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Cheap flights from Portland (PWM) to Chicago (CHI) 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 5/21. 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.
PWM — CHI
May 1 — May 81
From?
To?
Wed 5/1
Wed 5/8
1 adult, Economy
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The best prices from Portland to Chicago are usually found in September or July, booked 86 days in advance, depart on a Saturday or Thursday and return on a Tuesday

Cheap flight deals from Portland to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to Chicago (CHI). 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 April 26, 2024.

Popular in

April

Cheapest in

September

Round-trip from

$222

One-way from

$140
High demand for flights, 29% potential price rise
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Best time to find cheap flights, 22% potential price drop
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From Portland to Chicago (CHI)
Search Deals
One-way flight from Portland to Chicago (CHI)
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What is the cheapest day to fly round-trip from Portland, Maine to Chicago?

Flying to your destination on a Saturday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Chicago. Check prices with Cheapflights to find a great deal for your trip.

How far in advance should I book a flight from Portland, Maine to Chicago?

Users have found that booking a flight from Portland, Maine to Chicago at least 43 days early can save you up to 92% on average compared to booking a flight this week. If booking 43 days before your flight isn’t an option for you, users have found flights from Portland, Maine to Chicago for as little as $478 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $539 for flights departing within the next 3 days.

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

The best pricing can be found in the month of September. Prices to Chicago from Portland, Maine average $384. You can even find prices in September for less than $384, as users have found deals to Chicago from as low as $166. The month of April appears to be one of the more expensive times to travel to Chicago from Portland, Maine. Flying in the targeted month can save you up to 40%.

When is the cheapest time to fly from Portland, Maine to Chicago (PWM - CHI)?

One of the essential ways to save on airfare from Portland, Maine to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 52% on airfare.

Cheap Frontier flights from Portland to Chicago

Explore cheap flight options specifically provided by Frontier for the route between Portland and Chicago. 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 3,068,117 searches. Data last updated April 26, 2024.
Check out some of the cheapest Frontier flights we've come across from Portland to Chicago. Make sure to double check the flight details before booking.
Tue 10/2210:11 pmPWM - ORD
Nonstop2h 46mFrontier
Tue 10/296:00 pmORD - PWM
Nonstop2h 21mFrontier
Deal found 4/25$98
Tue 6/410:12 pmPWM - ORD
Nonstop2h 46mFrontier
Thu 6/65:52 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 4/26$101
Thu 6/610:02 pmPWM - ORD
Nonstop2h 46mFrontier
Sun 6/95:52 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 4/25$105
Thu 6/610:02 pmPWM - ORD
Nonstop2h 46mFrontier
Sun 6/95:52 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 4/26$112
Tue 7/910:11 pmPWM - ORD
Nonstop2h 46mFrontier
Thu 7/116:00 pmORD - PWM
Nonstop2h 21mFrontier
Deal found 4/25$126
Tue 6/411:40 amPWM - ORD
1 stop14h 28mFrontier
Thu 6/65:52 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 4/26$129
Thu 5/169:59 amPWM - ORD
1 stop9h 48mFrontier
Tue 5/216:02 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 4/25$138
Thu 6/611:40 amPWM - ORD
1 stop7h 38mFrontier
Sun 6/95:52 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 4/26$139
Thu 9/2611:46 amPWM - MDW
1 stop25h 37mFrontier
Mon 9/3011:38 amMDW - PWM
1 stop20h 24mFrontier
Deal found 4/25$148

