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BOS - ORD

Find cheap flights from Boston to Chicago from ₹ 5,757

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 26/5. 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
Sat 1/6
Sat 8/6

Search 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, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Chicago, as well as popular online travel agencies
In the last 7 days, travellers have searched 43,740,974 times on KAYAK, and here's 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
06:10 - 08:04BOS-ORD
2h 54mdirect
19:15 - 22:41ORD-BOS
2h 26mdirect
₹ 12,264JetBlue
Find Deal
Wed, 22 May - Sat, 25 May
11:00 - 12:50BOS-ORD
2h 50mdirect
13:50 - 17:18ORD-BOS
2h 28mdirect
₹ 13,599Delta
Find Deal
Thu, 15 Aug - Tue, 27 Aug
06:10 - 08:04BOS-ORD
2h 54mdirect
08:40 - 12:09ORD-BOS
2h 29mdirect
₹ 13,933JetBlue
Find Deal
Wed, 29 May - Wed, 5 Jun
17:05 - 19:03BOS-ORD
2h 58mdirect
06:30 - 09:58ORD-BOS
2h 28mdirect
₹ 14,350Delta
Find Deal
Sat, 13 Jul - Wed, 31 Jul
06:30 - 08:24BOS-ORD
2h 54mdirect
20:39 - 00:08ORD-BOS
2h 29mdirect
₹ 18,021Spirit Airlines
Find Deal
Sat, 22 Jun - Sat, 29 Jun
05:00 - 10:45BOS-ORD
6h 45m1 stop
06:30 - 15:25ORD-BOS
7h 55m1 stop
₹ 20,023Southwest
Find Deal
Fri, 14 Jun - Sat, 15 Jun
11:56 - 22:53BOS-ORD
11h 57m1 stop
20:39 - 00:08ORD-BOS
2h 29mdirect
₹ 20,440Spirit Airlines
Find Deal
Sat, 22 Jun - Sat, 29 Jun
11:39 - 18:12BOS-ORD
7h 33m1 stop
18:50 - 10:40ORD-BOS
14h 50m1 stop
₹ 22,109Sun Country Air
Find Deal
Fri, 25 Oct - Mon, 28 Oct
05:40 - 16:25BOS-ORD
11h 45m1 stop
11:25 - 18:35ORD-BOS
6h 10m1 stop
₹ 24,111Southwest
Find Deal
Mon, 13 May - Thu, 16 May
11:39 - 19:28BOS-ORD
8h 49m1 stop
19:30 - 10:40ORD-BOS
14h 10m1 stop
₹ 24,612Sun Country Air
Find Deal
Thu, 10 Oct - Mon, 14 Oct

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 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 February, where tickets cost ₹ 13,265 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is ₹ 30,452 and ₹ 27,198 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 87 days before departure.

Which airlines provide the cheapest flights from Boston to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the past 3 days, the cheapest one-way tickets to Chicago from Boston were found on JetBlue (₹ 5,757) and Delta (₹ 8,677), and the lowest return tickets were found on JetBlue (₹ 12,264) and Delta (₹ 13,599).

Which airlines fly most frequently between Boston and Chicago?

United Airlines connects Boston to Chicago up to 14 flights per day, followed by American Airlines (7 flights per day), and Delta (5 flights per day).

Which airlines fly direct 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 4 airlines that fly direct from Boston to Chicago O'Hare Intl Airport. They are: American Airlines, Delta, JetBlue and United Airlines. The cheapest price of all airlines flying this route was found with Delta at ₹ 13,153 for a one-way flight. On average, the best prices for this route can be found at Delta.

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

Each day, there are between 26 and 30 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 16:00 and most flights take off in the morning. Each week, there are 199 flights. The most frequent day of departure is Sunday, 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 2 cabin class options for the route. These are Business and 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 take?

Direct flights cover the 2,237 km separating Boston and Chicago in about 2h 45m.

What’s the earliest departure time from Boston to Chicago?

Early birds can take the earliest flight from Boston at 05:00 and will be landing in Chicago O'Hare Intl Airport at 06:55.

What’s the latest departure time from Boston to Chicago?

If you prefer to fly at night, the latest flight from Boston to Chicago O'Hare Intl Airport jets off at 20:16 and lands at 22:10.

Good to know

Low season

January

High season

November

Cheapest flight

₹ 5,757
Best time to beat the crowds (37% less expensive on average)
Most popular time to fly (13% more expensive on average)
Flight from Boston to Chicago

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 return price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns 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 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 ₹ 69 for a one-way ticket and ₹ 147 for a return.

  • 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 Chicago, also known as Chicago O'Hare Intl.

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

    American Airlines, Delta, JetBlue, and Alaska Airlines 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?

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

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

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

  • 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 travellers 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 return 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.

