$53 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, Jan 17 - Tue, Jan 20
MDW
Midway Intl.
BOS
Logan Intl.
$145 Roundtrip, found 5 days ago
$145
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Jan 17 from Midway Intl. to Logan Intl., returning Tue, Jan 20, priced at $145 found 5 days ago
Sat, Jan 17 - Tue, Jan 20
RFD
Greater Rockford
BOS
Logan Intl.
$158 Roundtrip, found 5 days ago
$158
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Jan 17 from Greater Rockford to Logan Intl., returning Tue, Jan 20, priced at $158 found 5 days ago
Sat, Jan 17 - Mon, Jan 19
ORD
O'Hare Intl.
BOS
Logan Intl.
$177 Roundtrip, found 7 hours ago
$177
Roundtrip
found 7 hours ago
Select United flight, departing Sat, Jan 17 from O'Hare Intl. to Logan Intl., returning Mon, Jan 19, priced at $177 found 7 hours ago
Fri, Jan 16 - Mon, Jan 19
ORD
O'Hare Intl.
MHT
Manchester-Boston Regional
$531 Roundtrip, found 4 days ago
$531
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Jan 16 from O'Hare Intl. to Manchester-Boston Regional, returning Mon, Jan 19, priced at $531 found 4 days ago

Airfares from $53 One Way, $104 Round Trip from Chicago to Portsmouth

Prices starting at $104 for return flights and $53 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.

Tue, Feb 17 - Wed, Feb 18
MDW
Chicago
BOS
Boston
$104 Roundtrip, found 3 days ago
$104
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Feb 17 from Chicago to Boston, returning Wed, Feb 18, priced at $104 found 3 days ago
Wed, Mar 18 - Tue, Mar 24
ORD
Chicago
BOS
Boston
$105 Roundtrip, found 8 hours ago
$105
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Wed, Mar 18 from Chicago to Boston, returning Tue, Mar 24, priced at $105 found 8 hours ago
Wed, Mar 18 - Tue, Mar 24
ORD
Chicago
BOS
Boston
$106 Roundtrip, found 8 hours ago
$106
Roundtrip
found 8 hours ago
Select JetBlue Airways flight, departing Wed, Mar 18 from Chicago to Boston, returning Tue, Mar 24, priced at $106 found 8 hours ago
Sat, Feb 7 - Wed, Feb 18
ORD
Chicago
BOS
Boston
$107 Roundtrip, found 2 days ago
$107
Roundtrip
found 2 days ago
Select United flight, departing Sat, Feb 7 from Chicago to Boston, returning Wed, Feb 18, priced at $107 found 2 days ago
Mon, Feb 2 - Tue, Feb 3
ORD
Chicago
BOS
Boston
$108 Roundtrip, found 18 hours ago
$108
Roundtrip
found 18 hours ago
Select Delta flight, departing Mon, Feb 2 from Chicago to Boston, returning Tue, Feb 3, priced at $108 found 18 hours ago

Portsmouth economy flight packages

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

The Whitney Hotel

9.6/10 Exceptional! (482 reviews)

Feb 9 - Feb 11

2 night stay

Chicago (CHI) to Boston (BOS)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $520, price is now $392 per person
$392
per person
found 1 day ago
What a gem in Boston! I've been to Boston many times and usually stay closer to the Downtown Crossing area. This time we stayed at the Whitney, choosing to try out that part of town. We loved it! Bigger than a boutique hotel, but small enough to feel intimate. Charles St is a great walking street, and we loved the location. The room was on the ground level (actually partly below ground) but was excellent! Well-appointed room, a good amount of space for Boston, and super professional staff. I'll be back when I come back to Boston

Reviewed on Jul 30, 2024

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,005 reviews)

Feb 9 - Feb 11

2 night stay

Chicago (CHI) to Boston (BOS)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $870, price is now $534 per person
$534
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 Atlas Hotel
3.5-star property

The Atlas Hotel

No reviews

Feb 15 - Feb 22

7 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,241, price is now $922 per person
$922
per person
found 11 hours ago
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Portsmouth packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Hotel & Suites Swansea by IHG
3.5-star property

Holiday Inn Express Hotel & Suites Swansea by IHG

7.8/10 Good! (1,001 reviews)

Feb 20 - Feb 23

3 night stay

Chicago (ORD) to Boston (BOS)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $623, price is now $540 per person
$540
per person
found 16 hours ago
Hotel was mostly fine. Could hear lots of noise outside the room through the door and walls. Was very expensive for the level of quality but it was a holiday weekend.

Reviewed on May 28, 2025

Red Roof Inn & Suites Swansea
2.0-star property

Red Roof Inn & Suites Swansea

6.8/10 (187 reviews)

Feb 20 - Feb 23

3 night stay

Chicago (ORD) to Boston (BOS)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $585, price is now $585 per person
$585
per person
found 16 hours ago
Was an OKAY stay. They say on the Orbitz app that rooms are kept open for a day before new people staying but that was a lie. Room had old scratch tickets laying around. Also, shower and all water didn't work. Turned shower on to get a few little streams of dark brown water that never stopped nor changed. So showering was not an option. Area is okay. But sketchy but if you know the area, you're okay. Highway is right outside the room so the view is so/so. The property says that the room was $110 but yet made me sign a paper saying that the rate was only $77. Maybe Orbitz needs to look into that? Would try again and hopefully these comments and concerns can be addressed in the near future

Reviewed on May 5, 2022

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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

When you’re searching for Chicago to Portsmouth flights for your family vacation, check out the guaranteed low prices at Orbitz. If you are looking for the best prices on hotels too, you’ll be sure to find great deals to suit your budget. You’ll also benefit from the following features:

Suitable Schedules

Orbitz simplifies the process of finding and booking budget flights from Chicago to Portsmouth. Since we monitor hundreds of flight fares, you can compare several flights from a range of different airlines to find the best fares and most suitable departure and arrival times. Mix and match your departure and return flight for even more discounts and travel flexibility.

Mobile Apps

Taking a lunch break or waiting to pick up the kids? Orbitz’s cutting-edge mobile tools will help you search for cheap Chicago to Portsmouth flights anywhere you are. Get exclusive mobile deals on flights, hotels, vacation packages, and cruises too.

Flight Alerts

Orbitz won’t leave you wondering whether your flight will take off on time. We can send you free alerts about your flights from Chicago to Portsmouth to your mobile phone and email. Whether your flights from Chicago to Portsmouth are running just a few minutes to a few hours late, we will let you know.

Miles and Points

If you travel regularly, you can still earn miles and points when you book qualifying Chicago to Portsmouth flights. Enter your frequent flyer number with your reservation to see the miles rack up.

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.