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$53+ 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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PWM
Dec 24 — Dec 311
Tue 12/24
Tue 12/31
1 adult, Economy
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Cheap flight deals from Chicago to Maine

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Maine (USME). 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 December 19, 2024.

Round-trip from

$116
(Mytrip)

One-way from

$53
(Mytrip)
From Chicago (CHI) to Maine
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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 December 19, 2024.

This FlightHub deal was found by Cheapflights users on 12/18. 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.
Mon 12/239:59 pmMDW - BOS
1 stop8h 02mFrontier
Tue 12/315:45 amBOS - MDW
1 stop10h 26mFrontier
Deal found 12/18$138
This Frontier deal was found by Cheapflights users on 12/18. 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.
Wed 12/2510:22 pmORD - BOS
1 stop8h 11mFrontier
Mon 1/611:55 amBOS - ORD
1 stop12h 02mFrontier
Deal found 12/18$178
This JetBlue Airways deal was found by Cheapflights users on 12/18. 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.
Wed 12/258:37 amORD - BOS
Nonstop2h 21mJetBlue
Tue 1/78:10 amBOS - ORD
Nonstop3h 02mJetBlue
Deal found 12/18$193
This American Airlines deal was found by Cheapflights users on 12/18. 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.
Wed 12/258:05 amORD - BOS
Nonstop2h 21mAmerican Airlines
Wed 1/16:45 amBOS - ORD
Nonstop3h 04mAmerican Airlines
Deal found 12/18$209
This Southwest deal was found by Cheapflights users on 12/18. 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 12/256:25 pmMDW - BOS
Nonstop2h 10mSouthwest
Mon 1/67:00 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 12/18$215
This United Airlines deal was found by Cheapflights users on 12/18. 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.
Wed 12/259:30 pmORD - BOS
Nonstop2h 24mUnited Airlines
Tue 12/316:02 amBOS - ORD
Nonstop3h 03mUnited Airlines
Deal found 12/18$235
This Delta deal was found by Cheapflights users on 12/18. 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.
Tue 12/245:57 pmORD - BOS
1 stop5h 53mDelta
Wed 1/83:30 pmBOS - ORD
Nonstop3h 06mDelta
Deal found 12/18$238
This CheapOair deal was found by Cheapflights users on 12/18. 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.
Wed 12/187:00 amORD - BOS
1 stop9h 26mSpirit Airlines
Tue 1/212:06 pmBOS - ORD
1 stop23h 51mSpirit Airlines
Deal found 12/18$249
This Booking.com deal was found by Cheapflights users on 12/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/201:24 pmORD - BOS
1 stop8h 51mMultiple Airlines
Tue 1/146:00 amBOS - ORD
1 stop8h 34mMultiple Airlines
Deal found 12/19$292
This Delta deal was found by Cheapflights users on 12/17. 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.
Wed 12/255:57 pmORD - PWM
1 stop5h 13mDelta
Wed 1/15:05 amPWM - ORD
1 stop5h 16mDelta
Deal found 12/17$317
This Delta deal was found by Cheapflights users on 12/18. 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.
Wed 12/2511:48 amMDW - BOS
1 stop6h 23mDelta
Thu 1/25:35 amBOS - MDW
1 stop6h 33mDelta
Deal found 12/18$317
This Southwest deal was found by Cheapflights users on 12/17. 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 12/3111:25 amORD - BOS
2 stops10h 00mSouthwest
Fri 1/35:00 amBOS - ORD
1 stop9h 00mSouthwest
Deal found 12/17$331

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 December 19, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/9

5:02 pm-12:30 am

1 stop6h 28m

Boston Logan Intl

Mon 1/13

11:37 am-10:23 pm

1 stop11h 46m

$116

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 1/7

5:24 pm-12:30 am

1 stop6h 06m

Boston Logan Intl

Fri 1/10

6:00 am-11:51 am

1 stop6h 51m

$116

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 2/9

4:18 pm-12:27 am

1 stop7h 09m

Boston Logan Intl

Wed 2/12

10:03 am-10:03 pm

1 stop13h 00m

$123

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 2/1

10:29 am-10:00 pm

1 stop10h 31m

Boston Logan Intl

Tue 2/4

11:31 am-8:13 pm

1 stop9h 42m

$144

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/9

4:15 pm-7:38 pm

Nonstop2h 23m

Boston Logan Intl

Sun 1/12

9:30 am-11:28 am

Nonstop2h 58m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/9

8:05 am-11:26 am

Nonstop2h 21m

Boston Logan Intl

Mon 1/13

6:00 am-8:08 am

Nonstop3h 08m

$158

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 1/9

10:05 am-1:20 pm

Nonstop2h 15m

Boston Logan Intl

Sat 1/11

5:50 am-7:50 am

Nonstop3h 00m

$158

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/16

7:00 am-10:15 am

Nonstop2h 15m

Boston Logan Intl

Sun 1/19

11:28 am-3:44 pm

1 stop5h 16m

$166

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 1/20

7:10 am-10:47 am

Nonstop2h 37m

Boston Logan Intl

Sat 1/25

7:15 am-9:25 am

Nonstop3h 10m

$187

ChicagoBangor

ORD - BGR

ORDBGR

Chicago O'Hare Intl

Wed 1/15

7:05 am-2:20 pm

1 stop6h 15m

Bangor

Sun 1/19

6:10 am-10:53 am

1 stop5h 43m

$248

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Showing 1-10 of 56 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 December 19, 2024.

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 December 19, 2024.
See what other customers who have flown with Frontier, Spirit Airlines and United Airlines 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
4,836 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Overall

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,836 reviews
Southwest
8.1
Very good
4,836 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Overall

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,551 reviews
Southwest
8.1
Very good
4,836 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Overall

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,600 reviews
Southwest
8.1
Very good
4,836 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Overall

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,274 reviews
Southwest
8.1
Very good
4,836 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Overall

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,048 reviews
Southwest
8.1
Very good
4,836 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Overall

8.1

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $53 on Frontier. Other airlines that offer cheap prices include JetBlue from $79 and Southwest from $79 one-way.

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

    While some choose either Chicago O'Hare Intl - Portland or Chicago Midway - Boston Logan Intl, 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 United Airlines (94%), SkyWest Airlines (93%) and Republic Airways (92%).

  • What are the cheapest flights from Chicago to Maine?

    The cheapest flight price from Chicago to Maine is $138. On average you can expect to pay $318. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $115.

  • 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 4 airlines flying from Chicago to Maine

Discover the top 4 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 December 19, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$92FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$184Average$360FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$340FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$217Average$469FlexibilityNo cancel feeOn-time69%
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