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Cheap flights from Chicago Midway Airport to Maine from $69

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 11/11. 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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Find the cheapest flights from Chicago Midway Airport to Maine

Cheap round-trip flights

Southwest Logo
9:20 pm - 12:40 amMDW-BOS
2h 20mnonstop
Southwest Logo
5:15 am - 6:55 amBOS-MDW
2h 40mnonstop
$137Southwest
Find Deal
vie., oct. 3 - mar., oct. 7
Southwest Logo
12:50 pm - 4:05 pmMDW-BOS
2h 15mnonstop
Southwest Logo
5:35 pm - 9:05 pmBOS-MDW
4h 30m1 stop
$143Southwest
Find Deal
sáb., dic. 13 - mié., dic. 17
Frontier Logo
6:21 am - 8:11 amMDW-BOS
24h 50m1 stop
Frontier Logo
8:56 am - 12:44 pmBOS-MDW
28h 48m1 stop
$144Frontier
Find Deal
vie., sep. 26 - sáb., oct. 4
Southwest Logo
2:35 pm - 11:00 pmMDW-BOS
7h 25m1 stop
Southwest Logo
3:15 pm - 4:50 pmBOS-MDW
2h 35mnonstop
$147Southwest
Find Deal
vie., sep. 19 - mar., sep. 23
Frontier Logo
6:21 am - 8:11 amMDW-BOS
24h 50m1 stop
Frontier Logo
8:56 am - 12:44 pmBOS-MDW
28h 48m1 stop
$150Frontier
Find Deal
vie., sep. 26 - sáb., oct. 4
Southwest Logo
6:05 am - 9:20 amMDW-BOS
2h 15mnonstop
Southwest Logo
3:20 pm - 11:35 pmBOS-MDW
9h 15m2 stops
$152Southwest
Find Deal
dom., oct. 12 - mié., oct. 15
Logo
7:50 pm - 9:43 amMDW-BOS
12h 53m1 stop
Logo
6:10 am - 3:58 pmBOS-MDW
10h 48m2 stops
$230
Find Deal
lun., sep. 15 - mar., sep. 23
Logo
7:50 pm - 9:43 amMDW-BOS
12h 53m1 stop
Logo
6:10 am - 3:58 pmBOS-MDW
10h 48m2 stops
$233
Find Deal
lun., sep. 15 - mar., sep. 23
Delta Logo
1:08 pm - 11:29 pmMDW-BGR
9h 21m2 stops
Delta Logo
5:23 am - 12:28 pmBGR-MDW
8h 05m2 stops
$234Delta
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mié., sep. 24 - mié., oct. 1
Delta Logo
6:00 am - 12:22 pmMDW-PWM
5h 22m1 stop
Delta Logo
11:41 am - 5:43 pmPWM-MDW
7h 02m1 stop
$251Delta
Find Deal
mié., oct. 22 - sáb., oct. 25

Frontier flights from Chicago Midway Airport to Maine

Our best Frontier deals on Chicago Midway Airport to Maine flight tickets
Frontier
Sep 26
MDW6:21 amChicago Midway
24h 50m
1 stop
BOS8:11 amBoston Logan Intl
Oct 4
BOS8:56 amBoston Logan Intl
28h 48m
1 stop
MDW12:44 pmChicago Midway
$144
Find similar
Frontier
Sep 26
MDW6:21 amChicago Midway
24h 50m
1 stop
BOS8:11 amBoston Logan Intl
Oct 4
BOS8:56 amBoston Logan Intl
28h 48m
1 stop
MDW12:44 pmChicago Midway
$150
Find similar
Frontier
Sep 12
MDW6:21 amChicago Midway
24h 50m
1 stop
BOS8:11 amBoston Logan Intl
Sep 20
BOS8:56 amBoston Logan Intl
28h 48m
1 stop
MDW12:44 pmChicago Midway
$160
Find similar

Southwest flights from Chicago Midway Airport to Maine

Our best Southwest deals on Chicago Midway Airport to Maine flight tickets
Southwest
Oct 3
MDW9:20 pmChicago Midway
2h 20m
BOS12:40 amBoston Logan Intl
Oct 7
BOS5:15 amBoston Logan Intl
2h 40m
MDW6:55 amChicago Midway
$137
Find similar
Southwest
Dec 13
MDW12:50 pmChicago Midway
2h 15m
BOS4:05 pmBoston Logan Intl
Dec 17
BOS5:35 pmBoston Logan Intl
4h 30m
1 stop
MDW9:05 pmChicago Midway
$143
Find similar
Southwest
Sep 19
MDW2:35 pmChicago Midway
7h 25m
1 stop
BOS11:00 pmBoston Logan Intl
Sep 23
BOS3:15 pmBoston Logan Intl
2h 35m
MDW4:50 pmChicago Midway
$147
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 agosto 28, 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

vie. 10/3

9:20 pm-12:40 am

Nonstop2h 20m

Boston Logan Intl

mar. 10/7

5:15 am-6:55 am

Nonstop2h 40m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

sáb. 12/13

12:50 pm-4:05 pm

Nonstop2h 15m

Boston Logan Intl

mié. 12/17

5:35 pm-9:05 pm

1 stop4h 30m

$143

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

vie. 9/26

6:21 am-8:11 am

1 stop24h 50m

Boston Logan Intl

sáb. 10/4

8:56 am-12:44 pm

1 stop28h 48m

$144

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

vie. 9/19

2:35 pm-11:00 pm

1 stop7h 25m

Boston Logan Intl

mar. 9/23

3:15 pm-4:50 pm

Nonstop2h 35m

$147

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

vie. 9/26

6:21 am-8:11 am

1 stop24h 50m

Boston Logan Intl

sáb. 10/4

8:56 am-12:44 pm

1 stop28h 48m

$150

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

dom. 10/12

6:05 am-9:20 am

Nonstop2h 15m

Boston Logan Intl

mié. 10/15

3:20 pm-11:35 pm

2 stops9h 15m

$152

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

lun. 9/15

7:50 pm-9:43 am

1 stop12h 53m

Boston Logan Intl

mar. 9/23

6:10 am-3:58 pm

2 stops10h 48m

$230

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

lun. 9/15

7:50 pm-9:43 am

1 stop12h 53m

Boston Logan Intl

mar. 9/23

6:10 am-3:58 pm

2 stops10h 48m

$233

ChicagoBangor

MDW - BGR

MDWBGR

Chicago Midway

mié. 9/24

1:08 pm-11:29 pm

2 stops9h 21m

Bangor

mié. 10/1

5:23 am-12:28 pm

2 stops8h 05m

$234

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

mié. 10/22

6:00 am-12:22 pm

1 stop5h 22m

Portland

sáb. 10/25

11:41 am-5:43 pm

1 stop7h 02m

$251

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 $371. 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 48% 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

Best Price Found

$387

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Maine

2 airports
The best flight deal from Chicago Midway Airport to Maine found on momondo in the last 72 hours is $387
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 2 airports near Maine: Portland (PWM), 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 $276Free CancellationRating
8.0
4,242 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.

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