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$78+ 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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
abr. 5 — abr. 121
sáb. 4/5
sáb. 4/12
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 marzo 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$132
(JetBlue)

One-way from

$78
(United Airlines)

Popular in

November

Cheapest in

September

Average price

$439

Good round-trip deal

$376 or less

Good one-way deal

$195 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. 9% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in March 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 marzo 31, 2025.

This JetBlue deal was found by Cheapflights users on 3/31. 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.
mar. 4/155:15 pmBOS - ORD
Nonstop3h 12mJetBlue
mar. 4/228:29 pmORD - BOS
Nonstop2h 29mJetBlue
Deal found 3/31$132
This Delta deal was found by Cheapflights users on 3/31. 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.
mié. 4/167:30 amBOS - ORD
Nonstop3h 00mDelta
mar. 4/2210:25 amORD - BOS
Nonstop2h 25mDelta
Deal found 3/31$137
This FlightHub deal was found by Cheapflights users on 3/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/238:00 amBOS - ORD
Nonstop2h 53mSpirit Airlines
lun. 10/276:00 amORD - BOS
1 stop10h 34mSpirit Airlines
Deal found 3/30$140
This United Airlines deal was found by Cheapflights users on 3/31. 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.
jue. 8/287:30 pmBOS - ORD
1 stop5h 12mUnited Airlines
lun. 9/16:30 amORD - BOS
Nonstop2h 26mUnited Airlines
Deal found 3/31$144
This Southwest deal was found by Cheapflights users on 3/30. 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.
jue. 4/105:45 amBOS - MDW
Nonstop2h 35mSouthwest
dom. 4/136:50 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 3/30$157
This FlightHub deal was found by Cheapflights users on 3/31. 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.
mié. 5/143:49 pmBOS - ORD
1 stop8h 15mMultiple Airlines
dom. 5/184:15 pmORD - BOS
1 stop7h 50mMultiple Airlines
Deal found 3/31$163
This American Airlines deal was found by Cheapflights users on 3/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/168:51 pmBOS - ORD
Nonstop3h 01mAmerican Airlines
mié. 5/217:37 amORD - BOS
Nonstop2h 35mAmerican Airlines
Deal found 3/30$179
This Southwest deal was found by Cheapflights users on 3/30. 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.
lun. 4/285:00 amBOS - ORD
1 stop8h 45mSouthwest
jue. 5/11:50 pmORD - BOS
1 stop7h 05mSouthwest
Deal found 3/30$182
This Frontier deal was found by Cheapflights users on 3/31. 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. 5/156:00 amBOS - MDW
1 stop7h 24mFrontier
lun. 5/191:19 pmMDW - BOS
1 stop10h 25mFrontier
Deal found 3/31$198
This Frontier deal was found by Cheapflights users on 3/31. 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.
vie. 5/912:52 pmBOS - ORD
1 stop11h 19mFrontier
dom. 5/114:15 pmORD - BOS
1 stop7h 50mFrontier
Deal found 3/31$198
This United Airlines deal was found by Cheapflights users on 3/31. 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. 9/176:00 amPWM - ORD
1 stop7h 37mUnited Airlines
sáb. 9/2011:05 amORD - PWM
Nonstop2h 28mUnited Airlines
Deal found 3/31$219
This American Airlines deal was found by Cheapflights users on 3/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/234:16 pmPWM - ORD
1 stop7h 31mAmerican Airlines
mié. 4/306:04 amORD - PWM
1 stop4h 20mAmerican Airlines
Deal found 3/30$228

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 marzo 31, 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

mar. 4/15

5:15 pm-7:27 pm

Nonstop3h 12m

Chicago O'Hare Intl

sáb. 4/19

8:29 pm-11:58 pm

Nonstop2h 29m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mié. 4/16

7:30 am-9:30 am

Nonstop3h 00m

Chicago O'Hare Intl

mar. 4/22

10:25 am-1:50 pm

Nonstop2h 25m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mié. 4/30

11:27 am-12:20 am

1 stop13h 53m

Chicago O'Hare Intl

lun. 5/5

9:09 am-6:43 pm

2 stops32h 34m

$143

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 8/28

7:30 pm-11:42 pm

1 stop5h 12m

Chicago O'Hare Intl

lun. 9/1

6:30 am-9:56 am

Nonstop2h 26m

$144

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

jue. 4/10

5:45 am-7:20 am

Nonstop2h 35m

Chicago Midway

dom. 4/13

6:50 am-10:05 am

Nonstop2h 15m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 5/1

6:10 am-8:18 am

Nonstop3h 08m

Chicago O'Hare Intl

lun. 5/5

6:35 pm-10:07 pm

Nonstop2h 32m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mié. 5/14

3:49 pm-11:04 pm

1 stop8h 15m

Chicago O'Hare Intl

dom. 5/18

4:15 pm-1:05 am

1 stop7h 50m

$163

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

lun. 4/28

5:00 am-12:45 pm

1 stop8h 45m

Chicago O'Hare Intl

lun. 5/5

4:00 pm-10:35 pm

1 stop5h 35m

$182

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

jue. 5/15

6:00 am-12:24 pm

1 stop7h 24m

Chicago Midway

lun. 5/19

1:19 pm-12:44 am

1 stop10h 25m

$198

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

vie. 5/9

12:52 pm-11:11 pm

1 stop11h 19m

Chicago O'Hare Intl

dom. 5/11

4:15 pm-1:05 am

1 stop7h 50m

$198

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

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 $323). 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 marzo 31, 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 marzo 31, 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
9,818 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,818 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,276 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,899 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,614 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
JetBlue
7.3
Good
2,924 reviews
Alaska Airlines
8.0
Very good
9,818 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 $78 on United Airlines. Other airlines that offer cheap prices include Delta from $79 and Spirit Airlines from $80 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 Emirates (100%), Air New Zealand (85%) or Republic Airways (80%) 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 $114. On average you can expect to pay $872. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $97.

  • 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 $323). 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
New Buffalo
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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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 marzo 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$109FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$158Average$344FlexibilityNo cancel feeOn-time71%
DeltaCheapest$189Average$361FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$193Average$396FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$281Average$390FlexibilityNo cancel feeOn-time63%
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