from AA. But other airlines were flying out. We needed our son in Chicago asap.i kept calling AA for a callback, but never received one. Finally i called back later in the afternoon and a representative answered the call. She told me there were no flights out till Tuesday morning. I asked how this is possible, I had seen flights from AA and other airlines leaving Monday. She said she checked all NYC airports and there were no AA flights till Tuesday AM. Then I asked about getting on another airline. She responded i would be responsible for that. When I asked how AA would reimburse. She became nasty and told me AA has not responsibility to reimburse anything they will put me in a flight for Tuesday morning. When i explained he must be there Monday by 8am, she told me there's nothing to do and practically hung up. At that point I just asked her to book the Tuesday morning flight. I had this experience with other airlines, cancelled due to weather and they and their reps were much more helpful. Either way Tuesday morning flight was delayed as well. Over an hour! I expect more from AA.

When you pay for Premium Economy on an 787 and you’re promised amenities for the extra money, you expect them to work. They didn’t. USB connector wouldn’t charge continuously. 120v outlet wouldn’t hold anything you plugged into it. The adapter would just fall out. The noise canceling headphones stopped noise cancelling in the first 15 minutes for EVERYONE. No one on the plane knew how to fix it so I couldn’t listen to any movies. I just put in my AirPods and went to sleep. Very unhappy with the crappy Panasonic entertainment system. I won’t buy premium again.

Our flight was delayed by 18 hours. Poor accommodations made and no apology.

This flight was awful all around. Delays on the tarmac at PHL before takeoff and at the tarmac in Chicago caused me to miss my final connection. This was completely avoidable, in my opinion.

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

You get what you pay for, but those tickets weren't cheap, so I expected better, but Spirit is just one of those airlines.

The worse experience ever from flight delays customer service and professionalism.

Terrible they delayed our flight then when we got on they had to fix the plane then finally we left hours later and when we got there since they had screwed up everything else we had to wait for a walkway so we had to sit on the plane and they turned off the AC and it was fuckin hot

Cancelled the return flight moments before boarding, horrible customer service in assisting with any rebooking. Never again will I fly Spirit.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Book cheap flights from Boston to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Boston to Chicago found on KAYAK in the last 72 hours.
8/27Tue
nonstopSpirit Airlines
2h 53mBOS-ORD
$23
9/24Tue
nonstopSpirit Airlines
2h 52mBOS-ORD
$24
9/25Wed
nonstopSpirit Airlines
2h 52mBOS-ORD
$26
9/24Tue
nonstopDelta
2h 48mBOS-ORD
$69
8/1Thu
nonstopAmerican Airlines
2h 56mBOS-ORD
$91
8/2Fri
nonstopAmerican Airlines
2h 56mBOS-ORD
$94
8/2Fri
nonstopUnited Airlines
2h 50mBOS-ORD
$111
7/31Wed
nonstopJetBlue
2h 54mBOS-ORD
$164
8/11Sun
nonstopUnited Airlines
2h 46mBOS-ORD
$189
7/31Wed
nonstopDelta
3h 00mBOS-ORD
$208

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Last minute flights from Boston to O'Hare Intl

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Boston to Chicago that are departing in the next 10 days.
7/30Tue
nonstopSpirit Airlines
2h 54mBOS-ORD
8/31Sat
nonstopSpirit Airlines
2h 28mORD-BOS
$142
7/30Tue
multi-stop
5h 44mBOS-ORD
8/6Tue
nonstop
2h 26mORD-BOS
$143
7/30Tue
multi-stop
5h 44mBOS-ORD
8/7Wed
nonstop
2h 28mORD-BOS
$148
7/30Tue
nonstopDelta
3h 01mBOS-ORD
8/6Tue
nonstopDelta
2h 42mORD-BOS
$254
7/30Tue
multi-stopDelta
4h 51mBOS-ORD
8/7Wed
nonstopDelta
2h 26mORD-BOS
$264
7/26Fri
nonstopAmerican Airlines
2h 56mBOS-ORD
7/31Wed
nonstopAmerican Airlines
2h 27mORD-BOS
$279
7/26Fri
nonstopJetBlue
2h 54mBOS-ORD
7/30Tue
nonstopJetBlue
2h 26mORD-BOS
$352
7/26Fri
nonstopAmerican Airlines
2h 59mBOS-ORD
7/28Sun
nonstopAmerican Airlines
2h 27mORD-BOS
$353
7/28Sun
nonstopJetBlue
2h 54mBOS-ORD
7/29Mon
multi-stopJetBlue
4h 40mORD-BOS
$361
7/26Fri
nonstopUnited Airlines
2h 45mBOS-ORD
7/27Sat
nonstopUnited Airlines
2h 22mORD-BOS
$377

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Boston - Chicago O'Hare Airport Flights

Departure:

Boston (BOS)United States

Destination:

Chicago O'Hare Airport (ORD)United States

Return flight deals:

Chicago O'Hare Airport - Boston

Cabin classes:

$373
$481
$364
$74