$70 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 $70 One Way, $130 Round Trip from Chicago to Brookline
Prices starting at $130 for return flights and $70 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
The Langham, Boston
May 10 - May 13
Chicago (CHI) to Boston (BOS)
Boston (BOS) to Chicago (CHI)
Reviewed on Jan 12, 2026
Boston Harbor Hotel
May 10 - May 13
Chicago (CHI) to Boston (BOS)
Boston (BOS) to Chicago (CHI)
Reviewed on Mar 24, 2024
The Inn at Hastings Park, Relais & Chateaux - Boston
May 25 - May 30
Chicago (ORD) to Boston (BOS)
Reviewed on Feb 13, 2025
Brookline first class flight packages
Eurostars The Boxer
Jun 3 - Jun 5
Chicago (ORD) to Boston (BOS)
Reviewed on May 6, 2025
Boston Harbor Hotel
Jun 3 - Jun 5
Chicago (ORD) to Boston (BOS)
Reviewed on Mar 24, 2024
The Colonnade Hotel Back Bay
Jun 3 - Jun 5
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 |
|---|---|
Destination Airport IATA Code | BOS |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Brookline
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Best Deals At Your Fingertips
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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.