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

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

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

364 flights are operational weekly from Chicago to Maine as of February 2026. The most popular departure day for this route is Mon, with 17% of flights per week taking off on this day.

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 day?

As of February 2026, there are 52 flights per day flying from Chicago to Maine. The most common time of day flights depart is 11:00AM, with 100% of flights taking off at noon.

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 6 as of February 2026.

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.

$69 Cheap Flights from Chicago to Maine in 2026

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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.

7:45 am - 2:15 pm

ORD

BOS

5h 30m

1 stop

7:10 am - 9:10 am

BOS

ORD

3h 00mnonstop

$130JetBlue

Sat, Apr 4 - Sat, Apr 11

4:30 pm - 8:03 pm

ORD

BOS

2h 33mnonstop

11:00 am - 12:52 pm

BOS

ORD

2h 52mnonstop

$131Delta

Sat, May 9 - Thu, Aug 20

5:15 am - 5:15 pm

ORD

BOS

11h 00m

1 stop

7:00 am - 9:10 am

BOS

ORD

3h 10mnonstop

$134Multiple Airlines

Wed, Mar 4 - Sun, Mar 8

6:05 am - 9:25 am

MDW

BOS

2h 20mnonstop

3:10 pm - 4:55 pm

BOS

MDW

2h 45mnonstop

$136Southwest

Thu, Feb 26 - Thu, Mar 5

7:55 am - 11:10 am

MDW

BOS

2h 15mnonstop

7:05 am - 9:00 am

BOS

MDW

2h 55mnonstop

$137Southwest

Fri, Mar 6 - Sun, Mar 8

4:28 pm - 12:51 am

ORD

BOS

7h 23m

1 stop

7:35 pm - 9:36 pm

BOS

ORD

3h 01mnonstop

$139Multiple Airlines

Fri, May 1 - Wed, May 6

7:05 am - 10:39 am

ORD

BOS

2h 34mnonstop

7:40 pm - 9:50 pm

BOS

ORD

3h 10mnonstop

$142American Airlines

Thu, Apr 9 - Sat, Apr 11

6:15 pm - 11:59 pm

ORD

PWM

4h 44m

1 stop

7:16 pm - 11:26 pm

PWM

ORD

5h 10m

1 stop

$193United Airlines

Sat, May 16 - Sat, May 23

6:15 pm - 11:59 pm

ORD

PWM

4h 44m

1 stop

6:25 pm - 8:34 pm

PWM

ORD

3h 09mnonstop

$201United Airlines

Sat, May 16 - Sat, May 23

8:02 pm - 11:34 pm

ORD

PWM

2h 32mnonstop

5:40 pm - 7:50 pm

PWM

ORD

3h 10mnonstop

$210American Airlines

Sun, Mar 29 - Sun, Apr 5

American Airlines flights from Chicago to Maine

Our best American Airlines deals on Chicago to Maine flight tickets

American Airlines

Apr 9

ORD7:05 amChicago O'Hare Intl

2h 34m

BOS10:39 amBoston Logan Intl

Apr 11

BOS7:40 pmBoston Logan Intl

3h 10m

ORD9:50 pmChicago O'Hare Intl

$142

American Airlines

Mar 12

ORD7:18 amChicago O'Hare Intl

2h 28m

BOS10:46 amBoston Logan Intl

Mar 18

BOS7:16 pmBoston Logan Intl

3h 14m

ORD9:30 pmChicago O'Hare Intl

$147

American Airlines

Feb 27

ORD7:40 pmChicago O'Hare Intl

2h 21m

BOS11:01 pmBoston Logan Intl

Mar 4

BOS7:16 pmBoston Logan Intl

3h 14m

ORD9:30 pmChicago O'Hare Intl

$156

Delta flights from Chicago to Maine

Our best Delta deals on Chicago to Maine flight tickets

Delta

May 9

ORD4:30 pmChicago O'Hare Intl

2h 33m

BOS8:03 pmBoston Logan Intl

Aug 20

BOS11:00 amBoston Logan Intl

2h 52m

ORD12:52 pmChicago O'Hare Intl

$131

Delta

Mar 4

ORD7:05 amChicago O'Hare Intl

2h 32m

BOS10:37 amBoston Logan Intl

Mar 10

BOS7:15 amBoston Logan Intl

3h 10m

ORD9:25 amChicago O'Hare Intl

$136

Delta

May 19

ORD7:15 pmChicago O'Hare Intl

2h 34m

BOS10:49 pmBoston Logan Intl

May 23

BOS5:30 pmBoston Logan Intl

3h 03m

ORD7:33 pmChicago O'Hare Intl

$137

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 4/4

7:45 am-2:15 pm

1 stop5h 30m

Boston Logan Intl

Sat 4/11

7:10 am-9:10 am

Nonstop3h 00m

$130

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/9

4:30 pm-8:03 pm

Nonstop2h 33m

Boston Logan Intl

Thu 8/20

11:00 am-12:52 pm

Nonstop2h 52m

$131

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 3/4

5:15 am-5:15 pm

1 stop11h 00m

Boston Logan Intl

Sun 3/8

7:00 am-9:10 am

Nonstop3h 10m

$134

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 2/26

6:05 am-9:25 am

Nonstop2h 20m

Boston Logan Intl

Thu 3/5

3:10 pm-4:55 pm

Nonstop2h 45m

$136

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 3/6

7:55 am-11:10 am

Nonstop2h 15m

Boston Logan Intl

Sun 3/8

7:05 am-9:00 am

Nonstop2h 55m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 5/1

4:28 pm-12:51 am

1 stop7h 23m

Boston Logan Intl

Wed 5/6

