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$68+ Cheap flights from Maine to Chicago (CHI)

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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Maine to Chicago

Keep the following information in mind while searching for Maine to Chicago flight deals. Data was last updated September 15, 2025.

Round-trip from

$125
(Kiwi.com)

One-way from

$68
(United Airlines)

Popular in

December

Cheapest in

September

Average price

$281

Good round-trip deal

$327 or less

Good one-way deal

$203 or less
From Maine to Chicago (CHI)
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One-way flight from Maine to Chicago (CHI)
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Highest demand for flights based on searches. 14% potential increase in price ($60 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 Maine to Chicago (CHI).
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Price to beat on a one-way flight from Maine to Chicago (CHI).
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Find flight deals from Maine to Chicago

Cheapest flights from Maine to Chicago
Explore the most affordable flight options available from Maine to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/46:10 amBOS - ORD
1 stop12h 29mSpirit Airlines
Tue 10/76:00 amORD - BOS
1 stop6h 20mSpirit Airlines
Deal found 9/13$125
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/156:16 amBOS - ORD
1 stop13h 22mSpirit Airlines
Tue 10/216:00 amORD - BOS
1 stop6h 20mSpirit Airlines
Deal found 9/13$126
This Southwest deal was found by Cheapflights users on 9/14. 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 10/25:35 amBOS - MDW
1 stop5h 40mSouthwest
Mon 10/66:05 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 9/14$127
This JetBlue deal was found by Cheapflights users on 9/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/307:00 amBOS - ORD
Nonstop2h 56mJetBlue
Wed 10/19:51 amORD - BOS
Nonstop2h 29mJetBlue
Deal found 9/13$127
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/153:00 pmBOS - ORD
1 stop9h 45mSpirit Airlines
Sat 10/1811:55 amORD - BOS
1 stop11h 04mSpirit Airlines
Deal found 9/14$129
This Priceline deal was found by Cheapflights users on 9/14. 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.
Sat 10/48:38 amBOS - ORD
1 stop9h 07mMultiple Airlines
Tue 10/76:00 amORD - BOS
1 stop6h 20mMultiple Airlines
Deal found 9/14$131
This American Airlines deal was found by Cheapflights users on 9/14. 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 9/232:40 pmBOS - ORD
Nonstop3h 04mAmerican Airlines
Tue 9/238:25 pmORD - BOS
Nonstop2h 28mAmerican Airlines
Deal found 9/14$132
This Southwest deal was found by Cheapflights users on 9/14. 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 10/301:05 pmBOS - MDW
Nonstop2h 40mSouthwest
Sun 11/25:45 amMDW - BOS
1 stop10h 25mSouthwest
Deal found 9/14$133
This United Airlines deal was found by Cheapflights users on 9/14. 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.
Sat 10/186:15 pmBOS - ORD
Nonstop2h 54mUnited Airlines
Sun 10/196:30 amORD - BOS
Nonstop2h 26mUnited Airlines
Deal found 9/14$133
This United Airlines deal was found by Cheapflights users on 9/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/48:00 amBOS - ORD
Nonstop2h 55mUnited Airlines
Sun 10/56:30 amORD - BOS
Nonstop2h 27mUnited Airlines
Deal found 9/13$134
This JetBlue deal was found by Cheapflights users on 9/15. 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 10/14:40 pmBOS - ORD
Nonstop3h 15mJetBlue
Fri 10/37:50 pmORD - BOS
Nonstop2h 35mJetBlue
Deal found 9/15$135
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/83:00 pmBOS - ORD
1 stop9h 45mSpirit Airlines
Sat 10/1111:55 amORD - BOS
1 stop11h 04mSpirit Airlines
Deal found 9/14$136

Cheapflights Fare Finder

 
Customize your flight search to find flights from Maine to Chicago 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 15, 2025.
Use the filters below to find and compare flights from Maine to Chicago that are best for you.

