Search Cheap Flights to
Portland

Photo by Rick Bucchino

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Portland Flights as Low as $82

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Breeze Airways
Wed, Jul 9 - Sun, Jul 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$82 Roundtrip, found 3 hours ago
$82
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Wed, Jul 9 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jul 13, priced at $82 found 3 hours ago
Breeze Airways
Wed, Jul 9 - Sun, Jul 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$87 Roundtrip, found 3 hours ago
$87
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Wed, Jul 9 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jul 13, priced at $87 found 3 hours ago
Breeze Airways
Wed, Jul 9 - Sun, Jul 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$92 Roundtrip, found 3 hours ago
$92
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Wed, Jul 9 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jul 13, priced at $92 found 3 hours ago
Breeze Airways
Fri, Jun 13 - Mon, Jun 30
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$96 Roundtrip, found 3 hours ago
$96
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Fri, Jun 13 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Jun 30, priced at $96 found 3 hours ago
Breeze Airways
Fri, Jun 13 - Mon, Jun 30
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$101 Roundtrip, found 3 hours ago
$101
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Fri, Jun 13 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Jun 30, priced at $101 found 3 hours ago
Avelo Airlines
Fri, Jun 13 - Mon, Jun 30
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$113 Roundtrip, found 3 hours ago
$113
Roundtrip
found 3 hours ago
Select Avelo Airlines flight, departing Fri, Jun 13 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Jun 30, priced at $113 found 3 hours ago
Breeze Airways
Sat, Jun 7 - Mon, Jun 9
MCO
Orlando Intl.
BDL
Bradley Intl.
$115 Roundtrip, just found
$115
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Jun 7 from Orlando Intl. to Bradley Intl., returning Mon, Jun 9, priced at $115 just found
Frontier Airlines
Thu, Jun 19 - Sat, Jun 21
MCO
Orlando Intl.
BDL
Bradley Intl.
$156 Roundtrip, found 1 day ago
$156
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Jun 19 from Orlando Intl. to Bradley Intl., returning Sat, Jun 21, priced at $156 found 1 day ago
Spirit Airlines
Sat, Jun 21 - Mon, Jun 23
MCO
Orlando Intl.
BDL
Bradley Intl.
$176 Roundtrip, found 1 day ago
$176
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Jun 21 from Orlando Intl. to Bradley Intl., returning Mon, Jun 23, priced at $176 found 1 day ago
Frontier Airlines
Sat, Jun 21 - Sat, Jun 28
BWI
Baltimore Washington Intl. Thurgood Marshall
BDL
Bradley Intl.
$193 Roundtrip, found 1 day ago
$193
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jun 21 from Baltimore Washington Intl. Thurgood Marshall to Bradley Intl., returning Sat, Jun 28, priced at $193 found 1 day ago
JetBlue Airways
Thu, Jul 10 - Thu, Jul 17
MCO
Orlando Intl.
BDL
Bradley Intl.
$211 Roundtrip, found 12 hours ago
$211
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Thu, Jul 10 from Orlando Intl. to Bradley Intl., returning Thu, Jul 17, priced at $211 found 12 hours ago
United
Wed, Jun 4 - Tue, Jun 10
MCO
Orlando Intl.
BDL
Bradley Intl.
$217 Roundtrip, found 17 hours ago
$217
Roundtrip
found 17 hours ago
Select United flight, departing Wed, Jun 4 from Orlando Intl. to Bradley Intl., returning Tue, Jun 10, priced at $217 found 17 hours ago
Delta
Wed, Jun 4 - Tue, Jun 10
MCO
Orlando Intl.
BDL
Bradley Intl.
$217 Roundtrip, found 17 hours ago
$217
Roundtrip
found 17 hours ago
Select Delta flight, departing Wed, Jun 4 from Orlando Intl. to Bradley Intl., returning Tue, Jun 10, priced at $217 found 17 hours ago
American Airlines
Sun, Jun 8 - Tue, Jun 10
MCO
Orlando Intl.
BDL
Bradley Intl.
$218 Roundtrip, found 9 hours ago
$218
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Sun, Jun 8 from Orlando Intl. to Bradley Intl., returning Tue, Jun 10, priced at $218 found 9 hours ago
Frontier Airlines
Thu, Jul 3 - Sun, Jul 13
BQN
Rafael Hernandez
BDL
Bradley Intl.
$278 Roundtrip, found 1 day ago
$278
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Jul 3 from Rafael Hernandez to Bradley Intl., returning Sun, Jul 13, priced at $278 found 1 day ago
United
Sat, May 31 - Mon, Jun 9
MSP
Minneapolis - St. Paul Intl.
BDL
Bradley Intl.
$673 Roundtrip, found 1 day ago
$673
Roundtrip
found 1 day ago
Select United flight, departing Sat, May 31 from Minneapolis - St. Paul Intl. to Bradley Intl., returning Mon, Jun 9, priced at $673 found 1 day ago

Cheap Flights to Portland

Fall in love at first flight with your vacation to Portland by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Portland on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Portland, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Portland

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Portland with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the HFD airport.

