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Cheap flights from Maine to Chicago from $34

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 8/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Maine to Chicago

Cheap round-trip flights

Southwest Logo
8:20 pm - 9:55 pmBOS-MDW
2h 35mnonstop
Southwest Logo
6:45 pm - 10:05 pmMDW-BOS
2h 20mnonstop
$67Southwest
Find Deal
Thu, Sep 4 - Mon, Sep 8
Southwest Logo
5:15 am - 6:45 amBOS-MDW
2h 30mnonstop
Southwest Logo
2:35 pm - 11:00 pmMDW-BOS
7h 25m1 stop
$77Southwest
Find Deal
Thu, Sep 4 - Mon, Sep 8
Southwest Logo
5:15 am - 6:45 amBOS-MDW
2h 30mnonstop
Southwest Logo
5:40 pm - 9:00 pmMDW-BOS
2h 20mnonstop
$79Southwest
Find Deal
Thu, Sep 18 - Sat, Sep 20
Southwest Logo
9:25 am - 11:05 amBOS-MDW
2h 40mnonstop
Southwest Logo
6:25 am - 3:25 pmMDW-BOS
8h 00m1 stop
$83Southwest
Find Deal
Wed, Sep 24 - Tue, Sep 30
Southwest Logo
5:35 pm - 9:05 pmBOS-MDW
4h 30m1 stop
Southwest Logo
6:15 pm - 9:35 pmMDW-BOS
2h 20mnonstop
$85Southwest
Find Deal
Tue, Nov 11 - Wed, Nov 12
Southwest Logo
5:15 am - 6:45 amBOS-MDW
2h 30mnonstop
Southwest Logo
5:55 am - 9:10 amMDW-BOS
2h 15mnonstop
$86Southwest
Find Deal
Fri, Sep 5 - Sun, Sep 7
Southwest Logo
10:45 am - 2:50 pmBOS-MDW
5h 05m1 stop
Southwest Logo
2:35 pm - 11:00 pmMDW-BOS
7h 25m1 stop
$87Southwest
Find Deal
Thu, Sep 4 - Mon, Sep 8
Southwest Logo
5:35 am - 9:00 amBOS-MDW
4h 25m1 stop
Southwest Logo
9:55 am - 1:20 pmMDW-BOS
2h 25mnonstop
$89Southwest
Find Deal
Mon, Sep 8 - Wed, Sep 10
Delta Logo
5:30 am - 8:45 amBOS-MDW
4h 15m1 stop
Delta Logo
6:00 am - 1:52 pmMDW-BOS
6h 52m1 stop
$137Delta
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Thu, Nov 27 - Sat, Dec 6
Delta Logo
6:00 am - 1:36 pmPWM-MDW
8h 36m1 stop
Delta Logo
4:25 pm - 12:03 amMDW-PWM
6h 38m1 stop
$217Delta
Find Deal
Tue, Aug 26 - Wed, Sep 3

Southwest flights from Maine to Chicago Midway Airport

Our best Southwest deals on Maine to Chicago Midway Airport flight tickets
Southwest
Sep 4
BOS8:20 pmBoston Logan Intl
2h 35m
MDW9:55 pmChicago Midway
Sep 8
MDW6:45 pmChicago Midway
2h 20m
BOS10:05 pmBoston Logan Intl
$67
Find similar
Southwest
Sep 4
BOS5:15 amBoston Logan Intl
2h 30m
MDW6:45 amChicago Midway
Sep 8
MDW2:35 pmChicago Midway
7h 25m
1 stop
BOS11:00 pmBoston Logan Intl
$77
Find similar
Southwest
Sep 18
BOS5:15 amBoston Logan Intl
2h 30m
MDW6:45 amChicago Midway
Sep 20
MDW5:40 pmChicago Midway
2h 20m
BOS9:00 pmBoston Logan Intl
$79
Find similar

Delta flights from Maine to Chicago Midway Airport

Our best Delta deals on Maine to Chicago Midway Airport flight tickets
Delta
Nov 27
BOS5:30 amBoston Logan Intl
4h 15m
1 stop
MDW8:45 amChicago Midway
Dec 6
MDW6:00 amChicago Midway
6h 52m
1 stop
BOS1:52 pmBoston Logan Intl
$137
Find similar
Delta
Aug 26
PWM6:00 amPortland
8h 36m
1 stop
MDW1:36 pmChicago Midway
Sep 3
MDW4:25 pmChicago Midway
6h 38m
1 stop
PWM12:03 amPortland
$217
Find similar
Delta
Sep 11
PWM6:00 amPortland
6h 48m
1 stop
MDW11:48 amChicago Midway
Sep 15
MDW12:43 pmChicago Midway
10h 51m
2 stops
PWM12:34 amPortland
$222
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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 August 7, 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 9/4

8:20 pm-9:55 pm

Nonstop2h 35m

Chicago Midway

Mon 9/8

6:45 pm-10:05 pm

Nonstop2h 20m

$67

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 9/4

5:15 am-6:45 am

Nonstop2h 30m

Chicago Midway

Mon 9/8

2:35 pm-11:00 pm

1 stop7h 25m

$77

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 9/18

5:15 am-6:45 am

Nonstop2h 30m

Chicago Midway

Sat 9/20

5:40 pm-9:00 pm

Nonstop2h 20m

$79

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 9/24

9:25 am-11:05 am

Nonstop2h 40m

Chicago Midway

Tue 9/30

6:25 am-3:25 pm

1 stop8h 00m

$83

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 11/11

5:35 pm-9:05 pm

1 stop4h 30m

Chicago Midway

Wed 11/12

6:15 pm-9:35 pm

Nonstop2h 20m

$85

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 9/5

5:15 am-6:45 am

Nonstop2h 30m

Chicago Midway

Sun 9/7

5:55 am-9:10 am

Nonstop2h 15m

$86

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 9/4

10:45 am-2:50 pm

1 stop5h 05m

Chicago Midway

Mon 9/8

2:35 pm-11:00 pm

1 stop7h 25m

$87

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 9/8

5:35 am-9:00 am

1 stop4h 25m

Chicago Midway

Wed 9/10

9:55 am-1:20 pm

Nonstop2h 25m

$89

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 11/27

5:30 am-8:45 am

1 stop4h 15m

Chicago Midway

Sat 12/6

6:00 am-1:52 pm

1 stop6h 52m

$137

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 8/26

6:00 am-1:36 pm

1 stop8h 36m

Chicago Midway

Wed 9/3

4:25 pm-12:03 am

1 stop6h 38m

$217

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 $401. 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, Saturday 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 $552.

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 $416 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $480. 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 are 1 cabin classes 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.

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

$34

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 $34. The best round-trip flight deal from Maine to Chicago Midway Airport found on momondo in the last 72 hours is $67.
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

  • 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
8.0
7,985 reviews
Search Delta flights
SouthwestPriceFrom $264Free CancellationRating
8.0
4,244 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
Lansing
Portage
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.

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