Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to Maine 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 Chicago Midway Airport to Maine departing on 12/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

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

Trusted and free

Trusted and free

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

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago Midway Airport to Maine

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:15 pm - 9:35 pmMDW-BOS
2h 20mnonstop
Southwest Logo
5:15 am - 7:00 amBOS-MDW
2h 45mnonstop
$117Southwest
Find Deal
Fri, Dec 5 - Sun, Dec 7
Southwest Logo
6:15 pm - 9:35 pmMDW-BOS
2h 20mnonstop
Southwest Logo
1:35 pm - 3:20 pmBOS-MDW
2h 45mnonstop
$122Southwest
Find Deal
Wed, Dec 3 - Wed, Dec 10
Frontier Logo
7:10 pm - 7:29 amMDW-BOS
11h 19m1 stop
Frontier Logo
11:28 am - 10:12 pmBOS-MDW
11h 44m1 stop
$124Frontier
Find Deal
Mon, Nov 24 - Thu, Dec 4
Southwest Logo
6:40 am - 12:55 pmMDW-BOS
5h 15m1 stop
Southwest Logo
5:30 am - 7:15 amBOS-MDW
2h 45mnonstop
$127Southwest
Find Deal
Wed, Dec 10 - Thu, Dec 11
Frontier Logo
7:23 pm - 10:22 amMDW-BOS
13h 59m1 stop
Frontier Logo
11:28 am - 6:08 pmBOS-MDW
7h 40m1 stop
$129Frontier
Find Deal
Thu, Dec 4 - Thu, Dec 11
Multiple Airlines Logo
3:10 pm - 10:01 amMDW-BOS
17h 51m1 stop
Multiple Airlines Logo
11:19 am - 7:42 pmBOS-MDW
9h 23m1 stop
$130Multiple Airlines
Find Deal
Mon, Dec 8 - Fri, Dec 12
Multiple Airlines Logo
3:52 pm - 10:01 amMDW-BOS
17h 09m1 stop
Multiple Airlines Logo
11:23 am - 10:12 pmBOS-MDW
11h 49m1 stop
$131Multiple Airlines
Find Deal
Fri, Dec 5 - Mon, Dec 8
Southwest Logo
6:15 pm - 9:35 pmMDW-BOS
2h 20mnonstop
Southwest Logo
6:00 pm - 10:35 pmBOS-MDW
5h 35m1 stop
$132Southwest
Find Deal
Thu, Dec 4 - Mon, Dec 8
Delta Logo
12:47 pm - 11:19 pmMDW-PWM
9h 32m2 stops
Delta Logo
6:08 am - 11:55 amPWM-MDW
6h 47m1 stop
$284Delta
Find Deal
Mon, Nov 17 - Sun, Dec 14
Delta Logo
1:05 pm - 9:59 pmMDW-PWM
7h 54m1 stop
Delta Logo
5:30 am - 12:01 pmPWM-MDW
7h 31m1 stop
$302Delta
Find Deal
Wed, Apr 1 - Sun, Apr 5

Frontier flights from Chicago Midway Airport to Maine

Our best Frontier deals on Chicago Midway Airport to Maine flight tickets
Frontier
Nov 24
MDW7:10 pmChicago Midway
11h 19m
1 stop
BOS7:29 amBoston Logan Intl
Dec 4
BOS11:28 amBoston Logan Intl
11h 44m
1 stop
MDW10:12 pmChicago Midway
$124
Find similar
Frontier
Dec 4
MDW7:23 pmChicago Midway
13h 59m
1 stop
BOS10:22 amBoston Logan Intl
Dec 11
BOS11:28 amBoston Logan Intl
7h 40m
1 stop
MDW6:08 pmChicago Midway
$129
Find similar
Frontier
Nov 24
MDW7:10 pmChicago Midway
11h 19m
1 stop
BOS7:29 amBoston Logan Intl
Dec 4
BOS11:28 amBoston Logan Intl
7h 40m
1 stop
MDW6:08 pmChicago Midway
$141
Find similar

