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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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$123
(Southwest)

One-way from

$60
(Kiwi.com)

Popular in

November

Cheapest in

September

Average price

$366

Good round-trip deal

$314 or less

Good one-way deal

$173 or less
From Maine to Chicago (CHI)
Search Deals
One-way flight from Maine to Chicago (CHI)
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Highest demand for flights based on searches. 12% potential increase in price ($52 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/11. 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 8/75:15 amBOS - MDW
Nonstop2h 30mSouthwest
Sun 8/1010:00 amMDW - BOS
Nonstop2h 25mSouthwest
Deal found 6/11$123
This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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.
Wed 7/25:45 amBOS - ORD
1 stop13h 59mSpirit Airlines
Wed 7/165:05 amORD - BOS
1 stop13h 29mSpirit Airlines
Deal found 6/10$124
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Tue 8/56:07 amBOS - ORD
Nonstop2h 58mUnited Airlines
Fri 8/87:49 pmORD - BOS
Nonstop2h 27mUnited Airlines
Deal found 6/10$125
This American Airlines deal was found by Cheapflights users on 6/12. 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 10/235:00 amBOS - ORD
Nonstop2h 58mAmerican Airlines
Mon 10/278:30 pmORD - BOS
Nonstop2h 44mAmerican Airlines
Deal found 6/12$126
This Southwest deal was found by Cheapflights users on 6/12. 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.
Tue 7/225:45 amBOS - ORD
1 stop7h 05mSouthwest
Fri 7/254:00 pmORD - BOS
1 stop7h 05mSouthwest
Deal found 6/12$142
This Delta deal was found by Cheapflights users on 6/10. 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 8/277:55 pmBOS - ORD
Nonstop2h 59mDelta
Tue 9/27:00 amORD - BOS
Nonstop2h 30mDelta
Deal found 6/10$158
This JetBlue deal was found by Cheapflights users on 6/11. 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 7/106:00 amBOS - ORD
Nonstop2h 55mJetBlue
Mon 7/148:40 amORD - BOS
Nonstop2h 24mJetBlue
Deal found 6/11$176
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Wed 7/96:20 amBGR - ORD
1 stop5h 19mUnited Airlines
Mon 7/146:10 pmORD - BGR
Nonstop2h 49mUnited Airlines
Deal found 6/11$201
This Mytrip deal was found by Cheapflights users on 6/9. 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 8/711:31 amBOS - MDW
1 stop20h 42mAllegiant Air
Mon 8/112:46 pmMDW - BOS
1 stop17h 29mAllegiant Air
Deal found 6/9$201
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Fri 8/111:42 amBOS - RFD
1 stop23h 31mMultiple Airlines
Sun 8/39:21 amRFD - BOS
1 stop5h 22mMultiple Airlines
Deal found 6/11$206
This American Airlines deal was found by Cheapflights users on 6/12. 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.
Tue 7/112:24 pmBGR - ORD
Nonstop2h 59mAmerican Airlines
Sat 7/58:10 amORD - BGR
Nonstop2h 36mAmerican Airlines
Deal found 6/12$210
This American Airlines deal was found by Cheapflights users on 6/11. 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 6/266:00 amPWM - ORD
Nonstop2h 57mAmerican Airlines
Mon 6/307:09 pmORD - PWM
Nonstop2h 38mAmerican Airlines
Deal found 6/11$219

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 June 12, 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 8/7

5:15 am-6:45 am

Nonstop2h 30m

Chicago Midway

Sun 8/10

10:00 am-1:25 pm

Nonstop2h 25m

$123

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 7/2

5:45 am-6:44 pm

1 stop13h 59m

Chicago O'Hare Intl

Wed 7/16

5:05 am-7:34 pm

1 stop13h 29m

$124

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 8/5

6:07 am-8:05 am

Nonstop2h 58m

Chicago O'Hare Intl

Fri 8/8

7:49 pm-11:16 pm

Nonstop2h 27m

$125

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 10/23

5:00 am-6:58 am

Nonstop2h 58m

Chicago O'Hare Intl

Mon 10/27

8:30 pm-12:14 am

Nonstop2h 44m

$126

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 7/8

6:00 am-7:55 am

Nonstop2h 55m

Chicago O'Hare Intl

Thu 7/10

4:27 pm-8:00 pm

Nonstop2h 33m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 7/22

5:45 am-11:50 am

1 stop7h 05m

Chicago O'Hare Intl

Fri 7/25

4:00 pm-12:05 am

1 stop7h 05m

$142

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 8/27

7:55 pm-9:54 pm

Nonstop2h 59m

Chicago O'Hare Intl

Tue 9/2

7:00 am-10:30 am

Nonstop2h 30m

$158

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 8/7

11:31 am-7:13 am

1 stop20h 42m

Chicago Midway

Mon 8/11

2:46 pm-9:15 am

1 stop17h 29m

$201

BangorChicago

BGR - ORD

BGRORD

Bangor

Wed 7/9

6:20 am-10:39 am

1 stop5h 19m

Chicago O'Hare Intl

Mon 7/14

6:10 pm-9:59 pm

Nonstop2h 49m

$201

BostonChicago

BOS - RFD

BOSRFD

Boston Logan Intl

Fri 8/1

11:42 am-10:13 am

1 stop23h 31m

Chicago Greater Rockford

Sun 8/3

9:21 am-3:43 pm

1 stop5h 22m

$206

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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 June 12, 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.

Weekly flight availability from Maine to Chicago

Explore weekly flight availability from Maine to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 12, 2025.

The most flights from USME to CHI are scheduled on a Tuesday (9 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

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 June 12, 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
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

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
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

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
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

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
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

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
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

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
2,925 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Comfort

7.8

Overall

8.0

Entertainment

7.1

Crew

8.5

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 $60 on Spirit Airlines. Other airlines that offer cheap prices include Southwest from $62 and United Airlines from $63 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 (100%), Qatar Airways (99%) or American Airlines (96%) 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 $129. On average you can expect to pay $796. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $112.

  • 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
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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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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Dallas/Fort Worth to O'Hare Intl flights
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Newark to O'Hare Intl flights
Boston to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Newark to Midway flights
John F Kennedy Intl to Midway flights
Seattle to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Ontario to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Hobby to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Denver to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
San Francisco to Midway flights
Atlanta to O'Hare Intl flights
LaGuardia to Midway flights
Burbank to O'Hare Intl flights
Dulles Intl to Midway flights
Raleigh to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Orlando to O'Hare Intl flights
Austin to O'Hare Intl flights
San Diego to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Atlanta to Midway flights
Portland to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Oakland to O'Hare Intl flights
Miami to O'Hare Intl flights
San Jose to O'Hare Intl flights
Tampa to O'Hare Intl flights
Love Field to O'Hare Intl flights
Los Angeles to Midway flights
Philadelphia to Midway flights
Boston to Midway flights
Minneapolis to O'Hare Intl flights
Hartford to O'Hare Intl flights
Baltimore to Midway flights
Minneapolis to Midway flights
Seattle to Midway flights
Newark to St. Louis flights
Salt Lake City to O'Hare Intl flights
Dulles Intl to St. Louis 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$127FlexibilityNo cancel feeOn-time62%
DeltaCheapest$124Average$353FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$158Average$338FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$209Average$378FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$264Average$371FlexibilityNo cancel feeOn-time63%

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