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Maine

$84+ Cheap flights from Chicago (CHI) 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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PWM
juni 8 — juni 151
man. 6/8
man. 6/15
1 adult, Economy
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Cheap flight deals from Chicago to Maine

Cheapest flights from Chicago to Maine
Explore the most affordable flight options available from Chicago to Maine. Find the lowest fares from popular airlines and budget airlines, with prices last updated on maj 9, 2026.

This Jetabroad deal was found by Cheapflights users on 5/5. 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.
ons. 6/2410:56 am
ORD
-
BOS
Nonstop2h 28m
JetBlue
tir. 6/308:10 am
BOS
-
ORD
Nonstop2h 56m
JetBlue
Deal found 5/5$166
This Delta deal was found by Cheapflights users on 5/6. 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.
lør. 5/307:00 am
ORD
-
BOS
Nonstop2h 35m
Delta
lør. 5/305:30 pm
BOS
-
ORD
Nonstop3h 03m
Delta
Deal found 5/6$167
This Southwest deal was found by Cheapflights users on 5/5. 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.
tir. 6/236:05 pm
MDW
-
BOS
Nonstop2h 15m
Southwest
ons. 6/245:35 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Deal found 5/5$167
This Delta deal was found by Cheapflights users on 5/5. 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.
lør. 5/304:30 pm
ORD
-
BOS
Nonstop2h 36m
Delta
søn. 5/317:35 am
BOS
-
ORD
Nonstop2h 52m
Delta
Deal found 5/5$172
This Southwest deal was found by Cheapflights users on 5/5. 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.
man. 6/19:25 am
MDW
-
BOS
Nonstop2h 15m
Southwest
tir. 6/27:20 am
BOS
-
MDW
Nonstop2h 45m
Southwest
Deal found 5/5$172
This Flysmarter deal was found by Cheapflights users on 5/6. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lør. 5/301:56 pm
ORD
-
BOS
Nonstop2h 31m
JetBlue
søn. 5/316:00 am
BOS
-
ORD
Nonstop3h 00m
JetBlue
Deal found 5/6$174
This United Airlines deal was found by Cheapflights users on 5/4. 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.
lør. 5/306:00 am
ORD
-
BOS
1 stop4h 16m
United Airlines
lør. 6/67:19 am
BOS
-
ORD
Nonstop2h 58m
United Airlines
Deal found 5/4$177
This Southwest deal was found by Cheapflights users on 5/5. 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.
fre. 6/54:00 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
man. 6/86:45 pm
BOS
-
MDW
Nonstop2h 50m
Southwest
Deal found 5/5$177
This Priceline deal was found by Cheapflights users on 5/5. 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.
ons. 5/278:30 pm
ORD
-
BOS
Nonstop2h 29m
Multiple Airlines
ons. 6/312:01 pm
BOS
-
ORD
1 stop8h 28m
Multiple Airlines
Deal found 5/5$179
This Frontier deal was found by Cheapflights users on 5/4. 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.
tor. 5/2812:27 pm
MDW
-
BOS
1 stop11h 57m
Frontier
man. 6/16:00 am
BOS
-
MDW
1 stop6h 09m
Frontier
Deal found 5/4$180
This Cheapflightsfares deal was found by Cheapflights users on 5/5. 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.
fre. 6/128:20 pm
ORD
-
BOS
Nonstop2h 31m
JetBlue
tir. 6/168:10 am
BOS
-
ORD
Nonstop2h 56m
JetBlue
Deal found 5/5$181
This United Airlines deal was found by Cheapflights users on 5/4. 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.
tor. 5/283:55 pm
ORD
-
BOS
Nonstop2h 35m
United Airlines
tir. 6/25:45 am
BOS
-
ORD
1 stop4h 51m
United Airlines
Deal found 5/4$182

Find flight deals from Chicago to Maine

Keep the following information in mind while searching for Chicago to Maine flight deals. Data was last updated maj 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$166
(Jetabroad)

One-way from

$84
(Delta)

