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$69+ 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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$137
(Southwest)

One-way from

$69
(Southwest)

Popular in

November

Cheapest in

August

Average price

$338

Good round-trip deal

$321 or less

Good one-way deal

$147 or less
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 ($46 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 July 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 July 30, 2025.

This Southwest deal was found by Cheapflights users on 7/28. 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 10/175:15 amBOS - MDW
Nonstop2h 40mSouthwest
Sun 10/199:05 pmMDW - BOS
Nonstop2h 20mSouthwest
Deal found 7/28$137
This United Airlines deal was found by Cheapflights users on 7/27. 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.
Fri 9/126:16 pmBOS - ORD
Nonstop2h 54mUnited Airlines
Wed 9/171:12 pmORD - BOS
Nonstop2h 31mUnited Airlines
Deal found 7/27$137
This FlightHub deal was found by Cheapflights users on 7/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/266:05 amBOS - ORD
1 stop14h 02mSpirit Airlines
Tue 8/268:12 pmORD - BOS
1 stop14h 06mSpirit Airlines
Deal found 7/29$138
This American Airlines deal was found by Cheapflights users on 7/27. 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 9/117:01 amBOS - ORD
Nonstop3h 04mAmerican Airlines
Thu 9/188:25 pmORD - BOS
Nonstop2h 28mAmerican Airlines
Deal found 7/27$139
This Trip.com deal was found by Cheapflights users on 7/28. 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.
Thu 8/216:00 amBOS - ORD
Nonstop2h 55mJetBlue
Thu 8/214:27 pmORD - BOS
Nonstop2h 33mJetBlue
Deal found 7/28$142
This Southwest deal was found by Cheapflights users on 7/28. 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 9/41:45 pmBOS - ORD
1 stop10h 20mSouthwest
Sun 9/71:50 pmORD - BOS
1 stop5h 45mSouthwest
Deal found 7/28$146
This Delta deal was found by Cheapflights users on 7/28. 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.
Thu 9/47:20 amBOS - ORD
Nonstop2h 55mDelta
Sun 9/77:00 amORD - BOS
Nonstop2h 30mDelta
Deal found 7/28$155
This Mytrip deal was found by Cheapflights users on 7/30. 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.
Fri 9/58:59 amBOS - MDW
1 stop8h 44mAllegiant Air
Mon 9/87:50 pmMDW - BOS
1 stop12h 53mAllegiant Air
Deal found 7/30$206
This Frontier deal was found by Cheapflights users on 7/30. 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.
Sat 8/169:40 amBOS - MDW
1 stop11h 42mFrontier
Sun 8/173:58 pmMDW - BOS
1 stop7h 40mFrontier
Deal found 7/30$208
This American Airlines deal was found by Cheapflights users on 7/28. 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 10/25:54 pmBGR - ORD
Nonstop2h 51mAmerican Airlines
Sun 10/56:30 pmORD - BGR
Nonstop2h 35mAmerican Airlines
Deal found 7/28$210
This Mytrip deal was found by Cheapflights users on 7/29. 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.
Fri 10/176:08 amBOS - RFD
2 stops13h 50mMultiple Airlines
Sun 10/194:45 pmRFD - BOS
1 stop16h 51mMultiple Airlines
Deal found 7/29$246
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/133:13 pmBGR - ORD
1 stop7h 27mDelta
Tue 9/167:00 amORD - BGR
1 stop6h 31mDelta
Deal found 7/29$249

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 July 30, 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

Fri 10/17

5:15 am-6:55 am

Nonstop2h 40m

Chicago Midway

Sun 10/19

9:05 pm-12:25 am

Nonstop2h 20m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 9/12

6:16 pm-8:10 pm

Nonstop2h 54m

Chicago O'Hare Intl

Wed 9/17

1:12 pm-4:43 pm

Nonstop2h 31m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 8/26

6:05 am-7:07 pm

1 stop14h 02m

Chicago O'Hare Intl

Tue 8/26

8:12 pm-11:18 am

1 stop14h 06m

$138

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/11

7:01 am-9:05 am

Nonstop3h 04m

Chicago O'Hare Intl

Thu 9/18

8:25 pm-11:53 pm

Nonstop2h 28m

$139

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 8/21

6:00 am-7:55 am

Nonstop2h 55m

Chicago O'Hare Intl

Thu 8/21

4:27 pm-8:00 pm

Nonstop2h 33m

$142

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/4

7:30 am-12:45 pm

1 stop6h 15m

Chicago O'Hare Intl

Sun 9/7

1:50 pm-8:35 pm

1 stop5h 45m

$146

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/4

7:20 am-9:15 am

Nonstop2h 55m

Chicago O'Hare Intl

Sun 9/7

7:00 am-10:30 am

Nonstop2h 30m

$155

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 9/5

8:59 am-4:43 pm

1 stop8h 44m

Chicago Midway

Mon 9/8

7:50 pm-9:43 am

1 stop12h 53m

$206

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 8/16

9:40 am-8:22 pm

1 stop11h 42m

Chicago Midway

Sun 8/17

3:58 pm-12:38 am

1 stop7h 40m

$208

BangorChicago

BGR - ORD

BGRORD

Bangor

Thu 10/2

5:54 pm-7:45 pm

Nonstop2h 51m

Chicago O'Hare Intl

Sun 10/5

6:30 pm-10:05 pm

Nonstop2h 35m

$210

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 57 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 July 30, 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 July 30, 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 (3 on average).

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 July 30, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Maine to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,896 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,913 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,241 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 $69 on Southwest. Other airlines that offer cheap prices include United Airlines from $69 and American Airlines from $70 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 Envoy Air (95%), American Airlines (92%) or SkyWest Airlines (90%) 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 $118. On average you can expect to pay $689. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $117.

  • 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 4 airlines flying from Maine to Chicago

Discover the top 4 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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$124Average$353FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$204Average$339FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$226Average$384FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$264Average$390FlexibilityNo cancel feeOn-time63%

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