$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
Eurostars The Boxer
May 14 - May 17
Chicago (CHI) to Boston (BOS)
Reviewed on May 6, 2025
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
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Your Perfect BrooklineVacation Package
Orbitz gives you access to exclusive deals and discounts on flights from Chicago to Brookline. Mix and match hotels and Chicago to Brookline flights to create your dream vacation. All your options are displayed at a glance with the Orbitz Matrix Display, which shows your package savings and built-in extras, such as free nights.
Stress free Searches Even on the Move
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Don’t Forget the Car Rental
Need a car after your Chicago to Brookline flights? Not only do you get great rental deals when you book in advance with Orbitz, we can send your flight details to the car rental company, so it knows when your flight from Chicago to Brookline is delayed.
Low Price Guarantee
With the best deals and easy searching options, Orbitz make it easy and fun to find cheap Chicago to Brookline flights, a great hotel, or a full vacation package. With Orbitz’s low price guarantee, you always get great discounts on air ticket prices.
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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.