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Cheap flights from Chicago (CHI) to Portland (PWM) from $40

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 6/25. 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.
CHI — PWM
May 11 — May 181
From?
To?
Sat 5/11
Sat 5/18
1 adult, Economy
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The best prices from Chicago to Portland are usually found in January or September, booked 10 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 6, 2024.

Popular in

December

Cheapest in

January

Round-trip from

$293

One-way from

$123
High demand for flights, 22% potential price rise
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Best time to find cheap flights, 24% potential price drop
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From Chicago (CHI) to Portland
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One-way flight from Chicago (CHI) to Portland
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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 79% on this flight, we recommend booking at least 11 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 $199 1-2 weeks out and tickets from $358 for flights departing within the next 72 hours.

What is the cheapest month to fly from Chicago to Portland, Maine?

January can be a great time to fly to Portland, Maine from Chicago with a flight ticket averaging about $410. Cheapflights users have found deals in the month of January for as cheap as $199. The most expensive prices can be found in the month of December.

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 2,689,106 searches. Data last updated May 6, 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.
Tue 6/115:42 pmORD - PWM
Nonstop2h 20mFrontier
Tue 6/189:55 pmPWM - ORD
Nonstop2h 43mFrontier
Deal found 5/5$78
Tue 6/115:42 pmORD - PWM
Nonstop2h 20mFrontier
Thu 6/1310:05 pmPWM - ORD
Nonstop2h 43mFrontier
Deal found 5/6$79
Tue 6/115:42 pmORD - PWM
Nonstop2h 20mFrontier
Thu 6/2010:05 pmPWM - ORD
Nonstop2h 43mFrontier
Deal found 5/6$89
Sun 6/95:52 pmORD - PWM
Nonstop2h 20mFrontier
Tue 6/189:55 pmPWM - ORD
Nonstop2h 43mFrontier
Deal found 5/6$99
Thu 6/65:52 pmORD - PWM
Nonstop2h 20mFrontier
Sun 6/910:05 pmPWM - ORD
Nonstop2h 43mFrontier
Deal found 5/6$100
Tue 5/286:02 pmORD - PWM
Nonstop2h 20mFrontier
Thu 5/3010:12 pmPWM - ORD
Nonstop2h 46mFrontier
Deal found 5/5$109
Thu 5/236:02 pmORD - PWM
Nonstop2h 20mFrontier
Sun 5/2610:26 pmPWM - ORD
Nonstop2h 46mFrontier
Deal found 5/5$110
Thu 6/65:52 pmORD - PWM
Nonstop2h 20mFrontier
Sun 6/910:05 pmPWM - ORD
Nonstop2h 43mFrontier
Deal found 5/4$111
Sat 9/72:06 pmORD - PWM
1 stop17h 56mFrontier
Tue 9/1010:11 pmPWM - ORD
Nonstop2h 46mFrontier
Deal found 5/5$114

