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$55+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PWM
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
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 January 21, 2025.

Round-trip from

$154
(CheapOair)

One-way from

$55
(Frontier)
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 January 21, 2025.

This CheapOair deal was found by Cheapflights users on 1/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/75:05 amORD - BOS
1 stop26h 07mFrontier
Tue 3/116:00 amBOS - ORD
1 stop28h 05mFrontier
Deal found 1/20$154
This FlightHub deal was found by Cheapflights users on 1/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/37:25 pmMDW - BOS
1 stop14h 08mFrontier
Fri 3/710:41 amBOS - MDW
1 stop11h 44mFrontier
Deal found 1/20$154
This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/56:45 amORD - BOS
1 stop11h 55mSpirit Airlines
Wed 3/128:48 amBOS - ORD
2 stops23h 56mSpirit Airlines
Deal found 1/20$156
This United Airlines deal was found by Cheapflights users on 1/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/209:15 amORD - BOS
Nonstop2h 23mUnited Airlines
Sun 2/2310:52 amBOS - ORD
Nonstop3h 02mUnited Airlines
Deal found 1/20$157
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/112:25 pmORD - BOS
1 stop8h 35mMultiple Airlines
Thu 2/66:00 amBOS - ORD
1 stop28h 52mMultiple Airlines
Deal found 1/20$159
This Booking.com deal was found by Cheapflights users on 1/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/110:20 amORD - PWM
1 stop21h 58mFrontier
Mon 3/38:35 pmPWM - ORD
1 stop17h 45mFrontier
Deal found 1/20$160
This JetBlue deal was found by Cheapflights users on 1/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/265:45 pmORD - BOS
Nonstop2h 35mJetBlue
Sat 3/12:00 pmBOS - ORD
Nonstop3h 05mJetBlue
Deal found 1/20$167
This Southwest deal was found by Cheapflights users on 1/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/266:25 pmMDW - BOS
Nonstop2h 15mSouthwest
Tue 3/48:10 amBOS - MDW
Nonstop2h 55mSouthwest
Deal found 1/19$167
This JetBlue Airways deal was found by Cheapflights users on 1/20. 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 JetBlue Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/316:20 amORD - PWM
1 stop6h 00mJetBlue
Sat 6/72:15 pmPWM - ORD
1 stop9h 05mJetBlue
Deal found 1/20$185
This American Airlines deal was found by Cheapflights users on 1/20. 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.
Sun 3/27:00 amORD - BOS
Nonstop2h 20mAmerican Airlines
Fri 3/76:59 amBOS - ORD
Nonstop3h 05mAmerican Airlines
Deal found 1/20$197
This American Airlines deal was found by Cheapflights users on 1/21. 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.
Sat 7/56:20 pmORD - PWM
Nonstop2h 30mAmerican Airlines
Wed 7/97:19 amPWM - ORD
Nonstop2h 51mAmerican Airlines
Deal found 1/21$209
This Delta deal was found by Cheapflights users on 1/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/316:25 pmORD - BOS
Nonstop2h 43mDelta
Mon 2/33:30 pmBOS - ORD
Nonstop3h 02mDelta
Deal found 1/20$212

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 3/7

5:05 am-8:12 am

1 stop26h 07m

Boston Logan Intl

Tue 3/11

6:00 am-9:05 am

1 stop28h 05m

$154

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 3/3

7:25 pm-10:33 am

1 stop14h 08m

Boston Logan Intl

Fri 3/7

10:41 am-9:25 pm

1 stop11h 44m

$154

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 3/1

5:15 am-5:32 pm

2 stops11h 17m

Boston Logan Intl

Wed 3/5

11:14 am-12:07 am

1 stop13h 53m

$155

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 2/20

7:10 am-10:43 am

Nonstop2h 33m

Boston Logan Intl

Mon 2/24

8:20 pm-10:19 pm

Nonstop2h 59m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 2/24

7:00 am-10:19 am

1 stop26h 19m

Boston Logan Intl

Fri 2/28

6:00 am-3:53 pm

1 stop10h 53m

$160

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 3/1

10:20 am-9:18 am

1 stop21h 58m

Portland

Mon 3/3

8:35 pm-1:20 pm

1 stop17h 45m

$160

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 2/7

7:00 am-10:15 am

Nonstop2h 15m

Boston Logan Intl

Wed 2/12

3:52 pm-5:55 pm

Nonstop3h 03m

$167

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 2/26

6:25 pm-9:40 pm

Nonstop2h 15m

Boston Logan Intl

Tue 3/4

8:10 am-10:05 am

Nonstop2h 55m

$167

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 3/14

9:30 pm-12:50 am

Nonstop2h 20m

Boston Logan Intl

Mon 3/24

4:30 pm-6:32 pm

Nonstop3h 02m

$188

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 2/21

2:55 pm-9:11 pm

1 stop5h 16m

Boston Logan Intl

Sun 2/23

1:15 pm-3:17 pm

Nonstop3h 02m

$207

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

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 January 21, 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 January 21, 2025.

The most flights from CHI to USME are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, 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 January 21, 2025.
See what other customers who have flown with Frontier, Spirit 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
4,659 reviews

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Entertainment

7.7

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
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Entertainment

7.7

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
9,696 reviews
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Entertainment

7.7

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
8,521 reviews
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Entertainment

7.7

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
3,201 reviews
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Entertainment

7.7

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
8,982 reviews
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Overall

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Entertainment

7.7

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 $55 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 (86%), United Airlines (85%) and Air New Zealand (85%).

  • What are the cheapest flights from Chicago to Maine?

    The cheapest flight price from Chicago to Maine is $104. On average you can expect to pay $301. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $113.

  • 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$92FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$182Average$356FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$191Average$333FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$331FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$221Average$470FlexibilityNo cancel feeOn-time69%
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