$101 Cheap flight deals from Chicago (CHI) to Brookline (BOS)

This Weekend's Flight Deals from Chicago to Brookline

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Oct 11 - Wed, Oct 14
MDW
Midway Intl.
BOS
Logan Intl.
$368 Roundtrip, found 1 day ago
$368
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Oct 11 from Midway Intl. to Logan Intl., returning Wed, Oct 14, priced at $368 found 1 day ago
Sun, Oct 11 - Sat, Oct 17
ORD
O'Hare Intl.
BOS
Logan Intl.
$378 Roundtrip, found 9 hours ago
$378
Roundtrip
found 9 hours ago
Select Delta flight, departing Sun, Oct 11 from O'Hare Intl. to Logan Intl., returning Sat, Oct 17, priced at $378 found 9 hours ago

Airfares from $101 One Way, $192 Round Trip from Chicago to Brookline

Prices starting at $192 for return flights and $101 for one-way flights to Brookline were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Nov 14 - Mon, Nov 16
ORD
Chicago
BOS
Boston
$192 Roundtrip, found 4 hours ago
$192
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Sat, Nov 14 from Chicago to Boston, returning Mon, Nov 16, priced at $192 found 4 hours ago
Thu, Dec 3 - Mon, Dec 7
ORD
Chicago
BOS
Boston
$192 Roundtrip, found 4 hours ago
$192
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Thu, Dec 3 from Chicago to Boston, returning Mon, Dec 7, priced at $192 found 4 hours ago
Mon, Dec 7 - Thu, Dec 10
ORD
Chicago
BOS
Boston
$197 Roundtrip, found 7 hours ago
$197
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Mon, Dec 7 from Chicago to Boston, returning Thu, Dec 10, priced at $197 found 7 hours ago
Sat, Nov 7 - Mon, Nov 9
ORD
Chicago
BOS
Boston
$201 Roundtrip, found 6 hours ago
$201
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Sat, Nov 7 from Chicago to Boston, returning Mon, Nov 9, priced at $201 found 6 hours ago
Sat, Nov 7 - Mon, Nov 9
ORD
Chicago
BOS
Boston
$201 Roundtrip, found 6 hours ago
$201
Roundtrip
found 6 hours ago
Select Delta flight, departing Sat, Nov 7 from Chicago to Boston, returning Mon, Nov 9, priced at $201 found 6 hours ago

Brookline economy flight packages

Price found within the past 48 hours. Click for updated prices.
Battery Wharf Hotel, Boston Waterfront
4.5-star property

Battery Wharf Hotel, Boston Waterfront

9/10 Wonderful! (2,041 reviews)

Nov 25 - Nov 27

2 night stay

Chicago (CHI) to Boston (BOS)

Delta • Roundtrip • Coach
Price was $715, price is now $497 per person
$497
per person
found 1 day ago

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,008 reviews)

Nov 25 - Nov 27

2 night stay

Chicago (CHI) to Boston (BOS)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was $1,143, price is now $732 per person
$732
per person
found 1 day ago
Great location. A bit pricey for the size room. Easy to get most places by walking .

Reviewed on Oct 4, 2026

Four Seasons Hotel Boston
5.0-star property

Four Seasons Hotel Boston

9.4/10 Exceptional! (485 reviews)

Nov 5 - Nov 8

3 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,974, price is now $1,415 per person
$1,415
per person
found 1 day ago
Beautiful hotel Wonderful rooms and kids absolutely loved the vault ! Looking forward to staying again :)

Reviewed on Oct 3, 2026

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Brookline first class flight packages

Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer
4.0-star property

Eurostars The Boxer

8.8/10 Excellent! (1,609 reviews)

Nov 7 - Nov 11

4 night stay

Chicago (CHI) to Boston (BOS)

Delta • Roundtrip • FirstClass
Save 100% on your flight
Price was $1,344, price is now $986 per person
$986
per person
found 14 hours ago

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,008 reviews)

Nov 7 - Nov 11

4 night stay

Chicago (CHI) to Boston (BOS)

Delta • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,436, price is now $1,611 per person
$1,611
per person
found 14 hours ago
Great location. A bit pricey for the size room. Easy to get most places by walking .

Reviewed on Oct 4, 2026

The Langham, Boston
5.0-star property

The Langham, Boston

9.8/10 Exceptional! (1,005 reviews)

Nov 7 - Nov 11

4 night stay

Chicago (CHI) to Boston (BOS)

Delta • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,173, price is now $1,656 per person
$1,656
per person
found 14 hours ago
The staff were incredibly helpful & nice. The hotel was beautiful & great location

Reviewed on Oct 4, 2026

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