Find Cheap Flights from Chicago (CHI) to Brookline (BOS) from CHF 158

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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 110 for one-way flights and CHF 158 for return flights, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, 12 Sept - Sat, 12 Sept
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 158 Return, found 16 hours ago
CHF 158
Return
found 16 hours ago
Select JetBlue Airways flight, departing Sat, 12 Sept from O'Hare Intl. to Logan Intl., returning Sat, 12 Sept, priced at CHF 158 found 16 hours ago
Sat, 12 Sept - Tue, 22 Sept
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 161 Return, found 16 hours ago
CHF 161
Return
found 16 hours ago
Select JetBlue Airways flight, departing Sat, 12 Sept from O'Hare Intl. to Logan Intl., returning Tue, 22 Sept, priced at CHF 161 found 16 hours ago
Mon, 14 Sept - Mon, 14 Sept
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 163 Return, found 16 hours ago
CHF 163
Return
found 16 hours ago
Select JetBlue Airways flight, departing Mon, 14 Sept from O'Hare Intl. to Logan Intl., returning Mon, 14 Sept, priced at CHF 163 found 16 hours ago
Thu, 10 Sept - Sat, 19 Sept
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 164 Return, found 16 hours ago
CHF 164
Return
found 16 hours ago
Select JetBlue Airways flight, departing Thu, 10 Sept from O'Hare Intl. to Logan Intl., returning Sat, 19 Sept, priced at CHF 164 found 16 hours ago
Wed, 16 Sept - Wed, 16 Sept
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 169 Return, found 16 hours ago
CHF 169
Return
found 16 hours ago
Select Delta flight, departing Wed, 16 Sept from O'Hare Intl. to Logan Intl., returning Wed, 16 Sept, priced at CHF 169 found 16 hours ago
Cheap Flights from Chicago to Brookline & Flight Information
Origin airport IATA code
ORD
Destination airport IATA code
BOS
Number of flight options
2
Return price
CHF 158
Average flight time
3 hours 28 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, United, JetBlue Airways
Distance
Direct Flight Time
Flight Price
CHF 158

Need a car after flight from Chicago to Brookline

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Place to stay after flight from Chicago to Brookline

Arcadian Hotel

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! (4,215 reviews)
"Good hotel but worst breakfast I’ve had when staying abroad"

Reviewed on 17 Jun 2026

Opens in a new windowArcadian Hotel
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! (4,750 reviews)
"Beautiful place to stay."

Reviewed on 18 Jun 2026

Opens in a new windowOmni Boston Hotel at the Seaport
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! (2,674 reviews)
"Was very g"

Reviewed on 17 Jun 2026

Opens in a new windowThe Revolution Hotel
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The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
505 Washington Street Boston MA
Dieses Hotel im Boutique-Stil bietet dir einen angenehmen Aufenthalt in Boston. Freu dich auf Frühstück (gegen Gebühr), Zimmerservice (bitte Zeiten beachten) ...
9.4/10 Exceptional! (5,096 reviews)
"Amazing location, great amenities, and friendly staff. Perfect stay, would go back in a heartbeat."

Reviewed on 18 Jun 2026

Opens in a new windowThe Godfrey Hotel Boston
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 ...
9.8/10 Exceptional! (1,001 reviews)
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Reviewed on 15 Jun 2026

Opens in a new windowThe Langham, Boston
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
Dieses Hotel für Geschäftsreisende bietet dir einen angenehmen Aufenthalt in Cambridge. Freu dich auf WLAN-Internetzugang (kostenlos), Frühstück (gegen Gebühr) ...
9/10 Wonderful! (2,366 reviews)
"Great stay, fantastic hotel and location"

Reviewed on 17 Jun 2026

Opens in a new windowHyatt Regency Boston/Cambridge
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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.