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Maine

$74+ Cheap flights from Chicago (CHI) to Maine

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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PWM
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
1 adult, Economy
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Cheap flight deals from Chicago to Maine

Keep the following information in mind while searching for Chicago to Maine flight deals. Data was last updated March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$116
(Southwest)

One-way from

$76
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$390

Good round-trip deal

$279 or less

Good one-way deal

$139 or less
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
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From Chicago (CHI) to Maine
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One-way flight from Chicago (CHI) to Maine
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Highest demand for flights based on searches. 10% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Maine.
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Price to beat on a one-way flight from Chicago (CHI) to Maine.
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Find flight deals from Chicago to Maine

Cheapest flights from Chicago to Maine
Explore the most affordable flight options available from Chicago to Maine. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 31, 2025.

This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/61:50 pmORD - BOS
1 stop4h 20mSouthwest
Fri 5/96:25 amBOS - ORD
1 stop8h 40mSouthwest
Deal found 3/31$116
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/306:50 amMDW - BOS
1 stop6h 10mSouthwest
Wed 5/71:30 pmBOS - MDW
1 stop7h 20mSouthwest
Deal found 3/31$116
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/187:00 amORD - BOS
Nonstop2h 30mDelta
Sat 10/258:10 pmBOS - ORD
Nonstop2h 52mDelta
Deal found 3/31$117
This FlightHub deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/16:00 amORD - BOS
1 stop10h 34mSpirit Airlines
Tue 10/76:10 amBOS - ORD
1 stop12h 27mSpirit Airlines
Deal found 3/31$118
This United Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/128:05 pmORD - BOS
Nonstop2h 27mUnited Airlines
Sat 8/167:44 amBOS - ORD
Nonstop2h 55mUnited Airlines
Deal found 3/30$124
This JetBlue deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/97:31 pmORD - BOS
Nonstop2h 29mJetBlue
Tue 5/136:00 amBOS - ORD
Nonstop3h 00mJetBlue
Deal found 3/30$132
This American Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/221:10 pmORD - BOS
Nonstop2h 25mAmerican Airlines
Fri 4/256:10 amBOS - ORD
Nonstop3h 08mAmerican Airlines
Deal found 3/29$138
This Frontier deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/81:19 pmMDW - BOS
1 stop10h 46mFrontier
Mon 5/1212:58 pmBOS - MDW
1 stop11h 49mFrontier
Deal found 3/31$198
This CheapOair deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/154:15 pmORD - BOS
1 stop7h 50mFrontier
Sun 5/1810:14 amBOS - ORD
1 stop28h 27mFrontier
Deal found 3/30$200
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/197:05 amORD - PWM
1 stop5h 30mDelta
Sat 4/265:32 amPWM - ORD
2 stops10h 33mDelta
Deal found 3/30$228
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/196:04 amMDW - PWM
1 stop6h 31mDelta
Sat 4/267:00 amPWM - MDW
2 stops11h 59mDelta
Deal found 3/30$228
This American Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/217:01 amORD - PWM
1 stop7h 19mAmerican Airlines
Sat 6/287:41 amPWM - ORD
1 stop5h 38mAmerican Airlines
Deal found 3/31$229

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Maine 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 2,558,603 searches. Data last updated March 31, 2025.
Use the filters below to find and compare flights from Chicago to Maine that are best for you.

