Find Cheap Flights from Chicago (CHI) to Brookline (BOS) from CHF 285

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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 73 for one-way flights and CHF 285 for return flights, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, 23 Aug - Mon, 24 Aug
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 285 Return, found 1 day ago
CHF 285
Return
found 1 day ago
Select Delta flight, departing Sun, 23 Aug from O'Hare Intl. to Logan Intl., returning Mon, 24 Aug, priced at CHF 285 found 1 day ago
Sun, 23 Aug - Mon, 24 Aug
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 289 Return, found 1 day ago
CHF 289
Return
found 1 day ago
Select Delta flight, departing Sun, 23 Aug from O'Hare Intl. to Logan Intl., returning Mon, 24 Aug, priced at CHF 289 found 1 day ago
Sun, 23 Aug - Mon, 24 Aug
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 293 Return, found 1 day ago
CHF 293
Return
found 1 day ago
Select Delta flight, departing Sun, 23 Aug from O'Hare Intl. to Logan Intl., returning Mon, 24 Aug, priced at CHF 293 found 1 day ago
Sun, 23 Aug - Mon, 24 Aug
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 297 Return, found 1 day ago
CHF 297
Return
found 1 day ago
Select American Airlines flight, departing Sun, 23 Aug from O'Hare Intl. to Logan Intl., returning Mon, 24 Aug, priced at CHF 297 found 1 day ago
Sun, 23 Aug - Mon, 24 Aug
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 300 Return, found 1 day ago
CHF 300
Return
found 1 day ago
Select United flight, departing Sun, 23 Aug from O'Hare Intl. to Logan Intl., returning Mon, 24 Aug, priced at CHF 300 found 1 day 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 284
Average flight time
3 hours 24 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, American Airlines
Distance
Direct Flight Time
Flight Price
CHF 285

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

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! (4,016 reviews)
I didn't feel parking was safe, and the room was not cleaned.

Reviewed on 14 Apr 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! (4,600 reviews)
Room was amazing, concier

Reviewed on 14 Apr 2026

Opens in a new windowOmni Boston Hotel at the Seaport
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! (4,198 reviews)
Only stayed for one night didn’t use any of the amenities. Room was clean

Reviewed on 14 Apr 2026

Opens in a new windowSeaport Hotel Boston
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Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Dieses Hotel im luxuriösen Stil bietet dir einen angenehmen Aufenthalt in Boston. Freu dich auf 2 Restaurants, 2 Bars/Lounges und Frühstück (gegen Gebühr). Die ...
8.4/10 Very Good! (3,162 reviews)
Clean room great location

Reviewed on 14 Apr 2026

Opens in a new windowHilton Boston Park Plaza
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! (6,464 reviews)
The ac could be a little cooler but other than that it was awesome

Reviewed on 14 Apr 2026

Opens in a new windowHarborside Inn Of Boston
Omni Parker House

Omni Parker House

4.5 out of 5
60 School 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 ...
9/10 Wonderful! (3,410 reviews)
Enjoyed our stay

Reviewed on 13 Apr 2026

Opens in a new windowOmni Parker House
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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.