$48 Cheap flight deals from Chicago (CHI) to Portsmouth (BOS)

Choose two or more items and save on your trip:

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 $48 One Way, $107 Round Trip from Chicago to Portsmouth

Prices starting at $107 for return flights and $48 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

Price found within the past 48 hours. Click for updated prices.
La Casa Inn & Suites - Middleboro
Sonesta Select Boston Lowell Chelmsford
Washington Park Motel
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
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Portsmouth

Orbitz guarantees you low prices on flights from Chicago to Portsmouth. In addition to low fares on Chicago to Portsmouth flights, Orbitz offers fantastic savings on hotels, cruises, vacation packages, and more.

Earn Miles While Saving

Besides helping you fly for the lowest fares, Orbitz lets you earn miles for your frequent flyer program for certain flights from Chicago to Portsmouth. If you are a member of the frequent flyer or loyalty program offered by the airline you booked through Orbitz or a partner airline’s, simply add your frequent flyer number to your Orbitz reservation to get credit for your Chicago to Portsmouth flights.

Travel Planning Made Easy

We help take some of the anxiety out of your Chicago to Portsmouth flights with free flight alerts. We will let you know of flight changes and delays to your flights from Chicago to Portsmouth by email, voicemail, or text messages to your mobile phone. Alerts can also be sent to up to six other contacts to keep family and business teams informed.

Use Mobile Apps with Orbitz

Orbitz lets you find the best deals on Chicago to Portsmouth flights while on the go, with our easy-to-use Android and iPhone mobile apps. Easily check flight status, gate numbers, and other flight details all in one place with our app—which is great when you are in a hurry. You can use the apps to access great mobile deals on flights and amazing hotel rooms.

Frequently asked questions

Are there non-stop flights from Chicago to Portsmouth?
Direct flights are offered by no less than 4 airlines from Chicago, IL (ORD-O’Hare Intl.) to BOS, which means you could be booking your fun-filled getaway within moments. Here are some reputable carriers to consider:

  • United Airlines
  • American Airlines
  • Delta
  • JetBlue

What is the shortest flight from Chicago to Portsmouth?
The journey from Chicago to Portsmouth can be as fast as 2 hours and 59 minutes. With a leisurely flight time like this, why not organize an impromptu getaway?
What airlines fly from Chicago to Portsmouth most frequently?
Feed your wanderlust and travel with one of the following carriers that offer the most frequent flights from Chicago to Portsmouth: United Airlines - (UA) with 208 flights every month American Airlines - (AA) with 199 flights every month Delta - (DL) with 147 flights every month JetBlue - (B6) with 56 flights every month
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

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.