Cheap American Airlines flights from Portland to Chicago

Explore cheap flight options specifically provided by American Airlines for the route between Portland and Chicago. 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 3,068,117 searches. Data last updated April 26, 2024.
Some of the lowest-priced American Airlines flights we've found at this time heading from Portland to Chicago. Deals are refreshing constantly so come back soon for more options.
Fri 6/77:17 amPWM - ORD
Nonstop2h 53mAmerican Airlines
Sun 6/97:15 pmORD - PWM
Nonstop2h 28mAmerican Airlines
Deal found 4/25$253
Wed 7/37:17 amPWM - ORD
Nonstop2h 53mAmerican Airlines
Fri 7/56:50 pmORD - PWM
Nonstop2h 39mAmerican Airlines
Deal found 4/25$254
Fri 6/74:00 pmPWM - ORD
1 stop6h 37mAmerican Airlines
Sun 6/97:15 pmORD - PWM
Nonstop2h 28mAmerican Airlines
Deal found 4/25$271
Fri 8/167:30 amPWM - ORD
Nonstop2h 50mAmerican Airlines
Mon 8/264:50 pmORD - PWM
1 stop5h 48mAmerican Airlines
Deal found 4/25$273
Fri 6/77:17 amPWM - ORD
Nonstop2h 53mAmerican Airlines
Mon 6/107:15 pmORD - PWM
Nonstop2h 28mAmerican Airlines
Deal found 4/26$304
Fri 6/77:17 amPWM - ORD
Nonstop2h 53mAmerican Airlines
Mon 6/105:30 amORD - PWM
1 stop5h 44mAmerican Airlines
Deal found 4/26$312
Tue 6/114:00 pmPWM - ORD
1 stop6h 37mAmerican Airlines
Fri 6/147:15 pmORD - PWM
Nonstop2h 28mAmerican Airlines
Deal found 4/26$321
Thu 7/257:14 amPWM - ORD
Nonstop2h 48mAmerican Airlines
Mon 7/294:45 pmORD - PWM
1 stop6h 01mAmerican Airlines
Deal found 4/25$322
Thu 7/257:14 amPWM - ORD
Nonstop2h 48mAmerican Airlines
Mon 7/296:50 pmORD - PWM
Nonstop2h 39mAmerican Airlines
Deal found 4/25$329

Cheap Portland to Chicago flights in April & May 2024

Find cheap flight options from Portland to Chicago specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,068,117 searches. Prices were last updated on April 26, 2024.
The lowest fares we've come across on flights traveling from Portland to Chicago in April and May 2024. For more flight deals, be sure to check back very soon.
Thu 5/169:59 amPWM - ORD
1 stop9h 48mFrontier
Tue 5/216:02 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 4/25$138
Thu 5/1610:12 pmPWM - ORD
Nonstop2h 46mFrontier
Tue 5/216:02 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 4/25$158
Fri 5/1012:56 pmPWM - MDW
1 stop10h 35mFrontier
Sun 5/126:31 pmMDW - PWM
1 stop12h 40mFrontier
Deal found 4/25$187
Thu 5/21:00 pmPWM - ORD
1 stop12h 59mFrontier
Sun 5/55:51 pmORD - PWM
1 stop13h 20mFrontier
Deal found 4/25$188
Thu 5/3010:12 pmPWM - ORD
Nonstop2h 46mFrontier
Sun 6/25:35 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 4/26$190
Thu 5/161:11 pmPWM - MDW
2 stops8h 06mFrontier
Mon 5/2012:14 pmMDW - PWM
1 stop21h 36mFrontier
Deal found 4/25$192
Fri 5/312:56 pmPWM - ORD
1 stop11h 47mFrontier
Mon 5/68:25 amORD - PWM
1 stop26h 45mFrontier
Deal found 4/25$198
Fri 5/312:56 pmPWM - MDW
1 stop10h 35mFrontier
Sun 5/56:31 pmMDW - PWM
1 stop12h 40mFrontier
Deal found 4/25$198
Thu 5/161:11 pmPWM - MDW
1 stop7h 29mFrontier
Mon 5/2012:14 pmMDW - PWM
1 stop21h 36mFrontier
Deal found 4/25$217

Portland to Chicago 2024 flight deals

Discover exclusive flight deals for travel between Portland and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,068,117 searches. Data last updated April 26, 2024.
The lowest fares we've come across on flights traveling from Portland to Chicago in April and May 2024. For more flight deals, be sure to check back very soon.
Tue 10/2210:11 pmPWM - ORD
Nonstop2h 46mFrontier
Tue 10/296:00 pmORD - PWM
Nonstop2h 21mFrontier
Deal found 4/25$98
Tue 6/410:12 pmPWM - ORD
Nonstop2h 46mFrontier
Thu 6/65:52 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 4/26$101
Thu 6/610:02 pmPWM - ORD
Nonstop2h 46mFrontier
Sun 6/95:52 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 4/25$105
Thu 6/610:02 pmPWM - ORD
Nonstop2h 46mFrontier
Sun 6/95:52 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 4/26$112
Tue 7/910:11 pmPWM - ORD
Nonstop2h 46mFrontier
Thu 7/116:00 pmORD - PWM
Nonstop2h 21mFrontier
Deal found 4/25$126
Tue 6/411:40 amPWM - ORD
1 stop14h 28mFrontier
Thu 6/65:52 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 4/26$129
Thu 5/169:59 amPWM - ORD
1 stop9h 48mFrontier
Tue 5/216:02 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 4/25$138
Thu 6/611:40 amPWM - ORD
1 stop7h 38mFrontier
Sun 6/95:52 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 4/26$139
Thu 9/2611:46 amPWM - MDW
1 stop25h 37mFrontier
Mon 9/3011:38 amMDW - PWM
1 stop20h 24mFrontier
Deal found 4/25$148

