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

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

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

As of April 2026, there are 316 flights per week flying from Maine to Chicago. The most common day of the week flights depart is Sun, with 22% of flights taking off on this day.

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 Bangor to Chicago O'Hare Intl Airport is 3h on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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

As of April 2026, 45 flights take off from Maine and land in Chicago each day. The most common flight departure time for this route is 4:00PM, with 45% 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 53% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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 April 2026, there are 6 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.

$68 Cheap Flights from Maine to Chicago in 2026

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Find the cheapest flights from Maine to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:02 am - 8:59 am

BOS

ORD

2h 57mnonstop

6:00 am - 9:15 am

ORD

BOS

2h 15mnonstop

$138JetBlue

Thu, Apr 30 - Sun, May 3

12:52 pm - 10:14 pm

BOS

MDW

10h 22m

1 stop

12:27 pm - 1:24 am

MDW

BOS

11h 57m

1 stop

$140Frontier

Tue, Apr 28 - Tue, May 5

12:31 pm - 11:01 pm

BOS

ORD

11h 30m

1 stop

6:08 pm - 1:31 am

ORD

BOS

6h 23m

1 stop

$140Frontier

Mon, Apr 27 - Wed, Apr 29

6:00 am - 5:00 pm

BOS

ORD

12h 00m

1 stop

11:28 am - 1:31 am

ORD

BOS

13h 03m

1 stop

$146Multiple Airlines

Tue, Apr 28 - Wed, Apr 29

6:55 pm - 8:45 pm

BOS

MDW

2h 50mnonstop

9:25 am - 12:40 pm

MDW

BOS

2h 15mnonstop

$157Southwest

Fri, May 1 - Fri, May 8

12:23 pm - 2:36 pm

BGR

ORD

3h 13mnonstop

8:00 am - 11:43 am

ORD

BGR

2h 43mnonstop

$261American Airlines

Wed, Jul 22 - Tue, Jul 28

7:40 am - 9:15 am

PWM

MDW

2h 35mnonstop

7:55 pm - 11:10 pm

MDW

PWM

2h 15mnonstop

$269Southwest

Fri, Jun 5 - Sun, Jun 7

7:19 pm - 9:45 pm

PWM

ORD

3h 26mnonstop

8:11 am - 11:46 am

ORD

PWM

2h 35mnonstop

$269American Airlines

Fri, May 22 - Mon, May 25

5:15 am - 12:43 pm

BGR

MDW

8h 28m

2 stops

1:24 pm - 11:31 pm

MDW

BGR

9h 07m

2 stops

$394Delta

Thu, Apr 23 - Mon, Apr 27

6:00 am - 5:56 pm

BGR

MDW

12h 56m

2 stops

1:22 pm - 11:33 pm

MDW

BGR

9h 11m

2 stops

$436Delta

Sat, May 16 - Wed, May 20

United Airlines flights from Maine to Chicago

Our best United Airlines deals on Maine to Chicago flight tickets

United Airlines

May 1

BOS6:39 pmBoston Logan Intl

3h 01m

ORD8:40 pmChicago O'Hare Intl

May 4

ORD6:00 amChicago O'Hare Intl

2h 25m

BOS9:25 amBoston Logan Intl

$157

United Airlines

May 2

BOS6:00 amBoston Logan Intl

3h 00m

ORD8:00 amChicago O'Hare Intl

May 9

ORD1:55 pmChicago O'Hare Intl

2h 27m

BOS5:22 pmBoston Logan Intl

$167

United Airlines

May 2

BOS9:20 amBoston Logan Intl

3h 00m

ORD11:20 amChicago O'Hare Intl

May 3

ORD9:30 pmChicago O'Hare Intl

2h 29m

BOS12:59 amBoston Logan Intl

$172

Southwest flights from Maine to Chicago

Our best Southwest deals on Maine to Chicago flight tickets

Southwest

May 1

BOS6:55 pmBoston Logan Intl

2h 50m

MDW8:45 pmChicago Midway

May 5

MDW3:15 pmChicago Midway

2h 20m

BOS6:35 pmBoston Logan Intl

$157

Southwest

May 2

BOS1:50 pmBoston Logan Intl

2h 40m

MDW3:30 pmChicago Midway

May 4

MDW5:40 pmChicago Midway

4h 30m

1 stop

BOS11:10 pmBoston Logan Intl

$167

Southwest

May 2

BOS9:25 amBoston Logan Intl

2h 40m

MDW11:05 amChicago Midway

May 4

MDW9:25 amChicago Midway

2h 15m

BOS12:40 pmBoston Logan Intl

$172

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/30

7:02 am-8:59 am

Nonstop2h 57m

Chicago O'Hare Intl

Sun 5/3

6:00 am-9:15 am

Nonstop2h 15m

$138

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 4/28

12:52 pm-10:14 pm

1 stop10h 22m

Chicago Midway

Tue 5/5

12:27 pm-1:24 am

1 stop11h 57m

$140

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 4/27

12:31 pm-11:01 pm

1 stop11h 30m

Chicago O'Hare Intl

Wed 4/29

6:08 pm-1:31 am

1 stop6h 23m

$140

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 4/28

6:00 am-5:00 pm

1 stop12h 00m

Chicago O'Hare Intl

Wed 4/29

11:28 am-1:31 am

1 stop13h 03m

$146

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 5/1

6:55 pm-8:45 pm

Nonstop2h 50m

Chicago Midway

Fri 5/8

9:25 am-12:40 pm

Nonstop2h 15m

$157

BangorChicago

BGR - ORD

BGRORD

Bangor

Wed 7/22

12:23 pm-2:36 pm

Nonstop3h 13m

Chicago O'Hare Intl

Tue 7/28

