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Maine

$88+ Cheap flights from Illinois to Maine

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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Aug 15 — Aug 221
Sat 8/15
Sat 8/22
1 adult, Economy
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Cheap flight deals from Illinois to Maine

Cheapest flights from Illinois to Maine
Explore the most affordable flight options available from Illinois to Maine. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 16, 2026.

This SmartFares deal was found by Cheapflights users on 7/13. 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.
Fri 8/285:27 pm
ORD
-
BOS
1 stop5h 32m
JetBlue
Fri 9/44:55 pm
BOS
-
ORD
1 stop6h 03m
JetBlue
Deal found 7/13$176
This Traveloka deal was found by Cheapflights users on 7/13. 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 Traveloka is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:27 pm
ORD
-
BOS
1 stop5h 32m
JetBlue
Tue 8/1812:44 pm
BOS
-
ORD
1 stop5h 51m
JetBlue
Deal found 7/13$181
This Super.com deal was found by Cheapflights users on 7/13. 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.
Tue 9/226:30 am
ORD
-
BOS
1 stop7h 10m
JetBlue
Fri 9/254:00 pm
BOS
-
ORD
1 stop7h 06m
JetBlue
Deal found 7/13$182
This SmartFares deal was found by Cheapflights users on 7/12. 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.
Wed 8/266:00 am
ORD
-
BOS
1 stop7h 22m
JetBlue
Wed 9/212:57 pm
BOS
-
ORD
1 stop5h 38m
JetBlue
Deal found 7/12$183
This Jetabroad deal was found by Cheapflights users on 7/11. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/108:20 pm
ORD
-
BOS
Nonstop2h 31m
JetBlue
Mon 8/175:21 pm
BOS
-
ORD
Nonstop3h 06m
JetBlue
Deal found 7/11$188
This Super.com deal was found by Cheapflights users on 7/15. 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.
Fri 8/149:42 am
ORD
-
BOS
1 stop6h 49m
JetBlue
Tue 8/182:45 pm
BOS
-
ORD
1 stop8h 13m
JetBlue
Deal found 7/15$193
This Super.com deal was found by Cheapflights users on 7/16. 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.
Wed 9/161:00 pm
ORD
-
BOS
1 stop6h 49m
JetBlue
Sun 9/203:13 pm
BOS
-
ORD
1 stop7h 53m
JetBlue
Deal found 7/16$194
This Southwest deal was found by Cheapflights users on 7/12. 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 9/166:40 am
MDW
-
BOS
Nonstop2h 15m
Southwest
Sat 9/197:05 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Deal found 7/12$197
This Southwest deal was found by Cheapflights users on 7/13. 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 10/179:55 am
MDW
-
BOS
Nonstop2h 20m
Southwest
Mon 10/195:50 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Deal found 7/13$206
This Southwest deal was found by Cheapflights users on 7/12. 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 10/1011:25 am
MDW
-
BOS
1 stop8h 05m
Southwest
Sat 10/179:40 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Deal found 7/12$213
This Southwest deal was found by Cheapflights users on 7/13. 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 8/205:45 am
MDW
-
BOS
Nonstop2h 15m
Southwest
Sat 8/227:05 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Deal found 7/13$215
This Southwest deal was found by Cheapflights users on 7/13. 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 11/118:30 am
MDW
-
BOS
Nonstop2h 25m
Southwest
Mon 11/161:10 pm
BOS
-
MDW
1 stop5h 35m
Southwest
Deal found 7/13$216

Find flight deals from Illinois to Maine

Keep the following information in mind while searching for Illinois to Maine flight deals. Data was last updated July 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$176
(SmartFares)

One-way from

$88
(SmartFares)

Popular in

July

Cheapest in

May

Average price

$432

Good round-trip deal

$341 or less

Good one-way deal

$140 or less
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
Search Deals
From Illinois to Maine
Search Deals
One-way flight from Illinois to Maine
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($32 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 July 2026
Search Deals
Price to beat on a round-trip flight from Illinois to Maine.
Search Deals
Price to beat on a one-way flight from Illinois to Maine.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Maine 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 16, 2026.
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
Quickest round-trip

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 8/14

5:45 am-9:00 am

Nonstop2h 15m

Boston Logan Intl

Tue 8/18

7:15 pm-8:50 pm

Nonstop2h 35m

$215

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sun 7/26

5:15 am-8:25 am

Nonstop2h 10m

Boston Logan Intl

Tue 8/4

7:20 pm-9:00 pm

Nonstop2h 40m

$215

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 10/15

6:10 am-9:33 am

Nonstop2h 23m

Boston Logan Intl

Tue 10/20

5:45 am-9:38 am

1 stop4h 53m

$216

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 10/3

9:24 pm-12:59 am

Nonstop2h 35m

Boston Logan Intl

Sun 10/4

7:01 am-9:00 am

Nonstop2h 59m

$216

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 8/29

9:40 am-6:57 pm

1 stop8h 17m

Boston Logan Intl

Tue 9/1

5:20 pm-7:26 pm

Nonstop3h 06m

$218

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 8/12

6:00 am-11:17 am

1 stop4h 17m

Boston Logan Intl

Wed 8/19

5:01 pm-7:00 pm

Nonstop2h 59m

$225

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 8/22

7:40 am-11:00 am

Nonstop2h 20m

Boston Logan Intl

Mon 8/24

5:25 am-11:00 am

1 stop6h 35m

$225

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 8/19

12:45 pm-9:25 pm

2 stops7h 40m

Boston Logan Intl

Tue 8/25

7:15 pm-8:50 pm

Nonstop2h 35m

$230

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 9/4

7:55 pm-8:00 am

1 stop11h 05m

Boston Logan Intl

Mon 9/7

8:20 pm-10:00 pm

Nonstop2h 40m

$231

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 8/1

6:12 pm-11:59 pm

1 stop4h 47m

Boston Logan Intl

Mon 8/3

9:50 am-11:43 am

Nonstop2h 53m

$235

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/11

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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
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 Illinois to Maine

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

Currently, July is the cheapest month in which you can book a flight from Illinois to Maine (average of $84). Flying from Illinois to Maine 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 IL to ME?

Find hourly flight availability from Illinois to Maine. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 16, 2026.

It’s optimal to fly from Illinois to Maine in the afternoon. By choosing this option you can save up to 15% on the cost of your flight, compared to a flight in the morning.

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

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

Booking 76 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?

Use this chart to determine the cheapest time to fly round-trip from Illinois to Maine. Price data was last updated on July 4, 2026.

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

Reviews of airlines servicing Maine

Get insights into the airlines that provide service to Maine. 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 Maine. Reviews last updated July 16, 2026.
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.
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
United Airlines
7.4
Good
9,993 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
American Airlines
7.1
Good
11,818 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

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

    There are many flights that can get you from Illinois to Maine in 2h 15m. Fly via Southwest, United Airlines, or JetBlue to get the fastest option. There are 857 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 American Airlines, with whom users have recently found tickets for as low as $99. However, be on the lookout for offers from United 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, July is the cheapest month in which you can book a flight from Illinois to Maine (average of $84). Flying from Illinois to Maine 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

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Alternative routes for Illinois to Maine

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Illinois to Maine

Discover the top 2 airlines that operate flights from Illinois to Maine. 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 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$229Average$420FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$229Average$401FlexibilityNo cancel feeOn-time69%

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