Southwest flights from Chicago Midway Airport to Maine

Our best Southwest deals on Chicago Midway Airport to Maine flight tickets
Southwest
Dec 5
MDW6:15 pmChicago Midway
2h 20m
BOS9:35 pmBoston Logan Intl
Dec 7
BOS5:15 amBoston Logan Intl
2h 45m
MDW7:00 amChicago Midway
$117
Find similar
Southwest
Dec 3
MDW6:15 pmChicago Midway
2h 20m
BOS9:35 pmBoston Logan Intl
Dec 10
BOS1:35 pmBoston Logan Intl
2h 45m
MDW3:20 pmChicago Midway
$122
Find similar
Southwest
Nov 14
MDW7:15 pmChicago Midway
2h 15m
BOS10:30 pmBoston Logan Intl
Nov 16
BOS5:15 amBoston Logan Intl
2h 45m
MDW7:00 amChicago Midway
$127
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Maine that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated November 5, 2025.
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

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 12/5

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Sun 12/7

5:15 am-7:00 am

Nonstop2h 45m

$117

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 12/3

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Wed 12/10

1:35 pm-3:20 pm

Nonstop2h 45m

$122

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 11/24

7:10 pm-7:29 am

1 stop11h 19m

Boston Logan Intl

Thu 12/4

11:28 am-10:12 pm

1 stop11h 44m

$124

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 12/10

6:40 am-12:55 pm

1 stop5h 15m

Boston Logan Intl

Thu 12/11

5:30 am-7:15 am

Nonstop2h 45m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 12/4

7:23 pm-10:22 am

1 stop13h 59m

Boston Logan Intl

Thu 12/11

11:28 am-6:08 pm

1 stop7h 40m

$129

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 12/8

3:10 pm-10:01 am

1 stop17h 51m

Boston Logan Intl

Fri 12/12

11:19 am-7:42 pm

1 stop9h 23m

$130

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 12/5

3:52 pm-10:01 am

1 stop17h 09m

Boston Logan Intl

Mon 12/8

11:23 am-10:12 pm

1 stop11h 49m

$131

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 12/4

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Mon 12/8

6:00 pm-10:35 pm

1 stop5h 35m

$132

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Mon 11/17

12:47 pm-11:19 pm

2 stops9h 32m

Portland

Sun 12/14

6:08 am-11:55 am

1 stop6h 47m

$284

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Wed 4/1

1:05 pm-9:59 pm

1 stop7h 54m

Portland

Sun 4/5

5:30 am-12:01 pm

1 stop7h 31m

$302

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Maine from

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

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 Tuesday. Travelers who choose to depart for Maine on a Tuesday will often find tickets for as low as $259. Flights from Chicago Midway Airport to Maine on a Thursday will generally be more expensive and average around $477. 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 at noon when flights can be purchased for as low as $372. Flights in the morning are often more expensive with an average ticket price of $411.

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 to Maine flights?

There is only 1 cabin class available to choose from on Chicago Midway 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 74% 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

1 airport
The fastest flight from Chicago Midway Airport to Maine takes 2h 10m
Direct flights go from Chicago Midway Airport to Maine every day.
There is 1 airport near Maine: Boston Logan Intl (BOS)
Search flight deals

  • 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?

  • 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?

Best airlines flying from Chicago Midway Airport to Maine

Compare and see reviews for airlines that fly from Chicago Midway Airport to Maine with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $313Free CancellationRating
8.0
4,240 reviews
Search Southwest flights

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.

An easier way to manage your Maine 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
Fri 12/5
Fri 12/12
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Maine

Popular cities in Maine

Popular flights according to clicks in the last 7 days on momondo
Flights to New Yorkfrom $44
Flights to Los Angelesfrom $49
Flights to Miamifrom $49
Flights to Chicagofrom $54
Flights to Orlandofrom $49
Flights to Las Vegasfrom $42
Flights to San Franciscofrom $57
Flights to Washington, D.C.from $49
Flights to Bostonfrom $49
Flights to Atlantafrom $40
Flights to Dallasfrom $59
Flights to Seattlefrom $58