Cheap United Airlines flights from Chicago to Portland

Explore cheap flight options specifically provided by United Airlines 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 2,689,106 searches. Data last updated May 6, 2024.
Browse through some of the cheapest United Airlines flights traveling from Chicago to Portland. Check back soon if you're not seeing flights that suit your needs.
Sat 6/86:03 pmORD - PWM
Nonstop2h 30mUnited Airlines
Wed 6/126:00 amPWM - ORD
Nonstop2h 49mUnited Airlines
Deal found 5/5$217
Sat 6/156:03 pmORD - PWM
Nonstop2h 30mUnited Airlines
Thu 6/206:00 amPWM - ORD
Nonstop2h 49mUnited Airlines
Deal found 5/6$239
Sat 6/86:03 pmORD - PWM
Nonstop2h 30mUnited Airlines
Wed 6/126:10 amPWM - ORD
1 stop5h 25mUnited Airlines
Deal found 5/5$241
Sat 6/151:12 pmORD - PWM
1 stop6h 54mUnited Airlines
Wed 6/196:00 amPWM - ORD
Nonstop2h 49mUnited Airlines
Deal found 5/6$285
Thu 5/1611:20 amORD - PWM
Nonstop2h 31mUnited Airlines
Sat 5/254:50 pmPWM - ORD
Nonstop2h 51mUnited Airlines
Deal found 5/6$584
Thu 5/1611:20 amORD - PWM
Nonstop2h 31mUnited Airlines
Sat 5/253:50 pmPWM - ORD
1 stop5h 20mUnited Airlines
Deal found 5/6$594
Thu 5/169:25 pmORD - PWM
2 stops12h 33mUnited Airlines
Sat 5/252:32 pmPWM - ORD
1 stop5h 20mUnited Airlines
Deal found 5/6$640
Thu 5/1611:20 amORD - PWM
Nonstop2h 31mUnited Airlines
Fri 5/174:31 pmPWM - ORD
Nonstop3h 03mUnited Airlines
Deal found 5/6$663
Tue 5/146:09 pmORD - PWM
Nonstop2h 34mUnited Airlines
Sat 5/186:05 amPWM - ORD
1 stop7h 34mUnited Airlines
Deal found 5/5$672

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 2,689,106 searches. Prices were last updated on May 6, 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.
Tue 5/286:02 pmORD - PWM
Nonstop2h 20mFrontier
Thu 5/3010:12 pmPWM - ORD
Nonstop2h 46mFrontier
Deal found 5/6$109
Sun 6/95:52 pmORD - PWM
Nonstop2h 20mFrontier
Sun 6/1610:05 pmPWM - ORD
Nonstop2h 43mFrontier
Deal found 5/6$110
Thu 6/205:52 pmORD - PWM
Nonstop2h 20mFrontier
Sun 6/2310:05 pmPWM - ORD
Nonstop2h 43mFrontier
Deal found 5/6$120
Thu 6/205:52 pmORD - PWM
Nonstop2h 20mFrontier
Thu 6/2710:05 pmPWM - ORD
Nonstop2h 43mFrontier
Deal found 5/6$128
Wed 5/158:25 amORD - PWM
1 stop23h 44mFrontier
Thu 5/2310:12 pmPWM - ORD
Nonstop2h 46mFrontier
Deal found 5/6$152
Wed 6/55:58 pmORD - PWM
1 stop14h 08mFrontier
Tue 6/119:55 pmPWM - ORD
Nonstop2h 43mFrontier
Deal found 5/6$156
Tue 6/115:42 pmORD - PWM
Nonstop2h 20mFrontier
Thu 6/1310:08 amPWM - ORD
1 stop9h 50mFrontier
Deal found 5/6$158
Wed 6/1912:57 pmMDW - PWM
1 stop23h 00mFrontier
Tue 6/253:23 pmPWM - MDW
1 stop6h 57mFrontier
Deal found 5/5$158
Sat 6/82:10 pmORD - PWM
1 stop17h 56mFrontier
Tue 6/119:55 pmPWM - ORD
Nonstop2h 43mFrontier
Deal found 5/5$159

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 2,689,106 searches. Data last updated May 6, 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.
Tue 5/286:02 pmORD - PWM
Nonstop2h 20mFrontier
Thu 5/3010:12 pmPWM - ORD
Nonstop2h 46mFrontier
Deal found 5/6$109
Sun 6/95:52 pmORD - PWM
Nonstop2h 20mFrontier
Sun 6/1610:05 pmPWM - ORD
Nonstop2h 43mFrontier
Deal found 5/6$110
Sat 9/72:06 pmORD - PWM
1 stop17h 56mFrontier
Tue 9/1010:11 pmPWM - ORD
Nonstop2h 46mFrontier
Deal found 5/5$114
Thu 6/205:52 pmORD - PWM
Nonstop2h 20mFrontier
Sun 6/2310:05 pmPWM - ORD
Nonstop2h 43mFrontier
Deal found 5/6$120
Thu 6/205:52 pmORD - PWM
Nonstop2h 20mFrontier
Thu 6/2710:05 pmPWM - ORD
Nonstop2h 43mFrontier
Deal found 5/6$128
Tue 8/136:00 pmORD - PWM
Nonstop2h 21mFrontier
Tue 8/2010:11 pmPWM - ORD
Nonstop2h 46mFrontier
Deal found 5/6$136
Tue 8/136:00 pmORD - PWM
Nonstop2h 21mFrontier
Sun 8/1810:11 pmPWM - ORD
Nonstop2h 46mFrontier
Deal found 5/6$147
Wed 5/158:25 amORD - PWM
1 stop23h 44mFrontier
Thu 5/2310:12 pmPWM - ORD
Nonstop2h 46mFrontier
Deal found 5/6$152
Wed 6/55:58 pmORD - PWM
1 stop14h 08mFrontier
Tue 6/119:55 pmPWM - ORD
Nonstop2h 43mFrontier
Deal found 5/6$156

