$70 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.

Sat, Apr 18 - Sun, Apr 26
ORD
O'Hare Intl.
BOS
Logan Intl.
$207 Roundtrip, found 1 hour ago
$207
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Sat, Apr 18 from O'Hare Intl. to Logan Intl., returning Sun, Apr 26, priced at $207 found 1 hour ago
Sat, Apr 18 - Mon, Apr 20
MDW
Midway Intl.
BOS
Logan Intl.
$258 Roundtrip, found 1 day ago
$258
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Apr 18 from Midway Intl. to Logan Intl., returning Mon, Apr 20, priced at $258 found 1 day ago
Sat, Apr 18 - Mon, Apr 20
RFD
Greater Rockford
BOS
Logan Intl.
$353 Roundtrip, found 1 day ago
$353
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Apr 18 from Greater Rockford to Logan Intl., returning Mon, Apr 20, priced at $353 found 1 day ago
Fri, Apr 17 - Tue, Apr 21
ORD
O'Hare Intl.
MHT
Manchester-Boston Regional
$730 Roundtrip, found 5 days ago
$730
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Apr 17 from O'Hare Intl. to Manchester-Boston Regional, returning Tue, Apr 21, priced at $730 found 5 days ago

Airfares from $70 One Way, $130 Round Trip from Chicago to Portsmouth

Prices starting at $130 for return flights and $70 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.

Mon, Apr 20 - Wed, Apr 22
ORD
Chicago
BOS
Boston
$130 Roundtrip, found 6 days ago
$130
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Mon, Apr 20 from Chicago to Boston, returning Wed, Apr 22, priced at $130 found 6 days ago
Thu, May 14 - Sun, May 17
MDW
Chicago
BOS
Boston
$140 Roundtrip, found 2 days ago
$140
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, May 14 from Chicago to Boston, returning Sun, May 17, priced at $140 found 2 days ago
Wed, May 6 - Tue, May 19
ORD
Chicago
BOS
Boston
$142 Roundtrip, found 4 days ago
$142
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Wed, May 6 from Chicago to Boston, returning Tue, May 19, priced at $142 found 4 days ago
Sat, May 2 - Tue, May 5
ORD
Chicago
BOS
Boston
$164 Roundtrip, found 3 hours ago
$164
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Sat, May 2 from Chicago to Boston, returning Tue, May 5, priced at $164 found 3 hours ago
Tue, Jul 28 - Tue, Aug 4
RFD
Rockford
BOS
Boston
$167 Roundtrip, found 1 hour ago
$167
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Jul 28 from Rockford to Boston, returning Tue, Aug 4, priced at $167 found 1 hour ago

Portsmouth economy flight packages

Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer
4.0-star property

Eurostars The Boxer

8.8/10 Excellent! (1,426 reviews)

May 27 - May 31

4 night stay

Chicago (CHI) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,140, price is now $763 per person
$763
per person
found 1 day ago
Third time staying here and it’s perfect for sports fans heading to games at TD Garden!

Reviewed on May 6, 2025

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,003 reviews)

Jun 4 - Jun 7

3 night stay

Chicago (CHI) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $2,330, price is now $1,524 per person
$1,524
per person
found 1 day ago
The staff is VERY attentive to all your needs. It just makes everything easy and more comfortable: room service to concierge to valet parking etc. etc.

Reviewed on Mar 24, 2024

The Langham, Boston
5.0-star property

The Langham, Boston

9.6/10 Exceptional! (1,000 reviews)

May 22 - May 25

3 night stay

Chicago (CHI) to Boston (BOS)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,217, price is now $830 per person
$830
per person
found 1 day ago
No complaints , everything . I would go back again and again.

Reviewed on Jan 12, 2026

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Portsmouth first class flight packages

Price found within the past 48 hours. Click for updated prices.
LivAway Suites Portland-Scarborough
2.0-star property

LivAway Suites Portland-Scarborough

8.2/10 Very Good! (195 reviews)

Jun 9 - Jun 12

3 night stay

Chicago (ORD) to Boston (BOS)

United • Roundtrip • FirstClass
Price was $758, price is now $704 per person
$704
per person
found 1 day ago
Quality Inn & Suites South Portland
2.5-star property

Quality Inn & Suites South Portland

6.6/10 (1,006 reviews)

Jun 8 - Jun 12

4 night stay

Chicago (ORD) to Boston (BOS)

United • Roundtrip • FirstClass
Price was $870, price is now $745 per person
$745
per person
found 2 hours ago
Room was clean and comfortable

Reviewed on Oct 20, 2025

Holiday Inn Express Hotel & Suites South Portland by IHG
2.5-star property

Holiday Inn Express Hotel & Suites South Portland by IHG

8.8/10 Excellent! (1,000 reviews)

Jun 8 - Jun 12

4 night stay

Chicago (ORD) to Boston (BOS)

United • Roundtrip • FirstClass
Price was $893, price is now $813 per person
$813
per person
found 2 hours ago
After an unexpected flight delay coming back home, I decided to stay overnight in Portland after we landed vs driving 3 hours home in the middle of the night. I called ahead to make sure I would be able to gain access as my arrival was well after midnight. When we arrived we were greeted wonderfully by the gentleman at the counter. He even set out a tea for me. I’m not sure how he knew what my favorite kind was but that was an unexpected gesture! The room was perfect for our family and breakfast in the morning was a great start to our drive home. I would definitely stay here again. The only complaint that I have is that the room wasn’t as clean as one would expect. There was some spots on the top of the comforter on one of the beds. This might have been a slight oversight by housekeeping. My room also had popcorn ceiling, and it looked as though there may have been a leak in the pastand there is some discoloration in the ceiling above the sleeping area, which had removed some of the popcorn ceiling. A little bit dated. This would not affect my decision to stay here again.

Reviewed on Sep 2, 2025

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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.