$51 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 $51 One Way, $101 Round Trip from Chicago to Rockport
Prices starting at $101 for return flights and $51 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
DoubleTree by Hilton Boston North Shore
Dec 12 - Dec 15
Chicago (ORD) to Boston (BOS)
Reviewed on Oct 17, 2025
The Revolution Hotel
Dec 27 - Dec 30
Chicago (MDW) to Boston (BOS)
Reviewed on Oct 30, 2025
AC Hotel by Marriott Boston Downtown
Dec 26 - Jan 2
Chicago (ORD) to Boston (BOS)
Boston (BOS) to Chicago (ORD)
Reviewed on Sep 23, 2025
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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Best Deals At Your Fingertips
Orbitz combines low prices on Chicago to Rockport flights with discounts on quality hotels. Using Orbitz’s Display Matrix, you can see all your options and savings easily. With our low price guarantee, you know you have the best deals at your fingertips.
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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.