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$60+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
1 adult, Economy
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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 octubre 30, 2025.

This Delta deal was found by Cheapflights users on 10/29. 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.
jue. 12/44:05 pmBOS - ORD
Nonstop2h 57mDelta
dom. 12/77:10 amORD - BOS
Nonstop2h 26mDelta
Deal found 10/29$118
This United Airlines deal was found by Cheapflights users on 10/28. 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.
lun. 11/1710:40 amBOS - ORD
Nonstop3h 00mUnited Airlines
jue. 2/197:30 amORD - BOS
Nonstop2h 19mUnited Airlines
Deal found 10/28$122
This Orbitz deal was found by Cheapflights users on 10/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/1511:43 amBOS - ORD
1 stop12h 46mMultiple Airlines
mar. 11/183:26 pmORD - BOS
1 stop7h 33mMultiple Airlines
Deal found 10/28$123
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
jue. 12/411:28 amBOS - MDW
1 stop7h 40mFrontier
jue. 12/117:23 pmMDW - BOS
1 stop13h 59mFrontier
Deal found 10/29$124
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
jue. 12/411:28 amBOS - ORD
1 stop6h 59mFrontier
jue. 12/1111:44 amORD - BOS
1 stop21h 38mFrontier
Deal found 10/29$124
This Priceline deal was found by Cheapflights users on 10/28. 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.
jue. 12/411:28 amBOS - ORD
1 stop6h 59mMultiple Airlines
mar. 12/93:26 pmORD - BOS
1 stop7h 30mMultiple Airlines
Deal found 10/28$125
This Southwest deal was found by Cheapflights users on 10/30. 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.
dom. 11/95:15 amBOS - MDW
Nonstop2h 45mSouthwest
lun. 11/109:35 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 10/30$127
This JetBlue deal was found by Cheapflights users on 10/28. 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.
sáb. 11/157:10 amBOS - ORD
Nonstop3h 05mJetBlue
lun. 11/176:55 pmORD - BOS
Nonstop2h 32mJetBlue
Deal found 10/28$127
This Frontier deal was found by Cheapflights users on 10/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/411:28 amBOS - ORD
1 stop6h 59mFrontier
dom. 12/76:00 amORD - BOS
1 stop5h 02mFrontier
Deal found 10/30$128
This JetBlue deal was found by Cheapflights users on 10/29. 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.
jue. 11/138:30 amBOS - ORD
Nonstop3h 05mJetBlue
sáb. 11/1510:00 amORD - BOS
Nonstop2h 20mJetBlue
Deal found 10/29$130
This United Airlines deal was found by Cheapflights users on 10/29. 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.
mié. 12/244:15 pmBOS - ORD
Nonstop3h 04mUnited Airlines
mié. 12/311:55 pmORD - BOS
Nonstop2h 22mUnited Airlines
Deal found 10/29$131
This United Airlines deal was found by Cheapflights users on 10/28. 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.
mié. 11/53:10 pmBOS - ORD
Nonstop3h 00mUnited Airlines
dom. 12/77:30 amORD - BOS
Nonstop2h 19mUnited Airlines
Deal found 10/28$132

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 octubre 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$118
(Delta)

One-way from

$60
(Flysmarter)

Popular in

December

Cheapest in

September

Average price

$344

Good round-trip deal

$339 or less

Good one-way deal

$189 or less
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-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. 13% potential increase in price ($54 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 octubre 30, 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 - ORD

BOSORD

Boston Logan Intl

vie. 12/12

7:52 pm-9:47 pm

Nonstop2h 55m

Chicago O'Hare Intl

lun. 12/15

7:10 am-10:36 am

Nonstop2h 26m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 11/20

9:40 am-11:43 am

Nonstop3h 03m

Chicago O'Hare Intl

jue. 12/4

8:38 pm-12:06 am

Nonstop2h 28m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mar. 12/16

4:05 pm-6:02 pm

Nonstop2h 57m

Chicago O'Hare Intl

dom. 1/18

7:05 am-10:40 am

Nonstop2h 35m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 12/4

7:30 am-9:33 am

Nonstop3h 03m

Chicago O'Hare Intl

dom. 12/7

7:10 am-10:36 am

Nonstop2h 26m

$129

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

dom. 11/16

7:30 am-9:35 am

Nonstop3h 05m

Chicago O'Hare Intl

lun. 11/17

3:50 pm-7:14 pm

Nonstop2h 24m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mié. 12/3

3:40 pm-9:52 pm

1 stop7h 12m

Chicago O'Hare Intl

mié. 12/10

11:25 am-2:49 pm

Nonstop2h 24m

$140

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

sáb. 11/15

7:10 am-9:15 am

Nonstop3h 05m

Chicago O'Hare Intl

lun. 11/17

6:45 am-3:00 pm

1 stop7h 15m

$140

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 11/13

3:37 pm-8:52 pm

1 stop6h 15m

Chicago O'Hare Intl

dom. 11/16

11:20 am-2:44 pm

Nonstop2h 24m

$140

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

dom. 11/16

5:15 am-7:00 am

Nonstop2h 45m

Chicago Midway

mar. 11/18

6:15 pm-9:35 pm

Nonstop2h 20m

$147

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

vie. 11/14

7:25 am-9:25 am

Nonstop3h 00m

Chicago O'Hare Intl

dom. 11/16

9:25 pm-12:45 am

Nonstop2h 20m

$147

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

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 April is currently the most expensive (average of $265). 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 octubre 30, 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 45m. Delta provides one of the quickest options available for as low as $147. 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 $64 on JetBlue. Other airlines that offer cheap prices include United Airlines from $64 and Southwest from $74 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 Air New Zealand (74%), American Airlines (70%) or Republic Airways (60%) 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 $137. On average you can expect to pay $1,077. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $114.

  • 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 April is currently the most expensive (average of $265). 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
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.
John F Kennedy Intl to O'Hare Intl flights
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San Francisco to O'Hare Intl flights
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Baltimore to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Seattle to O'Hare Intl flights
Denver to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
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John F Kennedy Intl to Midway flights
Baltimore to Midway flights
Dallas/Fort Worth to Midway flights
Ontario to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Los Angeles to Midway flights
Hobby to Midway flights
Atlanta to Midway flights
LaGuardia to Midway flights
Newark to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Newark to St. Louis flights
Denver to Midway flights
Philadelphia to Midway flights
Charlotte to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
San Francisco to Midway flights
George Bush Intcntl to O'Hare Intl flights
Dulles Intl to Midway flights
Hobby to O'Hare Intl flights
Tampa to O'Hare Intl flights
Miami to O'Hare Intl flights
Minneapolis to Midway flights
Raleigh to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
John F Kennedy Intl to St. Louis flights
Reagan-National to Midway flights
Austin to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Love Field to O'Hare Intl flights
Hartford to O'Hare Intl flights
Orlando to O'Hare Intl flights
San Diego to O'Hare Intl flights
Portland to O'Hare Intl flights
LaGuardia to St. Louis flights
Boston to Midway flights

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 octubre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$124Average$352FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$203Average$317FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$229Average$379FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$246Average$390FlexibilityNo cancel feeOn-time63%

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