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Cheap flights from Maine to Chicago from $68

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 10/30. 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

Southwest Logo
8:15 am - 11:40 amBOS-MDW
4h 25m1 stop
Southwest Logo
6:05 am - 9:20 amMDW-BOS
2h 15mnonstop
$127Southwest
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Sat, Oct 25 - Sun, Oct 26
Southwest Logo
5:05 am - 12:20 pmBOS-MDW
8h 15m2 stops
Southwest Logo
6:05 am - 9:20 amMDW-BOS
2h 15mnonstop
$132Southwest
Find Deal
Sat, Oct 25 - Sun, Oct 26
Southwest Logo
5:20 am - 7:00 amBOS-MDW
2h 40mnonstop
Southwest Logo
1:50 pm - 11:40 pmMDW-BOS
8h 50m1 stop
$133Southwest
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Sat, Nov 1 - Fri, Nov 7
Southwest Logo
5:30 am - 12:00 pmBOS-MDW
7h 30m1 stop
Southwest Logo
9:20 am - 4:35 pmMDW-BOS
6h 15m1 stop
$137Southwest
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Wed, Oct 29 - Wed, Nov 5
Frontier Logo
6:00 am - 9:32 pmBOS-MDW
16h 32m1 stop
Frontier Logo
6:00 am - 12:44 amMDW-BOS
17h 44m1 stop
$141Frontier
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Wed, Dec 10 - Sat, Dec 13
Frontier Logo
9:18 am - 4:20 pmBOS-MDW
8h 02m1 stop
Frontier Logo
9:26 pm - 8:55 amMDW-BOS
10h 29m1 stop
$144Frontier
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Fri, Oct 24 - Sun, Oct 26
Multiple Airlines Logo
8:24 pm - 10:47 pmBOS-MDW
27h 23m2 stops
Multiple Airlines Logo
9:32 am - 8:28 amMDW-BOS
21h 56m1 stop
$211Multiple Airlines
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Fri, Oct 24 - Fri, Oct 31
Multiple Airlines Logo
12:20 pm - 11:05 pmBOS-MDW
11h 45m2 stops
Multiple Airlines Logo
6:00 am - 12:44 amMDW-BOS
17h 44m1 stop
$214Multiple Airlines
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Thu, Dec 11 - Mon, Dec 15
Delta Logo
6:30 am - 5:43 pmPWM-MDW
12h 13m2 stops
Delta Logo
11:10 am - 4:03 pmMDW-PWM
3h 53m1 stop
$256Delta
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Sat, Oct 25 - Sat, Nov 8
Delta Logo
5:19 am - 4:09 pmBGR-MDW
11h 50m2 stops
Delta Logo
10:40 am - 11:28 pmMDW-BGR
11h 48m2 stops
$259Delta
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Wed, Oct 22 - Wed, Oct 29

Frontier flights from Maine to Chicago Midway Airport

Our best Frontier deals on Maine to Chicago Midway Airport flight tickets
Frontier
Dec 10
BOS6:00 amBoston Logan Intl
16h 32m
1 stop
MDW9:32 pmChicago Midway
Dec 13
MDW6:00 amChicago Midway
17h 44m
1 stop
BOS12:44 amBoston Logan Intl
$141
Find similar
Frontier
Oct 24
BOS9:18 amBoston Logan Intl
8h 02m
1 stop
MDW4:20 pmChicago Midway
Oct 26
MDW9:26 pmChicago Midway
10h 29m
1 stop
BOS8:55 amBoston Logan Intl
$144
Find similar
Frontier
Oct 23
BOS11:44 amBoston Logan Intl
24h 33m
1 stop
MDW11:17 amChicago Midway
Oct 26
MDW11:57 amChicago Midway
19h 36m
1 stop
BOS8:33 amBoston Logan Intl
$154
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Delta flights from Maine to Chicago Midway Airport

Our best Delta deals on Maine to Chicago Midway Airport flight tickets
Delta
Oct 25
PWM6:30 amPortland
12h 13m
2 stops
MDW5:43 pmChicago Midway
Nov 8
MDW11:10 amChicago Midway
3h 53m
1 stop
PWM4:03 pmPortland
$256
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Delta
Oct 22
BGR5:19 amBangor
11h 50m
2 stops
MDW4:09 pmChicago Midway
Oct 29
MDW10:40 amChicago Midway
11h 48m
2 stops
BGR11:28 pmBangor
$259
Find similar
Delta
Oct 25
PWM6:30 amPortland
6h 56m
2 stops
MDW12:26 pmChicago Midway
Nov 8
MDW1:06 pmChicago Midway
8h 13m
2 stops
PWM10:19 pmPortland
$261
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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 September 25, 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

Sat 10/25

8:15 am-11:40 am

1 stop4h 25m

Chicago Midway

Sun 10/26

6:05 am-9:20 am

Nonstop2h 15m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 10/25

5:05 am-12:20 pm

2 stops8h 15m

Chicago Midway

Sun 10/26

6:05 am-9:20 am

Nonstop2h 15m

$132

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 11/1

5:20 am-7:00 am

Nonstop2h 40m

Chicago Midway

Fri 11/7

1:50 pm-11:40 pm

1 stop8h 50m

$133

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 10/29

5:30 am-12:00 pm

1 stop7h 30m

Chicago Midway

Wed 11/5

9:20 am-4:35 pm

1 stop6h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 12/10

6:00 am-9:32 pm

1 stop16h 32m

Chicago Midway

Sat 12/13

6:00 am-12:44 am

1 stop17h 44m

$141

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 10/24

9:18 am-4:20 pm

1 stop8h 02m

Chicago Midway

Sun 10/26

9:26 pm-8:55 am

1 stop10h 29m

$144

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 10/24

8:24 pm-10:47 pm

2 stops27h 23m

Chicago Midway

Fri 10/31

9:32 am-8:28 am

1 stop21h 56m

$211

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 12/11

12:20 pm-11:05 pm

2 stops11h 45m

Chicago Midway

Mon 12/15

6:00 am-12:44 am

1 stop17h 44m

$214

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 10/25

6:30 am-5:43 pm

2 stops12h 13m

Chicago Midway

Sat 11/8

11:10 am-4:03 pm

1 stop3h 53m

$256

BangorChicago

BGR - MDW

BGRMDW

Bangor

Wed 10/22

5:19 am-4:09 pm

2 stops11h 50m

Chicago Midway

Wed 10/29

10:40 am-11:28 pm

2 stops11h 48m

$259

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 month to fly to Chicago Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Maine, with most prices found around $200. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Maine during the month June is also very affordable. Most momondo users find prices during this month for around $217.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Maine. The lowest ticket price found for a Wednesday departure recently was $294. 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 $425.

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 evening is the least expensive time of day to depart. momondo users have found prices as low as $318 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $348. 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

How far in advance should I book a flight to Chicago Midway Airport?

You are more likely to see cheaper flights to Chicago Midway Airport from Maine when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $257 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Maine for as low as $164 on momondo.

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?

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

$206

Fastest flight time

2h 35m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Maine in the past 72 hours is $206. The best round-trip flight deal from Maine to Chicago Midway Airport found on momondo in the last 72 hours is $393.
The fastest flight from Maine to Chicago Midway Airport takes 2h 35m
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
DeltaPriceFrom $253Free CancellationRating
7.9
7,973 reviews
Search Delta flights
SouthwestPriceFrom $264Free CancellationRating
8.0
4,246 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
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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