Maine

$145+ Cheap flights from Illinois to Maine

ORD — PWM
Dec 7 — Dec 141
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1. Tell us where you want to go

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Cheap flight deals from Illinois to Maine

Cheapest flights from Illinois to Maine

Mon 12/145:50 pm -
Nonstop2h 39m
Wed 12/164:47 pm -
Nonstop3h 13m
Deal found 11/4$289
Sat 12/55:50 pm -
Nonstop2h 39m
Sat 12/124:47 pm -
Nonstop3h 13m
Deal found 11/4$299
Mon 12/1411:39 am -
2 stops10h 41m
Wed 12/1611:40 am -
1 stop6h 24m
Deal found 11/4$314
Sat 12/53:00 pm -
1 stop6h 46m
Sat 12/122:57 pm -
1 stop7h 27m
Deal found 11/4$319
Sat 12/59:37 am -
1 stop5h 34m
Sat 12/1212:49 pm -
1 stop6h 12m
Deal found 11/4$319
Fri 12/115:50 pm -
Nonstop2h 39m
Sat 12/124:47 pm -
Nonstop3h 13m
Deal found 11/5$320
Sat 12/51:34 pm -
2 stops9h 47m
Sat 12/122:00 pm -
1 stop6h 25m
Deal found 11/4$324
Wed 12/211:59 am -
Nonstop2h 39m
Wed 12/94:47 pm -
Nonstop3h 13m
Deal found 11/4$326
Tue 12/13:36 pm -
1 stop6h 48m
Tue 12/84:47 pm -
Nonstop3h 13m
Deal found 11/4$334
Fri 12/45:12 pm -
1 stop5h 40m
Sun 12/66:00 am -
1 stop7h 04m
Deal found 11/4$339
Thu 12/32:30 pm -
1 stop5h 12m
Thu 12/109:51 am -
Nonstop3h 09m
Deal found 11/4$346
Fri 12/253:30 pm -
1 stop5h 19m
Tue 1/512:47 pm -
1 stop6h 13m
Deal found 11/4$346

Find flight deals from Illinois to Maine

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$289
(United Airlines)

One-way from

$145
(American Airlines)

Popular in

December

Cheapest in

May

Average price

$449

Good round-trip deal

$389 or less

Good one-way deal

$209 or less
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
From Illinois to Maine
One-way flight from Illinois to Maine
Highest demand for flights based on searches. 13% potential increase in price ($60 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Average for round-trip flights in November 2026
Price to beat on a round-trip flight from Illinois to Maine.
Price to beat on a one-way flight from Illinois to Maine.

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Illinois to Maine that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPortland

ORD Chicago O'Hare Intl - PWM Portland

ORDPWM

Chicago O'Hare Intl

Wed 12/9

8:50 am-4:39 pm

1 stop6h 49m

Portland

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$155

ChicagoPortland

ORD Chicago O'Hare Intl - PWM Portland

ORDPWM

Chicago O'Hare Intl

Fri 12/11

5:50 pm-9:29 pm

Nonstop2h 39m

Portland

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$170

ChicagoPortland

MDW Chicago Midway - PWM Portland

MDWPWM

Chicago Midway

Thu 11/26

6:00 am-1:06 pm

1 stop6h 06m

Portland

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$185

ChicagoPortland

MDW Chicago Midway - PWM Portland

MDWPWM

Chicago Midway

Tue 12/1

12:33 pm-11:48 am

3 stops22h 15m

Portland

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$189

ChicagoBangor

ORD Chicago O'Hare Intl - BGR Bangor

ORDBGR

Chicago O'Hare Intl

Thu 12/24

7:00 am-3:59 pm

1 stop7h 59m

Bangor

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$195

ChicagoBangor

ORD Chicago O'Hare Intl - BGR Bangor

ORDBGR

Chicago O'Hare Intl

Fri 12/25

9:42 am-3:59 pm

1 stop5h 17m

Bangor

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$195

ChicagoPortland

MDW Chicago Midway - PWM Portland

MDWPWM

Chicago Midway

Mon 11/23

5:05 am-10:30 am

1 stop4h 25m

Portland

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$200
Quickest round-trip

ChicagoPortland

ORD Chicago O'Hare Intl - PWM Portland

ORDPWM

Chicago O'Hare Intl

Fri 12/18

11:59 am-3:31 pm

Nonstop2h 32m

Portland

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$201

ChicagoPortland

MDW Chicago Midway - PWM Portland

MDWPWM

Chicago Midway

Sat 11/21

9:30 am-4:10 pm

1 stop5h 40m

Portland

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$205

ChicagoPortland

ORD Chicago O'Hare Intl - PWM Portland

ORDPWM

Chicago O'Hare Intl

Fri 11/20

6:18 pm-9:52 pm

Nonstop2h 34m

Portland

Wed 12/31

12:00 am-11:00 pm

Nonstop0h 00m

$210

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Illinois to Maine

Have a flexible travel schedule? Discover the best time to fly to Maine from Illinois with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Illinois to Maine

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

Currently, April is the cheapest month in which you can book a flight from Illinois to Maine (average of $334). Flying from Illinois to Maine in December is currently the most expensive (average of $482). 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 IL to ME?

It’s optimal to fly from Illinois to Maine in the evening. By choosing this option you can save up to 27% on the cost of your flight, compared to a flight in the morning.

Weekly flight availability from Illinois to Maine

The most flights from USIL to USME are scheduled on a Friday (7 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

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

Airfare is below average for this route at the moment.
Illinois to Maine flights typically cost between $429 and $526 in December.
The cheapest round-trip price found within the last 5 days was $289 on United Airlines (Dec 14-Dec 16).

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

Booking 55 days in advance of your planned departure date is, on average, the best time to get cheap flights from Illinois to Maine. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest day to fly from Illinois to Maine?

Travelers seeking maximum savings on their Illinois to Maine flight should consider departing on Sunday afternoons when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Maine

Read reviews from past customers who have flown Southwest,United Airlines, andAmerican Airlines from Illinois to Maine. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Related info for your journey

  • How long is the flight from Illinois to Maine?

    There are many flights that can get you from Illinois to Maine in 4h 52m. Fly via Delta, United Airlines, or American Airlines to get the fastest option. There are 975 mi between Illinois and Maine. Both multi-stop and nonstop flights can be found to your destination and back.

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

    The cheapest airline one-way is Southwest, with whom users have recently found tickets for as low as $98. However, be on the lookout for offers from American Airlines and Delta, as they are both options that can get you from Illinois to Maine for a low price.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Illinois to Maine (average of $334). Flying from Illinois to Maine in December is currently the most expensive (average of $482). 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

Alternative routes for Illinois to Maine

Top 2 airlines flying from Illinois to Maine

AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$229Average$512FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$234Average$410FlexibilityNo cancel feeOn-time69%

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