$109 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 $109 One Way, $198 Round Trip from Chicago to Brookline
Prices starting at $198 for return flights and $109 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 Cove at Yarmouth by Westgate Resorts
Oct 22 - Oct 27
Chicago (ORD) to Boston (BOS)
Reviewed on Jun 8, 2026
Furnished Apartment Near Longwood
Oct 8 - Oct 11
Chicago (ORD) to Boston (BOS)
Boston (BOS) to Chicago (ORD)
Reviewed on Jul 6, 2026
Brookline packages with premium economy flights
HomeAwhile
Oct 15 - Oct 18
Chicago (ORD) to Boston (BOS)
Reviewed on Sep 2, 2026
The Newbury Boston
Oct 15 - Oct 19
Chicago (CHI) to Boston (BOS)
Boston (BOS) to Chicago (CHI)
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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Booking a trip from Chicago to Brookline has never been easier. Not only will you find great deals on flights, we offer bargains on cruises, car rentals, top-notch hotels, and more. You can also research and add local activities in Brookline to your flight or hotel reservation to keep the kids happy and active.
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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.