BOS - ORD

$45 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 12/10. 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.
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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.
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Cheap Flight Deals from Boston to Chicago O'Hare Airport (BOS-ORD)

 
These are the cheapest deals for flights from Boston to O'Hare Intl currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Boston to O'Hare Intl

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Boston to O'Hare Intl.

Recent one-way flight deals from Boston to O'Hare Intl

Only flying one-way? Below are some of the best one-way flight deals from Boston to O'Hare Intl found on KAYAK recently.

Recent last minute flight deals from Boston to O'Hare Intl

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Boston to O'Hare Intl.

Recent direct flight deals from Boston to O'Hare Intl

The latest deals for direct flights from Boston to O'Hare Intl so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Boston to O'Hare Intl

Find recent round-trip train or bus tickets from Boston to O'Hare Intl.

All round-trip flight deals to O'Hare Intl

The cheapest plane tickets to O'Hare Intl found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
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10:34 am - 9:07 pmBOS-ORD
11h 33m1 stop
9:58 am - 12:38 amORD-BOS
13h 40m1 stop
$101Spirit Airlines
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Fri, Dec 6 - Tue, Dec 10
8:54 am - 3:43 pmBOS-ORD
7h 49m1 stop
9:58 am - 12:38 amORD-BOS
13h 40m1 stop
Mon, Dec 9 - Tue, Dec 10
6:00 am - 8:05 amBOS-ORD
3h 05mnonstop
8:51 am - 12:13 pmORD-BOS
2h 22mnonstop
$157JetBlue
Find Deal
Thu, Dec 5 - Tue, Dec 10
11:28 am - 3:44 pmBOS-ORD
5h 16m1 stop
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
$166JetBlue
Find Deal
Fri, Jan 10 - Tue, Jan 14
6:02 am - 8:05 amBOS-ORD
3h 03mnonstop
9:10 am - 3:41 pmORD-BOS
5h 31m1 stop
$183United Airlines
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Wed, Jan 1 - Mon, Feb 3
10:45 am - 12:41 pmBOS-ORD
2h 56mnonstop
9:20 am - 12:45 pmORD-BOS
2h 25mnonstop
$184United Airlines
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Tue, Dec 3 - Thu, Dec 5
12:00 pm - 1:59 pmBOS-ORD
2h 59mnonstop
8:35 pm - 12:10 amORD-BOS
2h 35mnonstop
$187American Airlines
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Tue, Dec 3 - Sun, Dec 8
6:45 am - 8:49 amBOS-ORD
3h 04mnonstop
8:30 pm - 12:15 amORD-BOS
2h 45mnonstop
$194American Airlines
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Tue, Dec 31 - Sun, Jan 5
7:40 pm - 9:41 pmBOS-ORD
3h 01mnonstop
7:10 am - 10:47 amORD-BOS
2h 37mnonstop
$199Delta
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Thu, Jan 2 - Mon, Jan 6
7:40 pm - 9:41 pmBOS-ORD
3h 01mnonstop
7:35 am - 11:03 amORD-BOS
2h 28mnonstop
$223Delta
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Sun, Dec 29 - Fri, Jan 3
5:00 am - 4:06 pmBOS-ORD
12h 06m1 stop
$45Spirit Airlines
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Tue, Dec 10
6:00 am - 11:47 amBOS-ORD
6h 47m1 stop
$53Frontier
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Wed, Jan 8
7:20 am - 9:29 amBOS-ORD
3h 09mnonstop
$78Delta
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Wed, Dec 4
3:52 pm - 5:55 pmBOS-ORD
3h 03mnonstop
$79JetBlue
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Wed, Feb 5
7:25 am - 9:28 amBOS-ORD
3h 03mnonstop
$83Delta
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Fri, Dec 6
11:28 am - 3:44 pmBOS-ORD
5h 16m1 stop
$88JetBlue
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Sun, Jan 19
6:02 am - 8:05 amBOS-ORD
3h 03mnonstop
$95United Airlines
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Tue, Dec 31
6:00 am - 7:56 amBOS-ORD
2h 56mnonstop
$124United Airlines
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Tue, Nov 26
8:30 am - 10:32 amBOS-ORD
3h 02mnonstop
$125American Airlines
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Wed, Nov 27
7:00 am - 11:13 amBOS-ORD
5h 13m1 stop
$133American Airlines
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Wed, Nov 27
