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$59+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Apr 27 — May 41
Sun 4/27
Sun 5/4
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 April 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$127
(Southwest)

One-way from

$59
(JetBlue)

Popular in

November

Cheapest in

September

Average price

$356

Good round-trip deal

$362 or less

Good one-way deal

$178 or less
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Portland-Chicago (CHI) flights.
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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. 11% potential increase in price ($45 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 22, 2025.

This Southwest deal was found by Cheapflights users on 4/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/313:00 pmBOS - MDW
1 stop7h 50mSouthwest
Thu 7/36:00 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 4/21$127
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/95:42 pmBOS - ORD
1 stop6h 47mSpirit Airlines
Wed 5/1412:41 pmORD - BOS
1 stop9h 48mSpirit Airlines
Deal found 4/21$129
This Southwest deal was found by Cheapflights users on 4/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/76:45 amBOS - ORD
1 stop9h 15mSouthwest
Wed 6/114:00 pmORD - BOS
1 stop6h 55mSouthwest
Deal found 4/21$136
This United Airlines deal was found by Cheapflights users on 4/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/57:45 amBOS - ORD
Nonstop2h 58mUnited Airlines
Mon 6/96:30 amORD - BOS
Nonstop2h 26mUnited Airlines
Deal found 4/21$137
This American Airlines deal was found by Cheapflights users on 4/22. 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.
Thu 5/16:10 amBOS - ORD
Nonstop3h 08mAmerican Airlines
Mon 5/54:40 pmORD - BOS
Nonstop2h 21mAmerican Airlines
Deal found 4/22$147
This JetBlue deal was found by Cheapflights users on 4/21. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/56:00 amBOS - ORD
Nonstop3h 00mJetBlue
Tue 6/107:31 pmORD - BOS
Nonstop2h 29mJetBlue
Deal found 4/21$152
This FlightHub deal was found by Cheapflights users on 4/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/143:49 pmBOS - ORD
1 stop8h 15mMultiple Airlines
Sat 5/174:15 pmORD - BOS
1 stop7h 29mMultiple Airlines
Deal found 4/21$153
This Delta deal was found by Cheapflights users on 4/20. 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.
Wed 5/78:20 pmBOS - ORD
Nonstop2h 54mDelta
Sun 5/117:00 amORD - BOS
Nonstop2h 25mDelta
Deal found 4/20$180
This Frontier deal was found by Cheapflights users on 4/22. 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.
Wed 5/2810:45 amBOS - MDW
1 stop12h 51mFrontier
Sun 6/19:12 pmMDW - BOS
1 stop10h 23mFrontier
Deal found 4/22$188
This Frontier deal was found by Cheapflights users on 4/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/298:47 amBOS - ORD
1 stop9h 21mFrontier
Sun 6/15:14 pmORD - BOS
1 stop14h 21mFrontier
Deal found 4/21$200
This United Airlines deal was found by Cheapflights users on 4/22. 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 6/146:00 amPWM - ORD
Nonstop2h 53mUnited Airlines
Tue 6/176:25 pmORD - PWM
Nonstop2h 31mUnited Airlines
Deal found 4/22$209
This Mytrip deal was found by Cheapflights users on 4/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/311:31 amBOS - MDW
1 stop20h 42mAllegiant Air
Mon 7/72:54 pmMDW - BOS
1 stop17h 21mAllegiant Air
Deal found 4/21$225

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 April 22, 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

Tue 5/20

3:49 pm-11:04 pm

1 stop8h 15m

Chicago O'Hare Intl

Wed 5/21

12:41 pm-11:29 pm

1 stop9h 48m

$118

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 5/31

3:00 pm-9:50 pm

1 stop7h 50m

Chicago Midway

Thu 7/3

6:00 am-9:15 am

Nonstop2h 15m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 6/7

6:45 am-3:00 pm

1 stop9h 15m

Chicago O'Hare Intl

Wed 6/11

4:00 pm-11:55 pm

1 stop6h 55m

$136

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 5/6

7:45 am-9:42 am

Nonstop2h 57m

Chicago O'Hare Intl

Thu 5/8

1:55 pm-5:19 pm

Nonstop2h 24m

$138

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 4/30

5:00 am-7:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Fri 5/2

4:49 pm-8:09 pm

Nonstop2h 20m

$147

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 6/5

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Sat 6/14

9:40 am-1:09 pm

Nonstop2h 29m

$152

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 5/14

3:49 pm-11:04 pm

1 stop8h 15m

Chicago O'Hare Intl

Sat 5/17

4:15 pm-12:44 am

1 stop7h 29m

$153

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 7/2

8:05 pm-10:05 pm

Nonstop3h 00m

Chicago O'Hare Intl

Tue 7/8

10:10 am-1:40 pm

Nonstop2h 30m

$177

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 5/28

10:45 am-10:36 pm

1 stop12h 51m

Chicago Midway

Sun 6/1

9:12 pm-8:35 am

1 stop10h 23m

$188

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 5/10

8:00 am-11:32 pm

1 stop16h 32m

Chicago O'Hare Intl

Mon 5/12

4:15 pm-12:44 am

1 stop7h 29m

$189

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

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 April 22, 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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, 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 73.4 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 Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated April 22, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest and Delta from Maine to Chicago by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,906 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,906 reviews
Alaska Airlines
8.0
Very good
9,906 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,286 reviews
Alaska Airlines
8.0
Very good
9,906 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,920 reviews
Alaska Airlines
8.0
Very good
9,906 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Avelo Airlines
7.5
Good
Alaska Airlines
8.0
Very good
9,906 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,683 reviews
Alaska Airlines
8.0
Very good
9,906 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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.

  • 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 $59 on JetBlue. Other airlines that offer cheap prices include United Airlines from $64 and Southwest from $68 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 (91%), Emirates (81%) or Air New Zealand (81%) 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 $124. On average you can expect to pay $906. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $115.

  • 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 Maine?

Book flights to Maine if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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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Philadelphia to Midway flights
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Los Angeles to Midway flights

Top 5 airlines flying from Maine to Chicago

Discover the top 5 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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$109FlexibilityNo cancel feeOn-time62%
DeltaCheapest$124Average$426FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$158Average$342FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$194Average$401FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$264Average$379FlexibilityNo cancel feeOn-time63%

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