$83 Cheap flight deals from Chicago (CHI) to Portsmouth (BOS)
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This Weekend's Flight Deals from Chicago to Portsmouth
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 $83 One Way, $156 Round Trip from Chicago to Portsmouth
Prices starting at $156 for return flights and $83 for one-way flights to Portsmouth were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Portsmouth economy flight packages
The Beverly
Oct 3 - Oct 6
Chicago (CHI) to Boston (BOS)
Reviewed on Aug 13, 2026
Good Hotels Boston
Sep 24 - Sep 27
Chicago (CHI) to Boston (BOS)
Reviewed on Aug 7, 2026
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
Sep 19 - Sep 26
Chicago (ORD) to Boston (BOS)
Boston (BOS) to Chicago (ORD)
Reviewed on Jul 27, 2026
Portsmouth packages with premium economy flights
The Langham, Boston
Oct 1 - Oct 4
Chicago (CHI) to Boston (BOS)
Reviewed on Aug 13, 2026
More About Flying To Portsmouth from Chicago
Route Information for Flights from Chicago to Portsmouth
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 Portsmouth
Low Cost Flights From Chicago to Portsmouth
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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.