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

As of November 2025, there are 457 flights per week flying from Maine to Chicago. The most common day of the week flights depart is Fri, with 18% of flights taking off on this day.

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

As of November 2025, 65 flights take off from Maine and land in Chicago each day. The most common flight departure time for this route is 9:00AM, with 61% of daily flights taking off in the afternoon.

What airlines fly to Chicago?

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Maine 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 Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How long does it take to fly to Chicago?

Average flight duration from Maine to Chicago depends on which airport you fly into and out of. Flying from Portland to Chicago O'Hare Intl Airport is 2h 55m on average, while flying from Augusta to Chicago O'Hare Intl Airport is 5h 35m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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

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

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

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

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

As of November 2025, there are 7 operators available to choose from for flights from Maine to Chicago.

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

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 Maine to Chicago.

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

The travel and health documents required for your trip to Chicago 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 Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$59 Cheap Flights from Maine to Chicago in 2025/26

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Cheap round-trip flights

Enter your travel dates to find the best prices.

7:52 pm - 9:47 pmBOS-ORD

2h 55mnonstop

7:10 am - 10:36 amORD-BOS

2h 26mnonstop

$117Delta

Find Deal

Thu, Dec 11 - Sun, Dec 14

7:30 am - 9:33 amBOS-ORD

3h 03mnonstop

7:10 am - 10:36 amORD-BOS

2h 26mnonstop

$118Delta

Find Deal

Thu, Dec 11 - Sun, Dec 14

5:30 am - 7:15 amBOS-MDW

2h 45mnonstop

9:35 am - 12:50 pmMDW-BOS

2h 15mnonstop

$122Southwest

Find Deal

Thu, Nov 20 - Mon, Nov 24

8:30 am - 10:35 amBOS-ORD

3h 05mnonstop

8:38 pm - 12:06 amORD-BOS

2h 28mnonstop

$122JetBlue

Find Deal

Thu, Dec 4 - Thu, Dec 11

7:00 am - 9:32 amBOS-ORD

3h 32mnonstop

6:10 am - 9:35 amORD-BOS

2h 25mnonstop

$123American Airlines

Find Deal

Sat, Dec 6 - Sat, Dec 13

5:30 am - 7:15 amBOS-MDW

2h 45mnonstop

7:15 pm - 10:30 pmMDW-BOS

2h 15mnonstop

$124Southwest

Find Deal

Mon, Dec 15 - Thu, Dec 18

7:00 am - 5:28 pmBOS-ORD

11h 28m1 stop

4:45 pm - 12:05 amORD-BOS

6h 20m1 stop

$125Multiple Airlines

Find Deal

Wed, Feb 25 - Wed, Mar 4

11:28 am - 5:27 pmBOS-ORD

6h 59m1 stop

2:26 pm - 10:01 amORD-BOS

18h 35m1 stop

$131Multiple Airlines

Find Deal

Thu, Dec 4 - Mon, Dec 8

8:30 am - 10:35 amBOS-ORD

3h 05mnonstop

7:00 am - 3:14 pmORD-BOS

7h 14m1 stop

$135JetBlue

Find Deal

Wed, Dec 10 - Tue, Dec 16

6:45 am - 8:52 amBOS-ORD

3h 07mnonstop

7:12 pm - 10:44 pmORD-BOS

2h 32mnonstop

$152American Airlines

Find Deal

Thu, Nov 20 - Mon, Nov 24

Delta flights from Maine to Chicago

Our best Delta deals on Maine to Chicago flight tickets

Delta

Dec 11

BOS7:52 pmBoston Logan Intl

2h 55m

ORD9:47 pmChicago O'Hare Intl

Dec 14

ORD7:10 amChicago O'Hare Intl

2h 26m

BOS10:36 amBoston Logan Intl

$117

Find similar

Delta

Dec 11

BOS7:30 amBoston Logan Intl

3h 03m

ORD9:33 amChicago O'Hare Intl

Dec 14

ORD7:10 amChicago O'Hare Intl

2h 26m

BOS10:36 amBoston Logan Intl

$118

Find similar

Delta

Dec 14

BOS7:30 amBoston Logan Intl

3h 03m

ORD9:33 amChicago O'Hare Intl

Dec 18

ORD7:10 amChicago O'Hare Intl

2h 26m

BOS10:36 amBoston Logan Intl

$124

Find similar

JetBlue flights from Maine to Chicago

Our best JetBlue deals on Maine to Chicago flight tickets

JetBlue

Dec 4

BOS8:30 amBoston Logan Intl

3h 05m

ORD10:35 amChicago O'Hare Intl

Dec 11

ORD8:38 pmChicago O'Hare Intl

2h 28m

BOS12:06 amBoston Logan Intl

$122

Find similar

JetBlue

Dec 10

BOS8:30 amBoston Logan Intl

3h 05m

ORD10:35 amChicago O'Hare Intl

Dec 16

ORD7:00 amChicago O'Hare Intl

7h 14m

1 stop

BOS3:14 pmBoston Logan Intl

$135

Find similar

JetBlue

Jan 30

BOS3:35 pmBoston Logan Intl

3h 09m

ORD5:44 pmChicago O'Hare Intl

Feb 11

ORD6:00 pmChicago O'Hare Intl

2h 29m

BOS9:29 pmBoston Logan Intl

$137

Find similar

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 12/11

7:52 pm-9:47 pm

Nonstop2h 55m

Chicago O'Hare Intl

Sun 12/14

7:10 am-10:36 am

Nonstop2h 26m

$117

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 12/11

7:30 am-9:33 am

Nonstop3h 03m

Chicago O'Hare Intl

Sun 12/14

7:10 am-10:36 am

Nonstop2h 26m

$118

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 11/20

5:30 am-7:15 am

Nonstop2h 45m

Chicago Midway

Mon 11/24

9:35 am-12:50 pm

Nonstop2h 15m

$122

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 12/4

8:30 am-10:35 am

Nonstop3h 05m

Chicago O'Hare Intl

Thu 12/11

8:38 pm-12:06 am

Nonstop2h 28m

$122

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 12/6

7:00 am-9:32 am

Nonstop3h 32m

Chicago O'Hare Intl

Sat 12/13

6:10 am-9:35 am

Nonstop2h 25m

$123

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 12/15

5:30 am-7:15 am

Nonstop2h 45m

Chicago Midway

Thu 12/18

7:15 pm-10:30 pm

Nonstop2h 15m

$124

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 2/25

7:00 am-5:28 pm

1 stop11h 28m

Chicago O'Hare Intl

Wed 3/4

4:45 pm-12:05 am

1 stop6h 20m

$125

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 12/4

11:28 am-5:27 pm

1 stop6h 59m

Chicago O'Hare Intl

Mon 12/8

2:26 pm-10:01 am

1 stop18h 35m

$131

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 12/10

8:30 am-10:35 am

Nonstop3h 05m

Chicago O'Hare Intl

Tue 12/16

7:00 am-3:14 pm

1 stop7h 14m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 11/20

6:45 am-8:52 am

Nonstop3h 07m

Chicago O'Hare Intl

Mon 11/24

7:12 pm-10:44 pm

Nonstop2h 32m

$152

Flights are sorted by cheapest round-trip flights first.

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How to get the cheapest flight ticket from Maine to Chicago

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 Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Maine, with most prices found around $279. If you’re not able to fly to Chicago in September, then May is your next best option. Flight prices from Maine to Chicago during May average around $303.

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

