$70 Cheap flight deals from Chicago (CHI) to Rye (BOS)
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This Weekend's Flight Deals from Chicago to Rye
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 $70 One Way, $130 Round Trip from Chicago to Rye
Prices starting at $130 for return flights and $70 for one-way flights to Rye were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Rye economy flight packages
Hotel 1620 Plymouth Harbor
May 21 - May 25
Chicago (CHI) to Boston (BOS)
Reviewed on Oct 3, 2025
The Inn at Hastings Park, Relais & Chateaux - Boston
May 25 - May 30
Chicago (ORD) to Boston (BOS)
Reviewed on Feb 13, 2025
The Langham, Boston
May 18 - May 21
Chicago (CHI) to Boston (BOS)
Boston (BOS) to Chicago (CHI)
Reviewed on Jan 12, 2026
Rye first class flight packages
Eurostars The Boxer
Jun 3 - Jun 5
Chicago (ORD) to Boston (BOS)
Reviewed on May 6, 2025
Boston Harbor Hotel
Jun 3 - Jun 5
Chicago (ORD) to Boston (BOS)
Reviewed on Mar 24, 2024
The Colonnade Hotel Back Bay
Jun 3 - Jun 5
Chicago (ORD) to Boston (BOS)
Reviewed on Aug 1, 2025
More About Flying To Rye from Chicago
Route Information for Flights from Chicago to Rye
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 Rye
Looking for cheap Chicago to Rye flights? Orbitz has the cheapest air fares for flights from Chicago to Rye. Plus, with our cutting-edge mobile tools, travel planning has never been easier or more wallet-friendly.
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Cheap Air Ticket Prices Guaranteed
Orbitz is your number one source for low fares for Chicago to Rye flights. Our low price guarantee on domestic and international air tickets give you great savings for a perfect trip to Rye. Need hotels too? You can book them last minute on your mobile phone.
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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.