ORD - BOS

£45 Find Cheap Flights from Chicago to Boston

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Boston departing on 3/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Boston

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Boston, 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 Chicago to Boston, as well as popular online travel agencies
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Expert advice
Booking Insights
Flights Deals

Cheap Flights from Chicago to Boston (ORD-BOS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from Chicago to Boston that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals from Chicago to Boston

Wed, 3 Sep - Wed, 3 Sep
United Airlines Logo
07:30 - 11:01ORD-BOS
2h 31mdirect
United Airlines Logo
16:27 - 18:21BOS-ORD
2h 54mdirect
£88United Airlines
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Mon, 18 Aug - Thu, 4 Sep
United Airlines Logo
06:00 - 09:26ORD-BOS
2h 26mdirect
United Airlines Logo
06:10 - 08:05BOS-ORD
2h 55mdirect
£96United Airlines
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Fri, 12 Sep - Wed, 17 Sep
Delta Logo
18:59 - 22:40ORD-BOS
2h 41mdirect
Delta Logo
11:55 - 13:43BOS-ORD
2h 48mdirect
£104Delta
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Sun, 31 Aug - Thu, 4 Sep
United Airlines Logo
06:30 - 09:56ORD-BOS
2h 26mdirect
United Airlines Logo
20:27 - 22:15BOS-ORD
2h 48mdirect
£105United Airlines
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Thu, 4 Sep - Wed, 10 Sep
Delta Logo
10:15 - 13:48ORD-BOS
2h 33mdirect
Delta Logo
19:55 - 21:56BOS-ORD
3h 01mdirect
£111Delta
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Fri, 12 Sep - Wed, 17 Sep
Southwest Logo
14:55 - 22:35ORD-BOS
6h 40m1 stop
Southwest Logo
05:40 - 11:50BOS-ORD
7h 10m1 stop
£119Southwest
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Sat, 27 Sep - Tue, 30 Sep
Southwest Logo
13:30 - 22:15ORD-BOS
7h 45m1 stop
Southwest Logo
05:40 - 11:50BOS-ORD
7h 10m1 stop
£122Southwest
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Wed, 27 Aug - Tue, 2 Sep
JetBlue Logo
06:15 - 12:15ORD-BOS
5h 00m1 stop
JetBlue Logo
13:40 - 15:32BOS-ORD
2h 52mdirect
£134JetBlue
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Thu, 4 Sep - Sun, 7 Sep
JetBlue Logo
09:42 - 13:10ORD-BOS
2h 28mdirect
JetBlue Logo
07:00 - 08:56BOS-ORD
2h 56mdirect
£135JetBlue
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Sun, 16 Nov - Thu, 20 Nov
American Airlines Logo
05:00 - 11:06ORD-BOS
5h 06m1 stop
American Airlines Logo
07:00 - 09:24BOS-ORD
3h 24mdirect
£147American Airlines
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Expert advice

Expert advice for your flight from Chicago to Boston

 
Snippets provided in this section are AI-generated based on a summarisation of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
JetBlue

JetBlue's Even More Space seats offer up to 18 cm extra legroom, ideal for added comfort.


JetBlue provides free gate-to-gate Wi-Fi and live TV, perfect for staying connected and entertained.

Read more about JetBlueby Harriet Baskas
Delta

Delta offers free Wi-Fi for SkyMiles members on domestic flights, enhancing productivity and connectivity.


Delta's Sky Priority check-in speeds up the process for premium cabin and elite status passengers.

Read more about Deltaby Stefanie Waldek
Airports
ORD

Security lines at ORD can be 30 minutes or longer during peak times. Plan accordingly to avoid delays.

Read more about ORDby Stefanie Waldek
BOS

The Silver Line bus from BOS to South Station is free and takes about 20-30 minutes, depending on traffic.

Read more about BOSby Blane Bachelor
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on JetBlue

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, The Points Guy, and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on Delta and ORD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or out at sea, likely en route to Antarctica or the Arctic.

Read more
Blane Bachelor

Blane Bachelor

Expert on BOS

Blane Bachelor

Blane Bachelor

Blane Bachelor is a journalist and editor specialising in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favourite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history.

Read more
Booking Insights

KAYAK's insights & trends for Chicago to Boston flights

Get data-powered insights and trends into flights from Chicago to Boston 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 Chicago to Boston?

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

For Chicago to Boston, Saturday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Boston back to Chicago, the best deals are generally found on Thursday, with Sunday being the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Boston, 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 Chicago O'Hare Intl Airport to Boston is September, where tickets cost £134 (return) on average. On the other hand, the most expensive months are February and March, where the average cost of round-trip tickets is £207 and £195 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to Boston, 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 Chicago O'Hare Intl Airport to Boston, you should book around 3 weeks before departure, which saves you about 37% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Find deals

Good to know - Cheap tickets from Chicago to Boston

Low seasonFebruary
Cheapest flight£45
Best time to beat the crowds but there is an average 19% increase in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Chicago to Boston

When to book flights from Chicago to Boston

Are your dates flexible? Find out the best times to travel from Chicago to Boston 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 Chicago to Boston flights

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

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Boston was £59 for a one-way ticket and £117 for a return.

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

    All the following airlines offer inflight Wi-Fi service on the Chicago to Boston flight route: American Airlines, JetBlue, Delta, Finnair, British Airways, and Iberia.

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

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

  • Which airline alliances offer flights from Chicago to Boston?

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

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

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

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

    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 Chicago to Boston.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Chicago 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 Chicago to Boston?

    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 Boston with an airline and back to Chicago with another airline.

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

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

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

  • Looking for a cheap flight from Boston to Chicago? 25% of our users found flights on this route for Boston or less round-trip.

Prefer to fly direct from Chicago to Boston?

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

Direct departures

Chicago O'Hare Intl to Boston Logan Intl

Monday

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

ANA, Air New Zealand, +22 more

Tuesday

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

ANA, Air New Zealand, +22 more

Wednesday

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

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

ANA, Air New Zealand, +23 more

Sunday

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

ANA, Air New Zealand, +23 more

See more direct flights

Direct returns

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, +20 more

ANA, Air New Zealand, +21 more

Wednesday

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

ANA, Air New Zealand, +23 more

Thursday

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

ANA, Air New Zealand, +24 more

Friday

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

ANA, Air New Zealand, +23 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

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

Information on your arrival and departure airports

Chicago (ORD)
Boston (BOS)

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