Find Cheap Flights from Chicago (CHI) to Brookline (BOS) from CHF 107

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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 53 for one-way flights and CHF 107 for return flights, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, 11 Feb - Wed, 11 Feb
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 107 Return, found 8 hours ago
CHF 107
Return
found 8 hours ago
Select JetBlue Airways flight, departing Wed, 11 Feb from O'Hare Intl. to Logan Intl., returning Wed, 11 Feb, priced at CHF 107 found 8 hours ago
Sat, 7 Feb - Wed, 11 Feb
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 111 Return, found 8 hours ago
CHF 111
Return
found 8 hours ago
Select JetBlue Airways flight, departing Sat, 7 Feb from O'Hare Intl. to Logan Intl., returning Wed, 11 Feb, priced at CHF 111 found 8 hours ago
Sat, 7 Feb - Tue, 17 Feb
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 144 Return, found 8 hours ago
CHF 144
Return
found 8 hours ago
Select JetBlue Airways flight, departing Sat, 7 Feb from O'Hare Intl. to Logan Intl., returning Tue, 17 Feb, priced at CHF 144 found 8 hours ago
Tue, 10 Feb - Thu, 12 Feb
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 158 Return, found 8 hours ago
CHF 158
Return
found 8 hours ago
Select Delta flight, departing Tue, 10 Feb from O'Hare Intl. to Logan Intl., returning Thu, 12 Feb, priced at CHF 158 found 8 hours ago
Thu, 12 Feb - Tue, 17 Feb
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 176 Return, found 8 hours ago
CHF 176
Return
found 8 hours ago
Select Delta flight, departing Thu, 12 Feb from O'Hare Intl. to Logan Intl., returning Tue, 17 Feb, priced at CHF 176 found 8 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 106
Average flight time
3 hours 20 mins

Best Day to Book Flight from Chicago to Brookline

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
JetBlue Airways, Delta
Distance
Direct Flight Time
Flight Price
CHF 107

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! (3,898 reviews)
Hotel was so cute and in a great spot, the only complaint I have is that the toilet was so low to the ground. Everything else was great

Reviewed on 1 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! (6,189 reviews)
Wonderful and friendly check in experience. The room was super nice and the bed very comfortable. This is my favorite place to stay in the area.

Reviewed on 29 Jan 2026

Opens in a new windowHarborside Inn Of Boston
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! (2,443 reviews)
Everything was perfect. Bed was extremely comfortable and the room was very clean. Would definitely recommend.

Reviewed on 2 Feb 2026

Opens in a new windowThe Revolution Hotel
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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)
Very nice hotel with excellent staff.

Reviewed on 28 Jan 2026

Opens in a new windowThe Langham, Boston
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
1 Broadway Everett MA
Dieses Hotel im luxuriösen Stil bietet dir einen angenehmen Aufenthalt in Everett. Freu dich auf WLAN-Internetzugang (kostenlos), Parken ohne Service (kostenlos) ...
9.6/10 Exceptional! (3,536 reviews)
Everything wonderful

Reviewed on 27 Jan 2026

Opens in a new windowEncore Boston Harbor
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Dieses Hotel für Geschäftsreisende bietet dir einen angenehmen Aufenthalt in Boston. Freu dich auf WLAN-Internetzugang (kostenlos), 2 Restaurants und Frühstück ...
9.6/10 Exceptional! (3,949 reviews)
Clean, comfortable and my son really enjoyed the indoor pool

Reviewed on 1 Feb 2026

Opens in a new windowSeaport Hotel 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.