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 2,689,106 searches. Data last updated May 6, 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.
Tue 5/286:02 pmORD - PWM
Nonstop2h 20mFrontier
Thu 5/3010:12 pmPWM - ORD
Nonstop2h 46mFrontier
Deal found 5/6$109
Sun 6/95:52 pmORD - PWM
Nonstop2h 20mFrontier
Sun 6/1610:05 pmPWM - ORD
Nonstop2h 43mFrontier
Deal found 5/6$110
Thu 6/205:52 pmORD - PWM
Nonstop2h 20mFrontier
Sun 6/2310:05 pmPWM - ORD
Nonstop2h 43mFrontier
Deal found 5/6$120
Thu 6/205:52 pmORD - PWM
Nonstop2h 20mFrontier
Thu 6/2710:05 pmPWM - ORD
Nonstop2h 43mFrontier
Deal found 5/6$128
Tue 7/96:00 pmORD - PWM
Nonstop2h 21mFrontier
Sun 7/1410:11 pmPWM - ORD
Nonstop2h 46mFrontier
Deal found 5/6$165
Thu 5/306:02 pmORD - PWM
Nonstop2h 20mFrontier
Sun 6/29:45 pmPWM - ORD
Nonstop2h 46mFrontier
Deal found 5/6$179
Thu 7/45:52 pmORD - PWM
Nonstop2h 20mFrontier
Sun 7/1410:11 pmPWM - ORD
Nonstop2h 46mFrontier
Deal found 5/6$197
Sun 7/286:00 pmORD - PWM
Nonstop2h 21mFrontier
Thu 8/110:11 pmPWM - ORD
Nonstop2h 46mFrontier
Deal found 5/5$207
Sat 6/86:03 pmORD - PWM
Nonstop2h 30mUnited Airlines
Wed 6/126:00 amPWM - ORD
Nonstop2h 49mUnited Airlines
Deal found 5/5$217

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 2,689,106 searches. Data last updated May 6, 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.
Wed 5/158:25 amORD - PWM
1 stop23h 44mFrontier
Thu 5/2310:12 pmPWM - ORD
Nonstop2h 46mFrontier
Deal found 5/6$152
Thu 5/166:02 pmORD - PWM
Nonstop2h 20mFrontier
Sun 5/2610:26 pmPWM - ORD
Nonstop2h 46mFrontier
Deal found 5/6$220
Wed 5/158:25 amORD - PWM
1 stop23h 44mFrontier
Thu 5/239:59 amPWM - ORD
1 stop9h 48mFrontier
Deal found 5/6$233
Thu 5/166:02 pmORD - PWM
Nonstop2h 20mFrontier
Thu 5/2310:12 pmPWM - ORD
Nonstop2h 46mFrontier
Deal found 5/6$241
Thu 5/166:02 pmORD - PWM
Nonstop2h 20mFrontier
Sun 5/2611:40 amPWM - ORD
1 stop14h 28mFrontier
Deal found 5/6$321
Thu 5/166:02 pmORD - PWM
Nonstop2h 20mFrontier
Sun 5/2610:09 amPWM - ORD
2 stops15h 59mFrontier
Deal found 5/6$327
Thu 5/166:02 pmORD - PWM
Nonstop2h 20mFrontier
Thu 5/2311:40 amPWM - ORD
1 stop14h 28mFrontier
Deal found 5/6$418
Tue 5/144:53 pmORD - PWM
1 stop4h 48mAmerican Airlines
Thu 5/163:41 pmPWM - ORD
1 stop7h 52mAmerican Airlines
Deal found 5/6$426
Thu 5/165:36 pmORD - PWM
2 stops22h 37mMultiple Airlines
Fri 5/241:05 pmPWM - ORD
2 stops21h 50mMultiple Airlines
Deal found 5/6$454

