$43 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, Jun 14 - Tue, Jun 17
MDW
Midway Intl.
BOS
Logan Intl.
$197 Roundtrip, found 3 days ago
$197
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Jun 14 from Midway Intl. to Logan Intl., returning Tue, Jun 17, priced at $197 found 3 days ago
Sat, Jun 14 - Mon, Jun 16
ORD
O'Hare Intl.
BOS
Logan Intl.
$221 Roundtrip, found 1 hour ago
$221
Roundtrip
found 1 hour ago
Select Bargain Flight flight, departing Sat, Jun 14 from O'Hare Intl. to Logan Intl., returning Mon, Jun 16, priced at $221 found 1 hour ago
Fri, Jun 13 - Tue, Jun 17
ORD
O'Hare Intl.
MHT
Manchester-Boston Regional
$832 Roundtrip, found 1 day ago
$832
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Fri, Jun 13 from O'Hare Intl. to Manchester-Boston Regional, returning Tue, Jun 17, priced at $832 found 1 day ago

Airfares from $43 One Way, $104 Round Trip from Chicago to Portsmouth

Prices starting at $104 for return flights and $43 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, Sep 2 - Tue, Sep 9
ORD
Chicago
BOS
Boston
$104 Roundtrip, found 6 days ago
$104
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Sep 2 from Chicago to Boston, returning Tue, Sep 9, priced at $104 found 6 days ago
Tue, Sep 2 - Tue, Sep 9
MDW
Chicago
BOS
Boston
$111 Roundtrip, found 6 days ago
$111
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Sep 2 from Chicago to Boston, returning Tue, Sep 9, priced at $111 found 6 days ago
Thu, Oct 16 - Thu, Oct 23
ORD
Chicago
BOS
Boston
$119 Roundtrip, found 1 hour ago
$119
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Thu, Oct 16 from Chicago to Boston, returning Thu, Oct 23, priced at $119 found 1 hour ago
Mon, Aug 11 - Thu, Aug 14
ORD
Chicago
BOS
Boston
$125 Roundtrip, found 2 hours ago
$125
Roundtrip
found 2 hours ago
Select United flight, departing Mon, Aug 11 from Chicago to Boston, returning Thu, Aug 14, priced at $125 found 2 hours ago
Mon, Aug 11 - Thu, Aug 14
ORD
Chicago
BOS
Boston
$125 Roundtrip, found 2 hours ago
$125
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Mon, Aug 11 from Chicago to Boston, returning Thu, Aug 14, priced at $125 found 2 hours ago

Portsmouth economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sea Mist Resort
3.0-star property

Sea Mist Resort

8.8/10 Excellent! (123 reviews)

Jul 17 - Jul 20

3 night stay

Chicago (CHI) to Boston (BOS)

United • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
I liked having 2 floors as it was a townhouse. Having an equipped kitchen and 2 baths was really a nice convenience for a family of 4. Plenty of closet space and a slider out to the back area where you can sit outside and also use their grills. The place does need updating. It is clearly showing wear. The furnishings and amenities like the TV's are out of date. Regardless, we enjoyed our stay and would stay again.

Reviewed on Dec 12, 2024

Holly Tree Resort
3.0-star property

Holly Tree Resort

9/10 Wonderful! (342 reviews)

Jul 24 - Jul 29

5 night stay

Chicago (CHI) to Boston (BOS)

United • Coach

Boston (BOS) to Chicago (CHI)

Southwest Airlines • Coach
Save 100% on your flight
per person
found 1 hour ago
good value for money

Reviewed on Oct 21, 2022

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,003 reviews)

Jul 31 - Aug 3

3 night stay

Chicago (ORD) to Boston (BOS)

United • Roundtrip • Coach
Save 100% on your flight
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

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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
863 mi
Direct Flight Airlines
JAL, Icelandair, Delta Air Lines, Air New Zealand, United Airlines, El Al, SAS, Iberia, Korean Air, WestJet, American Airlines, Qatar Airways, KLM, Emirates, Alaska Airlines, Etihad Airways, JetBlue, Avianca, Cathay Pacific, Royal Jordanian, Hawaiian Airlines, ANA, TAP Air Portugal, Virgin Atlantic, British Airways
Earliest Flight Arrival
2:08PM UTC
Latest Flight Arrival
4:20AM UTC

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.

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.