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$64+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
ene. 26 — feb. 21
dom. 1/26
dom. 2/2
1 adult, Economy
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Cheap flight deals from Maine to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Maine (USME) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated enero 21, 2025.

Round-trip from

$147
(Mytrip)

One-way from

$64
(Mytrip)

Good round-trip deal

$374 or less

Good one-way deal

$243 or less
From Maine to Chicago (CHI)
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One-way flight from Maine to Chicago (CHI)
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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 enero 21, 2025.

This Mytrip deal was found by Cheapflights users on 1/21. 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.
lun. 3/1010:21 pmBOS - ORD
2 stops16h 18mSpirit Airlines
mié. 3/126:45 amORD - BOS
1 stop8h 25mSpirit Airlines
Deal found 1/21$147
This Trip.com deal was found by Cheapflights users on 1/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/76:00 amBOS - ORD
1 stop15h 57mFrontier
lun. 2/104:41 pmORD - BOS
1 stop6h 58mFrontier
Deal found 1/21$148
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/105:10 amBOS - ORD
1 stop12h 21mMultiple Airlines
lun. 3/176:45 amORD - BOS
1 stop8h 25mMultiple Airlines
Deal found 1/21$149
This CheapOair deal was found by Cheapflights users on 1/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/110:24 amBOS - MDW
1 stop13h 16mFrontier
dom. 5/44:00 pmMDW - BOS
1 stop16h 34mFrontier
Deal found 1/21$150
This Southwest deal was found by Cheapflights users on 1/21. 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.
jue. 2/136:50 amBOS - MDW
Nonstop2h 55mSouthwest
mar. 2/187:00 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 1/21$157
This Delta deal was found by Cheapflights users on 1/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/218:20 pmBOS - ORD
Nonstop2h 59mDelta
mié. 2/267:10 amORD - BOS
Nonstop2h 33mDelta
Deal found 1/21$157
This JetBlue deal was found by Cheapflights users on 1/21. 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.
lun. 2/2410:00 amBOS - ORD
Nonstop3h 00mJetBlue
sáb. 3/112:38 pmORD - BOS
Nonstop2h 20mJetBlue
Deal found 1/21$167
This United Airlines deal was found by Cheapflights users on 1/21. 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.
lun. 3/104:17 pmBOS - ORD
1 stop6h 43mUnited Airlines
mié. 3/1211:15 amORD - BOS
Nonstop2h 19mUnited Airlines
Deal found 1/21$183
This American Airlines deal was found by Cheapflights users on 1/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/135:20 amBOS - ORD
Nonstop3h 01mAmerican Airlines
dom. 2/168:05 amORD - BOS
Nonstop2h 14mAmerican Airlines
Deal found 1/21$189
This Southwest deal was found by Cheapflights users on 1/21. 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.
jue. 2/135:45 amBOS - ORD
1 stop9h 15mSouthwest
mar. 2/1811:25 amORD - BOS
1 stop5h 20mSouthwest
Deal found 1/21$227
This United Airlines deal was found by Cheapflights users on 1/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/76:00 amPWM - ORD
1 stop5h 44mUnited Airlines
lun. 2/103:15 pmORD - PWM
1 stop6h 15mUnited Airlines
Deal found 1/20$239
This Kissandfly.com deal was found by Cheapflights users on 1/20. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/65:35 pmBOS - MDW
2 stops19h 19mMultiple Airlines
lun. 2/1011:33 amMDW - BOS
1 stop11h 54mMultiple Airlines
Deal found 1/20$241

Find flights from Maine to Chicago within your budget

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 enero 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

lun. 3/10

10:21 pm-1:39 pm

2 stops16h 18m

Chicago O'Hare Intl

mié. 3/12

6:45 am-4:10 pm

1 stop8h 25m

$147

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

lun. 2/24

5:10 am-4:51 pm

1 stop12h 41m

Chicago O'Hare Intl

jue. 2/27

12:59 pm-11:54 am

1 stop21h 55m

$148

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

lun. 3/10

5:10 am-4:31 pm

1 stop12h 21m

Chicago O'Hare Intl

lun. 3/17

6:45 am-4:10 pm

1 stop8h 25m

$149

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

vie. 2/21

11:11 am-9:25 pm

1 stop11h 14m

Chicago Midway

jue. 2/27

4:04 pm-10:21 am

1 stop17h 17m

$150

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

jue. 2/13

6:50 am-8:45 am

Nonstop2h 55m

Chicago Midway

dom. 2/16

8:20 pm-11:35 pm

Nonstop2h 15m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

vie. 2/21

8:20 pm-10:19 pm

Nonstop2h 59m

Chicago O'Hare Intl

mar. 2/25

2:35 pm-6:06 pm

Nonstop2h 31m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

lun. 2/24

10:00 am-12:00 pm

Nonstop3h 00m

Chicago O'Hare Intl

sáb. 3/1

12:38 pm-3:58 pm

Nonstop2h 20m

$167

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

lun. 3/10

4:17 pm-10:00 pm

1 stop6h 43m

Chicago O'Hare Intl

mié. 3/12

11:15 am-2:34 pm

Nonstop2h 19m

$183

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 2/13

5:20 am-7:21 am

Nonstop3h 01m

Chicago O'Hare Intl

mar. 2/18

7:00 am-10:21 am

Nonstop2h 21m

$187

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 2/13

5:45 am-2:00 pm

1 stop9h 15m

Chicago O'Hare Intl

dom. 2/16

7:00 am-2:00 pm

1 stop6h 00m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

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.

Travel insights for flights from Maine to Chicago

Get recent, data-driven insights about flights from Maine to Chicago including ideal travel times, pricing trends, and more.

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 $320). 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 enero 21, 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 enero 21, 2025.

The most flights from USME to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, 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 enero 21, 2025.
Get a feel of what it's like to fly with American Airlines, Frontier 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.
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,706 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,200 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,984 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Boarding

8.2

Overall

8.1

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $64 on Frontier. Other airlines that offer cheap prices include Southwest from $79 and Delta from $79 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 (90%), Republic Airways (89%) or United Airlines (88%) 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 $213. On average you can expect to pay $533. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $113.

  • 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 $320). 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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Hobby to Midway flights
George Bush Intcntl to O'Hare Intl flights
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Boston to Midway flights
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Portland to O'Hare Intl 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 enero 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$110FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$158Average$359FlexibilityNo cancel feeOn-time71%
DeltaCheapest$201Average$397FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$205Average$401FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$281Average$390FlexibilityNo cancel feeOn-time63%
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