ORD - BOS

£59 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 12/5. 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
1 adult, Economy, 0 bags

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
Travellers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest return fare
£117
Typical prices: £237-£118
Delta
Tue 12/5Tue 19/5
ORD - BOS • Direct
Cheapest one-way flight
£59
Typical prices: £81-£199
Delta
Tue 12/5
ORD - BOS • Direct
Advice from real travellers
AI-powered summary based on content written by travel experts. AI can make mistakes.
JetBlue's Even More Space seats add up to 18 cm legroom.
Expect 30-minute security lines at Chicago O'Hare.
Expert advice
Expert advice
Expert advice
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Direct flights
Every day
You can fly direct with American Airlines, Delta, and others. Average duration is 2h 30m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
JetBlue
Most punctual • 80% on-time
Morning flights
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to book
2 weeks
in advance
Our data shows that travellers who book at least 2 weeks in advance save around 37% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 16% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Boston!
Flight Deals
Booking Insights
Expert advice
Flight 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

Tue, 12 May - Tue, 19 May
Delta Logo
07:00 - 10:35
ORD
-
BOS
2h 35mdirect
Delta Logo
07:35 - 09:27
BOS
-
ORD
2h 52mdirect
£117Delta
Tue, 21 Apr - Wed, 22 Apr
United Airlines Logo
18:23 - 21:59
ORD
-
BOS
2h 36mdirect
United Airlines Logo
07:15 - 09:14
BOS
-
ORD
2h 59mdirect
£123United Airlines
Tue, 5 May - Tue, 12 May
Southwest Logo
14:40 - 22:30
ORD
-
BOS
6h 50m
1 stop
Southwest Logo
07:35 - 16:05
BOS
-
ORD
9h 30m
2 stops
£124Southwest
Tue, 12 May - Tue, 12 May
Delta Logo
06:00 - 14:15
ORD
-
BOS
7h 15m
1 stop
Delta Logo
20:40 - 22:35
BOS
-
ORD
2h 55mdirect
£124Delta
Tue, 28 Apr - Tue, 12 May
United Airlines Logo
18:23 - 21:59
ORD
-
BOS
2h 36mdirect
United Airlines Logo
15:00 - 16:58
BOS
-
ORD
2h 58mdirect
£126United Airlines
Wed, 13 May - Sun, 17 May
United Airlines Logo
06:00 - 09:25
ORD
-
BOS
2h 25mdirect
United Airlines Logo
06:00 - 08:00
BOS
-
ORD
3h 00mdirect
£127United Airlines
Tue, 12 May - Sat, 16 May
Delta Logo
07:00 - 10:35
ORD
-
BOS
2h 35mdirect
Delta Logo
17:30 - 19:33
BOS
-
ORD
3h 03mdirect
£129Delta
Sat, 2 May - Sun, 3 May
Delta Logo
06:00 - 09:26
ORD
-
BOS
2h 26mdirect
Delta Logo
06:00 - 08:09
BOS
-
ORD
3h 09mdirect
£130Delta
Sat, 2 May - Sun, 3 May
JetBlue Logo
06:00 - 09:15
ORD
-
BOS
2h 15mdirect
JetBlue Logo
07:02 - 08:59
BOS
-
ORD
2h 57mdirect
£130JetBlue
Tue, 5 May - Wed, 6 May
Delta Logo
06:25 - 13:59
ORD
-
BOS
6h 34m
1 stop
Delta Logo
12:00 - 16:47
BOS
-
ORD
5h 47m
1 stop
£132Delta
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.

How much is a return flight from Chicago O'Hare Intl Airport to Boston?

This analysis is based on the cheapest return trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to Boston departing in May.

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, Sunday is the cheapest day to fly on average and Monday is the most expensive. Flying from Boston back to Chicago, the best deals are generally found on Sunday, with Wednesday 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 £146 (return) on average. On the other hand, the most expensive months are April and March, where the average cost of round-trip tickets is £198 and £194 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 2 weeks before departure, which saves you about 37% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Find deals
Expert advice

Expert advice for your flight from Chicago to Boston

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on JetBlue

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 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 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

Good to know - Cheap tickets from Chicago to Boston

Low seasonJanuary
Cheapest flight£59
Best time to beat the crowds (12% less expensive on average)
Most popular time to fly (4% more expensive 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, British Airways, Iberia, and Finnair.

  • 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.

  • 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.

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

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Tuesday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Wednesday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Thursday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Friday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Saturday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Sunday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

See more direct flights

Direct returns

Boston Logan Intl to Chicago O'Hare Intl

Monday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Tuesday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Wednesday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Thursday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Friday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Saturday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 more

Sunday

American Airlines,Delta,JetBlue, +1 more

American Airlines,Delta, +2 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)