Find Cheap Flights from Chicago (CHI) to Brookline (BOS) from CHF 198

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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 56 for one-way flights and CHF 198 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 198 Return, found 4 days ago
CHF 198
Return
found 4 days ago
Select JetBlue Airways flight, departing Sun, 23 Aug from O'Hare Intl. to Logan Intl., returning Mon, 24 Aug, priced at CHF 198 found 4 days ago
Sun, 23 Aug - Mon, 24 Aug
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 203 Return, found 4 days ago
CHF 203
Return
found 4 days ago
Select United flight, departing Sun, 23 Aug from O'Hare Intl. to Logan Intl., returning Mon, 24 Aug, priced at CHF 203 found 4 days ago
Sun, 23 Aug - Mon, 24 Aug
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 210 Return, found 4 days ago
CHF 210
Return
found 4 days ago
Select Delta flight, departing Sun, 23 Aug from O'Hare Intl. to Logan Intl., returning Mon, 24 Aug, priced at CHF 210 found 4 days ago
Sun, 23 Aug - Mon, 24 Aug
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 213 Return, found 4 days ago
CHF 213
Return
found 4 days ago
Select JetBlue Airways flight, departing Sun, 23 Aug from O'Hare Intl. to Logan Intl., returning Mon, 24 Aug, priced at CHF 213 found 4 days ago
Sun, 23 Aug - Mon, 24 Aug
ORD
O'Hare Intl.
BOS
Logan Intl.
CHF 223 Return, found 4 days ago
CHF 223
Return
found 4 days ago
Select JetBlue Airways flight, departing Sun, 23 Aug from O'Hare Intl. to Logan Intl., returning Mon, 24 Aug, priced at CHF 223 found 4 days 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 197
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
JetBlue Airways, Delta, United
Distance
Direct Flight Time
Flight Price
CHF 198

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! (3,958 reviews)
Dirty footprint in the shower, broken mirror had to make your own bed. They have overcharged what was promised from Expedia. What seemed like a deal I have now been been charged triple

Reviewed on 25 Mar 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! (4,543 reviews)
PERFECT

Reviewed on 24 Mar 2026

Opens in a new windowOmni Boston Hotel at the Seaport
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! (3,135 reviews)
Best hotel experience I’ve ever had. The complementary waters made all the difference. Having access to an awesome gym was also amazing for people who enjoy fitness and gyms while traveling.

Reviewed on 24 Mar 2026

Opens in a new windowHilton Boston Park Plaza
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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! (4,094 reviews)
Clean, beautiful room

Reviewed on 25 Mar 2026

Opens in a new windowSeaport Hotel Boston
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! (6,380 reviews)
It was a great location spot and affordable compared to other hotels

Reviewed on 26 Mar 2026

Opens in a new windowHarborside Inn Of 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! (7,137 reviews)
Wonderful place to stay!!

Reviewed on 25 Mar 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.