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$62+ 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 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PWM
Feb 27 — Mar 61
Thu 2/27
Thu 3/6
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 February 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$150
(Frontier)

One-way from

$62
(Mytrip)

Popular in

April

Cheapest in

June

Average price

$357

Good round-trip deal

$331 or less

Good one-way deal

$233 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. 12% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 22, 2025.

This Frontier deal was found by Cheapflights users on 2/21. 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.
Mon 3/105:05 amORD - PWM
1 stop12h 29mFrontier
Thu 3/1310:08 amPWM - ORD
1 stop9h 46mFrontier
Deal found 2/21$150
This Frontier deal was found by Cheapflights users on 2/22. 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.
Mon 3/105:37 pmORD - BOS
1 stop6h 07mFrontier
Thu 3/136:00 amBOS - ORD
1 stop13h 54mFrontier
Deal found 2/22$150
This Frontier deal was found by Cheapflights users on 2/21. 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 5/151:19 pmMDW - BOS
1 stop10h 46mFrontier
Mon 5/1912:58 pmBOS - MDW
1 stop11h 49mFrontier
Deal found 2/21$150
This Mytrip deal was found by Cheapflights users on 2/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/112:14 pmORD - BOS
2 stops28h 00mSpirit Airlines
Tue 4/810:47 pmBOS - ORD
3 stops19h 54mSpirit Airlines
Deal found 2/21$151
This United Airlines deal was found by Cheapflights users on 2/21. 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.
Fri 3/711:15 amORD - BOS
Nonstop2h 19mUnited Airlines
Sat 3/156:00 amBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 2/21$157
This Southwest deal was found by Cheapflights users on 2/21. 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.
Thu 4/105:30 amMDW - BOS
Nonstop2h 15mSouthwest
Mon 4/145:45 amBOS - MDW
Nonstop2h 35mSouthwest
Deal found 2/21$157
This JetBlue deal was found by Cheapflights users on 2/21. 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 2/285:45 pmORD - BOS
Nonstop2h 35mJetBlue
Mon 3/33:00 pmBOS - ORD
Nonstop3h 00mJetBlue
Deal found 2/21$158
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Thu 2/277:00 amORD - BOS
Nonstop2h 20mAmerican Airlines
Sun 3/25:14 amBOS - ORD
Nonstop3h 01mAmerican Airlines
Deal found 2/20$161
This JetBlue Airways deal was found by Cheapflights users on 2/21. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/311:12 pmORD - PWM
1 stop7h 45mJetBlue
Sat 6/72:15 pmPWM - ORD
1 stop9h 05mJetBlue
Deal found 2/21$163
This CheapOair deal was found by Cheapflights users on 2/21. 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.
Sun 4/68:10 amORD - BOS
1 stop24h 25mMultiple Airlines
Wed 4/94:20 pmBOS - ORD
1 stop9h 01mMultiple Airlines
Deal found 2/21$165
This Delta deal was found by Cheapflights users on 2/21. 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.
Fri 3/146:55 pmORD - BOS
Nonstop2h 22mDelta
Mon 3/248:15 pmBOS - ORD
Nonstop3h 00mDelta
Deal found 2/21$178
This American Airlines deal was found by Cheapflights users on 2/21. 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 9/28:00 amORD - PWM
Nonstop2h 25mAmerican Airlines
Tue 9/96:02 pmPWM - ORD
Nonstop2h 48mAmerican Airlines
Deal found 2/21$209

Find flights from Chicago to Maine within your budget

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 February 22, 2025.

Fly from

Chicago

Fly to

Maine

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 3/10

5:05 am-6:34 pm

1 stop12h 29m

Portland

Thu 3/13

10:08 am-6:54 pm

1 stop9h 46m

$150

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 3/10

5:37 pm-12:44 am

1 stop6h 07m

Boston Logan Intl

Thu 3/13

6:00 am-6:54 pm

1 stop13h 54m

$150

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 5/15

1:19 pm-1:05 am

1 stop10h 46m

Boston Logan Intl

Mon 5/19

12:58 pm-11:47 pm

1 stop11h 49m

$150

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 4/1

12:14 pm-5:14 pm

2 stops28h 00m

Boston Logan Intl

Tue 4/8

10:47 pm-5:41 pm

3 stops19h 54m

$151

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 3/7

11:15 am-2:34 pm

Nonstop2h 19m

Boston Logan Intl

Sat 3/15

6:00 am-8:04 am

Nonstop3h 04m

$157

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 4/10

5:30 am-8:45 am

Nonstop2h 15m

Boston Logan Intl

Mon 4/14

5:45 am-7:20 am

Nonstop2h 35m

$157

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 5/31

1:12 pm-9:57 pm

1 stop7h 45m

Portland

Sat 6/7

2:15 pm-10:20 pm

1 stop9h 05m

$163

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 4/6

8:10 am-9:35 am

1 stop24h 25m

Boston Logan Intl

Wed 4/9

4:20 pm-12:21 am

1 stop9h 01m

$165

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 4/10

7:02 pm-10:32 pm

Nonstop2h 30m

Boston Logan Intl

Mon 4/14

7:05 am-9:05 am

Nonstop3h 00m

$167

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 3/14

6:55 pm-10:17 pm

Nonstop2h 22m

Boston Logan Intl

Mon 3/24

8:15 pm-10:15 pm

Nonstop3h 00m

$178

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

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.

Travel insights for flights from Chicago to Maine

Get recent, data-driven insights about flights from Chicago to Maine including ideal travel times, pricing trends, and more.

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 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.

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 February 22, 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.

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 February 22, 2025.
See what other customers who have flown with Southwest, Alaska Airlines 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.
Southwest
8.1
Very good
4,395 reviews

Entertainment

7.6

Food

7.1

Comfort

8.1

Crew

8.7

Overall

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,395 reviews
Southwest
8.1
Very good
4,395 reviews

Entertainment

7.6

Food

7.1

Comfort

8.1

Crew

8.7

Overall

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,700 reviews
Southwest
8.1
Very good
4,395 reviews

Entertainment

7.6

Food

7.1

Comfort

8.1

Crew

8.7

Overall

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,395 reviews

Entertainment

7.6

Food

7.1

Comfort

8.1

Crew

8.7

Overall

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,068 reviews
Southwest
8.1
Very good
4,395 reviews

Entertainment

7.6

Food

7.1

Comfort

8.1

Crew

8.7

Overall

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,754 reviews
Southwest
8.1
Very good
4,395 reviews

Entertainment

7.6

Food

7.1

Comfort

8.1

Crew

8.7

Overall

8.1

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $62 on Frontier. Other airlines that offer cheap prices include United Airlines from $79 and Southwest from $79 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 Republic Airways (92%), United Airlines (88%) and SkyWest Airlines (72%).

  • What are the cheapest flights from Chicago to Maine?

    The cheapest flight price from Chicago to Maine is $223. On average you can expect to pay $385. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $85.

  • 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 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.

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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 February 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$92FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$179Average$355FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$191Average$401FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$344FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$220Average$468FlexibilityNo cancel feeOn-time69%
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