How long does it take to fly to Chicago Midway Airport?

On average, it takes 2h 56m to fly from Maine to Chicago Midway Airport if you fly out of Portland (the most popular airport in Maine) and into Chicago O'Hare Intl Airport (the most popular airport in Chicago Midway Airport). If you’re flying out of Bangor and into Chicago O'Hare Intl Airport, then the flight time is around 3h.

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

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

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

The number of flights available between Maine and Chicago Midway Airport is 19 per week as of December 2025. The most frequent departure day is Mon, with 21% of weekly flights leaving on this day.

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

Prices for flights from Maine to Chicago Midway Airport are updated daily.

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

There are 2 operators available for flights from Maine to Chicago Midway Airport as of December 2025.

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

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Maine to Chicago Midway Airport.

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

The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

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.

4:55 pm - 6:45 pm

BOS

MDW

2h 50mnonstop

1:50 pm - 9:25 pm

MDW

BOS

6h 35m1 stop

$127Southwest

Sat, Jan 17 - Tue, Jan 20

8:50 am - 6:40 pm

BOS

MDW

10h 50m2 stops

6:35 pm - 9:50 pm

MDW

BOS

2h 15mnonstop

$129Southwest

Sat, Jan 24 - Sun, Jan 25

5:30 am - 7:20 am

BOS

MDW

2h 50mnonstop

6:40 am - 12:20 pm

MDW

BOS

4h 40m1 stop

$131Southwest

Wed, Jan 14 - Sat, Jan 17

1:20 pm - 6:35 pm

BOS

MDW

6h 15m2 stops

2:00 pm - 5:10 pm

MDW

BOS

2h 10mnonstop

$132Southwest

Tue, Jan 27 - Wed, Jan 28

5:30 am - 7:20 am

BOS

MDW

2h 50mnonstop

5:40 pm - 8:55 pm

MDW

BOS

2h 15mnonstop

$133Southwest

Wed, Jan 28 - Sat, Jan 31

5:30 am - 7:20 am

BOS

MDW

2h 50mnonstop

5:35 pm - 8:50 pm

MDW

BOS

2h 15mnonstop

$136Southwest

Sat, Jan 10 - Mon, Jan 12

12:10 pm - 5:55 pm

PWM

MDW

6h 45m1 stop

1:26 pm - 11:20 pm

MDW

PWM

8h 54m2 stops

$234Delta

Tue, Feb 3 - Tue, Feb 24

12:43 pm - 10:22 pm

PWM

MDW

10h 39m2 stops

1:26 pm - 11:20 pm

MDW

PWM

8h 54m2 stops

$239Delta

Tue, Feb 3 - Tue, Feb 24

5:04 am - 12:46 pm

BGR

MDW

8h 42m2 stops

6:25 am - 4:01 pm

MDW

BGR

8h 36m2 stops

$259Delta

Thu, Jan 29 - Sat, Jan 31

9:47 am - 7:52 pm

PWM

MDW

11h 05m1 stop

1:00 pm - 10:22 am

MDW

PWM

20h 22m1 stop

$263Multiple Airlines

Fri, Jan 23 - Fri, Jan 30

Southwest flights from Maine to Chicago Midway Airport

Our best Southwest deals on Maine to Chicago Midway Airport flight tickets

Southwest

Jan 17

BOS4:55 pmBoston Logan Intl

2h 50m

MDW6:45 pmChicago Midway

Jan 20

MDW1:50 pmChicago Midway

6h 35m

1 stop

BOS9:25 pmBoston Logan Intl

$127

Find similar

Southwest

Jan 24

BOS8:50 amBoston Logan Intl

10h 50m

2 stops

MDW6:40 pmChicago Midway

Jan 25

MDW9:40 amChicago Midway

2h 15m

BOS12:55 pmBoston Logan Intl

$129

Find similar

Southwest

Jan 14

BOS5:30 amBoston Logan Intl

2h 50m

MDW7:20 amChicago Midway

Jan 17

MDW6:40 amChicago Midway

4h 40m

1 stop

BOS12:20 pmBoston Logan Intl

$131

Find similar

Delta flights from Maine to Chicago Midway Airport

Our best Delta deals on Maine to Chicago Midway Airport flight tickets

Delta

Feb 3

PWM12:10 pmPortland

6h 45m

1 stop

MDW5:55 pmChicago Midway

Feb 24

MDW1:26 pmChicago Midway

8h 54m

2 stops

PWM11:20 pmPortland

$234

Find similar

Delta

Feb 3

PWM12:43 pmPortland

10h 39m

2 stops

MDW10:22 pmChicago Midway

Feb 24

MDW1:26 pmChicago Midway

8h 54m

2 stops

PWM11:20 pmPortland

$239

Find similar

Delta

Jan 29

BGR5:04 amBangor

8h 42m

2 stops

MDW12:46 pmChicago Midway

Jan 31

MDW6:25 amChicago Midway

8h 36m

2 stops

BGR4:01 pmBangor

$259

Find similar

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 1/17

4:55 pm-6:45 pm

Nonstop2h 50m

Chicago Midway

Tue 1/20

1:50 pm-9:25 pm

1 stop6h 35m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 1/24

8:50 am-6:40 pm

2 stops10h 50m

Chicago Midway

Sun 1/25

6:35 pm-9:50 pm

Nonstop2h 15m

$129

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 1/14

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Sat 1/17

6:40 am-12:20 pm

1 stop4h 40m

$131

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 1/27

1:20 pm-6:35 pm

2 stops6h 15m

Chicago Midway

Wed 1/28

2:00 pm-5:10 pm

Nonstop2h 10m

$132

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 1/28

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Sat 1/31

5:40 pm-8:55 pm

Nonstop2h 15m

$133

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 1/10

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Mon 1/12

5:35 pm-8:50 pm

Nonstop2h 15m

$136

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 2/3

12:10 pm-5:55 pm

1 stop6h 45m

Chicago Midway

Tue 2/24

1:26 pm-11:20 pm

2 stops8h 54m

$234

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 2/3

12:43 pm-10:22 pm

2 stops10h 39m

Chicago Midway

Tue 2/24

1:26 pm-11:20 pm

2 stops8h 54m

$239

BangorChicago

BGR - MDW

BGRMDW

Bangor

Thu 1/29

5:04 am-12:46 pm

2 stops8h 42m

Chicago Midway

Sat 1/31

6:25 am-4:01 pm

2 stops8h 36m

$259

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 1/23

9:47 am-7:52 pm

1 stop11h 05m

Chicago Midway

Fri 1/30

1:00 pm-10:22 am

1 stop20h 22m

$263

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 Midway Airport

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 day to depart on your flight to Chicago Midway Airport?

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Maine. The lowest ticket price found for a Thursday departure recently was $393. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Maine because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $581.

