$72 Cheap flight deals from Chicago (CHI) to Brookline (BOS)
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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.
Airfares from $72 One Way, $135 Round Trip from Chicago to Brookline
Prices starting at $135 for return flights and $72 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.
Brookline economy flight packages
Arcadian Hotel
Apr 28 - May 5
Chicago (CHI) to Boston (BOS)
Reviewed on Mar 20, 2026
Boston Harbor Hotel
May 14 - May 17
Chicago (CHI) to Boston (BOS)
Reviewed on Mar 24, 2024
The Langham, Boston
May 14 - May 17
Chicago (CHI) to Boston (BOS)
Reviewed on Jan 12, 2026
Brookline packages with premium economy flights
The Revolution Hotel
May 8 - May 11
Chicago (CHI) to Boston (BOS)
Reviewed on Jan 19, 2026
Boston Harbor Hotel
May 8 - May 11
Chicago (CHI) to Boston (BOS)
Reviewed on Mar 24, 2024
Eurostars The Boxer
May 8 - May 11
Chicago (CHI) to Boston (BOS)
Reviewed on May 6, 2025
Brookline first class flight packages
Arcadian Hotel
May 22 - May 24
Chicago (CHI) to Boston (BOS)
Reviewed on Mar 20, 2026
Eurostars The Boxer
May 22 - May 24
Chicago (CHI) to Boston (BOS)
Reviewed on May 6, 2025
More About Flying To Brookline from Chicago
Route Information for Flights from Chicago to Brookline
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | BOS |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Brookline
Orbitz is the best place to find guaranteed low prices on Chicago to Brookline flights. Because of our cutting-edge mobile tools and low fares on domestic and international flights, Orbitz is the best starting point for travelers.
Find Cheap Chicago to Brookline Flights
Orbitz offers free mobile apps for iPhone and Android devices—a great way to find fantastic deals on flights from Chicago to Brookline. Not only that, but you can check the status of your flight or even book low cost hotel rooms with the apps or on m.orbitz.com.
Get Miles and Points for Your Flight
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Flight Alerts Take Away the Stress
Orbitz does not want travelers to worry on their flights from Chicago to Brookline. We keep you updated on any flight changes for Chicago to Brookline flights with alerts sent directly to your email or a mobile device. These alerts can also be sent to friends and family.
Discount Travel Planning Made Simple
You will have no problems finding budget flights from Chicago to Brookline on Orbitz.com. If your travel plans are flexible, you can search for fares three days before and after a specific date to find the best price.
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.