What is the cheapest airline that flies from Chicago to Maine?

Delta, United Airlines, and Southwest are the most popular carriers operating from Chicago to Maine

What airlines fly to Maine?

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Maine from Chicago according to our data. United Airlines is the first choice among our users, with 51% of people opting to fly with this airline when traveling to Maine. Keep in mind that there are 4 different airlines that fly to Maine on a routine basis, so you have a few additional options to choose from.

How many flights depart from Chicago to Maine on average per week?

339 flights are operational weekly from Chicago to Maine as of December 2025. The most popular departure day for this route is Fri, with 20% of flights per week taking off on this day.

How many flights depart from Chicago to Maine on average per day?

As of December 2025, there are 48 flights per day flying from Chicago to Maine. The most common time of day flights depart is 5:00PM, with 56% of flights taking off in the afternoon.

When did momondo last update prices for flights from Chicago to Maine?

Prices for flights from Chicago to Maine were last updated today.

How many operators does momondo search for flights from Chicago to Maine?

The number of operators available for flights from Chicago to Maine is 7 as of December 2025.

How old do you have to be to fly from Chicago to Maine?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Maine.

What documentation or ID do you need to fly to Maine?

The travel and health documents required for your trip to Maine can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Maine. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$63 Cheap Flights from Chicago to Maine in 2025/26

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Find the cheapest flights from Chicago to Maine

