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$85+ 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 8/22. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Jul 26 — Aug 21
Sun 7/26
Sun 8/2
1 adult, Economy
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Cheap 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 26, 2026.

This Southwest deal was found by Cheapflights users on 6/23. 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.
Sat 8/228:40 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Thu 8/275:45 am
MDW
-
BOS
Nonstop2h 15m
Southwest
Deal found 6/23$175
This JetBlue deal was found by Cheapflights users on 6/22. 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.
Mon 8/105:01 am
BOS
-
ORD
1 stop4h 51m
JetBlue
Sat 8/159:40 am
ORD
-
BOS
1 stop6h 37m
JetBlue
Deal found 6/22$177
This Southwest deal was found by Cheapflights users on 6/22. 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.
Wed 7/85:35 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Mon 7/134:00 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Deal found 6/22$178
This United Airlines deal was found by Cheapflights users on 6/25. 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 7/158:15 am
BOS
-
ORD
Nonstop2h 57m
United Airlines
Thu 7/169:41 pm
ORD
-
BOS
Nonstop2h 33m
United Airlines
Deal found 6/25$178
This Southwest deal was found by Cheapflights users on 6/24. 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.
Sat 7/185:20 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Mon 7/207:35 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Deal found 6/24$179
This United Airlines deal was found by Cheapflights users on 6/22. 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.
Thu 7/98:15 am
BOS
-
ORD
Nonstop2h 57m
United Airlines
Wed 7/1510:30 am
ORD
-
BOS
Nonstop2h 37m
United Airlines
Deal found 6/22$179
This Southwest deal was found by Cheapflights users on 6/25. 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 7/285:35 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Tue 8/44:40 pm
MDW
-
BOS
1 stop4h 35m
Southwest
Deal found 6/25$180
This JetBlue deal was found by Cheapflights users on 6/22. 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 7/142:45 pm
BOS
-
ORD
1 stop8h 13m
JetBlue
Sat 7/181:09 pm
ORD
-
BOS
Nonstop2h 34m
JetBlue
Deal found 6/22$180
This Southwest deal was found by Cheapflights users on 6/24. 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 8/288:20 pm
BOS
-
MDW
Nonstop2h 40m
Southwest
Sat 9/123:10 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Deal found 6/24$181
This Cheapflightsfares deal was found by Cheapflights users on 6/23. 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 7/158:10 am
BOS
-
ORD
Nonstop2h 56m
JetBlue
Wed 7/226:00 am
ORD
-
BOS
1 stop7h 22m
JetBlue
Deal found 6/23$181
This Southwest deal was found by Cheapflights users on 6/24. 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.
Wed 7/153:45 pm
BOS
-
MDW
Nonstop2h 45m
Southwest
Fri 7/177:35 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Deal found 6/24$182
This Southwest deal was found by Cheapflights users on 6/22. 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.
Sat 7/185:20 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Sun 7/195:15 am
MDW
-
BOS
Nonstop2h 10m
Southwest
Deal found 6/22$183

Find 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 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$175
(Southwest)

One-way from

$85
(JetBlue)

Popular in

December

Cheapest in

September

Average price

$354

Good round-trip deal

$379 or less

Good one-way deal

$229 or less
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Chicago (CHI) flights.
Search Deals
From Maine to Chicago (CHI)
Search Deals
One-way flight from Maine to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals
Price to beat on a round-trip flight from Maine to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Maine to Chicago (CHI).
Search Deals

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 26, 2026.
Use the filters below to find and compare flights from Maine to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 8/11

12:44 pm-5:35 pm

1 stop5h 51m

Chicago O'Hare Intl

Thu 8/13

9:35 am-5:07 pm

1 stop6h 32m

$177

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 7/14

6:43 pm-8:40 pm

Nonstop2h 57m

Chicago O'Hare Intl

Fri 7/17

7:45 pm-11:21 pm

Nonstop2h 36m

$178

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 7/23

8:15 pm-10:15 pm

Nonstop3h 00m

Chicago O'Hare Intl

Tue 7/28

6:00 am-11:16 am

1 stop4h 16m

$180

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 7/22

5:45 am-9:36 am

1 stop4h 51m

Chicago O'Hare Intl

Thu 7/23

9:41 pm-1:14 am

Nonstop2h 33m

$180

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 8/19

8:15 am-10:11 am

Nonstop2h 56m

Chicago O'Hare Intl

Mon 8/24

6:00 am-2:43 pm

1 stop7h 43m

$188

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 7/9

5:45 am-9:36 am

1 stop4h 51m

Chicago O'Hare Intl

Tue 7/14

7:33 am-11:05 am

Nonstop2h 32m

$189
Quickest round-trip

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 7/16

5:25 am-7:00 am

Nonstop2h 35m

Chicago Midway

Sun 7/19

5:15 am-8:25 am

Nonstop2h 10m

$192

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 7/30

6:00 am-7:58 am

Nonstop2h 58m

Chicago O'Hare Intl

Mon 8/3

9:41 pm-1:14 am

Nonstop2h 33m

$195

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 7/7

8:45 pm-10:39 pm

Nonstop2h 54m

Chicago O'Hare Intl

Mon 7/13

7:25 pm-11:00 pm

Nonstop2h 35m

$200

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 8/18

5:35 am-11:50 am

1 stop7h 15m

Chicago Midway

Sat 8/22

9:05 am-12:25 pm

Nonstop2h 20m

$201

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/22

Showing 1-10 of 60 resultsSorted by cheapest first
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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, September is the cheapest month in which you can book a flight from Maine to Chicago (average of $130). Flying from Maine to Chicago in January is currently the most expensive (average of $209). 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 26, 2026.

When flying from Maine to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 25% versus a flight in the morning.

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 26, 2026.

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

How much does it cost to fly round-trip from Maine to Chicago?

How far ahead should I book a flight from Maine to Chicago?

The best time to book flights from Maine to Chicago is 83 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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.

  • How long is the flight from Maine to Chicago?

    A quick flight from Maine to Chicago can take about 2h 35m. JetBlue provides one of the quickest options available for as low as $192. The distance from Maine to Chicago is about 857 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $442 on Royal Jordanian. Other airlines that offer cheap prices include Qatar Airways from $575 and Turkish Airlines from $740 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 SkyWest Airlines (91%), United Airlines (90%) or Air New Zealand (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 $168. On average you can expect to pay $994. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for $149.

  • 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 $130). Flying from Maine to Chicago in January is currently the most expensive (average of $209). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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 June 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$209Average$348FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$229Average$379FlexibilityNo cancel feeOn-time69%
DeltaCheapest$234Average$346FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$267Average$397FlexibilityNo cancel feeOn-time63%

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