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

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

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

8 flights are operational weekly from Chicago Midway Airport to Maine as of June 2026. The most popular departure day for this route is Tue, with 50% of flights per week taking off on this day.

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

Prices for flights from Chicago Midway Airport to Maine are refreshed on a daily basis.

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

As of June 2026, there is 1 operator available to choose from for flights from Chicago Midway Airport to Maine.

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

$90 Cheap Flights from Chicago Midway Airport to Maine in 2026

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Find the cheapest flights from Chicago Midway Airport to Maine

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

3:10 pm - 6:30 pm

MDW

BOS

2h 20mnonstop

8:20 pm - 10:00 pm

BOS

MDW

2h 40mnonstop

$180Southwest

Sat, Sep 5 - Mon, Sep 14

5:25 am - 8:40 am

MDW

BOS

2h 15mnonstop

5:40 pm - 7:30 pm

BOS

MDW

2h 50mnonstop

$184Southwest

Sat, Jun 20 - Sat, Jul 4

4:40 pm - 10:15 pm

MDW

BOS

4h 35m

1 stop

1:20 pm - 7:05 pm

BOS

MDW

6h 45m

2 stops

$186Southwest

Wed, Sep 9 - Wed, Sep 16

6:40 am - 9:55 am

MDW

BOS

2h 15mnonstop

7:05 am - 8:40 am

BOS

MDW

2h 35mnonstop

$187Southwest

Wed, Aug 26 - Sat, Aug 29

5:15 am - 8:25 am

MDW

BOS

2h 10mnonstop

5:20 am - 6:55 am

BOS

MDW

2h 35mnonstop

$188Southwest

Sun, Jun 14 - Sat, Jun 20

5:45 am - 9:00 am

MDW

BOS

2h 15mnonstop

8:20 pm - 10:00 pm

BOS

MDW

2h 40mnonstop

$189Southwest

Thu, Aug 13 - Mon, Aug 17

5:45 am - 9:00 am

MDW

BOS

2h 15mnonstop

3:00 pm - 8:10 pm

BOS

MDW

6h 10m

1 stop

$191Southwest

Thu, Aug 27 - Mon, Aug 31

3:10 pm - 6:30 pm

MDW

BOS

2h 20mnonstop

8:40 am - 10:15 am

BOS

MDW

2h 35mnonstop

$192Southwest

Sat, Sep 5 - Sat, Sep 12

6:05 am - 1:19 pm

MDW

BGR

6h 14m

1 stop

6:00 am - 3:38 pm

BGR

MDW

10h 38m

2 stops

$286Delta

Sat, Aug 15 - Sat, Aug 22

12:46 pm - 11:40 pm

MDW

BGR

9h 54m

2 stops

5:20 am - 1:10 pm

BGR

MDW

8h 50m

2 stops

$291Delta

Tue, Aug 11 - Tue, Aug 18

Southwest flights from Chicago Midway Airport to Maine

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

Southwest

Jun 20

MDW5:25 amChicago Midway

2h 15m

BOS8:40 amBoston Logan Intl

Jul 4

BOS5:40 pmBoston Logan Intl

2h 50m

MDW7:30 pmChicago Midway

$184

Southwest

Aug 26

MDW6:40 amChicago Midway

2h 15m

BOS9:55 amBoston Logan Intl

Aug 29

BOS7:05 amBoston Logan Intl

2h 35m

MDW8:40 amChicago Midway

$187

Southwest

Jun 14

MDW5:15 amChicago Midway

2h 10m

BOS8:25 amBoston Logan Intl

Jun 20

BOS5:20 amBoston Logan Intl

2h 35m

MDW6:55 amChicago Midway

$188

Delta flights from Chicago Midway Airport to Maine

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

Delta

Aug 15

MDW6:05 amChicago Midway

6h 14m

1 stop

BGR1:19 pmBangor

Aug 22

BGR6:00 amBangor

10h 38m

2 stops

MDW3:38 pmChicago Midway

$286

Delta

Aug 11

MDW12:46 pmChicago Midway

9h 54m

2 stops

BGR11:40 pmBangor

Aug 18

BGR5:20 amBangor

8h 50m

2 stops

MDW1:10 pmChicago Midway

$291

Delta

Aug 15

MDW6:05 amChicago Midway

6h 14m

1 stop

BGR1:19 pmBangor

Aug 22

BGR2:33 pmBangor

9h 03m

1 stop

MDW10:36 pmChicago Midway

$295

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 9/5

3:10 pm-6:30 pm

Nonstop2h 20m

Boston Logan Intl

Mon 9/14

8:20 pm-10:00 pm

Nonstop2h 40m

$180

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 6/20

5:25 am-8:40 am

Nonstop2h 15m

Boston Logan Intl

Sat 7/4

5:40 pm-7:30 pm

Nonstop2h 50m

$184

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 9/9

4:40 pm-10:15 pm

1 stop4h 35m

Boston Logan Intl

Wed 9/16