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 2,689,106 searches. Data last updated May 6, 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.
Tue 6/255:42 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 5/6$40
Tue 5/216:02 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 5/5$49
Thu 6/65:52 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 5/5$50
Tue 7/236:00 pmORD - PWM
Nonstop2h 21mFrontier
Deal found 5/5$58
Wed 5/2212:09 pmMDW - PWM
1 stop21h 41mFrontier
Deal found 5/5$59
Sun 6/165:52 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 5/5$60
Sun 6/165:52 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 5/5$65
Sun 6/305:52 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 5/6$67
Thu 6/275:52 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 5/6$68

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 2,689,106 searches. Data last updated May 6, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$78 - $247

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

$78

Chicago O'Hare IntlPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 6/11

Nonstop2h 20m

Portland

Thu 6/13

Nonstop2h 43m

$79

Chicago O'Hare IntlPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 6/11

Nonstop2h 20m

Portland

Thu 6/20

Nonstop2h 43m

$89

Chicago O'Hare IntlPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 6/9

Nonstop2h 20m

Portland

Tue 6/18

Nonstop2h 43m

$99

Chicago O'Hare IntlPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 6/27

Nonstop2h 20m

Portland

Mon 7/1

1 stop7h 40m

$172

Chicago MidwayPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 6/18

1 stop8h 13m

Portland

Tue 6/25

1 stop4h 11m

$208

Chicago O'Hare IntlPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 6/8

Nonstop2h 30m

Portland

Wed 6/12

Nonstop2h 49m

$217

Chicago O'Hare IntlPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 7/4

1 stop17h 05m

Portland

Sat 7/13

1 stop9h 32m

$242

Chicago O'Hare IntlPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 6/8

Nonstop2h 28m

Portland

Wed 6/12

1 stop7h 28m

$247

Flights are sorted by cheapest first

Deals found on 5/5

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 May 3, 2024.
The best time to book flights from Chicago to Portland, Maine is 10 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.
Search Deals

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.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Chicago to Portland, Maine flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
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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 $57 while a round-trip flight costs $159. Price data was last updated on May 5, 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 $501). 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

$501

May

$433

June

$398

July

$447

August

$365

September

$339

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 6, 2024.
Read reviews from past customers who have flown Frontier, United Airlines and Sun Country Air from Chicago to Portland. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very good
6,082 reviews
Check prices

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Crew

8.7

Overall

8.2

Food

7.3

Reviews

1 / 10

The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.

Southwest
8.2
Very good
6,082 reviews
Southwest
8.2
Very good
6,082 reviews
Check prices

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Crew

8.7

Overall

8.2

Food

7.3

Reviews

1 / 10

The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.

Delta
8.1
Very good
10,818 reviews
Southwest
8.2
Very good
6,082 reviews
Check prices

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Crew

8.7

Overall

8.2

Food

7.3

Reviews

1 / 10

The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.

WestJet
7.6
Good
2,957 reviews
Southwest
8.2
Very good
6,082 reviews
Check prices

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Crew

8.7

Overall

8.2

Food

7.3

Reviews

1 / 10

The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.

United Airlines
7.4
Good
11,090 reviews
Southwest
8.2
Very good
6,082 reviews
Check prices

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Crew

8.7

Overall

8.2

Food

7.3

Reviews

1 / 10

The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.