11:35 am - 12:28 amBOS-ORD
13h 53m1 stop
11:45 am - 12:38 amORD-BOS
11h 53m1 stop
Sat, Nov 23 - Fri, Dec 6
11:35 am - 12:28 amBOS-ORD
13h 53m1 stop
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
Sat, Nov 23 - Thu, Nov 28
11:35 am - 12:28 amBOS-ORD
13h 53m1 stop
2:25 pm - 12:44 amORD-BOS
9h 19m1 stop
$139Frontier
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Sat, Nov 23 - Wed, Nov 27
7:20 am - 9:29 amBOS-ORD
3h 09mnonstop
12:40 pm - 3:58 pmORD-BOS
2h 18mnonstop
$252Delta
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Sun, Nov 24 - Sat, Dec 7
9:05 am - 12:50 pmBOS-ORD
4h 45m1 stop
7:15 am - 10:49 amORD-BOS
2h 34mnonstop
$262Delta
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Sat, Nov 23 - Sat, Dec 7
1:59 pm - 3:53 pmBOS-ORD
2h 54mnonstop
8:50 am - 12:12 pmORD-BOS
2h 22mnonstop
$282JetBlue
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Fri, Nov 22 - Wed, Dec 4
2:41 pm - 4:41 pmBOS-ORD
3h 00mnonstop
7:00 am - 10:19 amORD-BOS
2h 19mnonstop
$288American Airlines
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Fri, Nov 22 - Tue, Nov 26
9:30 am - 11:27 amBOS-ORD
2h 57mnonstop
8:20 am - 11:42 amORD-BOS
2h 22mnonstop
$297JetBlue
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Mon, Nov 25 - Fri, Nov 29
11:32 am - 3:43 pmBOS-ORD
5h 11m1 stop
11:59 pm - 3:18 amORD-BOS
2h 19mnonstop
$307United Airlines
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Mon, Nov 25 - Sun, Dec 1
8:00 am - 12:25 pmBOS-ORD
5h 25m1 stop
8:10 am - 3:23 pmORD-BOS
6h 13m1 stop
$311American Airlines
Find Deal
Mon, Nov 25 - Sat, Nov 30
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
8:51 am - 12:13 pmORD-BOS
2h 22mnonstop
$157JetBlue
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Fri, Dec 6 - Wed, Dec 11
11:05 am - 1:03 pmBOS-ORD
2h 58mnonstop
6:30 am - 10:00 amORD-BOS
2h 30mnonstop
$158Delta
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Thu, Dec 5 - Mon, Dec 9
11:05 am - 1:00 pmBOS-ORD
2h 55mnonstop
6:30 am - 10:00 amORD-BOS
2h 30mnonstop
$165Delta
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Thu, Dec 12 - Fri, Dec 13
1:59 pm - 3:53 pmBOS-ORD
2h 54mnonstop
8:50 am - 12:12 pmORD-BOS
2h 22mnonstop
$167JetBlue
Find Deal
Tue, Dec 3 - Thu, Dec 5
10:45 am - 12:41 pmBOS-ORD
2h 56mnonstop
9:20 am - 12:45 pmORD-BOS
2h 25mnonstop
$184United Airlines
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Tue, Dec 3 - Thu, Dec 5
12:12 pm - 2:10 pmBOS-ORD
2h 58mnonstop
7:30 am - 10:56 amORD-BOS
2h 26mnonstop
$185United Airlines
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Thu, Jan 16 - Mon, Jan 20
6:45 am - 8:49 amBOS-ORD
3h 04mnonstop
8:30 pm - 12:15 amORD-BOS
2h 45mnonstop
$194American Airlines
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Tue, Dec 31 - Sun, Jan 5
5:15 am - 7:19 amBOS-ORD
3h 04mnonstop
12:30 pm - 3:49 pmORD-BOS
2h 19mnonstop
$202American Airlines
Find Deal
Sun, Jan 5 - Wed, Jan 8
5:30 am - 7:37 amBOS-ORD
3h 07mnonstop
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
$425Spirit Airlines
Find Deal
Sat, Nov 30 - Mon, Dec 2
5:30 am - 7:37 amBOS-ORD
3h 07mnonstop
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
$433Spirit Airlines
Find Deal
Sat, Nov 30 - Mon, Dec 2

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 Sunday, 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 $194 on average. On the other hand, the most expensive months are May and November, where the average cost of tickets is $288 and $288 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.

Good to know

Low season

January

High season

November

Cheapest flight

$45
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 18% increase in price.
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 $45 for a one-way ticket and $101 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, Delta, JetBlue, 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 United Airlines?

    The two airlines most popular with KAYAK users for flights from Boston to Chicago are Delta and United Airlines. With an average price for the route of $252 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $300 and an overall rating of 7.4.

