$49 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 $49 One Way, $97 Round Trip from Chicago to Brookline
Prices starting at $97 for return flights and $49 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
Hyatt Regency Boston
Feb 24 - Mar 2
Chicago (ORD) to Boston (BOS)
Boston (BOS) to Chicago (ORD)
Reviewed on Dec 21, 2025
The Langham, Boston
Mar 13 - Mar 16
Chicago (CHI) to Boston (BOS)
Reviewed on Jan 12, 2026
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 guarantees you low prices on flights from Chicago to Brookline. In addition to low fares on Chicago to Brookline flights, Orbitz offers fantastic savings on hotels, cruises, vacation packages, and more.
Earn Miles While Saving
Besides helping you fly for the lowest fares, Orbitz lets you earn miles for your frequent flyer program for certain flights from Chicago to Brookline. If you are a member of the frequent flyer or loyalty program offered by the airline you booked through Orbitz or a partner airline’s, simply add your frequent flyer number to your Orbitz reservation to get credit for your Chicago to Brookline flights.
Travel Planning Made Easy
We help take some of the anxiety out of your Chicago to Brookline flights with free flight alerts. We will let you know of flight changes and delays to your flights from Chicago to Brookline by email, voicemail, or text messages to your mobile phone. Alerts can also be sent to up to six other contacts to keep family and business teams informed.
Use Mobile Apps with Orbitz
Orbitz lets you find the best deals on Chicago to Brookline flights while on the go, with our easy-to-use Android and iPhone mobile apps. Easily check flight status, gate numbers, and other flight details all in one place with our app—which is great when you are in a hurry. You can use the apps to access great mobile deals on flights and amazing hotel rooms.
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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.