Fly from

Maine

Fly to

Chicago

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 10/22

1:35 pm-6:10 pm

1 stop5h 35m

Chicago Midway

Thu 10/23

9:20 pm-12:40 am

Nonstop2h 20m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 10/4

2:35 pm-4:15 pm

Nonstop2h 40m

Chicago Midway

Tue 10/7

5:35 am-12:50 pm

1 stop6h 15m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 10/30

1:05 pm-2:45 pm

Nonstop2h 40m

Chicago Midway

Mon 11/3

6:40 am-12:55 pm

1 stop5h 15m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 10/2

5:35 am-10:15 am

1 stop5h 40m

Chicago Midway

Mon 10/6

9:20 pm-12:40 am

Nonstop2h 20m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 10/25

6:30 am-4:25 pm

1 stop10h 55m

Chicago Midway

Sun 10/26

9:05 pm-12:25 am

Nonstop2h 20m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 11/20

10:40 am-12:40 pm

Nonstop3h 00m

Chicago O'Hare Intl

Wed 11/26

9:25 pm-12:45 am

Nonstop2h 20m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 12/6

4:05 pm-6:02 pm

Nonstop2h 57m

Chicago O'Hare Intl

Mon 12/8

3:45 pm-7:12 pm

Nonstop2h 27m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/25

3:17 pm-5:07 pm

Nonstop2h 50m

Chicago O'Hare Intl

Sun 9/28

7:30 am-11:02 am

Nonstop2h 32m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 9/25

8:35 am-10:10 am

Nonstop2h 35m

Chicago Midway

Sun 9/28

5:55 am-9:10 am

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 11/14

12:05 pm-8:10 pm

1 stop9h 05m

Chicago Midway

Mon 11/17

6:40 am-4:35 pm

1 stop8h 55m

$142

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 60 results
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Best time to book a flight from Maine to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Maine 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 Maine to Chicago

What is the cheapest month to book a flight from Maine to Chicago?

Currently, August is the cheapest month in which you can book a flight from Maine to Chicago (average of $245). Flying from Maine to Chicago in March is currently the most expensive (average of $321). 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 ME to CHI?

Find hourly flight availability from Maine to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

When flying from Maine to Chicago, 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 Maine to Chicago

Explore weekly flight availability from Maine to Chicago. 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 15, 2025.

The most flights from USME to CHI are scheduled on a Friday (12 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (7 on average).

Related info for your journey

Find useful and relevant information for your journey from Maine to Chicago. 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 Maine to Chicago?

    A quick flight from Maine to Chicago can take about 2h 57m. Southwest provides one of the quickest options available for as low as $137. The distance from Maine to Chicago is about 864 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Maine to Chicago one-way?

    One-way options have recently been found by users for as low as $69 on Southwest. Other airlines that offer cheap prices include JetBlue from $69 and United Airlines from $69 one-way.

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

    Most travelers choose Boston Logan Intl - Chicago O'Hare Intl, Boston Logan Intl - Chicago Midway or Portland - Chicago O'Hare Intl when deciding on the best route from Maine to Chicago.

  • What are the most reliable airlines from Maine to Chicago?

    Consider Envoy Air (100%), American Airlines (85%) or Republic Airways (73%) when booking your flight. These represent the most reliable airlines when flying from Maine to Chicago.

  • What are the cheapest flights from Maine to Chicago?

    The cheapest flight price from Maine to Chicago is $135. On average you can expect to pay $858. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $117.

  • Can I find deals for flights from Maine to Chicago that include hotel bookings?

    Yes. In addition to deals on Maine to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Maine to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Maine to Chicago.

  • Can I find deals for business class flights from Maine to Chicago?

    Yes. Cheapflights offers flight deals from Maine to Chicago 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 Maine to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Maine to Chicago (average of $245). Flying from Maine to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Maine to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Maine to Chicago

Discover the top 4 airlines that operate flights from Maine to Chicago. 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 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$124Average$353FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$200Average$321FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$229Average$386FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$264Average$397FlexibilityNo cancel feeOn-time63%

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