Cheap flights from Chicago (CHI) to Portland (PWM) from $49
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
The best prices from Chicago to Portland are usually found in April or September, booked 65 days in advance, depart on a Tuesday or Saturday and return on a Saturday
Cheap flight deals from Chicago to Portland
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Portland (PWM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 4, 2024.
Popular in | November |
|---|---|
Cheapest in | April |
Round-trip from | $293 |
One-way from | $129 |
What is the cheapest day to fly round-trip from Chicago to Portland, Maine?
Flights from Chicago to Portland, Maine are found to be more expensive on Thursday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Portland, Maine.
How far in advance should I book a flight from Chicago to Portland, Maine?
To save up to 26% on this flight, we recommend booking at least 53 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago to Portland, Maine from $329 1-2 weeks out and tickets from $329 for flights departing within the next 72 hours.
What is the cheapest month to fly from Chicago to Portland, Maine?
April can be a great time to fly to Portland, Maine from Chicago with a flight ticket averaging about $386. Cheapflights users have found deals in the month of April for as cheap as $244. The most expensive prices can be found in the month of November.
When is the cheapest time to fly from Chicago to Portland, Maine (CHI - PWM)?
One of the essential ways to save on airfare from Chicago to Portland, Maine is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 21% on airfare.
Cheap Frontier flights from Chicago to Portland
Explore cheap flight options specifically provided by Frontier for the route between Chicago and Portland. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 4, 2024.
Find some of the cheapest Frontier flights traveling from Chicago to Portland. Come back soon if you're not finding the exact deal you're looking for.
Cheap Delta flights from Chicago to Portland
Explore cheap flight options specifically provided by Delta for the route between Chicago and Portland. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 4, 2024.
Browse through some of the cheapest Delta flights traveling from Chicago to Portland. Check back soon if you're not seeing flights that suit your needs.
Cheap Chicago to Portland flights in May & June 2024
Find cheap flight options from Chicago to Portland specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,795,183 searches. Prices were last updated on May 4, 2024.
Check out some of the best flight deals from Chicago to Portland in 2024. Check back in a little while for more flight options.
Chicago to Portland 2024 flight deals
Discover exclusive flight deals for travel between Chicago and Portland in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 4, 2024.
Check out some of the best flight deals from Chicago to Portland in 2024. Check back in a little while for more flight options.
Non-stop flights to Portland from Chicago
Discover non-stop flight options from Chicago to Portland. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 4, 2024.
Take a look at some of the direct flights traveling from Chicago to Portland in the near future. Those looking to potentially save on 1 or 2-stop flights from Chicago to Portland should utilize the search form at the the top of the page.
Chicago to Portland flights leaving soon
Find last-minute flight options from Chicago to Portland for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 4, 2024.
Have a look at some of the flights available from Chicago to Portland departing last-minute. Users should be sure to double check the price, date, and time of their last-minute flight.
One-way flights to Portland from Chicago
Search for one-way flight options from Chicago to Portland. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 4, 2024.
Users traveling one-way from Chicago to Portland can select one of these great deals. For those needing a return trip from Chicago, there is a search form available above.
Find flights from Chicago to Portland within your budget
Customize your flight search to find flights from Chicago to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 4, 2024.
Fly from
Fly to
Budget
$78 - $257
Route
Depart
Return
Price
Chicago O'Hare IntlPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Tue 6/11
Nonstop2h 20m
Portland
Tue 6/18
Nonstop2h 43m
Chicago O'Hare IntlPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Tue 6/4
Nonstop2h 20m
Portland
Tue 6/11
Nonstop2h 43m
Chicago O'Hare IntlPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Tue 6/18
Nonstop2h 20m
Portland
Tue 6/25
Nonstop2h 43m
Chicago O'Hare IntlPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Tue 7/9
Nonstop2h 21m
Portland
Tue 7/16
Nonstop2h 46m
Chicago O'Hare IntlPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Tue 7/9
Nonstop2h 21m
Portland
Tue 7/16
Nonstop2h 46m
Chicago O'Hare IntlPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Thu 6/13
Nonstop2h 20m
Portland
Sun 6/16
1 stop7h 56m
Chicago O'Hare IntlPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Tue 6/11
2 stops8h 35m
Portland
Tue 6/18
2 stops8h 14m
Chicago O'Hare IntlPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Wed 6/5
Nonstop2h 28m
Portland
Mon 6/10
1 stop6h 37m
Chicago O'Hare IntlPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Thu 7/4
1 stop17h 05m
Portland
Sat 7/13
1 stop9h 32m
When is the best time to book a flight from Chicago to Portland, Maine?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Portland. Price data was last updated on January 28, 2024.