See more FAQs

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 ₹ 6,687 or less one-way and ₹ 13,532 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 direct from Boston Logan Intl to Chicago O'Hare Intl?

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

Direct departures

Boston Logan Intl to Chicago O'Hare Intl

Monday

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

ANA, Air New Zealand, +22 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, +21 more

ANA, Air New Zealand, +22 more

Friday

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

ANA, Air New Zealand, +22 more

Saturday

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

ANA, Air New Zealand, +21 more

Sunday

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

ANA, Air New Zealand, +23 more

See more direct flights

Direct 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 airline flying 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 10858 reviews
7.9Comfort
8.2Boarding
8.6Crew
7.4Food
8.0Entertainment
Airline reviews

They did a fine job. Can't wait to use Delta in the future.

10.0 ExcellentRobert, Apr 2024BOS - RSW
Read more about Delta reviews

They did a fine job. Can't wait to use Delta in the future.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

Seats in first class on the E175 recline too far back. I was in 2A, and the man in 1A fully reclined almost the entire flight. It took 6-7 inches of space away from me and made it very difficult to work on my laptop.

Mario was great. Made a night flight on a small aircraft pleasant and memorable.

Crew were exceptional. Plane was quiet and quite empty, so I had a row to sleep across.

The seat could use more support or cushion. I'm in my 50's and have back issues so the seats are a bit hard for longer flights.

The plane was in bad condition. We were taxied for mode than an hour because a light panel had feel off. The bathroom in first class had broken panels as well. Overall poor aircraft maintenance

My only real complaint was how much turbulence there was-and that probably can't be avoided. I felt really sick getting off the plane. But boarding was super easy, the flight attendants were friendly, the bathroom was clean. Everything else about the flight was perfectly fine. Thanks!

Caroline (Supervisor) was great! Salute to the employees like her!

Boarding was good, staffs on the second flight to Korea was invisible all the time. Water was only offered 3 times during a 15 hours plus flight. It’s absolutely not enough for such a long flight!

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.
26/5Sun
directJetBlue
2h 54mBOS-ORD
₹ 5,757
22/5Wed
directJetBlue
2h 54mBOS-ORD
₹ 7,926
15/6Sat
directDelta
2h 58mBOS-ORD
₹ 8,677
27/7Sat
1 stopSun Country Air
6h 29mBOS-ORD
₹ 9,428
27/6Thu
1 stopAmerican Airlines
6h 24mBOS-ORD
₹ 10,763
19/7Fri
directDelta
2h 57mBOS-ORD
₹ 10,846
13/5Mon
1 stopSouthwest
10h 20mBOS-ORD
₹ 11,013
11/10Fri
1 stopSun Country Air
6h 33mBOS-ORD
₹ 13,599
8/5Wed
1 stopAmerican Airlines
5h 11mBOS-ORD
₹ 16,102
8/5Wed
1 stopSouthwest
7h 05mBOS-ORD
₹ 16,686

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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.
7/5Tue
directJetBlue
2h 54mBOS-ORD
14/5Tue
directJetBlue
2h 29mORD-BOS
₹ 23,611
3/5Fri
directJetBlue
2h 56mBOS-ORD
11/5Sat
directJetBlue
2h 29mORD-BOS
₹ 23,945
6/5Mon
multi-stopDelta
7h 59mBOS-ORD
11/5Sat
directDelta
2h 33mORD-BOS
₹ 24,362
3/5Fri
multi-stopDelta
5h 29mBOS-ORD
11/5Sat
directDelta
2h 31mORD-BOS
₹ 24,695
3/5Fri
directDelta
2h 55mBOS-ORD
9/5Thu
directDelta
2h 27mORD-BOS
₹ 24,862
6/5Mon
multi-stopSouthwest
4h 55mBOS-ORD
6/5Mon
multi-stopSouthwest
4h 55mORD-BOS
₹ 33,372
6/5Mon
directUnited Airlines
2h 52mBOS-ORD
6/5Mon
directUnited Airlines
2h 24mORD-BOS
₹ 34,540
6/5Mon
directUnited Airlines
2h 52mBOS-ORD
8/5Wed
directUnited Airlines
2h 24mORD-BOS
₹ 36,626
3/5Fri
multi-stopSouthwest
8h 55mBOS-ORD
4/5Sat
multi-stopSouthwest
15h 00mORD-BOS
₹ 52,144
6/5Mon
multi-stopAmerican Airlines
7h 07mBOS-ORD
6/5Mon
multi-stopAmerican Airlines
6h 44mORD-BOS
₹ 80,927

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Boston - Chicago Flights

Departure:

Boston (BOS)United States

Destination:

Chicago (ORD)United States

Cabin classes:

₹ 66,494
₹ 13,516

Browse origins:

  • Flights » 
  • Boston

Browse destinations:

  • Flights » 
  • Chicago O'Hare Airport