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

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

What airlines fly to Maine?

United Airlines, American Airlines and Southwest 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 56% of people opting to fly with this airline when traveling to Maine. Keep in mind that there are 5 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 July 2025, there are 65 flights per day flying from Chicago to Maine. The most common time of day flights depart is 6:00PM, with 43% of flights taking off in the evening.

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

459 flights are operational weekly from Chicago to Maine as of July 2025. The most popular departure day for this route is Thu, with 22% 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 7 as of July 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.

$55 Cheap Flights from Chicago to Maine in 2025

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Find the cheapest flights from Chicago to Maine

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

11:36 am - 11:49 pmORD-BOS

11h 13m1 stop

6:05 am - 7:07 pmBOS-ORD

14h 02m1 stop

$112Spirit Airlines

Find Deal

mié., ago. 27 - mié., sep. 3

7:30 am - 11:01 amORD-BOS

2h 31mnonstop

4:27 pm - 6:21 pmBOS-ORD

2h 54mnonstop

$117United Airlines

Find Deal

mié., sep. 3 - mié., sep. 3

7:10 pm - 10:40 pmORD-BOS

2h 30mnonstop

8:35 am - 10:32 amBOS-ORD

2h 57mnonstop

$120American Airlines

Find Deal

mié., sep. 3 - jue., sep. 4

6:45 am - 10:00 amMDW-BOS

2h 15mnonstop

5:30 am - 7:05 amBOS-MDW

2h 35mnonstop

$127Southwest

Find Deal

jue., sep. 4 - dom., sep. 7

8:25 pm - 11:53 pmORD-BOS

2h 28mnonstop

7:01 am - 9:05 amBOS-ORD

3h 04mnonstop

$128American Airlines

Find Deal

jue., sep. 4 - dom., sep. 7

2:35 pm - 11:00 pmMDW-BOS

7h 25m1 stop

5:40 pm - 7:20 pmBOS-MDW

2h 40mnonstop

$137Southwest

Find Deal

jue., sep. 4 - mié., sep. 10

10:15 am - 1:48 pmORD-BOS

2h 33mnonstop

7:55 pm - 9:56 pmBOS-ORD

3h 01mnonstop

$147Delta

Find Deal

jue., sep. 4 - mié., sep. 10

7:25 am - 10:55 amORD-BOS

2h 30mnonstop

7:20 am - 9:22 amBOS-ORD

3h 02mnonstop

$150Delta

Find Deal

mar., sep. 30 - mié., oct. 8

9:12 pm - 8:35 amMDW-BOS

10h 23m1 stop

9:40 am - 8:22 pmBOS-MDW

11h 42m1 stop

$208Frontier

Find Deal

jue., ago. 14 - sáb., ago. 16

6:21 am - 8:11 amMDW-BOS

24h 50m1 stop

8:56 am - 12:44 pmBOS-MDW

28h 48m1 stop

$209Frontier

Find Deal

vie., sep. 26 - sáb., oct. 4

JetBlue flights from Chicago to Maine

Our best JetBlue deals on Chicago to Maine flight tickets

JetBlue

Oct 28

ORD11:30 amChicago O'Hare Intl

2h 16m

BOS2:46 pmBoston Logan Intl

Oct 28

BOS4:55 pmBoston Logan Intl

3h 10m

ORD7:05 pmChicago O'Hare Intl

$132

Find similar

JetBlue

Sep 19

ORD7:50 pmChicago O'Hare Intl

2h 35m

BOS11:25 pmBoston Logan Intl

Sep 22

BOS7:00 amBoston Logan Intl

2h 56m

ORD8:56 amChicago O'Hare Intl

$137

Find similar

JetBlue

Oct 24

ORD9:42 amChicago O'Hare Intl

2h 28m

BOS1:10 pmBoston Logan Intl

Oct 27

BOS8:30 amBoston Logan Intl

2h 58m

ORD10:28 amChicago O'Hare Intl

$140

Find similar

Frontier flights from Chicago to Maine

Our best Frontier deals on Chicago to Maine flight tickets

Frontier

Aug 9

ORD12:20 pmChicago O'Hare Intl

11h 19m

1 stop

BOS12:39 amBoston Logan Intl

Aug 16

BOS6:00 amBoston Logan Intl

14h 12m

1 stop

ORD7:12 pmChicago O'Hare Intl

$198

Find similar

Frontier

Aug 14

MDW9:12 pmChicago Midway

10h 23m

1 stop

BOS8:35 amBoston Logan Intl

Aug 16

BOS9:40 amBoston Logan Intl

11h 42m

1 stop

MDW8:22 pmChicago Midway

$208

Find similar

Frontier

Sep 26

MDW6:21 amChicago Midway

24h 50m

1 stop

BOS8:11 amBoston Logan Intl

Oct 4

BOS8:56 amBoston Logan Intl

28h 48m

1 stop

MDW12:44 pmChicago Midway

$209

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mié. 8/27

11:36 am-11:49 pm

1 stop11h 13m

Boston Logan Intl

mié. 9/3

6:05 am-7:07 pm

1 stop14h 02m

$112

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mié. 9/3

7:30 am-11:01 am

Nonstop2h 31m

Boston Logan Intl

mié. 9/3

4:27 pm-6:21 pm

Nonstop2h 54m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mié. 9/3

7:10 pm-10:40 pm

Nonstop2h 30m

Boston Logan Intl

jue. 9/4

8:35 am-10:32 am

Nonstop2h 57m

$120

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

jue. 9/4

6:45 am-10:00 am

Nonstop2h 15m

Boston Logan Intl

dom. 9/7

5:30 am-7:05 am

Nonstop2h 35m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 9/4

8:25 pm-11:53 pm

Nonstop2h 28m

Boston Logan Intl

dom. 9/7

7:01 am-9:05 am

