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Cheap flights from Maine to Chicago from $96

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 7/28. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Maine to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:45 pm - 11:05 pm
BOS
-
MDW
5h 20m
1 stop
Southwest Logo
2:50 pm - 9:20 pm
MDW
-
BOS
5h 30m
2 stops
$162Southwest
ה', אוק' 1 - ב', אוק' 5
Southwest Logo
6:40 pm - 8:20 pm
BOS
-
MDW
2h 40mnonstop
Southwest Logo
5:55 am - 1:35 pm
MDW
-
BOS
6h 40m
1 stop
$163Southwest
ה', אוג' 13 - ב', אוג' 17
Southwest Logo
7:30 am - 9:05 am
BOS
-
MDW
2h 35mnonstop
Southwest Logo
11:55 am - 6:35 pm
MDW
-
BOS
5h 40m
2 stops
$164Southwest
ד', אוג' 12 - ג', אוג' 25
Southwest Logo
6:40 pm - 8:20 pm
BOS
-
MDW
2h 40mnonstop
Southwest Logo
6:00 am - 9:15 am
MDW
-
BOS
2h 15mnonstop
$165Southwest
ו', אוג' 21 - א', אוג' 23
Southwest Logo
5:25 am - 11:00 am
BOS
-
MDW
6h 35m
1 stop
Southwest Logo
7:55 am - 4:10 pm
MDW
-
BOS
7h 15m
2 stops
$166Southwest
ב', אוג' 24 - ב', אוג' 31
Southwest Logo
5:25 am - 9:00 am
BOS
-
MDW
4h 35m
1 stop
Southwest Logo
2:00 pm - 10:10 pm
MDW
-
BOS
7h 10m
2 stops
$167Southwest
ג', אוג' 18 - ג', אוג' 25
Southwest Logo
8:20 pm - 10:00 pm
BOS
-
MDW
2h 40mnonstop
Southwest Logo
11:55 am - 6:35 pm
MDW
-
BOS
5h 40m
2 stops
$168Southwest
ב', אוג' 24 - ד', אוג' 26
Southwest Logo
8:20 pm - 10:00 pm
BOS
-
MDW
2h 40mnonstop
Southwest Logo
8:50 am - 5:05 pm
MDW
-
BOS
7h 15m
2 stops
$169Southwest
ב', אוג' 10 - ד', אוג' 12
Delta Logo
5:20 am - 4:15 pm
BGR
-
MDW
11h 55m
2 stops
Delta Logo
10:54 am - 11:40 pm
MDW
-
BGR
11h 46m
2 stops
$305Delta
ד', אוג' 19 - ד', אוג' 26
Delta Logo
6:30 am - 3:44 pm
PWM
-
MDW
10h 14m
2 stops
Delta Logo
9:24 am - 4:01 pm
MDW
-
PWM
5h 37m
1 stop
$332Delta
ד', ספט' 2 - א', ספט' 6

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Southwest flights from Maine to Chicago Midway Airport

Our best Southwest deals on Maine to Chicago Midway Airport flight tickets
Southwest
Oct 1
BOS6:45 pmBoston Logan Intl
5h 20m
1 stop
MDW11:05 pmChicago Midway
Oct 5
MDW2:50 pmChicago Midway
5h 30m
2 stops
BOS9:20 pmBoston Logan Intl
$162
Southwest
Aug 13
BOS6:40 pmBoston Logan Intl
2h 40m
MDW8:20 pmChicago Midway
Aug 17
MDW5:55 amChicago Midway
6h 40m
1 stop
BOS1:35 pmBoston Logan Intl
$163
Southwest
Aug 12
BOS7:30 amBoston Logan Intl
2h 35m
MDW9:05 amChicago Midway
Aug 25
MDW11:55 amChicago Midway
5h 40m
2 stops
BOS6:35 pmBoston Logan Intl
$164

Delta flights from Maine to Chicago Midway Airport

Our best Delta deals on Maine to Chicago Midway Airport flight tickets
Delta
Aug 19
BGR5:20 amBangor
11h 55m
2 stops
MDW4:15 pmChicago Midway
Aug 26
MDW10:54 amChicago Midway
11h 46m
2 stops
BGR11:40 pmBangor
$305
Delta
Sep 25
PWM1:59 pmPortland
9h 46m
2 stops
MDW10:45 pmChicago Midway
Sep 28
MDW5:11 pmChicago Midway
5h 19m
1 stop
PWM11:30 pmPortland
$328
Delta
Sep 2
PWM6:30 amPortland
10h 14m
2 stops
MDW3:44 pmChicago Midway
Sep 6
MDW9:24 amChicago Midway
5h 37m
1 stop
PWM4:01 pmPortland
$332

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 יולי 11, 2026.
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

Cheapest round-trip

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

ה' 10/1

6:45 pm-11:05 pm

1 stop5h 20m

Chicago Midway

ב' 10/5

2:50 pm-9:20 pm

2 stops5h 30m

$162

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

ה' 8/13

6:40 pm-8:20 pm

Nonstop2h 40m

Chicago Midway

ב' 8/17

5:55 am-1:35 pm

1 stop6h 40m

$163

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

ד' 8/12

7:30 am-9:05 am

Nonstop2h 35m

Chicago Midway

ג' 8/25

11:55 am-6:35 pm

2 stops5h 40m

$164
Quickest round-trip

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

ו' 8/21

6:40 pm-8:20 pm

Nonstop2h 40m

Chicago Midway

א' 8/23

6:00 am-9:15 am

Nonstop2h 15m

$165

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

ב' 8/24

5:25 am-11:00 am

1 stop6h 35m

Chicago Midway

ב' 8/31

7:55 am-4:10 pm

2 stops7h 15m

$166

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

ג' 8/18

5:25 am-9:00 am

1 stop4h 35m

Chicago Midway

ג' 8/25

2:00 pm-10:10 pm

2 stops7h 10m

$167

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

ב' 8/24

8:20 pm-10:00 pm

Nonstop2h 40m

Chicago Midway

ד' 8/26

11:55 am-6:35 pm

2 stops5h 40m

$168

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

ב' 8/10

8:20 pm-10:00 pm

Nonstop2h 40m

Chicago Midway

ד' 8/12

8:50 am-5:05 pm

2 stops7h 15m

$169

BangorChicago

BGR - MDW

BGRMDW

Bangor

ד' 8/19

5:20 am-4:15 pm

2 stops11h 55m

Chicago Midway

ד' 8/26

10:54 am-11:40 pm

2 stops11h 46m

$305

PortlandChicago

PWM - MDW

PWMMDW

Portland

ד' 9/2

6:30 am-3:44 pm

2 stops10h 14m

Chicago Midway

א' 9/6

9:24 am-4:01 pm

1 stop5h 37m

$332

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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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, Friday is the cheapest day to fly to Chicago Midway Airport from Maine. The lowest ticket price found for a Friday departure recently was $426. 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 $628.

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 afternoon is the least expensive time of day to depart. momondo users have found prices as low as $389 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $489. 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 Airport flights?

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

No. A direct flight is the cheapest option for a flight between Maine 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

Best Price Found

$233

Fastest flight time

2h 30m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Maine in the past 72 hours is $233. The best round-trip flight deal from Maine to Chicago Midway Airport found on momondo in the last 72 hours is $401.
The fastest flight from Maine to Chicago Midway Airport takes 2h 30m
Direct flights go from Maine to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Maine to Chicago Midway Airport

  • 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 $267Free CancellationRating
7.9
4,248 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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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ב' 8/10
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