8:00 am-11:43 am

Nonstop2h 43m

$261

Quickest round-trip

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 6/5

7:40 am-9:15 am

Nonstop2h 35m

Chicago Midway

Sun 6/7

7:55 pm-11:10 pm

Nonstop2h 15m

$269

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 5/22

7:19 pm-9:45 pm

Nonstop3h 26m

Chicago O'Hare Intl

Mon 5/25

8:11 am-11:46 am

Nonstop2h 35m

$269

BangorChicago

BGR - MDW

BGRMDW

Bangor

Thu 4/23

5:15 am-12:43 pm

2 stops8h 28m

Chicago Midway

Mon 4/27

1:24 pm-11:31 pm

2 stops9h 07m

$394

BangorChicago

BGR - MDW

BGRMDW

Bangor

Sat 5/16

6:00 am-5:56 pm

2 stops12h 56m

Chicago Midway

Wed 5/20

1:22 pm-11:33 pm

2 stops9h 11m

$436

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 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 May is, on average, the cheapest month to fly to Chicago from Maine, with most prices found around $281. If you’re not able to fly to Chicago in May, then September is your next best option. Flight prices from Maine to Chicago during September average around $282.

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 $424. 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 $575.

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 in the afternoon. Flights from Maine to Chicago during this time can be as low as $414. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $470.

What is the cheapest Maine to Chicago flight route?

Fly from Portland to Chicago Midway 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 $341 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 $254 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?

You could potentially save up to 5% on your flight if you consider stops on a Maine to Chicago flight.

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	$181
Fastest flight time	2h 30m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Maine in the past 72 hours is $181. The best round-trip flight deal from Maine to Chicago found on momondo in the last 72 hours is $353.

The fastest flight from Maine to Chicago takes 2h 30m

Direct flights go from Maine to Chicago every day.

There are 3 airports in Chicago. From Maine there are direct flights to Chicago Midway (MDW).

Search flight deals

Frequently asked questions about flying 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 April 2026, there are 6 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 (30.21% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (30.09%), Boeing 737 MAX 8 (14.81%), and Boeing 737-800 (5.81%).

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
American Airlines	PriceFrom $209	Free Cancellation	Rating 7.1 11,555 reviews	Search American Airlines flights
United Airlines	PriceFrom $224	Free Cancellation	Rating 7.4 9,545 reviews	Search United Airlines flights
Southwest	PriceFrom $264	Free Cancellation	Rating 8.0 4,340 reviews	Search Southwest flights

Merrillville

New Buffalo

Hammond

Saint Joseph

Benton Harbor

Portage

Lansing

Valparaiso

Schererville

Munster

Crown Point

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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Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Cheap flights from Maine to Chicago from $68

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 4/22. 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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United Airlines flights from Maine to Chicago

Our best United Airlines deals on Maine to Chicago flight tickets

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Our best Southwest deals on Maine to Chicago flight tickets

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See travel insights to Chicago from

How to get the cheapest flight ticket from Maine to Chicago

What is the cheapest month to fly to Chicago?

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?

What is the cheapest Maine to Chicago flight route?

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

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

Can stopping save me money on Maine to Chicago flights?

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

What airlines fly to Chicago?

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

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

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

Frequently asked questions about flying 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?

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

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo

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