$55 Cheap flight deals from Chicago (CHI) to Dennis Port (PVC)

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This Weekend's Flight Deals from Chicago to Dennis Port

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 26 - Wed, Apr 30
ORD
O'Hare Intl.
BOS
Logan Intl.
$323 Roundtrip, found 1 hour ago
$323
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sat, Apr 26 from O'Hare Intl. to Logan Intl., returning Wed, Apr 30, priced at $323 found 1 hour ago
Sun, Apr 27 - Fri, May 2
MDW
Midway Intl.
BOS
Logan Intl.
$413 Roundtrip, found 6 days ago
$413
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sun, Apr 27 from Midway Intl. to Logan Intl., returning Fri, May 2, priced at $413 found 6 days ago
Sat, Apr 26 - Tue, Apr 29
ORD
O'Hare Intl.
ACK
Nantucket Memorial
$799 Roundtrip, found 4 days ago
$799
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Sat, Apr 26 from O'Hare Intl. to Nantucket Memorial, returning Tue, Apr 29, priced at $799 found 4 days ago
Sun, Apr 27 - Mon, May 5
ORD
O'Hare Intl.
MVY
Martha's Vineyard
$1,121 Roundtrip, found 1 day ago
$1,121
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Apr 27 from O'Hare Intl. to Martha's Vineyard, returning Mon, May 5, priced at $1,121 found 1 day ago

Airfares from $55 One Way, $109 Round Trip from Chicago to Dennis Port

Prices starting at $109 for return flights and $55 for one-way flights to Dennis Port 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, May 13 - Tue, May 20
ORD
Chicago
BOS
Boston
$109 Roundtrip, found 1 hour ago
$109
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Tue, May 13 from Chicago to Boston, returning Tue, May 20, priced at $109 found 1 hour ago
Thu, Oct 23 - Thu, Oct 30
ORD
Chicago
BOS
Boston
$109 Roundtrip, found 1 hour ago
$109
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Thu, Oct 23 from Chicago to Boston, returning Thu, Oct 30, priced at $109 found 1 hour ago
Sun, Jun 8 - Sat, Jun 14
MDW
Chicago
BOS
Boston
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sun, Jun 8 from Chicago to Boston, returning Sat, Jun 14, priced at $117 found 1 day ago
Sat, Sep 13 - Sat, Sep 20
ORD
Chicago
BOS
Boston
$117 Roundtrip, found 17 hours ago
$117
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Sat, Sep 13 from Chicago to Boston, returning Sat, Sep 20, priced at $117 found 17 hours ago
Thu, May 8 - Mon, May 12
ORD
Chicago
BOS
Boston
$117 Roundtrip, found 1 hour ago
$117
Roundtrip
found 1 hour ago
Select United flight, departing Thu, May 8 from Chicago to Boston, returning Mon, May 12, priced at $117 found 1 hour ago

Dennis Port economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sonesta Select Boston Danvers
3.0-star property

Sonesta Select Boston Danvers

8.6/10 Excellent! (1,004 reviews)

Jun 1 - Jun 3

2 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Non-stop • Coach

Boston (BOS) to Chicago (ORD)

American Airlines • Non-stop • Coach
per person
found 1 day ago
Dated, but clean, but not very inviting staff day or night

Reviewed on Mar 9, 2025

The Hotel Salem
3.0-star property

The Hotel Salem

9/10 Wonderful! (1,003 reviews)

Jun 1 - Jun 3

2 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Non-stop • Coach

Boston (BOS) to Chicago (ORD)

American Airlines • Non-stop • Coach
per person
found 1 day ago
The staff was very friendly and even left a card and cupcakes in my room for my birthday. It’s in the heart of Salem so it was easy to walk everywhere.

Reviewed on Apr 18, 2025

The Beverly
3.0-star property

The Beverly

8.4/10 Very Good! (277 reviews)

Jun 18 - Jun 21

3 night stay

Chicago (ORD) to Boston (BOS)

Spirit Airlines • Non-stop • Coach

Boston (BOS) to Chicago (ORD)

American Airlines • Non-stop • Coach
Save 100% on your flight
per person
found 4 hours ago
Expecting a modern, well-maintained hotel as depicted in their online photos. Unfortunately, it was clearly a motel, and this misleading information set unrealistic expectations for my stay. Despite being a non-smoking establishment, my room reeked of cigarette smoke and had a pervasive musty smell, making the stay very uncomfortable. The carpet was filthy, and the throw pillows were dirty and smelly, looking like they hadn’t been washed or replaced in years. The vent next to the bathroom sink was covered in a thick layer of dust, indicating a lack of proper cleaning and maintenance. The overall condition of the room was poor, with subpar cleanliness and unacceptable air quality due to the strong odors. There is no staff on-site, so you have to text them for assistance. When I texted about the awful smell, I received a response after 15 minutes: “I am so sorry to hear that. I am looking into the situation now and will get right back to you.” As we had been driving all day and were starving, I responded that we were heading out to eat and would deal with it when we returned. They never responded to that message. Upon returning from dinner, we struggled to fall asleep due to the thin walls. We could hear conversations from all neighboring rooms, including those above us, and any movement they made was very loud. Overall, was very disappointed with my stay and would not recommend this place to anyone looking for comfortable and clean accommodation.

Reviewed on Jul 28, 2024

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More About Flying To Dennis Port from Chicago

Route Information for Flights from Chicago to Dennis Port

Origin Airport IATA Code
CHI
Destination Airport IATA Code
PVC
Distance
863 mi
Direct Flight Airlines
American Airlines, KLM, Qatar Airways, JAL, Icelandair, Emirates, Delta Air Lines, Air New Zealand, United Airlines, El Al, Alaska Airlines, Etihad Airways, JetBlue, Cathay Pacific, Avianca, SAS, Royal Jordanian, Iberia, Hawaiian Airlines, ANA, Korean Air, TAP Air Portugal, WestJet, Virgin Atlantic, British Airways
Earliest Flight Arrival
2:26PM UTC
Latest Flight Arrival
4:45AM UTC

Chicago to Dennis Port

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Best Deals At Your Fingertips

Orbitz combines low prices on Chicago to Dennis Port flights with discounts on quality hotels. Using Orbitz’s Display Matrix, you can see all your options and savings easily. With our low price guarantee, you know you have the best deals at your fingertips.

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.