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $428. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Maine to Chicago for around $615.

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

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Maine to Chicago during this time can be as low as $432. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $485.

What is the cheapest Maine to Chicago flight route?

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

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

You are more likely to see cheaper flights to Chicago from Maine when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $363 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Maine for as low as $228 on momondo.

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

There are 4 cabin classes available to choose from on Maine to Chicago 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 Maine to Chicago flights?

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

Cheap Maine to Chicago flight deals and tips

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

Best Price Found	$189
Fastest flight time	2h 40m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Maine in the past 72 hours is $189. The best round-trip flight deal from Maine to Chicago found on momondo in the last 72 hours is $337.

The fastest flight from Maine to Chicago takes 2h 40m

Direct flights go from Maine to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

When did momondo last update prices for flights from Maine to Chicago?
Prices for flights from Maine to Chicago were last updated today.
How many operators does momondo search for flights from Maine to Chicago?
As of November 2025, there are 7 operators available to choose from for flights from Maine to Chicago.
How old do you have to be to fly from Maine to Chicago?
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 Maine to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago 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 Chicago. 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 Maine to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Maine to Chicago is Embraer 175 (Enhanced Winglets) (22.50% of total bookings). The next most popular plane models are Canadair (Bombardier) Regional Jet 700 (16.12%), Embraer 175 (15.60%), and Boeing 737 MAX 8 (12.41%).

Best airlines flying from Maine to Chicago

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

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $124	Free Cancellation	Rating 7.9 8,007 reviews	Search Delta flights
American Airlines	PriceFrom $203	Free Cancellation	Rating 7.2 11,045 reviews	Search American Airlines flights
United Airlines	PriceFrom $229	Free Cancellation	Rating 7.4 9,012 reviews	Search United Airlines flights
Southwest	PriceFrom $246	Free Cancellation	Rating 8.0 4,235 reviews	Search Southwest flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Maine to Chicago. momondo saves you time and could save you money on your trip.

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

momondo does allow users to show only those flights to Chicago from Maine which offer a flexible booking policy as well as other useful filters and features.

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

momondo provides multiple filters to help you find the best flight to Chicago from Maine. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Maine and alert you when they change.

An easier way to manage your Chicago 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 the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Cheap flights from Maine to Chicago from $59

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Maine to Chicago departing on 12/9. 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

Price Alerts

Price Alerts

Find the cheapest flights from Maine to Chicago

Cheap round-trip flights

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Cheap last minute flights

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Delta flights from Maine to Chicago

Our best Delta deals on Maine to Chicago flight tickets

JetBlue flights from Maine to Chicago

Our best JetBlue deals on Maine to Chicago flight tickets

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

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How to get the cheapest flight ticket from Maine to Chicago

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 Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Maine, with most prices found around $279. If you’re not able to fly to Chicago in September, then May is your next best option. Flight prices from Maine to Chicago during May average around $303.

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

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

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Maine to Chicago during this time can be as low as $432. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $485.

What is the cheapest Maine to Chicago flight route?

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

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

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

There are 4 cabin classes available to choose from on Maine to Chicago 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 Maine to Chicago flights?

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

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

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

What airlines fly to Chicago?

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

As of November 2025, 65 flights take off from Maine and land in Chicago each day. The most common flight departure time for this route is 9:00AM, with 61% of daily flights taking off in the afternoon.

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

As of November 2025, there are 457 flights per week flying from Maine to Chicago. The most common day of the week flights depart is Fri, with 18% of flights taking off on this day.

How long does it take to fly to Chicago?

Cheap Maine to Chicago flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

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

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

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

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

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

Best airlines flying from Maine to Chicago

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

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago 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 the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago