What airlines fly to Maine?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Maine from Chicago according to our data. American Airlines is the first choice among our users, with 52% 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 April 2026, there are 54 flights per day flying from Chicago to Maine. The most common time of day flights depart is 1:00PM, with 47% of flights taking off in the afternoon.

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

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

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

381 flights are operational weekly from Chicago to Maine as of April 2026. The most popular departure day for this route is Fri, with 18% of flights per week taking off on this day.

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 April 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.

$76 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.

1:59 pm - 1:24 am

ORD

BOS

10h 25m

1 stop

9:31 am - 7:51 pm

BOS

ORD

11h 20m

1 stop

$140Frontier

Tue, May 5 - Tue, May 12

2:15 pm - 1:31 am

MDW

BOS

10h 16m

1 stop

12:55 pm - 10:14 pm

BOS

MDW

10h 19m

1 stop

$140Frontier

Tue, Apr 28 - Wed, Apr 29

7:15 pm - 10:15 am

ORD

BOS

14h 00m

1 stop

6:00 am - 5:00 pm

BOS

ORD

12h 00m

1 stop

$145Multiple Airlines

Tue, Apr 21 - Tue, Apr 28

12:45 pm - 4:05 pm

MDW

BOS

2h 20mnonstop

6:00 pm - 10:15 pm

BOS

MDW

5h 15m

1 stop

$149Southwest

Tue, May 12 - Tue, May 12

6:00 pm - 9:20 pm

MDW

BOS

2h 20mnonstop

3:30 pm - 5:15 pm

BOS

MDW

2h 45mnonstop

$153Southwest

Tue, May 5 - Sat, May 9

6:00 am - 9:26 am

ORD

BOS

2h 26mnonstop

4:55 pm - 6:59 pm

BOS

ORD

3h 04mnonstop

$153Delta

Sat, May 2 - Wed, May 6

7:00 am - 10:35 am

ORD

BOS

2h 35mnonstop

7:35 am - 9:27 am

BOS

ORD

2h 52mnonstop

$155Delta

Tue, May 12 - Tue, May 19

1:01 pm - 4:43 pm

ORD

BGR

2h 42mnonstop

5:13 pm - 7:21 pm

BGR

ORD

3h 08mnonstop

$261American Airlines

Wed, Aug 19 - Wed, Sep 2

8:54 pm - 12:35 am

ORD

PWM

2h 41mnonstop

7:19 pm - 9:45 pm

PWM

ORD

3h 26mnonstop

$269American Airlines

Thu, Jun 11 - Tue, Jun 23

10:55 am - 2:26 pm

ORD

PWM

2h 31mnonstop

6:25 pm - 8:34 pm

PWM

ORD

3h 09mnonstop

$293United Airlines

Sun, Jul 5 - Thu, Jul 9

JetBlue flights from Chicago to Maine

Our best JetBlue deals on Chicago to Maine flight tickets

JetBlue

Apr 22

ORD9:41 amChicago O'Hare Intl

2h 26m

BOS1:07 pmBoston Logan Intl

Apr 29

BOS7:35 pmBoston Logan Intl

3h 01m

ORD9:36 pmChicago O'Hare Intl

$147

JetBlue

May 2

ORD6:00 amChicago O'Hare Intl

2h 15m

BOS9:15 amBoston Logan Intl

May 3

BOS7:02 amBoston Logan Intl

2h 57m

ORD8:59 amChicago O'Hare Intl

$151

JetBlue

Jun 6

ORD1:55 pmChicago O'Hare Intl

2h 29m

BOS5:24 pmBoston Logan Intl

Jun 9

BOS5:26 pmBoston Logan Intl

3h 08m

ORD7:34 pmChicago O'Hare Intl

$161

American Airlines flights from Chicago to Maine

Our best American Airlines deals on Chicago to Maine flight tickets

American Airlines

Apr 28

ORD8:56 pmChicago O'Hare Intl

2h 29m

BOS12:25 amBoston Logan Intl

Apr 30

BOS6:30 amBoston Logan Intl

3h 14m

ORD8:44 amChicago O'Hare Intl

$166

American Airlines

Jun 12

ORD8:45 pmChicago O'Hare Intl

2h 30m

BOS12:15 amBoston Logan Intl

Jun 15

BOS5:05 amBoston Logan Intl

2h 57m

ORD7:02 amChicago O'Hare Intl

$191

American Airlines

Apr 18

ORD8:56 pmChicago O'Hare Intl

2h 29m

BOS12:25 amBoston Logan Intl

Apr 22

BOS3:59 pmBoston Logan Intl

3h 14m

ORD6:13 pmChicago O'Hare Intl

$206

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 5/5

1:59 pm-1:24 am

1 stop10h 25m

Boston Logan Intl

Tue 5/12

9:31 am-7:51 pm

1 stop11h 20m

$140

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 4/28

2:15 pm-1:31 am

1 stop10h 16m

Boston Logan Intl

Wed 4/29

12:55 pm-10:14 pm

1 stop10h 19m

$140

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 4/21

7:15 pm-10:15 am

1 stop14h 00m

Boston Logan Intl

Tue 4/28

6:00 am-5:00 pm

1 stop12h 00m

$145

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 5/12

