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Illinois

$61+ Cheap flights from Maine to Illinois

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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Maine to Illinois

Cheapest flights from Maine to Illinois
Explore the most affordable flight options available from Maine to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Orbitz deal was found by Cheapflights users on 1/26. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/255:27 am
BOS
-
ORD
1 stop14h 44m
Multiple Airlines
Wed 3/410:00 am
ORD
-
BOS
Nonstop2h 20m
Multiple Airlines
Deal found 1/26$132
This Super.com deal was found by Cheapflights users on 1/29. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/53:35 pm
BOS
-
ORD
Nonstop3h 08m
JetBlue
Mon 2/97:40 am
ORD
-
BOS
Nonstop2h 25m
JetBlue
Deal found 1/29$133
This Cheapflightsfares deal was found by Cheapflights users on 1/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/313:35 pm
BOS
-
ORD
Nonstop3h 08m
JetBlue
Wed 2/47:40 am
ORD
-
BOS
Nonstop2h 25m
JetBlue
Deal found 1/28$134
This Southwest deal was found by Cheapflights users on 1/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/305:30 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Tue 2/32:00 pm
MDW
-
BOS
Nonstop2h 10m
Southwest
Deal found 1/27$135
This United Airlines deal was found by Cheapflights users on 1/27. 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 1/304:16 pm
BOS
-
ORD
Nonstop3h 00m
United Airlines
Sun 2/17:30 am
ORD
-
BOS
Nonstop2h 22m
United Airlines
Deal found 1/27$135
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:15 am
BOS
-
ORD
Nonstop3h 13m
Delta
Sat 2/287:05 am
ORD
-
BOS
Nonstop2h 32m
Delta
Deal found 1/27$136
This American Airlines deal was found by Cheapflights users on 1/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/277:16 pm
BOS
-
ORD
Nonstop3h 14m
American Airlines
Mon 3/28:45 pm
ORD
-
BOS
Nonstop2h 14m
American Airlines
Deal found 1/29$137
This Delta deal was found by Cheapflights users on 1/28. 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.
Wed 2/257:45 pm
BOS
-
ORD
Nonstop3h 03m
Delta
Mon 3/25:37 pm
ORD
-
BOS
1 stop4h 49m
Delta
Deal found 1/28$138
This Delta deal was found by Cheapflights users on 1/28. 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.
Sat 2/289:00 am
BOS
-
MDW
1 stop4h 46m
Delta
Mon 3/26:20 pm
MDW
-
BOS
1 stop4h 06m
Delta
Deal found 1/28$139
This Delta deal was found by Cheapflights users on 1/28. 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.
Sat 2/284:58 pm
BOS
-
ORD
1 stop4h 46m
Delta
Tue 3/37:10 am
ORD
-
BOS
1 stop5h 09m
Delta
Deal found 1/28$139
This lastminute.com deal was found by Cheapflights users on 1/27. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/245:38 pm
BOS
-
ORD
1 stop6h 21m
JetBlue
Wed 2/2510:00 am
ORD
-
BOS
Nonstop2h 20m
JetBlue
Deal found 1/27$140
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Thu 2/266:00 am
BOS
-
ORD
1 stop17h 39m
Frontier
Mon 3/24:42 pm
ORD
-
BOS
1 stop7h 31m
Frontier
Deal found 1/26$141

Find flight deals from Maine to Illinois

Keep the following information in mind while searching for Maine to Illinois flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$132
(Orbitz)

One-way from

$61
(Trip.com)

Popular in

December

Cheapest in

September

Average price

$357

Good round-trip deal

$365 or less

Good one-way deal

$205 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 Illinois
Search Deals
One-way flight from Maine to Illinois
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Maine to Illinois.
Search Deals
Price to beat on a one-way flight from Maine to Illinois.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Maine to Illinois 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 January 29, 2026.
Use the filters below to find and compare flights from Maine to Illinois that are best for you.

Fly from

Maine

Fly to

Illinois

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 2/28

5:45 pm-7:35 pm

Nonstop2h 50m

Chicago Midway

Mon 3/2

6:35 pm-9:50 pm

Nonstop2h 15m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 6/3

6:35 pm-8:35 pm

Nonstop3h 00m

Chicago O'Hare Intl

Thu 6/4

9:26 pm-12:59 am

Nonstop2h 33m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 4/8

7:10 am-9:10 am

Nonstop3h 00m

Chicago O'Hare Intl

Wed 4/15

6:00 am-9:15 am

Nonstop2h 15m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 6/3

7:00 am-8:58 am

Nonstop2h 58m

Chicago O'Hare Intl

Sat 6/6

7:00 am-10:28 am

Nonstop2h 28m

$135

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 2/25

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Wed 3/4

5:35 pm-8:50 pm

Nonstop2h 15m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 5/30

7:00 am-8:58 am

Nonstop2h 58m

Chicago O'Hare Intl

Sat 6/6

7:00 am-10:28 am

Nonstop2h 28m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 4/14

6:52 am-8:51 am

Nonstop2h 59m

Chicago O'Hare Intl

Wed 4/22

6:00 am-9:15 am

Nonstop2h 15m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 4/7

4:25 pm-6:31 pm

Nonstop3h 06m

Chicago O'Hare Intl

Fri 4/10

7:35 pm-11:02 pm

Nonstop2h 27m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 5/2

8:55 am-11:00 am

Nonstop3h 05m

Chicago O'Hare Intl

Sat 5/9

7:00 am-10:28 am

Nonstop2h 28m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 3/31

4:25 pm-6:31 pm

Nonstop3h 06m

Chicago O'Hare Intl

Wed 4/8

10:40 am-2:04 pm

Nonstop2h 24m

$135

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 60 results
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Best time to book a flight from Maine to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois 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 Illinois

What is the cheapest month to book a flight from Maine to Illinois?

Currently, May is the cheapest month in which you can book a flight from Maine to Illinois (average of $182). Flying from Maine to Illinois 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 IL?

Find hourly flight availability from Maine to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 29, 2026.

One of the essential ways to save on airfare from Maine to Illinois is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 29% on airfare.

Weekly flight availability from Maine to Illinois

Explore weekly flight availability from Maine to Illinois. 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 January 29, 2026.

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

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated January 29, 2026.
See what other customers who have flown with Southwest, Delta, and United Airlines from Maine to Illinois have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,128 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,215 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,205 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Maine to Illinois. 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 Illinois?

    There are many flights that can get you from Maine to Illinois in 2h 50m. Fly via Southwest, United Airlines, or JetBlue to get the fastest option. Maine and Illinois are separated by a distance of 857 mi. Generally, flights for this route are nonstop.

  • What are the cheapest airlines to fly from Maine to Illinois one-way?

    $442 is the cheapest one-way deal found within the past few days, from Royal Jordanian. You may also be able to find cheap deals on Turkish Airlines and Qatar Airways, with prices starting from $740 and $756, respectively.

  • Can I find deals for flights from Maine to Illinois that include hotel bookings?

    Yes. In addition to deals on Maine to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Maine to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Maine to Illinois.

  • Can I find deals for business class flights from Maine to Illinois?

    Yes. Cheapflights offers flight deals from Maine to Illinois 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 Illinois?

    Currently, May is the cheapest month in which you can book a flight from Maine to Illinois (average of $182). Flying from Maine to Illinois 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Maine to Illinois

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 Illinois

Discover the top 4 airlines that operate flights from Maine to Illinois. 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$114Average$350FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$209Average$354FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$228Average$428FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$246Average$397FlexibilityNo cancel feeOn-time63%

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