The best time to book flights from Chicago to Portland, Maine is 65 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
When is the cheapest time to fly from Chicago to Portland, Maine?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Portland. Price data was last updated on April 28, 2024.
Average price of flights to Portland by month
Plan your trip from Chicago to Portland by taking into account the cheapest months to travel. The average price of a one-way flight from Chicago to Portland is currently $71 while a round-trip flight costs $152. Price data was last updated on April 28, 2024.
Currently, January is the cheapest month in which you can book a flight from Chicago to Portland, Maine (average of $293). Flying from Chicago to Portland, Maine in April is currently the most expensive (average of $498). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
January
$293
February
$332
March
$414
April
$498
May
$439
June
$410
July
$448
August
$364
September
$341
October
$323
November
$333
December
$333
Temperature and rainfall in Portland by month
Plan your trip to Portland by taking into account the average temperature and rainfall totals by month.
PWM Temperature | 23 - 68 °F |
|---|
Reviews of airlines servicing Portland
Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated May 4, 2024.
Read reviews from past customers who have flown Frontier, Delta and American Airlines from Chicago to Portland. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
Boarding
Entertainment
Food
Overall
Crew
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Comfort
Boarding
Entertainment
Food
Overall
Crew
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Comfort
Boarding
Entertainment
Food
Overall
Crew
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Comfort
Boarding
Entertainment
Food
Overall
Crew
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Comfort
Boarding
Entertainment
Food
Overall
Crew
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Comfort
Boarding
Entertainment
Food
Overall
Crew
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Related info for your journey
Find useful and relevant information for your journey from Chicago to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to PortlandSee prices for flight routes from nearby airports that may be better suited for you.
See prices for flight routes from nearby airports that may be better suited for you.
Top 4 airlines flying from Chicago to Portland
Discover the top 4 airlines that operate flights from Chicago to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 4, 2024.
Search flights from Chicago to Portland by cabin class
Find flights from Chicago to Portland, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Hourly flight availability from Chicago to Portland
Find hourly flight availability from Chicago to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 4, 2024.
| 0%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 40%of flight departures | Morning6 am to noon |
| 60%of flight departures | AfternoonNoon to 6 pm |
| 0%of flight departures | Evening6 pm to midnight |
Weekly flight availability from Chicago to Portland
Explore weekly flight availability from Chicago to Portland. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 4, 2024.
| Sunday | 4daily flights |
|---|---|
| Monday | 5daily flights |
| Tuesday | 5daily flights |
| Wednesday | 5daily flights |
| Thursday | 5daily flights |
| Friday | 5daily flights |
| Saturday | 6daily flights |
Book a flight to one of these trending destinations
User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
Fly with Cheapflights
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How does Cheapflights help users find flights from Chicago to Portland?
Cheapflights makes it easy to find Chicago to Portland flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.
Why should you use Cheapflights to find cheap flight tickets from Chicago to Portland?
It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chicago to Portland.
Can Cheapflights find flights from Chicago to Portland with no change fees?
Cheapflights does show flights with no change fees to all users. To see these options for flights from Chicago to Portland, users can toggle the no change fees filter when performing a flight search.
Can Cheapflights notify me if prices for flights from Chicago to Portland become cheaper?
Yes, Cheapflights offers price alerts on Chicago to Portland flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.