  • 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 $123 or less one-way and $208 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, +18 more

ANA, Air New Zealand, +19 more

Thursday

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

ANA, Air New Zealand, +21 more

Friday

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

ANA, Air New Zealand, +23 more

Saturday

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

ANA, Air New Zealand, +20 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, +21 more

ANA, Air New Zealand, +22 more

Wednesday

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

ANA, Air New Zealand, +21 more

Thursday

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

ANA, Air New Zealand, +23 more

Friday

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

ANA, Air New Zealand, +22 more

Saturday

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

ANA, Air New Zealand, +22 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 8765 reviews
7.9Entertainment
7.9Comfort
8.5Crew
8.2Boarding
7.3Food
Airline reviews

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

8.0 ExcellentAndrew, Nov 2024MCO - LGA
Read more Delta reviews

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Crew was nice. Flight was timely. Seats could be better as well as the food considering it’s first class.

Left on time and arrived early this extending our 31 minute transfer. Bags made it also!

Good and consistent Printer in lounge did not work for me :(

Most of my discomfort was going through TSA. However, the Delta seats had inadequate leg room and I tried my very best to connect to the wi-fi and it was a cumbersome process that finally gave me the info that I needed to sign in AFTER I had completed the flight...Why make it so difficult to use? That said I really really appreciate the pilot taking a little extra time to avoid a bad storm area and both landings in Atlanta and Orlando were flawless to my delight!!!

Delayed in taking off because no flight crew. The in seat entertainment was working properly.

I upgraded to first class only to find out that I still had no access to the sky lounge without a sky miles card or AmEx (something that should be emphasized outside of the fine print!) Also, no food or drink service provided during the flight, so I basically paid 4x more just for “free” checked baggage and a bigger seat. Not worth it.

Delta was really good about being transparent with why we were delayed it’s just that’s the plane was really old and outdated and a lot of the comfort and amenities we know Delta to have did not shine through

Bottom seat cushion is almost non existent. Very uncomfortable seat.

Delta was great the entertainment was outdated. Screen was very small and didn’t work.

Smooth boarding and friendly crew. Unfortunately as soon as we boarded the unit that provides air circulation failed. The pilot informed us and requested maintenance technicians to check it out. The plane became uncomfortably warm without any fresh air coming in. Plus the repair delayed our departure. I am glad the maintenance crew were able to fix the problem. I also was without use of my tv monitor for the first 1/3rd of the trip.

Communication with the customer and stay is important. Staff off with a minor inconvenience but it worked out of course. Also this was a very old Mint Class plane. They snuck this one in on us. The updated aircraft are much better.

The flight itself was fine, but the boarding process was extremely frustrating. There is no one scanning boarding passes - passengers just scan themselves and enter the jetway. By the time my husband and I got on the plane and were halfway to our seats they determined there were too many bags on the plane and everything at that point needed to be checked. This created a lot of unnecessary chaos. They should have alerted people before getting on the plane that they would need to start checking bags instead of waiting until people were already on the plane.

The best flight I’ve had in a while. The plane was like 25% capacity, if that. Smoothest boarding and deplaning process I’ve ever experienced. Wish all flights were this smooth.

Did not enjoy this flight at all. All of my coworkers flew delta and I chose JetBlue because I really value how simple the WiFi and entertainment is and this flight I didn’t get either. Crew staff was unsympathetic to my system not working, everyone I asked for help with was extremely bothered by my request for help.

Little snafu at boarding. Staff communicated with gate poorly. Flight attendant was rude making disembark early. This was an older mint class. Needs an overhaul for sure. Food was good. The male flight attendant was really nice.

My encounter with the entertainment services provided on board was moderate; the functionality of the Wi-Fi connection was either sluggish or nonoperational, while the display screens were antiquated and suffered from poor visibility. On the positive side, the cabin exuded a sense of expansiveness, and the crew exhibited amiable and accommodating behavior throughout the journey.

Everything was great except for some reason crew and ground crew could not figure out how to deal with an electric wheelchair and it delayed us 20-30mins. Was pretty frustrating for passengers and the captain.

Like the space, did not like the snack options, there was no power outlet in seats, no entertainment, no flyfi.

Traveling with JetBlue from NYC was convenient as accessing JFK airport was straightforward via the LIRR to the AirTrain. Maneuvering through the terminal was hassle-free, which was a pleasant start to the journey. However, the flight experience itself left much to be desired. The seating arrangement was notably uncomfortable; despite securing a window seat, space felt cramped. This was exacerbated by the middle seat passenger encroaching on my area, which made the flight less enjoyable. Additionally, while the in-flight entertainment system initially seemed like a reprieve, the sound outlet on my seat was inoperable. This issue turned what could have been a manageable three-hour flight into a rather tedious ordeal, as I was unable to use the entertainment system effectively. While JetBlue provided a smooth process in terms of airport logistics, the on-board experience highlighted areas in need of improvement, particularly in terms of comfort and entertainment system maintenance.

