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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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(Southwest)

One-way from

$59
(Southwest)

Popular in

November

Cheapest in

September

Average price

$330

Good round-trip deal

$356 or less

Good one-way deal

$193 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 ($47 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 May 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 May 1, 2025.

This Southwest deal was found by Cheapflights users on 4/30. 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.
Thu 6/55:15 amBOS - MDW
Nonstop2h 35mSouthwest
Sun 6/86:00 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 4/30$117
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/77:15 amBOS - ORD
Nonstop2h 54mDelta
Wed 5/147:00 amORD - BOS
Nonstop2h 25mDelta
Deal found 4/30$117
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Sat 5/103:52 pmBOS - ORD
Nonstop3h 02mAmerican Airlines
Mon 5/126:35 pmORD - BOS
Nonstop2h 32mAmerican Airlines
Deal found 4/30$118
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/43:49 pmBOS - ORD
1 stop8h 15mSpirit Airlines
Wed 6/115:05 amORD - BOS
1 stop8h 39mSpirit Airlines
Deal found 4/30$120
This Southwest deal was found by Cheapflights users on 4/30. 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.
Sat 6/76:45 amBOS - ORD
1 stop9h 15mSouthwest
Tue 6/104:00 pmORD - BOS
1 stop6h 55mSouthwest
Deal found 4/30$136
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/196:00 amBOS - ORD
Nonstop2h 57mUnited Airlines
Tue 5/204:20 pmORD - BOS
Nonstop2h 28mUnited Airlines
Deal found 4/30$140
This JetBlue deal was found by Cheapflights users on 4/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/36:00 amBOS - ORD
Nonstop2h 55mJetBlue
Fri 7/115:51 pmORD - BOS
Nonstop2h 35mJetBlue
Deal found 4/30$152
This Mytrip deal was found by Cheapflights users on 4/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2910:30 amBOS - RFD
1 stop5h 54mMultiple Airlines
Sun 6/14:16 pmRFD - BOS
1 stop16h 19mMultiple Airlines
Deal found 4/29$176
This Mytrip deal was found by Cheapflights users on 4/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1210:30 amBOS - ORD
1 stop6h 55mMultiple Airlines
Sat 5/174:15 pmORD - BOS
1 stop7h 29mMultiple Airlines
Deal found 4/29$176
This Booking.com deal was found by Cheapflights users on 4/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/107:30 pmPWM - ORD
1 stop29h 02mFrontier
Sat 5/174:15 pmORD - PWM
1 stop26h 18mFrontier
Deal found 4/30$208
This Frontier deal was found by Cheapflights users on 4/30. 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.
Wed 5/2810:45 amBOS - MDW
1 stop12h 51mFrontier
Sun 6/19:12 pmMDW - BOS
1 stop10h 23mFrontier
Deal found 4/30$208
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/912:52 pmBOS - ORD
1 stop11h 19mFrontier
Sat 5/104:15 pmORD - BOS
1 stop7h 29mFrontier
Deal found 4/29$208

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 May 1, 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

Thu 6/5

5:15 am-6:50 am

Nonstop2h 35m

Chicago Midway

Sun 6/8

6:00 am-9:15 am

Nonstop2h 15m

$117

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 6/4

8:20 pm-10:14 pm

Nonstop2h 54m

Chicago O'Hare Intl

Wed 6/11

10:18 am-1:51 pm

Nonstop2h 33m

$117

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 5/10

3:52 pm-5:54 pm

Nonstop3h 02m

Chicago O'Hare Intl

Mon 5/12

6:35 pm-10:07 pm

Nonstop2h 32m

$118

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 6/4

3:49 pm-11:04 pm

1 stop8h 15m

Chicago O'Hare Intl

Wed 6/11

5:05 am-2:44 pm

1 stop8h 39m

$120

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 6/7

6:45 am-3:00 pm

1 stop9h 15m

Chicago O'Hare Intl

Tue 6/10

4:00 pm-11:55 pm

1 stop6h 55m

$136

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 5/19

6:00 am-7:57 am

Nonstop2h 57m

Chicago O'Hare Intl

Wed 5/21

9:20 am-12:48 pm

Nonstop2h 28m

$140

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 7/3

6:00 am-7:55 am

Nonstop2h 55m

Chicago O'Hare Intl

Fri 7/11

5:51 pm-9:26 pm

Nonstop2h 35m

$152

BostonChicago

BOS - RFD

BOSRFD

Boston Logan Intl

Thu 5/29

10:30 am-3:24 pm

1 stop5h 54m

Chicago Greater Rockford

Sun 6/1

4:16 pm-9:35 am

1 stop16h 19m

$176

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 5/12

10:30 am-4:25 pm

1 stop6h 55m

Chicago O'Hare Intl

Sat 5/17

4:15 pm-12:44 am

1 stop7h 29m

$176

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

$208

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 $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 May 1, 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 May 1, 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
9,972 reviews

Comfort

7.9

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,294 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,922 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Comfort

7.9

Food

7.1

Crew

8.5

Entertainment

7.1

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 Southwest. Other airlines that offer cheap prices include JetBlue from $59 and Spirit Airlines from $60 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 $153. On average you can expect to pay $930. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $109.

  • 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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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$108FlexibilityNo cancel feeOn-time62%
DeltaCheapest$124Average$361FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$158Average$343FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$205Average$428FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$264Average$371FlexibilityNo cancel feeOn-time63%

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