Nonstop3h 04m

$128

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

jue. 9/4

2:35 pm-11:00 pm

1 stop7h 25m

Boston Logan Intl

mié. 9/10

5:40 pm-7:20 pm

Nonstop2h 40m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 9/4

10:15 am-1:48 pm

Nonstop2h 33m

Boston Logan Intl

mié. 9/10

7:55 pm-9:56 pm

Nonstop3h 01m

$147

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mar. 9/30

7:25 am-10:55 am

Nonstop2h 30m

Boston Logan Intl

mié. 10/8

7:20 am-9:22 am

Nonstop3h 02m

$150

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

jue. 8/14

9:12 pm-8:35 am

1 stop10h 23m

Boston Logan Intl

sáb. 8/16

9:40 am-8:22 pm

1 stop11h 42m

$208

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

vie. 9/26

6:21 am-8:11 am

1 stop24h 50m

Boston Logan Intl

sáb. 10/4

8:56 am-12:44 pm

1 stop28h 48m

$209

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 February. Flight prices, which tend to average around $285, 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 February, then flying in March is also cheap. Prices for this month can be found on momondo for an average of $303.

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 $328. Flights from Chicago to Maine on a Friday will generally be more expensive and average around $405. 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 morning are often more expensive with an average ticket price of $374.

What is the cheapest Chicago to Maine flight route?

Fly from Chicago Midway 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 $394 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 $282 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	$55
Fastest flight time	2h 10m
Direct flights	Every day
Airports in Maine	2 airports

The best one-way flight to Maine from Chicago in the past 72 hours is $55. The best round-trip flight deal from Chicago to Maine found on momondo in the last 72 hours is $112.

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

Direct flights go from Chicago to Maine every day.

There are 2 airports near Maine: 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 July 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, representing 24.37% of all bookings. The subsequent popular models are Embraer 175 (Enhanced Winglets) at 17.01%, Boeing 737-800 at 13.91%, and Embraer 170 at 12.26%.

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
Frontier	PriceFrom $68	Free Cancellation	Rating 5.9 3,239 reviews	Search Frontier flights
Delta	PriceFrom $163	Free Cancellation	Rating 8.0 7,981 reviews	Search Delta flights
Southwest	PriceFrom $191	Free Cancellation	Rating 8.0 4,246 reviews	Search Southwest flights
American Airlines	PriceFrom $203	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $213	Free Cancellation	Rating 7.4 8,900 reviews	Search United Airlines 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

Flights to New Yorkfrom $39

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Flights to Orlandofrom $54

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Flights to San Franciscofrom $49

Flights to Washington, D.C.from $49

Flights to Bostonfrom $77

Flights to Atlantafrom $29

Flights to Dallasfrom $55

Flights to Seattlefrom $93

Cheap flights from Chicago to Maine from $55

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 8/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

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Price Alerts

Find the cheapest flights from Chicago to Maine

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

JetBlue flights from Chicago to Maine

Our best JetBlue deals on Chicago to Maine flight tickets

Frontier flights from Chicago to Maine

Our best Frontier 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

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

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 $301. Flights in the morning are often more expensive with an average ticket price of $374.

What is the cheapest Chicago to Maine flight route?

Fly from Chicago Midway 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?

Spirit Airlines, JetBlue, 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 July 2025, there are 65 flights per day flying from Chicago to Maine. The most common time of day flights depart is 6:00PM, with 43% of flights taking off in the evening.

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

459 flights are operational weekly from Chicago to Maine as of July 2025. The most popular departure day for this route is Thu, with 22% 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