BOS - ORD

₹ 4,852 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 O'Hare Intl departing on 15/4. 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, 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
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Cheap Flight Deals from Boston to Chicago (BOS-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return 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.

Recent return flight deals from Boston to O'Hare Intl

Recommended return deals departing in the coming months from the most popular airlines that fly from Boston to O'Hare Intl.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
20:15 - 22:15BOS-ORD
3h 00mdirect
07:00 - 10:25ORD-BOS
2h 25mdirect
₹ 13,429Delta
Find Deal
Mon, 10 Mar - Wed, 12 Mar
12:05 - 14:05BOS-ORD
3h 00mdirect
07:00 - 10:25ORD-BOS
2h 25mdirect
₹ 13,603Delta
Find Deal
Sat, 8 Mar - Wed, 12 Mar
07:30 - 09:34BOS-ORD
3h 04mdirect
07:10 - 10:38ORD-BOS
2h 28mdirect
₹ 13,689United Airlines
Find Deal
Sat, 15 Mar - Sun, 13 Apr
05:30 - 09:38BOS-ORD
5h 08m1 stop
16:05 - 19:25ORD-BOS
2h 20mdirect
₹ 14,122United Airlines
Find Deal
Sat, 8 Mar - Wed, 12 Mar
05:30 - 09:38BOS-ORD
5h 08m1 stop
09:20 - 12:43ORD-BOS
2h 23mdirect
₹ 14,209United Airlines
Find Deal
Thu, 6 Mar - Tue, 11 Mar
16:25 - 18:32BOS-ORD
3h 07mdirect
06:20 - 12:25ORD-BOS
5h 05m1 stop
₹ 14,469JetBlue
Find Deal
Wed, 7 May - Sat, 10 May
05:20 - 10:59BOS-ORD
6h 39m1 stop
13:00 - 16:20ORD-BOS
2h 20mdirect
₹ 14,816JetBlue
Find Deal
Thu, 27 Mar - Thu, 27 Mar
05:35 - 11:00BOS-ORD
6h 25m1 stop
07:00 - 13:10ORD-BOS
5h 10m1 stop
₹ 18,281Southwest
Find Deal
Thu, 6 Mar - Fri, 14 Mar
17:40 - 21:30BOS-ORD
4h 50m1 stop
07:00 - 17:50ORD-BOS
9h 50m2 stops
₹ 18,714Southwest
Find Deal
Thu, 6 Mar - Fri, 14 Mar
07:08 - 12:35BOS-ORD
6h 27m1 stop
06:17 - 12:20ORD-BOS
5h 03m1 stop
₹ 25,906American Airlines
Find Deal
Mon, 31 Mar - Thu, 3 Apr

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?

The average price of all round-trip flights from Boston to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.
For Boston to Chicago, Thursday is the cheapest day to fly on average and Saturday is the most expensive. Flying from Chicago back to Boston, the best deals are generally found on Sunday, with Wednesday being 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 round-trip 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 September, where tickets cost ₹ 16,982 (return) on average. On the other hand, the most expensive months are May and December, where the average cost of round-trip tickets is ₹ 24,953 and ₹ 24,606 respectively.

Can I save money by flying with a stopover from Boston to Chicago O'Hare Intl Airport?

The average return price for all direct flights, flights with one stopover, and flights with two stopovers for the route found by users searching on KAYAK in the last 2 weeks.
Yes, flying with a stopover may cost you more time, but you can also save money on the route, with a 1 stop stopover the cheapest option at ₹ 22,150 on average.

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

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 O'Hare Intl Airport, 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 O'Hare Intl Airport, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Good to know

Low season

January

High season

August

Cheapest flight

₹ 4,852
Best time to beat the crowds (15% less expensive on average)
Most popular time to fly and prices are also 17% lower 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 ₹ 56 for a one-way ticket and ₹ 155 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?

    All the following airlines offer inflight Wi-Fi service on the Boston to Chicago flight route: American Airlines, Delta, JetBlue, Aeromexico, Alaska Airlines, and KLM.

  • 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.

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

    The two airlines most popular with KAYAK users for flights from Boston to Chicago are Delta and American Airlines. With an average price for the route of ₹ 19,838 and an overall rating of 8.0, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of ₹ 28,684 and an overall rating of 7.2.

  • 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

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

  • 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 Boston Logan Intl Airport to Chicago O'Hare Intl Airport, 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, +23 more

ANA, Air New Zealand, +24 more

Tuesday

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

ANA, Air New Zealand, +22 more

Wednesday

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

ANA, Air New Zealand, +22 more

Thursday

ANA, Air New Zealand, Alaska Airlines, +23 more

ANA, Air New Zealand, +24 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, +23 more

ANA, Air New Zealand, +24 more

See more direct flights

Direct returns

Chicago O'Hare Intl to Boston Logan Intl

Monday

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

ANA, Air New Zealand, +23 more

Tuesday

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

ANA, Air New Zealand, +22 more

Wednesday

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

ANA, Air New Zealand, +22 more

Thursday

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

ANA, Air New Zealand, +23 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, +22 more

ANA, Air New Zealand, +23 more

See more direct flights
See more direct flights

Top airlines 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 8220 reviews
7.9Entertainment
8.5Crew
7.3Food
8.0Comfort
8.2Boarding
Airline reviews

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

10.0 ExcellentStephen, Feb 2025SFO - JFK
Read more Delta reviews

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

I loved having a most black flight crew during Black History Month; rather by design or accident I appreciated the representation. ❤️

This was the second flight this week with flight attendant Marcus I’m not sure if his last name is Lane or Lang but this guy is awesome. He funny, attentive and his service is 5 stars. Marcus makes business travel more enjoyable !

Although the flight left late, we arrived early. It was one of the quickest boarding and off boarding experiences I’ve had. It was kind of annoying the only drinks they had were water, coffee, and tea. The flight was very smooth, temperature was just right, and flight attendants were friendly.

Lower number on this flight so spaced out passengers. Able to enjoy more room to relax during flight. It was lovely.

Kind staff. Snacks are small but that’s the new normal.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

Flight left early and arrived early. the whole trip was excellent.

Seats were really tight and the seat belts did not give enough slack.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

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.

Travelling to a place near O'Hare Intl?

Book flights to O'Hare Intl if you plan to visit one of these locations
Schaumburg
Lake Geneva
Naperville
Elk Grove Village
Oak Brook
Des Plaines
Benton Harbor
Itasca
Skokie
Elgin
Rosemont
Tinley Park
Evanston
Janesville
Glenview
Hoffman Estates
Northbrook
South Holland
Aurora
Rockford

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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