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

4:41 pm - 1:13 am

ORD

BOS

7h 32m1 stop

5:23 pm - 8:18 am

BOS

ORD

15h 55m1 stop

$125Multiple Airlines

Sat, Jan 17 - Tue, Jan 20

8:40 am - 4:10 pm

MDW

BOS

6h 30m1 stop

4:55 pm - 6:45 pm

BOS

MDW

2h 50mnonstop

$126Southwest

Sat, Jan 10 - Sat, Jan 17

6:05 pm - 9:38 pm

ORD

BOS

2h 33mnonstop

9:30 am - 11:34 am

BOS

ORD

3h 04mnonstop

$127United Airlines

Sat, Jan 17 - Tue, Jan 20

5:25 pm - 8:45 pm

ORD

BOS

2h 20mnonstop

7:00 am - 9:05 am

BOS

ORD

3h 05mnonstop

$128American Airlines

Sat, Jan 17 - Sun, Jan 18

10:00 am - 1:23 pm

ORD

BOS

2h 23mnonstop

7:00 am - 9:10 am

BOS

ORD

3h 10mnonstop

$129JetBlue

Fri, Feb 27 - Sun, Mar 1

7:45 am - 11:10 am

ORD

BOS

2h 25mnonstop

3:35 pm - 5:43 pm

BOS

ORD

3h 08mnonstop

$130JetBlue

Tue, Jan 13 - Tue, Jan 20

2:00 pm - 5:24 pm

ORD

BOS

2h 24mnonstop

6:00 am - 8:04 am

BOS

ORD

3h 04mnonstop

$132United Airlines

Sat, Jan 17 - Mon, Jan 19

1:29 pm - 4:54 pm

ORD

PWM

2h 25mnonstop

5:57 pm - 8:10 pm

PWM

ORD

3h 13mnonstop

$209American Airlines

Mon, Mar 23 - Sat, Mar 28

8:55 am - 4:15 pm

ORD

PWM

6h 20m1 stop

3:00 pm - 8:45 pm

PWM

ORD

6h 45m1 stop

$229Delta

Sat, May 9 - Tue, May 12

9:35 am - 4:06 pm

MDW

PWM

5h 31m1 stop

12:51 pm - 5:54 pm

PWM

MDW

6h 03m1 stop

$229Delta

Mon, Mar 23 - Sat, Mar 28

Southwest flights from Chicago to Maine

Our best Southwest deals on Chicago to Maine flight tickets

Southwest

Jan 10

MDW8:40 amChicago Midway

6h 30m

1 stop

BOS4:10 pmBoston Logan Intl

Jan 17

BOS4:55 pmBoston Logan Intl

2h 50m

MDW6:45 pmChicago Midway

$126

Find similar

Southwest

Jan 17

MDW10:15 amChicago Midway

2h 15m

BOS1:30 pmBoston Logan Intl

Jan 18

BOS9:35 amBoston Logan Intl

6h 20m

1 stop

MDW2:55 pmChicago Midway

$128

Find similar

Southwest

Jan 17

MDW10:15 amChicago Midway

2h 15m

BOS1:30 pmBoston Logan Intl

Jan 24

BOS5:30 amBoston Logan Intl

2h 50m

MDW7:20 amChicago Midway

$132

Find similar

United Airlines flights from Chicago to Maine

Our best United Airlines deals on Chicago to Maine flight tickets

United Airlines

Jan 17

ORD6:05 pmChicago O'Hare Intl

2h 33m

BOS9:38 pmBoston Logan Intl

Jan 20

BOS9:30 amBoston Logan Intl

3h 04m

ORD11:34 amChicago O'Hare Intl

$127

Find similar

United Airlines

Dec 24

ORD6:11 pmChicago O'Hare Intl

2h 33m

BOS9:44 pmBoston Logan Intl

Jan 1

BOS7:45 amBoston Logan Intl

3h 04m

ORD9:49 amChicago O'Hare Intl

$137

Find similar

United Airlines

Jan 5

ORD9:12 pmChicago O'Hare Intl

2h 33m

BOS12:45 amBoston Logan Intl

Jan 7

BOS12:45 pmBoston Logan Intl

3h 04m

ORD2:49 pmChicago O'Hare Intl

$147

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/17

4:41 pm-1:13 am

1 stop7h 32m

Boston Logan Intl

Tue 1/20

5:23 pm-8:18 am

1 stop15h 55m

$125

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 1/10

8:40 am-4:10 pm

1 stop6h 30m

Boston Logan Intl

Sat 1/17

4:55 pm-6:45 pm

Nonstop2h 50m

$126

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/17

6:05 pm-9:38 pm

Nonstop2h 33m

Boston Logan Intl

Tue 1/20

9:30 am-11:34 am

Nonstop3h 04m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/17

5:25 pm-8:45 pm

Nonstop2h 20m

Boston Logan Intl

Sun 1/18

7:00 am-9:05 am

Nonstop3h 05m

$128

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 2/27

10:00 am-1:23 pm

Nonstop2h 23m

Boston Logan Intl

Sun 3/1

7:00 am-9:10 am

Nonstop3h 10m

$129

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 1/13

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

Tue 1/20

3:35 pm-5:43 pm

Nonstop3h 08m

$130

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/17

2:00 pm-5:24 pm

Nonstop2h 24m

Boston Logan Intl

Mon 1/19

6:00 am-8:04 am

Nonstop3h 04m

$132

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 3/23

1:29 pm-4:54 pm

Nonstop2h 25m

Portland

Sat 3/28

5:57 pm-8:10 pm

Nonstop3h 13m

$209

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 5/9

8:55 am-4:15 pm

1 stop6h 20m

Portland

Tue 5/12

3:00 pm-8:45 pm

1 stop6h 45m

$229

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Mon 3/23

9:35 am-4:06 pm

1 stop5h 31m

Portland

Sat 3/28

12:51 pm-5:54 pm

1 stop6h 03m

$229

Flights are sorted by cheapest round-trip flights first.

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How to get the cheapest flight ticket from Chicago to Maine

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Maine?

The cheapest month to fly to Maine from Chicago is in January. Flight prices, which tend to average around $207, are often lower during this time because this is during the off-season. If you aren’t able to travel to Maine during the month of January, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $207.

What is the cheapest day to depart on your flight to Maine?

The cheapest day to depart from Chicago to Maine is on a Thursday. Travelers who choose to depart for Maine on a Thursday will often find tickets for as low as $241. Flights from Chicago to Maine on a Monday will generally be more expensive and average around $306. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Maine?

The cheapest time of day to fly to Maine is in the evening when flights can be purchased for as low as $214. Flights at noon are often more expensive with an average ticket price of $298.

What is the cheapest Chicago to Maine flight route?

Fly from Chicago O'Hare Intl to Portland for the best Chicago - Maine flight prices

How far in advance should I book a flight to Maine?

You are more likely to see cheaper flights to Maine from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Maine for around $231 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Maine from Chicago for as low as $183 on momondo.

What cabin class options are available on Chicago to Maine flights?

There are 4 cabin classes available to choose from on Chicago to Maine flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Maine flights?

No. A direct flight is the cheapest option for a flight between Chicago to Maine.

Cheap Chicago to Maine flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Maine

Best Price Found	$358
Fastest flight time	2h 15m
Direct flights	Every day
Airports in Maine	49 airports

The best one-way flight to Maine from Chicago in the past 72 hours is $358. The best round-trip flight deal from Chicago to Maine found on momondo in the last 72 hours is $305.