7:35 pm-9:36 pm

Nonstop3h 01m

$139

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 4/9

7:05 am-10:39 am

Nonstop2h 34m

Boston Logan Intl

Sat 4/11

7:40 pm-9:50 pm

Nonstop3h 10m

$142

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 5/16

6:15 pm-11:59 pm

1 stop4h 44m

Portland

Sat 5/23

7:16 pm-11:26 pm

1 stop5h 10m

$193

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 5/16

6:15 pm-11:59 pm

1 stop4h 44m

Portland

Sat 5/23

6:25 pm-8:34 pm

Nonstop3h 09m

$201

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 3/29

8:02 pm-11:34 pm

Nonstop2h 32m

Portland

Sun 4/5

5:40 pm-7:50 pm

Nonstop3h 10m

$210

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Showing 1-10 of 20 resultsSorted by cheapest first

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 March. Flight prices, which tend to average around $292, 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 March, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $314.

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

The cheapest day to depart from Chicago to Maine is on a Tuesday. Travelers who choose to depart for Maine on a Tuesday will often find tickets for as low as $307. Flights from Chicago to Maine on a Thursday will generally be more expensive and average around $388. 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 $311. Flights in the afternoon are often more expensive with an average ticket price of $376.

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 $375 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 $289 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?

You could potentially save up to 34% on your flight if you consider stops on a Chicago to Maine flight.

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	$172
Fastest flight time	2h 10m
Direct flights	Every day
Airports in Maine	49 airports

The best one-way flight to Maine from Chicago in the past 72 hours is $172. The best round-trip flight deal from Chicago to Maine found on momondo in the last 72 hours is $274.

The fastest flight from Chicago to Maine takes 2h 10m

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 6 as of February 2026.
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, representing 31.86% of all bookings. The subsequent popular models are Embraer 175 (Enhanced Winglets) at 29.30%, Boeing 737-700 at 10.93%, and Canadair (Bombardier) Regional Jet 700 at 6.28%.

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 $108	Free Cancellation	Rating 7.9 8,205 reviews	Search Delta flights
United Airlines	PriceFrom $209	Free Cancellation	Rating 7.4 9,296 reviews	Search United Airlines flights
American Airlines	PriceFrom $229	Free Cancellation	Rating 7.2 11,297 reviews	Search American Airlines flights
Southwest	PriceFrom $259	Free Cancellation	Rating 8.0 4,286 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.

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Popular cities in Maine

Flights to New Yorkfrom $52

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Flights to Las Vegasfrom $50

Flights to Washington, D.C.from $25

Flights to Bostonfrom $69

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Flights to Dallasfrom $54

Flights to Seattlefrom $65

Cheap flights from Chicago to Maine from $69

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 4/21. 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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American Airlines flights from Chicago to Maine

Our best American Airlines deals on Chicago to Maine flight tickets

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Our best Delta deals on Chicago to Maine flight tickets

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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?

What is the cheapest Chicago to Maine flight route?

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

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

Can stopping save me money on Chicago to Maine flights?

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

What airlines fly to Maine?

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

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

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

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

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