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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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Dec 27 — Jan 31
Fri 12/27
Fri 1/3
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 December 22, 2024.

Round-trip from

$137
(Mytrip)

One-way from

$60
(Mytrip)
From Maine to Chicago (CHI)
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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 December 22, 2024.

This Priceline deal was found by Cheapflights users on 12/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/318:01 amBOS - MDW
1 stop6h 08mFrontier
Mon 1/62:20 pmMDW - BOS
1 stop9h 21mFrontier
Deal found 12/20$188
This United Airlines deal was found by Cheapflights users on 12/21. 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.
Tue 12/317:42 pmBOS - ORD
1 stop4h 43mUnited Airlines
Thu 1/29:30 pmORD - BOS
Nonstop2h 24mUnited Airlines
Deal found 12/21$228
This American Airlines deal was found by Cheapflights users on 12/21. 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.
Tue 12/316:00 amPWM - ORD
1 stop7h 15mAmerican Airlines
Sat 1/45:42 pmORD - PWM
1 stop4h 19mAmerican Airlines
Deal found 12/21$238
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Tue 12/315:45 amBOS - ORD
1 stop11h 43mFrontier
Sat 1/44:45 pmORD - BOS
1 stop17h 20mFrontier
Deal found 12/21$241
This Delta deal was found by Cheapflights users on 12/21. 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.
Tue 12/315:05 amPWM - MDW
1 stop4h 45mDelta
Sat 1/46:25 pmMDW - PWM
1 stop3h 57mDelta
Deal found 12/21$242
This Delta deal was found by Cheapflights users on 12/21. 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.
Tue 12/315:05 amPWM - ORD
1 stop5h 16mDelta
Sat 1/41:50 pmORD - PWM
2 stops9h 20mDelta
Deal found 12/21$247
This American Airlines deal was found by Cheapflights users on 12/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/316:45 amBOS - ORD
Nonstop3h 04mAmerican Airlines
Sat 1/48:30 pmORD - BOS
Nonstop2h 45mAmerican Airlines
Deal found 12/20$248
This Booking.com deal was found by Cheapflights users on 12/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3110:34 amBOS - ORD
1 stop10h 17mSpirit Airlines
Thu 1/28:14 pmORD - BOS
1 stop12h 44mSpirit Airlines
Deal found 12/21$253
This Southwest deal was found by Cheapflights users on 12/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/317:00 amBOS - MDW
Nonstop2h 45mSouthwest
Mon 1/68:30 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 12/20$255
This Delta deal was found by Cheapflights users on 12/21. 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.
Tue 12/3112:20 pmBOS - ORD
1 stop5h 20mDelta
Sat 1/44:45 pmORD - BOS
Nonstop2h 29mDelta
Deal found 12/21$259
This JetBlue deal was found by Cheapflights users on 12/21. 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.
Tue 12/316:00 amBOS - ORD
Nonstop3h 07mJetBlue
Sun 1/58:42 amORD - BOS
Nonstop2h 29mJetBlue
Deal found 12/21$262
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Wed 12/2512:35 pmBOS - ORD
1 stop8h 16mMultiple Airlines
Sat 1/44:45 pmORD - BOS
1 stop17h 20mMultiple Airlines
Deal found 12/21$300

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 December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 1/7

6:00 am-1:34 pm

1 stop8h 34m

Chicago O'Hare Intl

Sun 1/12

4:11 pm-12:30 am

1 stop7h 19m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 1/6

11:55 am-11:20 pm

1 stop12h 25m

Chicago Midway

Fri 1/10

3:37 pm-12:30 am

1 stop7h 53m

$138

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 1/18

11:31 am-8:13 pm

1 stop9h 42m

Chicago O'Hare Intl

Thu 1/23

4:41 pm-12:39 am

1 stop6h 58m

$142

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 1/11

7:15 am-9:25 am

Nonstop3h 10m

Chicago O'Hare Intl

Sun 1/12

7:10 am-10:47 am

Nonstop2h 37m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 1/15

8:10 am-10:05 am

Nonstop2h 55m

Chicago Midway

Tue 1/21

6:25 pm-9:40 pm

Nonstop2h 15m

$158

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/10

6:00 am-8:08 am

Nonstop3h 08m

Chicago O'Hare Intl

Sun 1/12

6:30 am-10:03 am

Nonstop2h 33m

$158

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 2/4

10:00 am-4:10 pm

1 stop7h 10m

Chicago O'Hare Intl

Tue 2/11

5:11 am-12:13 am

2 stops18h 02m

$160

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/17

9:30 am-11:28 am

Nonstop2h 58m

Chicago O'Hare Intl

Sun 1/19

7:10 am-2:07 pm

1 stop5h 57m

$167

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 2/11

3:52 pm-5:55 pm

Nonstop3h 03m

Chicago O'Hare Intl

Sat 2/15

12:45 pm-4:13 pm

Nonstop2h 28m

$173

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 1/11

3:50 pm-11:29 pm

1 stop8h 39m

Chicago Midway

Sun 1/12

7:45 am-2:40 pm

1 stop29h 55m

$210

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 54 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 $317). 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 December 22, 2024.

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 December 22, 2024.

The most flights from USME to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, 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 December 22, 2024.
Get a feel of what it's like to fly with JetBlue, American Airlines and Spirit Airlines 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
4,804 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

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
4,804 reviews
Southwest
8.1
Very good
4,804 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

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
9,537 reviews
Southwest
8.1
Very good
4,804 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

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
8,594 reviews
Southwest
8.1
Very good
4,804 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

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
3,265 reviews
Southwest
8.1
Very good
4,804 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

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
9,028 reviews
Southwest
8.1
Very good
4,804 reviews

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

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 $60 on Frontier. Other airlines that offer cheap prices include Southwest from $79 and JetBlue 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 Qatar Airways (97%), SkyWest Airlines (96%) or Republic Airways (92%) 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 $167. On average you can expect to pay $993. 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 $317). 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.

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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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$110FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$158Average$362FlexibilityNo cancel feeOn-time71%
DeltaCheapest$201Average$387FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$206Average$409FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$281Average$387FlexibilityNo cancel feeOn-time63%
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