Cheap Flight Deals From Chicago (CHI) to Portsmouth (BOS) Starting at $40

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

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 $40 One Way, $79 Round Trip from Chicago to Portsmouth

Prices starting at $79 for return flights and $40 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

Boston Marriott Burlington
Sheraton Boston, a Marriott Hotel
Hilton Boston Downtown/Faneuil Hall
Don't see what you're looking for?
See all available trips from Chicago to Portsmouth
View all trips

Portsmouth first class flight packages

The Ritz-Carlton, Boston
Boston Marriott Burlington
Hilton Boston Downtown/Faneuil Hall
Don't see what you're looking for?
See all available trips from Chicago to Portsmouth
View all trips

More About Flying To Portsmouth from Chicago

Route Information for Flights from Chicago to Portsmouth

Origin Airport IATA Code CHI
Destination Airport IATA Code BOS
Distance 863 mi
Direct Flight Airlines American Airlines, KLM, Qatar Airways, JAL, Azul, Icelandair, Emirates, Delta Air Lines, Air New Zealand, United Airlines, Alaska Airlines, JetBlue Airways, Southwest Airlines, Royal Jordanian, SAS, Iberia, Hawaiian Airlines, Korean Air, ANA, TAP Air Portugal, Virgin Atlantic, British Airways
Earliest Flight Arrival 2:18PM UTC
Latest Flight Arrival 4:27AM UTC

Chicago to Portsmouth

Planning a romantic getaway, traveling the world at last or flying out to see the kids and grandkids? Orbitz On-the-Go saves you both time and money. Our cutting edge mobile tools and guaranteed low prices leave plenty of room in your budget for the important things in life. Find same-day deals on domestic flights from Chicago to Portsmouth, and bargain sales on international Chicago to Portsmouth flights.

Family Matters, and So Do Cheap Tickets

Don’t miss another birthday, graduation or wedding, wherever they are. Take advantage of Orbitz On-the-Go’s discount travel planning features to save on flights from Chicago to Portsmouth and Chicago to Portsmouth flights. Tell them you’ll be there, every single time.

Escape to Romance

Treat yourself and the one you love to a romantic hideaway. Orbitz budget air flights from Chicago to Portsmouth and Chicago to Portsmouth flights can be bundled into packages for extravagant savings at spa resorts and hotels.

See the World

It’s finally your time. Go wherever the wind takes you. Orbitz On-the-Go makes dreams come true. Book low fare flights from Chicago to Portsmouth, the world is at your fingertips.

Flight or Gate Changes? No Problem

Once you’ve reserved your low cost air ticket on Chicago to Portsmouth flights or flights from Chicago to Portsmouth, stay informed with Orbitz On-the-Go free alerts. Choose from email, voice and text notification. You’ll always know your flight status and gate number, and where and how to pick up your bags.

Frequently asked questions

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.