Find Cheap Flights from Chicago (CHI) to Brookline (BOS) from CHF 113

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Selected flight deals from Chicago to Brookline

The lowest prices found within the past 7 days from Chicago to Brookline were CHF 57 for one-way flights and CHF 113 for return flights, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, 14 Oct - Wed, 21 Oct
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 113 Return, found 20 hours ago
CHF 113
Return
found 20 hours ago
Select Delta flight, departing Wed, 14 Oct from O'Hare Intl. to Logan Intl., returning Wed, 21 Oct, priced at CHF 113 found 20 hours ago
Wed, 14 Oct - Wed, 21 Oct
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 133 Return, found 20 hours ago
CHF 133
Return
found 20 hours ago
Select Delta flight, departing Wed, 14 Oct from O'Hare Intl. to Logan Intl., returning Wed, 21 Oct, priced at CHF 133 found 20 hours ago
Wed, 14 Oct - Wed, 21 Oct
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 139 Return, found 20 hours ago
CHF 139
Return
found 20 hours ago
Select Delta flight, departing Wed, 14 Oct from O'Hare Intl. to Logan Intl., returning Wed, 21 Oct, priced at CHF 139 found 20 hours ago
Wed, 14 Oct - Wed, 21 Oct
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 147 Return, found 20 hours ago
CHF 147
Return
found 20 hours ago
Select Delta flight, departing Wed, 14 Oct from O'Hare Intl. to Logan Intl., returning Wed, 21 Oct, priced at CHF 147 found 20 hours ago
Wed, 14 Oct - Wed, 21 Oct
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 148 Return, found 20 hours ago
CHF 148
Return
found 20 hours ago
Select Delta flight, departing Wed, 14 Oct from O'Hare Intl. to Logan Intl., returning Wed, 21 Oct, priced at CHF 148 found 20 hours ago
Cheap Flights from Chicago to Brookline & Flight Information
Origin airport IATA code
ORD
Destination airport IATA code
BOS
Number of flight options
1
Return price
CHF 112
Average flight time
3 hours 20 mins

Brookline Flight Information

Traveling From
Chicago
Origin Airport IATA Code
CHI
Traveling To
Brookline
Destination Airport IATA Code
BOS
Number of Airlines Serving
Available Airlines
Delta, American Airlines
Distance
Direct Flight Time
Flight Price
CHF 113

Need a car after flight from Chicago to Brookline

Economy

Chevrolet Spark or similar
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Jeep Compass
SUV Jeep Compass

Place to stay after flight from Chicago to Brookline

The Arcadian Hotel

The Arcadian Hotel

3.5 out of 5
1200 Beacon St Brookline MA
Dieses Hotel bietet dir einen angenehmen Aufenthalt in Brookline. Freu dich auf inbegriffenes Frühstück, WLAN-Internetzugang (kostenlos) und Fitnessbereich (rund ...
8/10 Very Good! (3,903 reviews)
Decent room. Great staff. On-site parking. 24 hour coffee and tea in lobby.

Reviewed on 19 Feb 2026

Opens in a new windowThe Arcadian Hotel
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
Dieses Hotel bietet dir einen angenehmen Aufenthalt in Boston. Freu dich auf WLAN-Internetzugang (kostenlos), eine rund um die Uhr besetzte Rezeption und Businesscenter. ...
9.2/10 Wonderful! (6,280 reviews)
Great location!

Reviewed on 19 Feb 2026

Opens in a new windowHarborside Inn Of Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Dieses Hotel im luxuriösen Stil bietet dir einen angenehmen Aufenthalt in Boston. Freu dich auf WLAN-Internetzugang (kostenlos), Wellnessbereich und 4 Restaurants. ...
9.2/10 Wonderful! (4,491 reviews)
Yes

Reviewed on 20 Feb 2026

Opens in a new windowOmni Boston Hotel at the Seaport
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The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Dieses Hotel bietet dir einen angenehmen Aufenthalt in Boston. Freu dich auf WLAN-Internetzugang (kostenlos), Frühstück (gegen Gebühr) und Fitnessbereich (rund ...
9/10 Wonderful! (2,482 reviews)
Staff, rooms and hotels were clean

Reviewed on 20 Feb 2026

Opens in a new windowThe Revolution Hotel
The Langham, Boston

The Langham, Boston

5 out of 5
250 Franklin St Boston MA
Dieses Hotel im luxuriösen Stil bietet dir einen angenehmen Aufenthalt in Boston. Freu dich auf WLAN-Internetzugang (kostenlos), Frühstück (gegen Gebühr) und ...
9.6/10 Exceptional! (1,001 reviews)
It’s very clean

Reviewed on 19 Feb 2026

Opens in a new windowThe Langham, Boston
The Dagny Boston

The Dagny Boston

4 out of 5
89 Broad Street Boston MA
Dieses Hotel im luxuriösen Stil bietet dir einen angenehmen Aufenthalt in Boston. Freu dich auf WLAN-Internetzugang (kostenlos), Frühstück (gegen Gebühr) und ...
9.4/10 Exceptional! (7,078 reviews)
Staff was incredibly friendly. Bed was a bit uncomfortable.

Reviewed on 19 Feb 2026

Opens in a new windowThe Dagny Boston
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

^Savings based on all holiday package bookings with Flight + Hotel made on ebookers.ie from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.