Popular in

December

Cheapest in

May

Average price

$299

Good round-trip deal

$269 or less

Good one-way deal

$173 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 Chicago (CHI) to Maine
Search Deals
One-way flight from Chicago (CHI) to Maine
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 ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Maine.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Maine.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago 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 maj 9, 2026.
Use the filters below to find and compare flights from Chicago to Maine that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

tor. 8/6

8:20 pm-11:51 pm

Nonstop2h 31m

Boston Logan Intl

ons. 8/12

5:20 pm-7:25 pm

Nonstop3h 05m

$172

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

tor. 7/23

6:05 am-9:29 am

Nonstop2h 24m

Boston Logan Intl

man. 7/27

8:15 pm-10:15 pm

Nonstop3h 00m

$177

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

fre. 6/5

9:41 pm-1:14 am

Nonstop2h 33m

Boston Logan Intl

man. 6/8

8:15 am-10:12 am

Nonstop2h 57m

$177
Quickest round-trip

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

ons. 6/17

6:05 pm-9:20 pm

Nonstop2h 15m

Boston Logan Intl

ons. 6/24

5:35 am-7:10 am

Nonstop2h 35m

$182

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

lør. 5/30

1:56 pm-5:27 pm

Nonstop2h 31m

Boston Logan Intl

søn. 5/31

6:00 am-8:00 am

Nonstop3h 00m

$182

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

fre. 6/19

1:55 pm-5:29 pm

Nonstop2h 34m

Boston Logan Intl

tir. 6/23

6:40 pm-8:40 pm

Nonstop3h 00m

$186

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

fre. 6/12

8:20 pm-11:51 pm

Nonstop2h 31m

Boston Logan Intl

tir. 6/16

8:10 am-10:06 am

Nonstop2h 56m

$186

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

tir. 7/14

6:05 pm-9:20 pm

Nonstop2h 15m

Boston Logan Intl

tor. 7/16

5:25 am-7:00 am

Nonstop2h 35m

$187

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

ons. 6/10

5:20 pm-11:30 pm

1 stop5h 10m

Boston Logan Intl

fre. 6/12

5:25 am-7:00 am

Nonstop2h 35m

$196

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

man. 7/27

4:00 pm-7:20 pm

Nonstop2h 20m

Boston Logan Intl

lør. 8/1

5:20 am-6:55 am

Nonstop2h 35m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/4

Showing 1-10 of 60 resultsSorted by cheapest first
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6

Best time to book a flight from Chicago to Maine

Have a flexible travel schedule? Discover the best time to fly to Maine from Chicago 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 Chicago to Maine

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

The price you pay for your flight from Chicago to Maine may vary depending on when you book. For the best chance of a lower fare, look to book 90 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, July is the cheapest month in which you can book a flight from Chicago to Maine (average of $101). Flying from Chicago 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 CHI to ME?

Find hourly flight availability from Chicago 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 maj 9, 2026.

When flying from Chicago to Maine, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 12% versus a flight in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from Chicago to Maine. Price data was last updated on May 2, 2026.

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

Weekly flight availability from Chicago to Maine

Explore weekly flight availability from Chicago to Maine. 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 maj 9, 2026.

The most flights from CHI to USME are scheduled on a Wednesday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).

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

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 maj 9, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Chicago to Maine by reading reviews from past customers. 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
4,302 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,302 reviews
Southwest
8.0
Very good
4,302 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,692 reviews
Southwest
8.0
Very good
4,302 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,669 reviews
Southwest
8.0
Very good
4,302 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

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

    Departing from Chicago to Maine will take you 2h 15m. Chicago and Maine are separated by a distance of 857 mi. Generally, flights for this route are nonstop.

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

    One-way options have recently been found by users for as low as $416 on Royal Jordanian. Other airlines that offer cheap prices include Air France from $476 and Turkish Airlines from $478 one-way.

  • What are the most popular routes from Chicago to Maine?

    While some choose either Chicago Midway - Boston Logan Intl or Chicago O'Hare Intl - Portland, Chicago O'Hare Intl - Boston Logan Intl is the most popular route from Chicago to Maine.

  • What are the most reliable airlines from Chicago to Maine?

    The top 3 most reliable airlines when flying from Chicago to Maine are American Airlines (73%), Envoy Air (73%) and Republic Airways (72%).

  • What are the cheapest flights from Chicago to Maine?

    The cheapest flight price from Chicago to Maine is $134. On average you can expect to pay $401. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $172.

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

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

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

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

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

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

    Currently, July is the cheapest month in which you can book a flight from Chicago to Maine (average of $101). Flying from Chicago 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 Chicago to Maine

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Chicago to Maine

Discover the top 3 airlines that operate flights from Chicago 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 maj 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$229Average$406FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$229Average$373FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$259Average$434FlexibilityNo cancel feeOn-time63%

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