Non-stop flights to Chicago from Portland

Discover non-stop flight options from Portland to Chicago. 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 3,068,117 searches. Data last updated April 26, 2024.
Take a look at some of the direct flights traveling from Portland to Chicago in the near future. Users can also choose from other Portland to Chicago flights by using the search form above.
Tue 10/2210:11 pmPWM - ORD
Nonstop2h 46mFrontier
Tue 10/296:00 pmORD - PWM
Nonstop2h 21mFrontier
Deal found 4/25$98
Tue 6/410:12 pmPWM - ORD
Nonstop2h 46mFrontier
Thu 6/65:52 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 4/26$101
Thu 6/610:02 pmPWM - ORD
Nonstop2h 46mFrontier
Sun 6/95:52 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 4/25$105
Thu 6/610:02 pmPWM - ORD
Nonstop2h 46mFrontier
Sun 6/95:52 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 4/26$112
Tue 7/910:11 pmPWM - ORD
Nonstop2h 46mFrontier
Thu 7/116:00 pmORD - PWM
Nonstop2h 21mFrontier
Deal found 4/25$126
Tue 10/2210:11 pmPWM - ORD
Nonstop2h 46mFrontier
Thu 10/316:00 pmORD - PWM
Nonstop2h 21mFrontier
Deal found 4/25$157
Thu 5/1610:12 pmPWM - ORD
Nonstop2h 46mFrontier
Tue 5/216:02 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 4/25$158
Tue 10/2210:11 pmPWM - ORD
Nonstop2h 46mFrontier
Sun 10/276:00 pmORD - PWM
Nonstop2h 21mFrontier
Deal found 4/25$189
Thu 5/3010:12 pmPWM - ORD
Nonstop2h 46mFrontier
Sun 6/25:35 pmORD - PWM
Nonstop2h 20mFrontier
Deal found 4/26$190

Portland to Chicago flights leaving soon

Find last-minute flight options from Portland to Chicago 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 3,068,117 searches. Data last updated April 26, 2024.
Users seeking a last-minute flight from Portland to Chicago should consider booking one of these fares. To prevent any unwanted surprises, users should verify their flight info before booking.
Thu 5/21:00 pmPWM - ORD
1 stop12h 59mFrontier
Sun 5/55:51 pmORD - PWM
1 stop13h 20mFrontier
Deal found 4/25$188
Fri 5/312:56 pmPWM - ORD
1 stop11h 47mFrontier
Mon 5/68:25 amORD - PWM
1 stop26h 45mFrontier
Deal found 4/25$198
Fri 5/312:56 pmPWM - MDW
1 stop10h 35mFrontier
Sun 5/56:31 pmMDW - PWM
1 stop12h 40mFrontier
Deal found 4/25$198
Fri 5/36:05 amPWM - ORD
1 stop6h 35mUnited Airlines
Sun 5/56:09 pmORD - PWM
Nonstop2h 34mUnited Airlines
Deal found 4/25$494
Fri 5/32:55 pmPWM - ORD
2 stops9h 57mDelta
Mon 5/65:25 pmORD - PWM
1 stop5h 19mDelta
Deal found 4/25$519
Fri 5/39:20 amPWM - ORD
Nonstop2h 59mUnited Airlines
Sun 5/56:09 pmORD - PWM
Nonstop2h 34mUnited Airlines
Deal found 4/25$544
Fri 5/39:20 amPWM - ORD
Nonstop2h 59mUnited Airlines
Mon 5/68:48 amORD - PWM
1 stop5h 11mUnited Airlines
Deal found 4/26$553
Fri 5/36:05 amPWM - ORD
1 stop5h 35mUnited Airlines
Mon 5/66:09 pmORD - PWM
Nonstop2h 34mUnited Airlines
Deal found 4/25$608
Thu 5/29:20 amPWM - ORD
Nonstop2h 59mUnited Airlines
Sun 5/56:09 pmORD - PWM
Nonstop2h 34mUnited Airlines
Deal found 4/25$612