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

when you can say you don't remember being at any point upset during a flight, the airline is winning .

The staff was very friendly. The seats seemed quite small. Overall the flight was pleasant.

It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!

Charging and entertainment didn't work. The meal was horrible. They only came by with the drink cart one time for the 8 hour flight. They did come by with water a couple times.

Exceptional, I’d like to specifically recognize Robert for his outstanding customer service. He is professional, pleasant, and personable.

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

The flight from Buffalo to Chicago was on an older and smaller plane. Seating was tight. Looking closely at the interior of the aircraft there were definitely signs of aging and wear.

The flight encountered a delay exceeding 4 hours. The food voucher issued was valued at $12, insufficient to cover our meal expenses. Consequently, I was unable to take my medication, leading to a drop in blood sugar levels and exacerbating my anxiety.

Airplane was cold. Flight attendants were rude. Phone charger did not work. No food available.

3hour delay In the last 3 months i had 3 flights and 2 of these had a more than 2:40 hrs delayed

My initial flight to ORD was extended without reason. We circled the airport a few time and then drove on the ground for at least 20 minutes. These kinds of delays are annoying but somewhat expected… it would be nice if the crew would make an announcement to give updates on how long we could expect to be delayed.

The flight was uneventful. What was a problem was I was delayed getting home one entire day because the flight from Sacramento was delayed. That made getting to my connecting flight impossible. I had to stay another night at the hotel and incur that expense as a result.

This flight was fine but had no time to breathe as the connection was late from Sea to ORD.. Super stressful. If we checked bags, the trip would have been very distressed.

Seats were very uncomfortable. I paid extra for a seat with more leg room, the seat was no different than a seat at the back of the plane. Flight attendant was rude.

the food choice of packaged chips and popcorn was utterly ridiculous for first class

The flight landed with a delay and we had to wait almost an hour to be off boarded. So typical of spirit.

The gate employees and the flight crew were friendly and professional. Afterboarding we waited 20 minutes for another flight; a complimentary beverage would have ben appreciated for the inconvenience.

Spirit literally broke parts of two of our suitcases and call it “normal wear and tear.” Not worth the low price if we have to replace bags.

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.

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.
12/10Tue
1 stopSpirit Airlines
12h 06mBOS-ORD
$45
1/8Wed
1 stopFrontier
6h 47mBOS-ORD
$53
12/4Wed
nonstopDelta
3h 09mBOS-ORD
$78
2/5Wed
nonstopJetBlue
3h 03mBOS-ORD
$79
12/6Fri
nonstopDelta
3h 03mBOS-ORD
$83
1/19Sun
1 stopJetBlue
5h 16mBOS-ORD
$88
12/31Tue
nonstopUnited Airlines
3h 03mBOS-ORD
$95
11/26Tue
nonstopUnited Airlines
2h 56mBOS-ORD
$124
11/27Wed
nonstopAmerican Airlines
3h 02mBOS-ORD
$125
11/27Wed
1 stopAmerican Airlines
5h 13mBOS-ORD
$133

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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.
11/23Sat
multi-stop
13h 53mBOS-ORD
12/6Fri
multi-stop
11h 53mORD-BOS
$134
11/23Sat
multi-stop
13h 53mBOS-ORD
11/28Thu
nonstop
2h 19mORD-BOS
$138
11/23Sat
multi-stopFrontier
13h 53mBOS-ORD
11/27Wed
multi-stopFrontier
9h 19mORD-BOS
$139
11/24Sun
nonstopDelta
3h 09mBOS-ORD
12/7Sat
nonstopDelta
2h 18mORD-BOS
$252
11/23Sat
multi-stopDelta
4h 45mBOS-ORD
12/7Sat
nonstopDelta
2h 34mORD-BOS
$262
11/22Fri
nonstopJetBlue
2h 54mBOS-ORD
12/4Wed
nonstopJetBlue
2h 22mORD-BOS
$282
11/22Fri
nonstopAmerican Airlines
3h 00mBOS-ORD
11/26Tue
nonstopAmerican Airlines
2h 19mORD-BOS
$288
11/25Mon
nonstopJetBlue
2h 57mBOS-ORD
11/29Fri
nonstopJetBlue
2h 22mORD-BOS
$297
11/25Mon
multi-stopUnited Airlines
5h 11mBOS-ORD
12/1Sun
nonstopUnited Airlines
2h 19mORD-BOS
$307
11/25Mon
multi-stopAmerican Airlines
5h 25mBOS-ORD
11/30Sat
multi-stopAmerican Airlines
6h 13mORD-BOS
$311

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Everything you need to know for your flight from Boston to O'Hare Intl

Information on your arrival and departure airports

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