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Maine

$59+ 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PWM
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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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 November 13, 2025.

This Delta deal was found by Cheapflights users on 11/12. 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 12/127:10 pmORD - BOS
Nonstop2h 24mDelta
Sun 12/1412:50 pmBOS - ORD
Nonstop2h 57mDelta
Deal found 11/12$117
This Southwest deal was found by Cheapflights users on 11/11. 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 12/116:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Sun 12/145:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 11/11$117
This Delta deal was found by Cheapflights users on 11/11. 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.
Thu 12/117:10 amORD - BOS
Nonstop2h 26mDelta
Sun 12/147:30 amBOS - ORD
Nonstop3h 03mDelta
Deal found 11/11$118
This Trip.com deal was found by Cheapflights users on 11/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/128:38 pmORD - BOS
Nonstop2h 28mJetBlue
Mon 12/158:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 11/13$120
This JetBlue deal was found by Cheapflights users on 11/12. 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.
Mon 12/811:25 amORD - BOS
Nonstop2h 24mJetBlue
Tue 12/98:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 11/12$122
This Southwest deal was found by Cheapflights users on 11/12. 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 12/116:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Sat 12/135:20 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 11/12$122
This Trip.com deal was found by Cheapflights users on 11/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/48:38 pmORD - BOS
Nonstop2h 28mJetBlue
Mon 12/85:29 pmBOS - ORD
Nonstop3h 14mJetBlue
Deal found 11/12$123
This American Airlines deal was found by Cheapflights users on 11/11. 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.
Fri 12/128:40 pmORD - BOS
Nonstop2h 33mAmerican Airlines
Sat 1/36:36 amBOS - ORD
Nonstop3h 11mAmerican Airlines
Deal found 11/11$124
This JetBlue deal was found by Cheapflights users on 11/12. 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.
Sat 12/611:25 amORD - BOS
Nonstop2h 24mJetBlue
Mon 12/88:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 11/12$125
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:15 amMDW - BOS
1 stop15h 59mFrontier
Thu 1/16:00 amBOS - MDW
1 stop12h 38mFrontier
Deal found 11/12$125
This JetBlue deal was found by Cheapflights users on 11/12. 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.
Thu 12/48:38 pmORD - BOS
Nonstop2h 28mJetBlue
Sun 12/78:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 11/12$127
This Southwest deal was found by Cheapflights users on 11/11. 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.
Fri 12/56:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Mon 12/85:30 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 11/11$127

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 November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(Delta)

One-way from

$59
(United Airlines)

Popular in

November

Cheapest in

February

Average price

$473

Good round-trip deal

$271 or less

Good one-way deal

$225 or less
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
Search Deals
From Chicago (CHI) to Maine
Search Deals
One-way flight from Chicago (CHI) to Maine
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($61 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Maine.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Maine.
Search Deals

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 November 13, 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

Thu 12/11

10:35 am-1:59 pm

Nonstop2h 24m

Boston Logan Intl

Sun 12/14

12:50 pm-2:47 pm

Nonstop2h 57m

$117

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 12/25

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Thu 1/1

5:30 am-7:15 am

Nonstop2h 45m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 12/12

7:10 pm-10:34 pm

Nonstop2h 24m

Boston Logan Intl

Sun 12/14

12:50 pm-2:47 pm

Nonstop2h 57m

$117

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 12/11

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Sun 12/14

5:15 am-7:00 am

Nonstop2h 45m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 2/14

7:05 am-10:40 am

Nonstop2h 35m

Boston Logan Intl

Sat 2/21

5:15 pm-7:26 pm

Nonstop3h 11m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 12/6

11:25 am-2:49 pm

Nonstop2h 24m

Boston Logan Intl

Sun 12/7

8:30 am-10:35 am

Nonstop3h 05m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 12/5

8:38 pm-12:06 am

Nonstop2h 28m

Boston Logan Intl

Sun 12/7

8:30 am-10:35 am

Nonstop3h 05m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 12/24

7:41 pm-11:10 pm

Nonstop2h 29m

Boston Logan Intl

Wed 12/31

4:31 pm-6:46 pm

Nonstop3h 15m

$131

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 12/9

1:30 pm-4:45 pm

Nonstop2h 15m

Boston Logan Intl

Tue 12/16

7:45 am-1:00 pm

2 stops6h 15m

$132

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 12/11

9:20 am-4:35 pm

1 stop6h 15m

Boston Logan Intl

Sat 12/13

5:20 am-7:05 am

Nonstop2h 45m

$132

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

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, October is the cheapest month in which you can book a flight from Chicago to Maine (average of $205). Flying from Chicago to Maine in November is currently the most expensive (average of $289). 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 November 13, 2025.

When flying from Chicago to Maine, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 40% versus a flight in the morning.

What is the cheapest day to fly from Chicago to Maine?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Maine. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Maine flight should consider departing on Sunday afternoons when fares are most often at their lowest. Thursday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 November 13, 2025.

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

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 November 13, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Chicago to Maine 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.
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,007 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,017 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,051 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,907 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Chicago to Maine?

    Departing from Chicago to Maine will take you 2h 20m. Chicago and Maine are separated by a distance of 857 mi. Generally, flights for this route are nonstop.

  • 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 $59 on United Airlines. Other airlines that offer cheap prices include Delta from $59 and Southwest from $59 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 Air New Zealand (85%), United Airlines (84%) and Republic Airways (83%).

  • What are the cheapest flights from Chicago to Maine?

    The cheapest flight price from Chicago to Maine is $165. On average you can expect to pay $412. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $71.

  • 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, October is the cheapest month in which you can book a flight from Chicago to Maine (average of $205). Flying from Chicago to Maine in November is currently the most expensive (average of $289). 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 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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$163Average$413FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$226Average$420FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$229Average$376FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$313Average$411FlexibilityNo cancel feeOn-time63%

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