
$75 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 $75 One Way, $149 Round Trip from Chicago to Brookline
Prices starting at $149 for return flights and $75 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


Sunbird Cape Cod Resort
Aug 8 - Aug 16
Chicago (CHI) to Boston (BOS)
Reviewed on Oct 12, 2025

Nantucket Inn
Aug 11 - Aug 15
Chicago (CHI) to Boston (BOS)
Reviewed on Aug 19, 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
Chicago to Brookline flights are offered at fantastic discount by Orbitz. Book air tickets now and cut those extra costs out of your travel budget to ensure a rewarding travel experience. With guaranteed low prices like these, can you afford to miss this discount?
Book cheap flights from Chicago to Brookline
Cheap airfares are available on flights from Chicago to Brookline. Use Orbitz to find the best flights that suit both your budget and the travel times that you need. Travelers who are looking for discounted rates on domestic or international flights need to look no further than Orbitz.
Orbitz goes mobile
As the world of technology rapidly expands around us, we are continuously finding new ways to improve our services, communications, and accessibility. With our cutting-edge mobile tools now available on Android, iPhone, and tablets, you can access detailed information on your bookings for flights from Chicago to Brookline at any time or anywhere. See your itinerary for your Chicago to Brookline flights, baggage and gate claim details, as well as hotel deals with our easy-to-use apps.
Get a great package with your Chicago to Brookline flights
With frequent updates on your flight status, including delays and changes in bookings, traveling becomes more hassle-free than ever. Not only do we offer huge discounted deals on flights from Chicago to Brookline, we also have fantastic savings on vacation packages, hotel room, cruises, activities, and car rentals so you can pick and choose and create the best travel package for you.
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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.