12:45 pm-4:05 pm

Nonstop2h 20m

Boston Logan Intl

Tue 5/12

6:00 pm-10:15 pm

1 stop5h 15m

$149

Quickest round-trip

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 5/5

6:00 pm-9:20 pm

Nonstop2h 20m

Boston Logan Intl

Sat 5/9

3:30 pm-5:15 pm

Nonstop2h 45m

$153

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/2

6:00 am-9:26 am

Nonstop2h 26m

Boston Logan Intl

Wed 5/6

4:55 pm-6:59 pm

Nonstop3h 04m

$153

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 5/12

7:00 am-10:35 am

Nonstop2h 35m

Boston Logan Intl

Tue 5/19

7:35 am-9:27 am

Nonstop2h 52m

$155

ChicagoBangor

ORD - BGR

ORDBGR

Chicago O'Hare Intl

Wed 8/19

1:01 pm-4:43 pm

Nonstop2h 42m

Bangor

Wed 9/2

5:13 pm-7:21 pm

Nonstop3h 08m

$261

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 6/11

8:54 pm-12:35 am

Nonstop2h 41m

Portland

Tue 6/23

7:19 pm-9:45 pm

Nonstop3h 26m

$269

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 7/5

10:55 am-2:26 pm

Nonstop2h 31m

Portland

Thu 7/9

6:25 pm-8:34 pm

Nonstop3h 09m

$293

Flights are sorted by cheapest round-trip flights first.

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 September. Flight prices, which tend to average around $307, 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 September, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $319.

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 $305. Flights from Chicago to Maine on a Sunday 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 $301. Flights in the afternoon are often more expensive with an average ticket price of $375.

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 $368 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 $285 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.

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	$174
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 $174. The best round-trip flight deal from Chicago to Maine found on momondo in the last 72 hours is $308.

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

Frequently asked questions about flying from Chicago to Maine

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 April 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 33.10% of all bookings. The subsequent popular models are Embraer 175 (Enhanced Winglets) at 27.06%, Boeing 737 MAX 8 at 11.22%, and Canadair (Bombardier) Regional Jet 700 at 6.12%.

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
United Airlines	PriceFrom $210	Free Cancellation	Rating 7.4 9,569 reviews	Search United Airlines flights
American Airlines	PriceFrom $229	Free Cancellation	Rating 7.1 11,572 reviews	Search American Airlines flights
Southwest	PriceFrom $259	Free Cancellation	Rating 8.0 4,335 reviews	Search Southwest flights
Delta	PriceFrom $263	Free Cancellation	Rating 7.9 8,406 reviews	Search Delta 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 $55

Flights to Los Angelesfrom $48

Flights to Orlandofrom $49

Flights to Miamifrom $56

Flights to Chicagofrom $60

Flights to San Franciscofrom $56

Flights to Las Vegasfrom $48

Flights to Washington, D.C.from $56

Flights to Bostonfrom $69

Flights to Atlantafrom $51

Flights to Dallasfrom $59

Flights to Fort Lauderdalefrom $53

Cheap flights from Chicago to Maine from $76

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 5/5. 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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JetBlue flights from Chicago to Maine

Our best JetBlue deals on Chicago to Maine flight tickets

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Our best American Airlines 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?

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

Frequently asked questions about flying 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?

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

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According to popular flight searches on momondo this year

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