Fly from

Chicago

Fly to

Maine

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 5/6

1:50 pm-7:10 pm

1 stop4h 20m

Boston Logan Intl

Fri 5/9

6:25 am-2:05 pm

1 stop8h 40m

$116

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 4/30

6:50 am-2:00 pm

1 stop6h 10m

Boston Logan Intl

Wed 5/7

1:30 pm-7:50 pm

1 stop7h 20m

$116

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 4/11

8:29 pm-11:58 pm

Nonstop2h 29m

Boston Logan Intl

Tue 4/15

5:15 pm-7:27 pm

Nonstop3h 12m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 8/12

8:05 pm-11:32 pm

Nonstop2h 27m

Boston Logan Intl

Sat 8/16

7:44 am-9:39 am

Nonstop2h 55m

$124

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/31

7:00 am-10:25 am

Nonstop2h 25m

Boston Logan Intl

Sat 6/7

11:25 am-1:14 pm

Nonstop2h 49m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 4/22

1:10 pm-4:35 pm

Nonstop2h 25m

Boston Logan Intl

Fri 4/25

6:10 am-8:18 am

Nonstop3h 08m

$138

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 4/29

7:47 pm-10:22 am

1 stop13h 35m

Boston Logan Intl

Wed 4/30

11:27 am-12:20 am

1 stop13h 53m

$139

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 5/8

1:19 pm-1:05 am

1 stop10h 46m

Boston Logan Intl

Mon 5/12

12:58 pm-11:47 pm

1 stop11h 49m

$198

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 4/19

7:05 am-1:35 pm

1 stop5h 30m

Portland

Sat 4/26

5:32 am-3:05 pm

2 stops10h 33m

$228

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Sat 4/19

6:04 am-1:35 pm

1 stop6h 31m

Portland

Sat 4/26

7:00 am-5:59 pm

2 stops11h 59m

$228

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Maine

Have a flexible travel schedule? Discover the best time to fly to Maine from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Maine

What is the cheapest month to book a flight from Chicago to Maine?

Currently, January is the cheapest month in which you can book a flight from Chicago to Maine (average of $296). Flying from Chicago to Maine in May is currently the most expensive (average of $416). 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.

What is the cheapest time of day to fly from CHI to ME?

Find hourly flight availability from Chicago to Maine. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 31, 2025.

When flying from Chicago to Maine, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Chicago to Maine

Explore weekly flight availability from Chicago to Maine. 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 March 31, 2025.

The most flights from CHI to USME are scheduled on a Monday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Maine by month

Plan your trip to Maine by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Maine ranges from 2.9 - 4.5 inches per month. November is typically the wettest month, when rainfall can reach 4.5 in. August is typically the driest time to visit Maine when rainfall is around 2.9 in.

Temperature in Maine by month

Plan your trip to Maine by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Maine, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Maine

Get insights into the airlines that provide service to Maine. 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 Maine. Reviews last updated March 31, 2025.
See what other customers who have flown with Alaska Airlines, Southwest and Delta from Chicago to Maine have to say. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,818 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,818 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,275 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,899 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,614 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
JetBlue
7.3
Good
2,924 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Related info for your journey

Find useful and relevant information for your journey from Chicago to Maine. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    One-way options have recently been found by users for as low as $76 on Spirit Airlines. Other airlines that offer cheap prices include Delta from $79 and United Airlines from $83 one-way.

  • What are the most popular routes from Chicago to Maine?

    While some choose either Chicago Midway - Boston Logan Intl or Chicago O'Hare Intl - Portland, Chicago O'Hare Intl - Boston Logan Intl is the most popular route from Chicago to Maine.

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

    The top 3 most reliable airlines when flying from Chicago to Maine are SkyWest Airlines (77%), Air New Zealand (70%) and United Airlines (66%).

  • What are the cheapest flights from Chicago to Maine?

    The cheapest flight price from Chicago to Maine is $89. On average you can expect to pay $285. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $92.

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

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

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

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

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

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

  • What is the cheapest month to book a flight from Chicago to Maine?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Maine (average of $296). Flying from Chicago to Maine in May is currently the most expensive (average of $416). 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.

See more FAQs

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Alternative routes for Chicago to Maine

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Chicago to Maine

Discover the top 5 airlines that operate flights from Chicago to Maine. 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 2,558,603 searches. Data last updated March 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$89FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$179Average$350FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$191Average$406FlexibilityNo cancel feeOn-time63%
DeltaCheapest$217Average$358FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$218Average$462FlexibilityNo cancel feeOn-time69%
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