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$45+ 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Nov 19 — Nov 261
Tue 11/19
Tue 11/26
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 November 14, 2024.

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 November 14, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 11/13. 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.
Fri 11/225:30 amBOS - ORD
Nonstop3h 07mSpirit Airlines
Wed 12/411:45 amORD - BOS
1 stop11h 53mSpirit Airlines
Deal found 11/13$123
This Frontier deal was found by Cheapflights users on 11/14. 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 12/46:00 amBOS - MDW
1 stop6h 42mFrontier
Wed 12/1112:57 pmMDW - BOS
1 stop10h 33mFrontier
Deal found 11/14$124
This FlightHub deal was found by Cheapflights users on 11/13. 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.
Sat 11/1610:55 amBOS - ORD
1 stop11h 50mFrontier
Wed 11/202:15 pmORD - BOS
1 stop9h 14mFrontier
Deal found 11/13$124
This CheapOair deal was found by Cheapflights users on 11/13. 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.
Wed 11/206:00 amBOS - ORD
1 stop8h 10mMultiple Airlines
Wed 12/411:45 amORD - BOS
1 stop11h 53mMultiple Airlines
Deal found 11/13$133
This eDestinos deal was found by Cheapflights users on 11/12. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/76:00 amBOS - MDW
1 stop18h 29mMultiple Airlines
Mon 12/912:36 pmMDW - BOS
1 stop7h 12mMultiple Airlines
Deal found 11/12$153
This Delta deal was found by Cheapflights users on 11/14. 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 12/411:05 amBOS - ORD
Nonstop2h 58mDelta
Thu 12/126:50 pmORD - BOS
Nonstop2h 30mDelta
Deal found 11/14$157
This Southwest deal was found by Cheapflights users on 11/14. 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.
Fri 12/66:00 pmBOS - MDW
Nonstop2h 45mSouthwest
Mon 12/96:25 pmMDW - BOS
Nonstop2h 10mSouthwest
Deal found 11/14$158
This JetBlue deal was found by Cheapflights users on 11/13. 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.
Sat 12/76:00 amBOS - ORD
Nonstop3h 06mJetBlue
Sat 12/710:14 amORD - BOS
1 stop4h 29mJetBlue
Deal found 11/13$161
This United Airlines deal was found by Cheapflights users on 11/14. 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 12/45:45 amBOS - ORD
1 stop4h 49mUnited Airlines
Thu 12/59:20 amORD - BOS
Nonstop2h 25mUnited Airlines
Deal found 11/14$167
This American Airlines deal was found by Cheapflights users on 11/14. 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
Sun 1/58:20 amORD - BOS
Nonstop2h 23mAmerican Airlines
Deal found 11/14$194
This Mytrip deal was found by Cheapflights users on 11/14. 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 12/65:05 amBOS - RFD
1 stop13h 05mMultiple Airlines
Sun 12/84:11 pmRFD - BOS
1 stop17h 30mMultiple Airlines
Deal found 11/14$244
This Delta deal was found by Cheapflights users on 11/14. 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.
Sat 12/73:40 pmBGR - ORD
1 stop7h 16mDelta
Thu 12/126:00 amORD - BGR
1 stop5h 35mDelta
Deal found 11/14$248

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 2,752,363 searches. Data last updated November 14, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 12/4

6:00 am-11:42 am

1 stop6h 42m

Chicago Midway

Wed 12/11

12:57 pm-12:30 am

1 stop10h 33m

$124

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 1/9

6:00 am-9:54 am

1 stop28h 54m

Chicago O'Hare Intl

Sun 1/12

7:00 am-10:47 am

1 stop26h 47m

$125

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 12/3

8:10 am-10:21 am

Nonstop3h 11m

Chicago O'Hare Intl

Tue 12/10

9:58 am-12:38 am

1 stop13h 40m

$126

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 12/11

5:00 am-4:06 pm

1 stop12h 06m

Chicago O'Hare Intl

Fri 12/13

10:59 am-12:30 am

1 stop12h 31m

$130

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 12/7

6:00 am-11:29 pm

1 stop18h 29m

Chicago Midway

Mon 12/9

12:36 pm-8:48 pm

1 stop7h 12m

$153

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 12/9

6:00 am-8:06 am

Nonstop3h 06m

Chicago O'Hare Intl

Mon 12/16

8:51 am-12:13 pm

Nonstop2h 22m

$156

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 12/4

7:50 pm-9:51 pm

Nonstop3h 01m

Chicago O'Hare Intl

Fri 12/13

2:05 pm-5:34 pm

Nonstop2h 29m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 12/6

7:00 am-8:45 am

Nonstop2h 45m

Chicago Midway

Sun 12/8

8:00 am-11:15 am

Nonstop2h 15m

$158

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 12/31

6:45 am-8:49 am

Nonstop3h 04m

Chicago O'Hare Intl

Sun 1/5

8:20 am-11:43 am

Nonstop2h 23m

$194

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 12/3

2:05 pm-8:14 pm

1 stop7h 09m

Chicago O'Hare Intl

Fri 12/6

1:55 pm-5:16 pm

Nonstop2h 21m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/14

Showing 1-10 of 58 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, September is the cheapest month in which you can book a flight from Maine to Chicago (average of $232). Flying from Maine to Chicago in June is currently the most expensive (average of $308). 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 November 14, 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 November 14, 2024.

The most flights from USME to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 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 November 14, 2024.
Get a feel of what it's like to fly with Southwest, Spirit Airlines and United 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
5,045 reviews

Entertainment

7.7

Boarding

8.3

Crew

8.7

Overall

8.1

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,045 reviews
Southwest
8.1
Very good
5,045 reviews

Entertainment

7.7

Boarding

8.3

Crew

8.7

Overall

8.1

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,439 reviews
Southwest
8.1
Very good
5,045 reviews

Entertainment

7.7

Boarding

8.3

Crew

8.7

Overall

8.1

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,788 reviews
Southwest
8.1
Very good
5,045 reviews

Entertainment

7.7

Boarding

8.3

Crew

8.7

Overall

8.1

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

JetBlue
7.5
Good
3,447 reviews
Southwest
8.1
Very good
5,045 reviews

Entertainment

7.7

Boarding

8.3

Crew

8.7

Overall

8.1

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,194 reviews
Southwest
8.1
Very good
5,045 reviews

Entertainment

7.7

Boarding

8.3

Crew

8.7

Overall

8.1

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 $45 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $49 and Southwest 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 (96%), American Airlines (92%) or Envoy Air (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 $182. On average you can expect to pay $953. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $104.

  • 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, September is the cheapest month in which you can book a flight from Maine to Chicago (average of $232). Flying from Maine to Chicago in June is currently the most expensive (average of $308). 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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Los Angeles to Midway flights
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Reagan-National to Midway flights
Minneapolis to Midway flights
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LaGuardia to Midway flights
San Francisco to Midway flights
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Tampa to Midway flights
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Columbus 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 2,752,363 searches. Data last updated November 14, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$112FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$158Average$362FlexibilityNo cancel feeOn-time71%
DeltaCheapest$201Average$354FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$206Average$410FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$281Average$387FlexibilityNo cancel feeOn-time63%
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