$109 Cheap flight deals from Chicago (CHI) to Truro (PVC)

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This Weekend's Flight Deals from Chicago to Truro

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, Sep 6 - Sat, Sep 12
MDW
Midway Intl.
BOS
Logan Intl.
$295 Roundtrip, found 3 days ago
$295
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sun, Sep 6 from Midway Intl. to Logan Intl., returning Sat, Sep 12, priced at $295 found 3 days ago
Sat, Sep 5 - Sun, Sep 6
RFD
Greater Rockford
BOS
Logan Intl.
$318 Roundtrip, found 4 days ago
$318
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Sep 5 from Greater Rockford to Logan Intl., returning Sun, Sep 6, priced at $318 found 4 days ago
Sun, Sep 6 - Tue, Sep 8
ORD
O'Hare Intl.
BOS
Logan Intl.
$322 Roundtrip, found 1 hour ago
$322
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Sun, Sep 6 from O'Hare Intl. to Logan Intl., returning Tue, Sep 8, priced at $322 found 1 hour ago
Fri, Sep 4 - Tue, Sep 8
ORD
O'Hare Intl.
PVC
Provincetown Municipal
$890 Roundtrip, found 1 day ago
$890
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Fri, Sep 4 from O'Hare Intl. to Provincetown Municipal, returning Tue, Sep 8, priced at $890 found 1 day ago

Airfares from $109 One Way, $198 Round Trip from Chicago to Truro

Prices starting at $198 for return flights and $109 for one-way flights to Truro 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, Oct 21 - Wed, Nov 4
ORD
Chicago
BOS
Boston
$198 Roundtrip, found 3 hours ago
$198
Roundtrip
found 3 hours ago
Select Delta flight, departing Wed, Oct 21 from Chicago to Boston, returning Wed, Nov 4, priced at $198 found 3 hours ago
Fri, Oct 16 - Wed, Nov 18
ORD
Chicago
BOS
Boston
$200 Roundtrip, found 18 hours ago
$200
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Fri, Oct 16 from Chicago to Boston, returning Wed, Nov 18, priced at $200 found 18 hours ago
Fri, Nov 6 - Tue, Nov 10
MDW
Chicago
BOS
Boston
$217 Roundtrip, found 5 days ago
$217
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Fri, Nov 6 from Chicago to Boston, returning Tue, Nov 10, priced at $217 found 5 days ago
Wed, Oct 21 - Wed, Nov 4
ORD
Chicago
BOS
Boston
$217 Roundtrip, found 3 hours ago
$217
Roundtrip
found 3 hours ago
Select Delta flight, departing Wed, Oct 21 from Chicago to Boston, returning Wed, Nov 4, priced at $217 found 3 hours ago
Thu, Feb 4 - Tue, Feb 9
ORD
Chicago
BOS
Boston
$217 Roundtrip, just found
$217
Roundtrip
just found
Select JetBlue Airways flight, departing Thu, Feb 4 from Chicago to Boston, returning Tue, Feb 9, priced at $217 just found

Truro economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Cove at Yarmouth by Westgate Resorts
3.0-star property

The Cove at Yarmouth by Westgate Resorts

9.2/10 Wonderful! (268 reviews)

Oct 22 - Oct 27

5 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $818, price is now $571 per person
$571
per person
found 1 day ago
P Indoor pool and hot tub loved and the outdoor Shack was great

Reviewed on Jun 8, 2026

Furnished Apartment Near Longwood
3.0-star property

Furnished Apartment Near Longwood

7/10 Good! (6 reviews)

Oct 8 - Oct 11

3 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Coach

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Coach
Save 100% on your flight
Price was $1,382, price is now $956 per person
$956
per person
found 1 day ago
This is more like university housing than anything else. The building is full of students and poorly maintained, with visitors following others into the entrance. Carpeting is stained, paint is chipping, blinds are broken, the a/c didn't work, the hallway smells. Communication with the Evonify owners was poor, and we had to go through Hotels.com to receive our access code/registration in time for our arrival and, ultimately, a refund. We left a few minutes after we entered the unit. Not recommended. It is not the sunny, pristine, and secure apartment that appears in the photos.

Reviewed on Jul 6, 2026

Harbor Hotel Provincetown
3.0-star property

Harbor Hotel Provincetown

8.4/10 Very Good! (1,022 reviews)

Oct 22 - Oct 27

5 night stay

Chicago (ORD) to Provincetown (PVC)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $860, price is now $607 per person
$607
per person
found 1 day ago
Clean, shuttle, week kept, pretty

Reviewed on Sep 1, 2026

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Truro packages with premium economy flights

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

HomeAwhile

9.4/10 Exceptional! (229 reviews)

Oct 15 - Oct 18

3 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $852, price is now $723 per person
$723
per person
found 1 day ago

The Newbury Boston
5.0-star property

The Newbury Boston

9.4/10 Exceptional! (713 reviews)

Oct 15 - Oct 19

4 night stay

Chicago (CHI) to Boston (BOS)

JetBlue Airways • PremiumEconomy

Boston (BOS) to Chicago (CHI)

Frontier Airlines • PremiumEconomy
Price was $2,964, price is now $2,270 per person
$2,270
per person
found 1 day ago

The Whitney Hotel
4.0-star property

The Whitney Hotel

9.6/10 Exceptional! (609 reviews)

Oct 15 - Oct 19

4 night stay

Chicago (CHI) to Boston (BOS)

JetBlue Airways • PremiumEconomy

Boston (BOS) to Chicago (CHI)

Frontier Airlines • PremiumEconomy
Price was $2,378, price is now $1,894 per person
$1,894
per person
found 1 day ago

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More About Flying To Truro from Chicago

Route Information for Flights from Chicago to Truro

Origin Airport IATA Code
CHI
Destination Airport IATA Code
PVC
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Truro

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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.