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

As of September 2025, 57 flights take off from Maine and land in Chicago each day. The most common flight departure time for this route is 4:00PM, with 58% of daily flights taking off in the afternoon.

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

As of September 2025, there are 404 flights per week flying from Maine to Chicago. The most common day of the week flights depart is Wed, with 21% of flights taking off on this day.

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 57% 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.

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

United Airlines, Frontier, and JetBlue are the most popular carriers operating from Maine to Chicago

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 51m on average, while flying from Bangor to Chicago O'Hare Intl Airport is 3h 06m on average. Chicago O'Hare Intl Airport is the most popular airport in 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 September 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.

$64 Cheap Flights from Maine to Chicago in 2025/26

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Find the cheapest flights from Maine to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

6:16 am - 6:38 pmBOS-ORD

13h 22m1 stop

6:00 am - 1:20 pmORD-BOS

6h 20m1 stop

$126Spirit Airlines

Find Deal

Wed, Oct 15 - Tue, Oct 21

5:20 am - 7:00 amBOS-MDW

2h 40mnonstop

5:50 am - 1:50 pmMDW-BOS

7h 00m1 stop

$127Southwest

Find Deal

Sat, Oct 25 - Mon, Oct 27

7:30 pm - 9:19 pmBOS-ORD

2h 49mnonstop

7:05 am - 10:29 amORD-BOS

2h 24mnonstop

$127Delta

Find Deal

Tue, Oct 28 - Thu, Oct 30

6:00 am - 7:56 amBOS-ORD

2h 56mnonstop

6:30 am - 9:56 amORD-BOS

2h 26mnonstop

$131United Airlines

Find Deal

Wed, Oct 15 - Sun, Oct 19

6:00 am - 7:56 amBOS-ORD

2h 56mnonstop

6:30 am - 9:56 amORD-BOS

2h 26mnonstop

$134United Airlines

Find Deal

Sat, Oct 18 - Sun, Oct 19

7:09 am - 9:22 amBOS-ORD

3h 13mnonstop

7:13 pm - 10:46 pmORD-BOS

2h 33mnonstop

$135JetBlue

Find Deal

Wed, Oct 15 - Mon, Oct 20

7:50 pm - 9:46 pmBOS-ORD

2h 56mnonstop

7:10 am - 10:37 amORD-BOS

2h 27mnonstop

$137Delta

Find Deal

Fri, Dec 5 - Sun, Dec 7

5:00 am - 6:51 amBOS-ORD

2h 51mnonstop

8:25 pm - 11:54 pmORD-BOS

2h 29mnonstop

$138American Airlines

Find Deal

Sat, Oct 4 - Mon, Oct 6

7:09 am - 9:22 amBOS-ORD

3h 13mnonstop

7:13 pm - 10:46 pmORD-BOS

2h 33mnonstop

$145JetBlue

Find Deal

Tue, Oct 7 - Wed, Oct 15

6:57 am - 8:55 amBOS-ORD

2h 58mnonstop

6:05 am - 9:32 amORD-BOS

2h 27mnonstop

$146American Airlines

Find Deal

Thu, Oct 23 - Sun, Oct 26

Delta flights from Maine to Chicago

Our best Delta deals on Maine to Chicago flight tickets

Delta

Oct 28

BOS7:30 pmBoston Logan Intl

2h 49m

ORD9:19 pmChicago O'Hare Intl

Oct 30

ORD7:05 amChicago O'Hare Intl

2h 24m

BOS10:29 amBoston Logan Intl

$127

Find similar

Delta

Dec 5

BOS7:50 pmBoston Logan Intl

2h 56m

ORD9:46 pmChicago O'Hare Intl

Dec 7

ORD7:10 amChicago O'Hare Intl

2h 27m

BOS10:37 amBoston Logan Intl

$137

Find similar

Delta

Oct 27

BOS7:30 pmBoston Logan Intl

2h 49m

ORD9:19 pmChicago O'Hare Intl

Nov 5

ORD10:25 amChicago O'Hare Intl

2h 30m

BOS1:55 pmBoston Logan Intl

$147

Find similar

American Airlines flights from Maine to Chicago

Our best American Airlines deals on Maine to Chicago flight tickets

American Airlines

Oct 4

BOS5:00 amBoston Logan Intl

2h 51m

ORD6:51 amChicago O'Hare Intl

Oct 6

ORD8:25 pmChicago O'Hare Intl

2h 29m

BOS11:54 pmBoston Logan Intl

$138

Find similar

American Airlines

Oct 23

BOS6:57 amBoston Logan Intl

2h 58m

ORD8:55 amChicago O'Hare Intl

Oct 26

ORD6:05 amChicago O'Hare Intl

2h 27m

BOS9:32 amBoston Logan Intl

$146

Find similar

American Airlines

Oct 16

BOS5:24 amBoston Logan Intl

3h 01m

ORD7:25 amChicago O'Hare Intl

Oct 20

ORD7:00 amChicago O'Hare Intl

2h 21m

BOS10:21 amBoston Logan Intl

$149

Find similar

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 10/15

6:16 am-6:38 pm

1 stop13h 22m

