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Cheap flights from Maine to Chicago 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 Maine to Chicago departing on 12/9. 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 Maine to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:30 am - 7:15 amBOS-MDW
2h 45mnonstop
Southwest Logo
9:35 am - 12:50 pmMDW-BOS
2h 15mnonstop
$122Southwest
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Thu, Nov 20 - Mon, Nov 24
Southwest Logo
5:30 am - 7:15 amBOS-MDW
2h 45mnonstop
Southwest Logo
7:15 pm - 10:30 pmMDW-BOS
2h 15mnonstop
$124Southwest
Find Deal
Mon, Dec 15 - Thu, Dec 18
Southwest Logo
5:30 am - 7:15 amBOS-MDW
2h 45mnonstop
Southwest Logo
6:15 pm - 9:35 pmMDW-BOS
2h 20mnonstop
$127Southwest
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Mon, Nov 17 - Tue, Nov 18
Southwest Logo
5:30 am - 7:15 amBOS-MDW
2h 45mnonstop
Southwest Logo
7:50 pm - 11:05 pmMDW-BOS
2h 15mnonstop
$129Southwest
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Mon, Dec 8 - Mon, Dec 22
Frontier Logo
11:28 am - 6:08 pmBOS-MDW
7h 40m1 stop
Frontier Logo
6:15 am - 10:22 amMDW-BOS
27h 07m1 stop
$130Frontier
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Thu, Dec 11 - Sun, Dec 14
Frontier Logo
11:28 am - 6:08 pmBOS-MDW
7h 40m1 stop
Frontier Logo
6:15 am - 10:22 amMDW-BOS
27h 07m1 stop
$131Frontier
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Thu, Dec 11 - Sun, Dec 14
Multiple Airlines Logo
11:28 am - 6:08 pmBOS-MDW
7h 40m1 stop
Multiple Airlines Logo
3:10 pm - 10:01 amMDW-BOS
17h 51m1 stop
$145Multiple Airlines
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Thu, Dec 11 - Mon, Dec 15
Multiple Airlines Logo
11:28 am - 6:08 pmBOS-MDW
7h 40m1 stop
Multiple Airlines Logo
8:42 pm - 11:56 pmMDW-BOS
26h 14m2 stops
$148Multiple Airlines
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Thu, Dec 4 - Mon, Dec 8
Delta Logo
5:31 am - 12:01 pmPWM-MDW
7h 30m1 stop
Delta Logo
12:46 pm - 11:22 pmMDW-PWM
9h 36m2 stops
$234Delta
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Thu, Feb 26 - Mon, Mar 2
Delta Logo
4:43 pm - 11:47 pmPWM-MDW
8h 04m2 stops
Delta Logo
9:29 am - 10:23 pmMDW-PWM
11h 54m2 stops
$239Delta
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Wed, Dec 3 - Sat, Dec 6

Southwest flights from Maine to Chicago Midway Airport

Our best Southwest deals on Maine to Chicago Midway Airport flight tickets
Southwest
Nov 20
BOS5:30 amBoston Logan Intl
2h 45m
MDW7:15 amChicago Midway
Nov 24
MDW9:35 amChicago Midway
2h 15m
BOS12:50 pmBoston Logan Intl
$122
Find similar
Southwest
Dec 15
BOS5:30 amBoston Logan Intl
2h 45m
MDW7:15 amChicago Midway
Dec 18
MDW7:15 pmChicago Midway
2h 15m
BOS10:30 pmBoston Logan Intl
$124
Find similar
Southwest
Nov 17
BOS5:30 amBoston Logan Intl
2h 45m
MDW7:15 amChicago Midway
Nov 18
MDW6:15 pmChicago Midway
2h 20m
BOS9:35 pmBoston Logan Intl
$127
Find similar

Frontier flights from Maine to Chicago Midway Airport

Our best Frontier deals on Maine to Chicago Midway Airport flight tickets
Frontier
Dec 11
BOS11:28 amBoston Logan Intl
7h 40m
1 stop
MDW6:08 pmChicago Midway
Dec 14
MDW6:15 amChicago Midway
27h 07m
1 stop
BOS10:22 amBoston Logan Intl
$130
Find similar
Frontier
Dec 11
BOS11:28 amBoston Logan Intl
7h 40m
1 stop
MDW6:08 pmChicago Midway
Dec 14
MDW6:15 amChicago Midway
27h 07m
1 stop
BOS10:22 amBoston Logan Intl
$131
Find similar
Frontier
Dec 11
BOS11:28 amBoston Logan Intl
7h 40m
1 stop
MDW6:08 pmChicago Midway
Dec 14
MDW6:15 amChicago Midway
27h 07m
1 stop
BOS10:22 amBoston Logan Intl
$135
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Maine to Chicago Midway Airport 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 10, 2025.
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

Thu 11/20

5:30 am-7:15 am

Nonstop2h 45m

Chicago Midway

Mon 11/24

9:35 am-12:50 pm

Nonstop2h 15m

$122

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 12/15

5:30 am-7:15 am

Nonstop2h 45m

Chicago Midway

Thu 12/18

7:15 pm-10:30 pm

Nonstop2h 15m

$124

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 11/17

5:30 am-7:15 am

Nonstop2h 45m

Chicago Midway

Tue 11/18

6:15 pm-9:35 pm

Nonstop2h 20m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 12/8

5:30 am-7:15 am

Nonstop2h 45m

Chicago Midway

Mon 12/22

7:50 pm-11:05 pm

Nonstop2h 15m

$129

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 12/11

11:28 am-6:08 pm

1 stop7h 40m

Chicago Midway

Sun 12/14

6:15 am-10:22 am

1 stop27h 07m

$130

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 12/11

11:28 am-6:08 pm

1 stop7h 40m

Chicago Midway

Sun 12/14

6:15 am-10:22 am

1 stop27h 07m

$131

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 12/11

11:28 am-6:08 pm

1 stop7h 40m

Chicago Midway

Mon 12/15

3:10 pm-10:01 am

1 stop17h 51m

$145

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 12/4

11:28 am-6:08 pm

1 stop7h 40m

Chicago Midway

Mon 12/8

8:42 pm-11:56 pm

2 stops26h 14m

$148

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 2/26

5:31 am-12:01 pm

1 stop7h 30m

Chicago Midway

Mon 3/2

12:46 pm-11:22 pm

2 stops9h 36m

$234

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 12/3

4:43 pm-11:47 pm

2 stops8h 04m

Chicago Midway

Sat 12/6

9:29 am-10:23 pm

2 stops11h 54m

$239

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 Chicago from

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

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 $394 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 74% 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 40m

Direct flights

Every day
The fastest flight from Maine to Chicago Midway Airport takes 2h 40m
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?

  • 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?

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
SouthwestPriceFrom $246Free CancellationRating
8.0
4,235 reviews
Search Southwest flights
DeltaPriceFrom $253Free CancellationRating
7.9
8,006 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
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

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