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Maine

$67+ 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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PWM
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$131
(Southwest)

One-way from

$67
(American Airlines)

Popular in

December

Cheapest in

February

Average price

$323

Good round-trip deal

$272 or less

Good one-way deal

$194 or less
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. 9% potential increase in price ($36 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 September 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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/11. 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.
Mon 9/296:45 pmMDW - BOS
Nonstop2h 20mSouthwest
Tue 9/305:20 amBOS - MDW
2 stops10h 40mSouthwest
Deal found 9/11$131
This JetBlue deal was found by Cheapflights users on 9/9. 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 10/19:51 amORD - BOS
Nonstop2h 29mJetBlue
Wed 10/14:40 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 9/9$132
This Southwest deal was found by Cheapflights users on 9/11. 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 11/137:15 pmMDW - BOS
Nonstop2h 15mSouthwest
Sun 11/165:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 9/11$132
This JetBlue deal was found by Cheapflights users on 9/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/17:50 pmORD - BOS
Nonstop2h 35mJetBlue
Tue 10/77:09 amBOS - ORD
Nonstop3h 13mJetBlue
Deal found 9/11$133
This JetBlue deal was found by Cheapflights users on 9/10. 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 9/249:51 amORD - BOS
Nonstop2h 29mJetBlue
Wed 10/17:00 amBOS - ORD
Nonstop2h 56mJetBlue
Deal found 9/10$135
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/1111:55 amORD - BOS
1 stop11h 04mSpirit Airlines
Tue 10/142:15 pmBOS - ORD
1 stop8h 18mSpirit Airlines
Deal found 9/9$136
This United Airlines deal was found by Cheapflights users on 9/10. 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 9/172:15 pmORD - BOS
Nonstop2h 31mUnited Airlines
Fri 9/1911:00 amBOS - ORD
Nonstop2h 50mUnited Airlines
Deal found 9/10$137
This Southwest deal was found by Cheapflights users on 9/11. 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.
Sat 9/203:55 pmMDW - BOS
Nonstop2h 20mSouthwest
Mon 9/228:20 pmBOS - MDW
Nonstop2h 35mSouthwest
Deal found 9/11$137
This American Airlines deal was found by Cheapflights users on 9/9. 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 9/205:36 pmORD - BOS
Nonstop2h 24mAmerican Airlines
Sat 9/272:40 pmBOS - ORD
Nonstop3h 04mAmerican Airlines
Deal found 9/9$138
This American Airlines deal was found by Cheapflights users on 9/11. 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 10/248:25 pmORD - BOS
Nonstop2h 29mAmerican Airlines
Sun 10/265:24 amBOS - ORD
Nonstop3h 01mAmerican Airlines
Deal found 9/11$139
This Priceline deal was found by Cheapflights users on 9/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/216:00 amORD - BOS
1 stop6h 20mSpirit Airlines
Wed 10/223:00 pmBOS - ORD
1 stop9h 45mSpirit Airlines
Deal found 9/11$140
This JetBlue deal was found by Cheapflights users on 9/10. 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 11/136:55 pmORD - BOS
Nonstop2h 32mJetBlue
Sun 11/168:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 9/10$141

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 September 11, 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

Sat 10/25

4:09 pm-1:13 am

1 stop8h 04m

Boston Logan Intl

Sat 11/1

5:40 am-12:16 pm

1 stop7h 36m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 10/31

4:55 pm-8:10 pm

Nonstop2h 15m

Boston Logan Intl

Sat 11/1

5:20 am-7:00 am

Nonstop2h 40m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 11/6

7:05 am-10:29 am

Nonstop2h 24m

Boston Logan Intl

Wed 11/12

4:05 pm-6:13 pm

Nonstop3h 08m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 10/25

9:20 am-5:12 pm

1 stop6h 52m

Boston Logan Intl

Sat 11/1

5:45 am-1:08 pm

1 stop8h 23m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 11/11

11:25 am-9:40 pm

1 stop9h 15m

Boston Logan Intl

Sun 11/16

6:50 am-3:40 pm

1 stop9h 50m

$141

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 11/18

10:30 am-1:59 pm

Nonstop2h 29m

Boston Logan Intl

Sun 11/23

7:30 am-9:35 am

Nonstop3h 05m

$147

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 11/14

1:55 pm-5:15 pm

Nonstop2h 20m

Boston Logan Intl

Sun 11/16

5:30 am-9:46 am

1 stop5h 16m

$149

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 12/4

7:10 am-10:37 am

Nonstop2h 27m

Boston Logan Intl

Sun 12/7

5:45 am-11:48 am

1 stop7h 03m

$149

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 10/25

6:30 am-9:56 am

Nonstop2h 26m

Boston Logan Intl

Sat 10/25

5:19 pm-9:44 pm

1 stop5h 25m

$150

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 10/30

7:05 am-10:29 am

Nonstop2h 24m

Boston Logan Intl

Sat 11/1

5:40 am-12:16 pm

1 stop7h 36m

$153

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

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 July is currently the most expensive (average of $394). 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 September 11, 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 September 11, 2025.

The most flights from CHI to USME are scheduled on a Monday (12 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (10 on average).

How much does it cost to fly round-trip from Chicago to Maine?

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 September 11, 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
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

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
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

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
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

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
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

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
2,913 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

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 15m. Chicago and Maine are separated by a distance of 857 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $67 on United Airlines. Other airlines that offer cheap prices include Delta from $69 and JetBlue from $69 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 Envoy Air (100%), SkyWest Airlines (74%) and United Airlines (72%).

  • What are the cheapest flights from Chicago to Maine?

    The cheapest flight price from Chicago to Maine is $129. On average you can expect to pay $281. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $117.

  • 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 July is currently the most expensive (average of $394). 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$163Average$516FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$228Average$427FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$229Average$368FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$276Average$411FlexibilityNo cancel feeOn-time63%

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