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

Flying to Chicago Midway Airport from Maine in the morning is the least expensive time of day to depart. momondo users have found prices as low as $404 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $462. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Maine to Chicago Midway flight route?

Fly from Portland to Chicago Midway for the best Maine - Chicago Midway flight prices

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

There is only 1 cabin class available to choose from on Maine to Chicago Midway 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 Midway Airport flights?

You could potentially save up to 42% on your flight if you consider stops on a Maine to Chicago Midway Airport flight.

Cheap Maine to Chicago Midway Airport flight deals and tips

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

Fastest flight time	2h 35m
Direct flights	Every day

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

Direct flights go from Maine to Chicago Midway Airport every day.

Search flight deals

When did momondo last update prices for flights from Maine to Chicago Midway Airport?
Prices for flights from Maine to Chicago Midway Airport are updated daily.
How many operators does momondo search for flights from Maine to Chicago Midway Airport?
There are 2 operators available for flights from Maine to Chicago Midway Airport as of December 2025.
How old do you have to be to fly from Maine to Chicago Midway Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Maine to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Maine to Chicago Midway Airport?
Based on momondo bookings for flights between Maine and Chicago Midway Airport, the leading plane model is Boeing 737 MAX 8, making up 10.00% of the total bookings. Other popular models include Boeing 737-900 with 10.00%, Boeing 737-800 Passenger/BBJ2 (winglets) with 10.00%, and Boeing 737-700 with 10.00%.

Best airlines flying from Maine to Chicago Midway Airport

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

Airline	Rating	Free Cancellation	Price
Southwest	PriceFrom $246	Free Cancellation	Rating 8.0 4,256 reviews		Search Southwest flights
Delta	PriceFrom $253	Free Cancellation	Rating 7.9 8,019 reviews		Search Delta flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

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?

Finding the right flight to Chicago from Maine is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

Yes. momondo enables you to select and highlight flights to Chicago from Maine with this policy.

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

Once you have performed a search for Maine to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes momondo offers price alerts on flights to Chicago from Maine. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago Midway Airport 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.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Tue 1/27

Tue 2/3

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago

Popular cities in the United States

Flights to New York John F Kennedy Intl Airportfrom $58

Flights to Newark Airportfrom $53

Flights to New York LaGuardia Airportfrom $51

Flights to Dallas/Fort Worth Airportfrom $51

Flights to Chicago O'Hare Intl Airportfrom $51

Flights to Washington, D.C. Dulles Intl Airportfrom $58

Flights to Washington, D.C. Reagan-National Airportfrom $72

Flights to Orlando Airportfrom $49

Flights to Dallas Love Field Airport

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 1/17. 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

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Southwest flights from Maine to Chicago Midway Airport

Our best Southwest deals on Maine to Chicago Midway Airport flight tickets

Delta flights from Maine to Chicago Midway Airport

Our best Delta deals on Maine to Chicago Midway Airport flight tickets

momondo Fare Finder

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

See travel insights to Chicago from

How to get the cheapest flight ticket from Maine to Chicago Midway Airport

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

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

What is the cheapest Maine to Chicago Midway flight route?

Fly from Portland to Chicago Midway for the best Maine - Chicago Midway flight prices

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

There is only 1 cabin class available to choose from on Maine to Chicago Midway 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 Midway Airport flights?

You could potentially save up to 42% on your flight if you consider stops on a Maine to Chicago Midway Airport flight.

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

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

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

The number of flights available between Maine and Chicago Midway Airport is 19 per week as of December 2025. The most frequent departure day is Mon, with 21% of weekly flights leaving on this day.

How long does it take to fly to Chicago Midway Airport?

Cheap Maine to Chicago Midway Airport flight deals and tips

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

Fastest flight time

Direct flights

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

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

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

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

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

Best airlines flying from Maine to Chicago Midway Airport

Compare and see reviews for airlines that fly from Maine to Chicago Midway Airport 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 Midway Airport 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 Chicago

Popular cities in the United States

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