1:20 pm-7:05 pm

2 stops6h 45m

$186

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 8/26

6:40 am-9:55 am

Nonstop2h 15m

Boston Logan Intl

Sat 8/29

7:05 am-8:40 am

Nonstop2h 35m

$187

Quickest round-trip

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sun 6/14

5:15 am-8:25 am

Nonstop2h 10m

Boston Logan Intl

Sat 6/20

5:20 am-6:55 am

Nonstop2h 35m

$188

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 8/13

5:45 am-9:00 am

Nonstop2h 15m

Boston Logan Intl

Mon 8/17

8:20 pm-10:00 pm

Nonstop2h 40m

$189

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 8/27

5:45 am-9:00 am

Nonstop2h 15m

Boston Logan Intl

Mon 8/31

3:00 pm-8:10 pm

1 stop6h 10m

$191

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 9/5

3:10 pm-6:30 pm

Nonstop2h 20m

Boston Logan Intl

Sat 9/12

8:40 am-10:15 am

Nonstop2h 35m

$192

ChicagoBangor

MDW - BGR

MDWBGR

Chicago Midway

Sat 8/15

6:05 am-1:19 pm

1 stop6h 14m

Bangor

Sat 8/22

6:00 am-3:38 pm

2 stops10h 38m

$286

ChicagoBangor

MDW - BGR

MDWBGR

Chicago Midway

Tue 8/11

12:46 pm-11:40 pm

2 stops9h 54m

Bangor

Tue 8/18

5:20 am-1:10 pm

2 stops8h 50m

$291

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 Midway Airport 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 day to depart on your flight to Maine?

The cheapest day to depart from Chicago Midway Airport to Maine is on a Wednesday. Travelers who choose to depart for Maine on a Wednesday will often find tickets for as low as $245. Flights from Chicago Midway Airport to Maine on a Sunday will generally be more expensive and average around $490. 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 afternoon when flights can be purchased for as low as $308. Flights in the morning are often more expensive with an average ticket price of $403.

What is the cheapest Chicago Midway to Maine flight route?

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

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

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

You could potentially save up to 2% on your flight if you consider stops on a Chicago Midway Airport to Maine flight.

Cheap Chicago Midway Airport to Maine flight deals and tips

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

Fastest flight time	2h 10m
Direct flights	Every day
Airports in Maine	49 airports

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

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

There are 49 airports in Maine. From Chicago Midway Airport there are direct flights to Boston Logan Intl (BOS), Portland (PWM).

Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Maine

When did momondo last update prices for flights from Chicago Midway Airport to Maine?
Prices for flights from Chicago Midway Airport to Maine are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to Maine?
As of June 2026, there is 1 operator available to choose from for flights from Chicago Midway Airport to Maine.
How old do you have to be to fly from Chicago Midway Airport 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 Midway Airport 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 Midway Airport to Maine?
momondo data reveals that the most frequently booked plane model on the route from Chicago Midway Airport to Maine is Boeing 737 MAX 8, representing 23.91% of all bookings. The subsequent popular models are Embraer 175 at 21.74%, Embraer 175 (Enhanced Winglets) at 17.39%, and Boeing 737-800 Passenger/BBJ2 (winglets) at 13.04%.

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. momondo allows you to filter the results for Chicago to Maine flights to just show those with flexible booking policies.

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

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

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.