$71 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.

Sun, Jul 12 - Wed, Jul 15
MDW
Midway Intl.
BOS
Logan Intl.
$287 Roundtrip, found 2 days ago
$287
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sun, Jul 12 from Midway Intl. to Logan Intl., returning Wed, Jul 15, priced at $287 found 2 days ago
Fri, Jul 10 - Sat, Jul 11
RFD
Greater Rockford
BOS
Logan Intl.
$292 Roundtrip, found 3 days ago
$292
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Jul 10 from Greater Rockford to Logan Intl., returning Sat, Jul 11, priced at $292 found 3 days ago
Fri, Jul 10 - Sun, Jul 12
ORD
O'Hare Intl.
BOS
Logan Intl.
$334 Roundtrip, found 4 hours ago
$334
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Fri, Jul 10 from O'Hare Intl. to Logan Intl., returning Sun, Jul 12, priced at $334 found 4 hours ago

Airfares from $71 One Way, $141 Round Trip from Chicago to Portsmouth

Prices starting at $141 for return flights and $71 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.

Wed, Sep 16 - Sat, Sep 19
ORD
Chicago
BOS
Boston
$141 Roundtrip, found 6 hours ago
$141
Roundtrip
found 6 hours ago
Select Delta flight, departing Wed, Sep 16 from Chicago to Boston, returning Sat, Sep 19, priced at $141 found 6 hours ago
Thu, Oct 1 - Mon, Oct 5
ORD
Chicago
BOS
Boston
$141 Roundtrip, found 3 hours ago
$141
Roundtrip
found 3 hours ago
Select United flight, departing Thu, Oct 1 from Chicago to Boston, returning Mon, Oct 5, priced at $141 found 3 hours ago
Thu, Oct 1 - Wed, Oct 14
ORD
Chicago
BOS
Boston
$141 Roundtrip, found 5 hours ago
$141
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Thu, Oct 1 from Chicago to Boston, returning Wed, Oct 14, priced at $141 found 5 hours ago
Wed, Aug 26 - Sat, Aug 29
RFD
Rockford
BOS
Boston
$144 Roundtrip, found 1 day ago
$144
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Aug 26 from Rockford to Boston, returning Sat, Aug 29, priced at $144 found 1 day ago
Wed, Aug 26 - Sat, Aug 29
MDW
Chicago
BOS
Boston
$145 Roundtrip, found 1 day ago
$145
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Aug 26 from Chicago to Boston, returning Sat, Aug 29, priced at $145 found 1 day ago

Portsmouth economy flight packages

Price found within the past 48 hours. Click for updated prices.
Good Hotels Boston
2.0-star property

Good Hotels Boston

8/10 Very Good! (55 reviews)

Aug 27 - Aug 30

3 night stay

Chicago (CHI) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $975, price is now $603 per person
$603
per person
found 1 day ago
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,001 reviews)

Aug 27 - Aug 30

3 night stay

Chicago (CHI) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Price was $1,530, price is now $818 per person
$818
per person
found 1 day ago
From the moment I checked in with Natalie, our 4 days were superb! Natalie was so friendly and explained the property and amenities (our first time there). Even though I researched the property, and am originally from close to Boston, it was the 4th of July weekend, and there was Sooo much going on. Head concierge Nathan provided lots of tips about the best places to see certain events. So helpful. Our room was beautiful and well appointed. I miss the days of the shower cap, sewing kit, slippers, robes, etc. and they provided all that. The bed was extremely comfortable and the housekeeping staff wonderful. We go to Boston a few times a year and will be looking forward to returning here. Fabulous location!

Reviewed on Jul 8, 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
3.0-star property

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

10/10 Exceptional! (9 reviews)

Aug 12 - Aug 17

5 night stay

Chicago (CHI) to Boston (BOS)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $5,471, price is now $3,391 per person
$3,391
per person
found 1 day ago
I can't express how much I appreciate the hosts very fine people Indeed, the property is just awesome! The view gorgeous clearly they went out of their way to think of everything highly recommended. Tim Lawler

Reviewed on Oct 8, 2025

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Portsmouth first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Godfrey Hotel Boston
4.0-star property

The Godfrey Hotel Boston

9.4/10 Exceptional! (5,105 reviews)

Sep 2 - Sep 6

4 night stay

Chicago (ORD) to Boston (BOS)

United • Roundtrip • FirstClass
Price was $1,286, price is now $972 per person
$972
per person
found 10 hours ago
Very clean room, helpful staff and just all around nice, good location close to a lot of things

Reviewed on Jul 8, 2026

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,001 reviews)

Sep 2 - Sep 6

4 night stay

Chicago (ORD) to Boston (BOS)

United • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,488, price is now $1,505 per person
$1,505
per person
found 10 hours ago
From the moment I checked in with Natalie, our 4 days were superb! Natalie was so friendly and explained the property and amenities (our first time there). Even though I researched the property, and am originally from close to Boston, it was the 4th of July weekend, and there was Sooo much going on. Head concierge Nathan provided lots of tips about the best places to see certain events. So helpful. Our room was beautiful and well appointed. I miss the days of the shower cap, sewing kit, slippers, robes, etc. and they provided all that. The bed was extremely comfortable and the housekeeping staff wonderful. We go to Boston a few times a year and will be looking forward to returning here. Fabulous location!

Reviewed on Jul 8, 2026

The Langham, Boston
5.0-star property

The Langham, Boston

9.8/10 Exceptional! (1,005 reviews)

Sep 2 - Sep 6

4 night stay

Chicago (ORD) to Boston (BOS)

United • Roundtrip • FirstClass
Save 100% on your flight
Price was $1,836, price is now $1,362 per person
$1,362
per person
found 10 hours ago

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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

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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.

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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.