American Airlines
7.3
Good
14,697 reviews
Southwest
8.2
Very good
6,082 reviews
Check prices

Boarding

8.3

Comfort

8.1

Entertainment

7.8

Crew

8.7

Overall

8.2

Food

7.3

Reviews

1 / 10

The seats are too narrow and uncomfortable. I do appreciate that there was room for my knees. I hate the boarding circus.

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.

  • What airport do you fly into for flights to Portland from Chicago?

    Most people fly into Portland (PWM) if they book a flight to Portland from Chicago. On average, Portland has 5 inbound flights from Chicago per day from 4 airlines. Portland is conveniently located just 2.9 mi from Portland’s city center.

  • Can I find flights from Chicago to Portland, Maine for under $100 on Cheapflights?

    Yes, there are multiple flights from Chicago to Portland, Maine for under $100. The cheapest flight booked recently is on Frontier for just $78, but on average you can expect to pay $122.

  • Are there nonstop flights from Chicago to Portland, Maine for under $200 on Cheapflights?

    Cheapflights has at least 20 direct flights from Chicago to Portland, Maine under $200. A good price for a nonstop flight from Chicago to Portland, Maine is less than $219.

  • Are there last-minute flights available from Chicago to Portland, Maine for under $200?

    There are currently 20+ open flights from Chicago to Portland, Maine within the next 7 days for less than $200.

  • What is the cheapest airline to fly from Chicago to Portland, Maine round-trip?

    Frontier, at $78, was found to be the cheapest airline from Chicago to Portland, Maine.. Frontier is 80% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Chicago to Portland, Maine one-way?

    One-way options have recently been found by users for as low as $40 on Frontier. Other airlines that offer cheap prices include Delta from $104 and American Airlines from $121 one-way.

  • What are the most popular airlines that fly from Chicago to Portland, Maine?

    When booking a flight from Chicago to Portland, Maine, you may want to consider flying on American Airlines, Delta or Frontier as they are the most popular for this route.

  • What are the most reliable airlines from Chicago to Portland, Maine?

    No one likes to see their flight delayed. When booking a flight from Chicago to Portland, Maine consider choosing Republic Airways (82%), Air New Zealand (78%) or United Airlines (74%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Chicago to Portland, Maine?

    Looking for the cheapest flight from Chicago to Portland, Maine? While on average our users pay $265, our data indicates the cheapest price to be $49. The most popular route (Chicago O'Hare Intl - Portland), is priced around $131.

  • What does ORD to PWM mean?

    ORD and PWM are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. ORD to PWM refers to a flight route from Chicago O'Hare Intl Airport to Portland Airport. This flight route has multiple associated airports, so we think it might be helpful to learn the name and codes of them as well. They are Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from Chicago to Portland that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Portland flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Portland with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Portland flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Chicago to Portland that include hotel bookings?

    Yes. In addition to deals on Chicago to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Portland.

  • Can I find deals for business class flights from Chicago to Portland?

    Yes. Cheapflights offers flight deals from Chicago to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Chicago to Portland that allow pets onboard?

    Many airlines flying from Chicago to Portland offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Portland?

    Yes, you can often find last-minute deals on Chicago to Portland flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Portland, Maine flight deals updated?

    The Chicago to Portland, Maine flight deals you see on this page were last updated on 5/6.

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Alternative routes for Chicago to Portland
See prices for flight routes from nearby airports that may be better suited for you.

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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 2,689,106 searches. Data last updated May 6, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$28Average$107FlexibilityNo cancel feeOn-time62%
Search Frontier flights
American AirlinesCheapest$199Average$372FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
United AirlinesCheapest$204Average$420FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
DeltaCheapest$214Average$340FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
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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.
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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 6, 2024.
0%of flight departuresEarly morningMidnight to 6 am
40%of flight departuresMorning6 am to noon
60%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
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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 6, 2024.
Sunday4daily flights
Monday5daily flights
Tuesday5daily flights
Wednesday5daily flights
Thursday5daily flights
Friday5daily flights
Saturday6daily flights

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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.

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