What is the cheapest month to fly to Portland?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Portland are in July, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Portland?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Portland.

What airport is best to fly into Portland?

When you’re planning your trip to Portland, convenience is the name of the game. Luckily, Portland Tweed - New Haven Regional Airport is nearby so you can deplane and get going on checking off everything on your Portland must-do list.

How much are flights to Portland?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Portland on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $82, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Portland?

The trick to saving a stack of cash on your flight to Portland? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $82 right now, why wait?

Portland Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$81

Last Minute Hotel Deals in Portland

Solano Inn
Solano Inn
2.5 out of 5
1503 Portland-Cobalt Rd, Portland, CT
Stay at this hotel in Portland. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Arrigoni Winery and Dart Island State Park are located ...
8.8/10 Excellent! (134 reviews)
Nice place!
"Cycling down the Airline rail trail as part of a 5 day tour. Wonderful location close to trail, clean, quiet and a relaxing bath and bed. Breakfast spot across the street has superb breakfast bowls."

Reviewed on May 24, 2025

Get rates
Solano Inn
Clarion Inn
Clarion Inn
3 out of 5
201 Washington Avenue, North Haven, CT
Book a stay at this business-friendly hotel in North Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.4/10 Good! (1,014 reviews)
"Stayed one night as we were passing through!! Clean, quiet, and staff was friendly"

Reviewed on May 21, 2025

Get rates
Clarion Inn
Holiday Inn Express Southington by IHG
Holiday Inn Express Southington by IHG
2.5 out of 5
120 Laning St, Southington, CT
Book a stay at this business-friendly hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,004 reviews)
"Property was in a quiet location staff was great but needs some deep cleaning. Stayed in RM 306 bathroom sink cracked,wall had some brown dried pigment by toilet paper, toilet had ring around the bowl, Desk area had dried sticky liquid on it. Bathroom sink counter and floor dusty. Breakfast was ..."

Reviewed on May 25, 2025

Get rates
Holiday Inn Express Southington by IHG
The Goodwin Hotel
The Goodwin Hotel
3.5 out of 5
1 Haynes St, Hartford, CT
Stay at this 3.5-star hotel in Hartford. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,003 reviews)
"Hotel was beautiful! The valets were amazing! Would definitely stay there again"

Reviewed on May 22, 2025

Get rates
The Goodwin Hotel
Best Western Hartford Hotel & Suites
Best Western Hartford Hotel & Suites
2.5 out of 5
185 Brainard Rd, Hartford, CT
Stay at this hotel in Hartford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
7.6/10 Good! (1,006 reviews)
"Clean cozy quiet environment family friendly and I will love to stay again"

Reviewed on May 25, 2025

Get rates
Best Western Hartford Hotel & Suites
Hampton Inn & Suites Hartford/East Hartford
Hampton Inn & Suites Hartford/East Hartford
2.5 out of 5
351 Pitkin Steet, East Hartford, CT
Stay at this hotel in East Hartford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9/10 Wonderful! (1,000 reviews)
"We enjoyed everything from early check in to the indoor pool and breakfast as early as 6am! I just questioned how often the pool is clean it kinda smelled other than that fantastic stay, clean rooms thanks this was East Hartford CT! Me and little one will be going back for sure"

Reviewed on May 27, 2025

Get rates
Hampton Inn & Suites Hartford/East Hartford
Motel 6 Wethersfield, CT - Hartford
Motel 6 Wethersfield, CT - Hartford
2 out of 5
1341 Silas Deane Hwy, Wethersfield, CT
Stay at this motel in Wethersfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
6.4/10 (1,015 reviews)
"Good staff take care of you for all you need."

Reviewed on May 20, 2025

Get rates
Motel 6 Wethersfield, CT - Hartford
Extended Stay America Suites Hartford Farmington
Extended Stay America Suites Hartford Farmington
2.5 out of 5
1 Batterson Park Rd, Farmington, CT
Book a stay at this business-friendly hotel in Farmington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7.8/10 Good! (938 reviews)
Good and not so good.
"The room was clean and the bed was pretty comfortable (but could have had a couple more pillows and the sheets were not soft). There was a kitchen in the room which was a big plus for me (except for the noisy fridge in the middle of the night). There were a couple of areas which need touch-up painting. ..."

Reviewed on May 17, 2025

Get rates
Extended Stay America Suites Hartford Farmington
See all 662 properties in Portland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.