$86 Cheap flight deals from Chicago (CHI) to Watertown (BOS)
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This Weekend's Flight Deals from Chicago to Watertown
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 $86 One Way, $167 Round Trip from Chicago to Watertown
Prices starting at $167 for return flights and $86 for one-way flights to Watertown were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Watertown economy flight packages
The Cove at Yarmouth by Westgate Resorts
Oct 11 - Oct 14
Chicago (CHI) to Boston (BOS)
Boston (BOS) to Chicago (CHI)
Reviewed on Jun 8, 2026
Furnished Apartment Near Longwood
Sep 26 - Sep 29
Chicago (CHI) to Boston (BOS)
Reviewed on Jul 6, 2026
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
Oct 9 - Oct 12
Chicago (ORD) to Boston (BOS)
Reviewed on Jul 27, 2026
Watertown packages with premium economy flights
Watertown first class flight packages
Battery Wharf Hotel, Boston Waterfront
Sep 26 - Sep 28
Chicago (ORD) to Boston (BOS)
Reviewed on Aug 18, 2026
The Langham, Boston
Sep 26 - Sep 28
Chicago (ORD) to Boston (BOS)
Reviewed on Aug 18, 2026
More About Flying To Watertown from Chicago
Route Information for Flights from Chicago to Watertown
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 Watertown
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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.