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$64+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This JetBlue deal was found by Cheapflights users on 12/15. 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.
Thu 12/254:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Mon 12/297:41 pmORD - BOS
Nonstop2h 29mJetBlue
Deal found 12/15$132
This Expedia deal was found by Cheapflights users on 12/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2312:08 pmBOS - ORD
1 stop23h 10mMultiple Airlines
Wed 1/77:45 amORD - BOS
Nonstop2h 25mMultiple Airlines
Deal found 12/15$156
This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Fri 12/197:45 amORD - BOS
Nonstop2h 22mUnited Airlines
Deal found 12/15$157
This Expedia deal was found by Cheapflights users on 12/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2312:08 pmBOS - ORD
1 stop23h 10mFrontier
Wed 1/74:49 pmORD - BOS
1 stop7h 30mFrontier
Deal found 12/15$162
This Priceline deal was found by Cheapflights users on 12/16. 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 12/2311:02 amBOS - ORD
1 stop8h 50mMultiple Airlines
Thu 12/257:41 pmORD - BOS
Nonstop2h 29mMultiple Airlines
Deal found 12/16$166
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:40 pmBOS - ORD
Nonstop3h 12mAmerican Airlines
Fri 1/235:25 pmORD - BOS
Nonstop2h 20mAmerican Airlines
Deal found 12/17$177
This American Airlines deal was found by Cheapflights users on 12/14. 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.
Wed 12/176:00 amBOS - ORD
Nonstop3h 17mAmerican Airlines
Fri 12/197:25 amORD - BOS
Nonstop2h 33mAmerican Airlines
Deal found 12/14$187
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Mon 12/296:23 pmBOS - ORD
Nonstop3h 02mUnited Airlines
Sun 1/47:45 amORD - BOS
Nonstop2h 23mUnited Airlines
Deal found 12/16$189
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/206:23 pmBOS - ORD
Nonstop3h 02mUnited Airlines
Thu 12/251:55 pmORD - BOS
Nonstop2h 22mUnited Airlines
Deal found 12/17$192
This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Sun 1/49:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/15$196
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/206:23 pmBOS - ORD
Nonstop3h 02mUnited Airlines
Sun 12/219:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/17$197
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.
Wed 12/315:35 pmBOS - MDW
1 stop4h 30mSouthwest
Fri 1/25:30 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 12/17$258

Find flight deals from Maine to Chicago

Keep the following information in mind while searching for Maine to Chicago flight deals. Data was last updated December 18, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$124
(Kiwi.com)

One-way from

$64
(Southwest)

Popular in

April

Cheapest in

September

Average price

$253

Good round-trip deal

$400 or less

Good one-way deal

$298 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
Search Deals
From Maine to Chicago (CHI)
Search Deals
One-way flight from Maine to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Maine to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Maine to Chicago (CHI).
Search Deals

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 December 18, 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 2/25

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Fri 2/27

7:40 pm-10:55 pm

Nonstop2h 15m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 2/21

7:00 am-9:10 am

Nonstop3h 10m

Chicago O'Hare Intl

Sat 3/7

10:00 am-1:23 pm

Nonstop2h 23m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 2/26

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Mon 3/2

11:05 am-2:30 pm

Nonstop2h 25m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/23

7:30 am-9:41 am

Nonstop3h 11m

Chicago O'Hare Intl

Sun 1/25

7:05 am-10:40 am

Nonstop2h 35m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 2/7

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Sat 2/14

6:10 pm-9:25 pm

Nonstop2h 15m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/14

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Sun 1/18

7:45 am-11:10 am

Nonstop2h 25m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 1/1

6:01 am-8:05 am

Nonstop3h 04m

Chicago O'Hare Intl

Fri 1/2

9:12 pm-12:45 am

Nonstop2h 33m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 1/24

7:30 am-9:41 am

Nonstop3h 11m

Chicago O'Hare Intl

Sun 1/25

7:05 am-10:40 am

Nonstop2h 35m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 2/24

7:00 am-9:10 am

Nonstop3h 10m

Chicago O'Hare Intl

Fri 3/6

10:00 am-1:23 pm

Nonstop2h 23m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/7

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Fri 1/16

7:45 am-11:10 am

Nonstop2h 25m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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, May is the cheapest month in which you can book a flight from Maine to Chicago (average of $182). Flying from Maine to Chicago in December is currently the most expensive (average of $264). 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 December 18, 2025.

When flying from Maine to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 36% versus a flight in the morning.

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

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

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

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

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 50m. Southwest provides one of the quickest options available for as low as $137. The distance from Maine to Chicago is about 857 mi. Most flights are nonstop.

  • 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 $442 on Royal Jordanian. Other airlines that offer cheap prices include Qatar Airways from $689 and Turkish Airlines from $740 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 Republic Airways (85%), American Airlines (70%) or United Airlines (66%) 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 $193. On average you can expect to pay $1,152. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $116.

  • 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, May is the cheapest month in which you can book a flight from Maine to Chicago (average of $182). Flying from Maine to Chicago in December is currently the most expensive (average of $264). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$124Average$426FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$209Average$336FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$229Average$388FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$246Average$397FlexibilityNo cancel feeOn-time63%

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