The fastest flight from Chicago to Maine takes 2h 15m

Direct flights go from Chicago to Maine every day.

There are 49 airports in Maine. From Chicago there are direct flights to Boston Logan Intl (BOS), Portland (PWM).

Search flight deals

When did momondo last update prices for flights from Chicago to Maine?
Prices for flights from Chicago to Maine were last updated today.
How many operators does momondo search for flights from Chicago to Maine?
The number of operators available for flights from Chicago to Maine is 7 as of December 2025.
How old do you have to be to fly from Chicago to Maine?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Maine.
What documentation or ID do you need to fly to Maine?
The travel and health documents required for your trip to Maine can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Maine. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to Maine?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Maine is Embraer 175 (Enhanced Winglets), representing 22.10% of all bookings. The subsequent popular models are Embraer 175 at 20.95%, Boeing 737-800 at 15.05%, and Canadair (Bombardier) Regional Jet 700 at 15.05%.

Best airlines flying from Chicago to Maine

Compare and see reviews for airlines that fly from Chicago to Maine with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $163	Free Cancellation	Rating 7.9 8,014 reviews	Search Delta flights
United Airlines	PriceFrom $218	Free Cancellation	Rating 7.4 9,105 reviews	Search United Airlines flights
American Airlines	PriceFrom $229	Free Cancellation	Rating 7.2 11,054 reviews	Search American Airlines flights
Southwest	PriceFrom $313	Free Cancellation	Rating 8.0 4,253 reviews	Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Maine?

It is quick and easy to find Chicago to Maine flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Maine that suits you.

Can I find flights from Chicago to Maine with flexible booking policies on momondo?

Yes. All flights to Maine from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Maine?

Once all potential Chicago to Maine flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Maine right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Maine flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Maine trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Find better results for your trip to Maine

Popular cities in Maine

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Flights to Seattlefrom $55

Cheap flights from Chicago to Maine from $63

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Maine departing on 1/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Chicago to Maine

Cheap round-trip flights

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Southwest flights from Chicago to Maine

Our best Southwest deals on Chicago to Maine flight tickets

United Airlines flights from Chicago to Maine

Our best United Airlines deals on Chicago to Maine flight tickets

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

See travel insights to Maine from

How to get the cheapest flight ticket from Chicago to Maine

What is the cheapest month to fly to Maine?

What is the cheapest day to depart on your flight to Maine?

What is the cheapest time of day to depart on your flight to Maine?

The cheapest time of day to fly to Maine is in the evening when flights can be purchased for as low as $214. Flights at noon are often more expensive with an average ticket price of $298.

What is the cheapest Chicago to Maine flight route?

Fly from Chicago O'Hare Intl to Portland for the best Chicago - Maine flight prices

How far in advance should I book a flight to Maine?

What cabin class options are available on Chicago to Maine flights?

There are 4 cabin classes available to choose from on Chicago to Maine flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Maine flights?

No. A direct flight is the cheapest option for a flight between Chicago to Maine.

What is the cheapest airline that flies from Chicago to Maine?

Delta, United Airlines, and Southwest are the most popular carriers operating from Chicago to Maine

What airlines fly to Maine?

How many flights depart from Chicago to Maine on average per day?

As of December 2025, there are 48 flights per day flying from Chicago to Maine. The most common time of day flights depart is 5:00PM, with 56% of flights taking off in the afternoon.

How many flights depart from Chicago to Maine on average per week?

339 flights are operational weekly from Chicago to Maine as of December 2025. The most popular departure day for this route is Fri, with 20% of flights per week taking off on this day.

Cheap Chicago to Maine flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Maine

Best Price Found

Fastest flight time

Direct flights

Airports in Maine

When did momondo last update prices for flights from Chicago to Maine?

How many operators does momondo search for flights from Chicago to Maine?

How old do you have to be to fly from Chicago to Maine?

What documentation or ID do you need to fly to Maine?

What is the most popular plane model from Chicago to Maine?

Best airlines flying from Chicago to Maine

Compare and see reviews for airlines that fly from Chicago to Maine with momondo

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Maine?

Can I find flights from Chicago to Maine with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to Maine?

I’m not ready to book a flight from Chicago to Maine right now. Can momondo alert me if prices change?

An easier way to manage your Maine trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Maine

Popular cities in Maine

Popular flights according to clicks in the last 7 days on momondo