$51 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 $51 One Way, $115 Round Trip from Chicago to Brookline
Prices starting at $115 for return flights and $51 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
Club Quarters Hotel Faneuil Hall, Boston
Jan 8 - Jan 11
Chicago (CHI) to Boston (BOS)
Reviewed on Nov 11, 2025
Boston Lodge and Suites
Dec 15 - Dec 19
Chicago (CHI) to Boston (BOS)
Boston (BOS) to Chicago (CHI)
Reviewed on Jul 19, 2019
The Colonnade Hotel Back Bay
Dec 26 - Dec 31
Chicago (ORD) to Boston (BOS)
Reviewed on Aug 1, 2025
More About Flying To Brookline from Chicago
Route Information for Flights from Chicago to Brookline
Origin Airport IATA Code | CHI |
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Destination Airport IATA Code | BOS |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Brookline
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Mobile Apps for Chicago to Brookline Flights
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Budget Flying Made Simple
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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.