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$70+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Apr 22 — Apr 291
Wed 4/22
Wed 4/29
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 March 23, 2026.

This Southwest deal was found by Cheapflights users on 3/22. 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.
Tue 5/2610:45 am
BOS
-
MDW
Nonstop2h 40m
Southwest
Tue 6/26:00 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Deal found 3/22$136
This Frontier deal was found by Cheapflights users on 3/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1412:40 pm
BOS
-
MDW
1 stop7h 51m
Frontier
Wed 4/152:15 pm
MDW
-
BOS
1 stop10h 16m
Frontier
Deal found 3/20$140
This Frontier deal was found by Cheapflights users on 3/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1312:45 pm
BOS
-
ORD
1 stop6h 45m
Frontier
Tue 4/146:08 pm
ORD
-
BOS
1 stop6h 23m
Frontier
Deal found 3/20$140
This Southwest deal was found by Cheapflights users on 3/22. 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.
Mon 4/137:10 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Tue 4/146:00 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Deal found 3/22$146
This Cheapflightsfares deal was found by Cheapflights users on 3/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:26 pm
BOS
-
ORD
Nonstop3h 09m
JetBlue
Sat 5/301:55 pm
ORD
-
BOS
Nonstop2h 29m
JetBlue
Deal found 3/20$152
This SmartFares deal was found by Cheapflights users on 3/20. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/47:35 pm
BOS
-
ORD
Nonstop3h 01m
JetBlue
Mon 5/116:00 am
ORD
-
BOS
Nonstop2h 15m
JetBlue
Deal found 3/20$154
This SmartFares deal was found by Cheapflights users on 3/18. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:05 am
BOS
-
ORD
Nonstop3h 00m
JetBlue
Mon 4/138:58 am
ORD
-
BOS
Nonstop2h 30m
JetBlue
Deal found 3/18$155
This Southwest deal was found by Cheapflights users on 3/20. 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.
Sat 5/23:30 pm
BOS
-
MDW
Nonstop2h 45m
Southwest
Thu 5/79:25 am
MDW
-
BOS
Nonstop2h 15m
Southwest
Deal found 3/20$157
This Delta deal was found by Cheapflights users on 3/18. 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.
Fri 5/17:35 pm
BOS
-
ORD
Nonstop2h 54m
Delta
Sun 5/36:50 am
ORD
-
BOS
Nonstop2h 21m
Delta
Deal found 3/18$157
This American Airlines deal was found by Cheapflights users on 3/20. 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.
Sat 4/113:16 pm
BOS
-
ORD
Nonstop3h 14m
American Airlines
Sun 4/126:00 am
ORD
-
BOS
Nonstop2h 27m
American Airlines
Deal found 3/20$158
This Priceline deal was found by Cheapflights users on 3/20. 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.
Sat 4/116:05 am
BOS
-
ORD
Nonstop3h 03m
Multiple Airlines
Tue 4/146:08 pm
ORD
-
BOS
1 stop6h 23m
Multiple Airlines
Deal found 3/20$159
This Frontier deal was found by Cheapflights users on 3/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/712:42 pm
BOS
-
MDW
1 stop10h 37m
Frontier
Tue 4/142:15 pm
MDW
-
BOS
1 stop10h 16m
Frontier
Deal found 3/20$160

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 March 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$136
(Southwest)

One-way from

$70
(Frontier)

Popular in

December

Cheapest in

September

Average price

$391

Good round-trip deal

$350 or less

Good one-way deal

$190 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. 11% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 23, 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

Wed 5/6

9:20 am-11:20 am

Nonstop3h 00m

Chicago O'Hare Intl

Sat 5/9

9:30 pm-12:59 am

Nonstop2h 29m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 7/23

7:19 am-9:17 am

Nonstop2h 58m

Chicago O'Hare Intl

Mon 7/27

9:35 pm-1:08 am

Nonstop2h 33m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 6/2

10:45 am-12:25 pm

Nonstop2h 40m

Chicago Midway

Tue 6/9

5:30 pm-11:20 pm

1 stop4h 50m

$167

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 4/27

4:45 pm-10:20 pm

1 stop6h 35m

Chicago Midway

Wed 4/29

3:15 pm-6:35 pm

Nonstop2h 20m

$167

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 6/13

7:27 pm-11:26 pm

1 stop4h 59m

Chicago O'Hare Intl

Tue 6/16

9:26 pm-12:59 am

Nonstop2h 33m

$177

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/30

8:25 pm-10:20 pm

Nonstop2h 55m

Chicago O'Hare Intl

Sat 5/2

10:40 am-4:36 pm

1 stop4h 56m

$177

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 5/1

5:50 pm-11:55 pm

1 stop7h 05m

Chicago Midway

Tue 5/5

7:50 am-5:15 pm

2 stops8h 25m

$182

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 5/5

6:20 am-10:40 am

1 stop5h 20m

Chicago Midway

Sat 5/9

2:15 pm-11:40 pm

2 stops8h 25m

$182

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 4/15

8:10 am-12:50 pm

1 stop5h 40m

Chicago O'Hare Intl

Fri 4/17

2:40 pm-11:55 pm

2 stops8h 15m

$182

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 4/11

7:05 am-1:15 pm

1 stop7h 10m

Chicago O'Hare Intl

Sat 4/11

6:23 pm-9:59 pm

Nonstop2h 36m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/19

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, May is the cheapest month in which you can book a flight from Maine to Chicago (average of $182). Flying from Maine to Chicago in December is currently the most expensive (average of $259). 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 March 23, 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 46% versus a flight in the evening.

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 March 23, 2026.

The most flights from USME to CHI are scheduled on a Tuesday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 on average).

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

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 40m. United Airlines provides one of the quickest options available for as low as $167. The distance from Maine to Chicago is about 857 mi. Most flights are nonstop.

  • 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 $104 on American Airlines. Other airlines that offer cheap prices include Delta from $114 and United Airlines from $115 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 (100%), Republic Airways (83%) or American Airlines (76%) 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 $124. On average you can expect to pay $991. 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, May is the cheapest month in which you can book a flight from Maine to Chicago (average of $182). Flying from Maine to Chicago in December is currently the most expensive (average of $259). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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.
John F Kennedy Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Boston to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Denver to O'Hare Intl flights
Seattle to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Ontario to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Atlanta to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Hobby to O'Hare Intl flights
Orlando to O'Hare Intl flights
Los Angeles to Midway flights
Austin to O'Hare Intl flights
Dulles Intl to Midway flights
Baltimore to Midway flights
George Bush Intcntl to O'Hare Intl flights
Tampa to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Atlanta to Midway flights
San Diego to O'Hare Intl flights
LaGuardia to Midway flights
Charlotte to O'Hare Intl flights
Newark to Midway flights
San Jose to O'Hare Intl flights
Miami to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Newark to St. Louis flights
Denver to Midway flights
Sacramento to O'Hare Intl flights
Portland to O'Hare Intl flights
Minneapolis to Midway flights
Orlando to Midway flights
Hartford to O'Hare Intl flights
San Francisco to Midway flights
Boston to Midway flights
LaGuardia to St. Louis flights
John F Kennedy Intl to St. Louis flights
Burbank to O'Hare Intl flights
Love Field to O'Hare Intl flights

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 March 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$114Average$373FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$209Average$358FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$224Average$398FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$264Average$387FlexibilityNo cancel feeOn-time63%

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