Chicago O'Hare Intl

Tue 10/21

6:00 am-1:20 pm

1 stop6h 20m

$126

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 10/25

5:20 am-7:00 am

Nonstop2h 40m

Chicago Midway

Mon 10/27

5:50 am-1:50 pm

1 stop7h 00m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 10/28

7:30 pm-9:19 pm

Nonstop2h 49m

Chicago O'Hare Intl

Thu 10/30

7:05 am-10:29 am

Nonstop2h 24m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 10/15

6:00 am-7:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Sun 10/19

6:30 am-9:56 am

Nonstop2h 26m

$131

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 10/18

6:00 am-7:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Sun 10/19

6:30 am-9:56 am

Nonstop2h 26m

$134

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 10/15

7:09 am-9:22 am

Nonstop3h 13m

Chicago O'Hare Intl

Mon 10/20

7:13 pm-10:46 pm

Nonstop2h 33m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 12/5

7:50 pm-9:46 pm

Nonstop2h 56m

Chicago O'Hare Intl

Sun 12/7

7:10 am-10:37 am

Nonstop2h 27m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 10/4

5:00 am-6:51 am

Nonstop2h 51m

Chicago O'Hare Intl

Mon 10/6

8:25 pm-11:54 pm

Nonstop2h 29m

$138

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 10/7

7:09 am-9:22 am

Nonstop3h 13m

Chicago O'Hare Intl

Wed 10/15

7:13 pm-10:46 pm

Nonstop2h 33m

$145

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 10/23

6:57 am-8:55 am

Nonstop2h 58m

Chicago O'Hare Intl

Sun 10/26

6:05 am-9:32 am

Nonstop2h 27m

$146

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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 $283. 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 $304.

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 $437. 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 $619.

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 $493.

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 $379 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	$182
Fastest flight time	2h 35m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Maine in the past 72 hours is $182. The best round-trip flight deal from Maine to Chicago found on momondo in the last 72 hours is $316.

The fastest flight from Maine to Chicago takes 2h 35m

Direct flights go from Maine to Chicago every day.

There is 1 airport near Chicago: 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 September 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 (18.94% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (17.87%), Boeing 737-700 (11.89%), and Canadair (Bombardier) Regional Jet 700 (11.36%).

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 7,973 reviews	Search Delta flights
American Airlines	PriceFrom $203	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $229	Free Cancellation	Rating 7.4 8,928 reviews	Search United Airlines flights
Southwest	PriceFrom $264	Free Cancellation	Rating 8.0 4,244 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 $64

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 11/19. 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

Cheap direct flights

Delta flights from Maine to Chicago

Our best Delta deals on Maine to Chicago flight tickets

American Airlines flights from Maine to Chicago

Our best American Airlines 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 $283. 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 $304.

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 $493.

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?

United Airlines, Frontier, 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 September 2025, 57 flights take off from Maine and land in Chicago each day. The most common flight departure time for this route is 4:00PM, with 58% of daily flights taking off in the afternoon.

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

As of September 2025, there are 404 flights per week flying from Maine to Chicago. The most common day of the week flights depart is Wed, with 21% 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