One-way flights to Chicago from Portland

Search for one-way flight options from Portland to Chicago. 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 3,068,117 searches. Data last updated April 26, 2024.
Some of the best available deals we've found on one-way flights from Portland to Chicago. Users needing a return flight from Portland to Chicago should utilize the search form above.
Tue 5/2110:12 pmPWM - ORD
Nonstop2h 46mFrontier
Deal found 4/25$49
Thu 6/1310:02 pmPWM - ORD
Nonstop2h 46mFrontier
Deal found 4/25$56
Tue 5/2111:40 amPWM - MDW
1 stop20h 14mFrontier
Deal found 4/25$59
Tue 8/1310:11 pmPWM - ORD
Nonstop2h 46mFrontier
Deal found 4/24$69
Sun 6/2310:02 pmPWM - ORD
Nonstop2h 46mFrontier
Deal found 4/25$88
Tue 5/2111:40 amPWM - ORD
1 stop14h 28mFrontier
Deal found 4/26$94
Tue 5/141:06 pmPWM - ORD
1 stop12h 53mFrontier
Deal found 4/25$95
Wed 6/267:15 pmPWM - ORD
1 stop5h 05mUnited Airlines
Deal found 4/26$99
Sun 5/59:40 amPWM - MDW
1 stop9h 00mFrontier
Deal found 4/25$99

Find flights from Portland to Chicago within your budget

Customize your flight search to find flights from Portland to Chicago 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 3,068,117 searches. Data last updated April 26, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$98 - $315

Route

Depart

Return

Price

PortlandChicago O'Hare Intl

PWM - ORD

PWMORD

Portland

Tue 10/22

Nonstop2h 46m

Chicago O'Hare Intl

Tue 10/29

Nonstop2h 21m

$98

PortlandChicago O'Hare Intl

PWM - ORD

PWMORD

Portland

Tue 6/4

Nonstop2h 46m

Chicago O'Hare Intl

Thu 6/6

Nonstop2h 20m

$101

PortlandChicago O'Hare Intl

PWM - ORD

PWMORD

Portland

Thu 6/6

Nonstop2h 46m

Chicago O'Hare Intl

Sun 6/9

Nonstop2h 20m

$105

PortlandChicago O'Hare Intl

PWM - ORD

PWMORD

Portland

Thu 6/6

Nonstop2h 46m

Chicago O'Hare Intl

Sun 6/9

Nonstop2h 20m

$112

PortlandChicago O'Hare Intl

PWM - ORD

PWMORD

Portland

Tue 6/25

Nonstop2h 46m

Chicago O'Hare Intl

Wed 6/26

1 stop15h 23m

$223

PortlandChicago O'Hare Intl

PWM - ORD

PWMORD

Portland

Thu 6/13

1 stop4h 44m

Chicago O'Hare Intl

Tue 6/18

1 stop6h 28m

$238

PortlandChicago O'Hare Intl

PWM - ORD

PWMORD

Portland

Fri 6/7

Nonstop2h 53m

Chicago O'Hare Intl

Sun 6/9

Nonstop2h 28m

$253

PortlandChicago O'Hare Intl

PWM - ORD

PWMORD

Portland

Thu 9/5

Nonstop2h 46m

Chicago O'Hare Intl

Sat 9/7

Nonstop2h 31m

$299

PortlandChicago O'Hare Intl

PWM - ORD

PWMORD

Portland

Fri 7/26

1 stop22h 49m

Chicago O'Hare Intl

Sun 7/28

1 stop15h 23m

$315

Flights are sorted by cheapest first

Deals found on 4/25

When is the best time to book a flight from Portland, Maine to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Portland to Chicago. Price data was last updated on January 28, 2024.
Booking 86 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland, Maine to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Search Deals

When is the cheapest time to fly from Portland, Maine to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Portland to Chicago. Price data was last updated on April 21, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Portland, Maine to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Average price of flights to Chicago by month

Plan your trip from Portland to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight from Portland to Chicago is currently $79 while a round-trip flight costs $194. Price data was last updated on April 21, 2024.

Currently, February is the cheapest month in which you can book a flight from Portland, Maine to Chicago (average of $245). Flying from Portland, Maine to Chicago in June is currently the most expensive (average of $356). 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

$248

February

$245

March

$280

April

$273

May

$282

June

$356

July

$336

August

$276

September

$258

October

$248

November

$270

December

$248

Temperature and rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

23 - 73.4 °F

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated April 26, 2024.
Get a feel of what it's like to fly with Frontier, American Airlines and United Airlines from Portland to Chicago by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.1
Very good
10,966 reviews
Check prices

Overall

8.1

Food

7.4

Entertainment

8.0

Comfort

7.9

Crew

8.6

Boarding

8.2

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

Delta
8.1
Very good
10,966 reviews
Delta
8.1
Very good
10,966 reviews
Check prices

