$104 Cheap flight deals from Chicago (CHI) to Rockport (BOS)
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This Weekend's Flight Deals from Chicago to Rockport
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 $104 One Way, $198 Round Trip from Chicago to Rockport
Prices starting at $198 for return flights and $104 for one-way flights to Rockport were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Rockport economy flight packages
The Cove at Yarmouth by Westgate Resorts
Oct 23 - Oct 28
Chicago (CHI) to Boston (BOS)
Boston (BOS) to Chicago (CHI)
Reviewed on Jun 8, 2026
Inn on the Square
Oct 23 - Oct 28
Chicago (CHI) to Boston (BOS)
Boston (BOS) to Chicago (CHI)
Reviewed on Sep 1, 2026
Rockport first class flight packages
Hampton Inn & Suites Springfield/Downtown
Oct 22 - Oct 25
Chicago (CHI) to Boston (BOS)
Reviewed on Aug 30, 2026
Hampton Inn West Springfield
Oct 22 - Oct 25
Chicago (CHI) to Boston (BOS)
Reviewed on Sep 4, 2026
More About Flying To Rockport from Chicago
Route Information for Flights from Chicago to Rockport
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | BOS |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Rockport
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You can always find affordable flights from Chicago to Rockport on Orbitz. Use different airlines to book arrival and departure flights, take advantage of vacation package deals, and secure exclusive rewards.
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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.