Overall

8.1

Food

7.4

Entertainment

8.0

Comfort

7.9

Crew

8.6

Boarding

8.2

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

JetBlue
7.6
Good
4,606 reviews
Delta
8.1
Very good
10,966 reviews
Check prices

Overall

8.1

Food

7.4

Entertainment

8.0

Comfort

7.9

Crew

8.6

Boarding

8.2

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

WestJet
7.5
Good
2,981 reviews
Delta
8.1
Very good
10,966 reviews
Check prices

Overall

8.1

Food

7.4

Entertainment

8.0

Comfort

7.9

Crew

8.6

Boarding

8.2

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

United Airlines
7.4
Good
11,228 reviews
Delta
8.1
Very good
10,966 reviews
Check prices

Overall

8.1

Food

7.4

Entertainment

8.0

Comfort

7.9

Crew

8.6

Boarding

8.2

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

American Airlines
7.3
Good
14,889 reviews
Delta
8.1
Very good
10,966 reviews
Check prices

Overall

8.1

Food

7.4

Entertainment

8.0

Comfort

7.9

Crew

8.6

Boarding

8.2

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

Related info for your journey

Find useful and relevant information for your journey from Portland to Chicago. 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 from for flights from Portland to Chicago?

    For a flight from Portland to Chicago, you will be flying from Portland. Portland (PWM) is just 2.9 mi from the center of the city. Portland is the only Portland airport and it handles 4 outbound flights to Chicago per day. 4 airlines have flights to Chicago from Portland on a regular basis.

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

    Yes, there are multiple flights from Portland, Maine to Chicago for under $100. The cheapest flight booked recently is on Frontier for just $98, but on average you can expect to pay $151.

  • Are there nonstop flights from Portland, Maine to Chicago for under $100 on Cheapflights?

    Cheapflights has at least 20 direct flights from Portland, Maine to Chicago under $100. A good price for a nonstop flight from Portland, Maine to Chicago is less than $209.

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

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

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

    Cheapflights users have booked flights from Portland, Maine to Chicago round-trip from $98. This flight start at 74% lower than the current average price 3 months from now.

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

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $49. Users have also found prices from $99 and $119 on United Airlines and Delta, respectively.

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

    The most popular airlines flying from Portland, Maine to Chicago are American Airlines, Delta and Frontier. Something to consider prior to booking your flight.

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

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Portland, Maine to Chicago on time: Air New Zealand (88%), Republic Airways (88%), United Airlines (87%).

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

    On average you can expect to pay $896 for a flight from Portland, Maine to Chicago. The cheapest flight overall is $154 while the most popular route, (Portland - Chicago O'Hare Intl) is currently priced at $131.

  • What does PWM to ORD mean?

    Great question - PWM to ORD just means Portland Airport to Chicago O'Hare Intl Airport. Now you’ll know what these unique codes when you look for flights! Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.

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

    The amount of baggage you can bring on your Portland to Chicago 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 Portland to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Portland to Chicago 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 Portland to Chicago that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Portland to Chicago 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 Portland to Chicago that allow pets onboard?

    Many airlines flying from Portland to Chicago 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 Portland to Chicago?

    Yes, you can often find last-minute deals on Portland to Chicago 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 Portland, Maine to Chicago flight deals updated?

    The Portland, Maine to Chicago flight deals you see on this page were last updated on 4/26.

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

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Top 4 airlines flying from Portland to Chicago

Discover the top 4 airlines that operate flights from Portland to Chicago. 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 3,068,117 searches. Data last updated April 26, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$99Average$178FlexibilityNo cancel feeOn-time62%
Search Frontier flights
American AirlinesCheapest$194Average$378FlexibilityNo cancel feeOn-time71%
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DeltaCheapest$207Average$381FlexibilityNo cancel feeOn-timeN/A
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United AirlinesCheapest$216Average$380FlexibilityNo cancel feeOn-time69%
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Search flights from Portland to Chicago by cabin class

Find flights from Portland to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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Hourly flight availability from Portland to Chicago

Find hourly flight availability from Portland to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 26, 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 Portland to Chicago

Explore weekly flight availability from Portland to Chicago. 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 April 26, 2024.
Sunday4daily flights
Monday4daily flights
Tuesday3daily flights
Wednesday4daily flights
Thursday4daily flights
Friday4daily flights
Saturday6daily flights

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Why should you use Cheapflights to find cheap flight tickets from Portland to Chicago?

Millions of users choose and trust Cheapflights to book the best flight deals from Portland to Chicago for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

Can Cheapflights find flights from Portland to Chicago with no change fees?

Certainly. Search results for flights to Chicago from Portland shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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Not ready to book yet? You can track prices for flights from Portland to Chicago on Cheapflights with our Price Alert feature and get notified when better prices are available.

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