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Cheap flights from Maine to Chicago from $104

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
9:40 am - 11:15 amBOS  Boston Logan Intl-MDW Chicago Midway
2h 35mnonstop
Southwest Logo
11:00 am - 2:25 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 25mnonstop
$217Southwest
Sat, Oct 24 - Mon, Oct 26
Southwest Logo
5:50 am - 7:25 amBOS  Boston Logan Intl-MDW Chicago Midway
2h 35mnonstop
Southwest Logo
6:10 pm - 9:25 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 15mnonstop
$217Southwest
Thu, Oct 15 - Tue, Oct 20
Southwest Logo
10:05 am - 11:35 amBOS  Boston Logan Intl-MDW Chicago Midway
2h 30mnonstop
Southwest Logo
6:40 am - 9:55 amMDW  Chicago Midway-BOS Boston Logan Intl
2h 15mnonstop
$217Southwest
Tue, Sep 22 - Tue, Sep 29
Southwest Logo
5:55 pm - 7:40 pmBOS  Boston Logan Intl-MDW Chicago Midway
2h 45mnonstop
Southwest Logo
6:45 pm - 10:00 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 15mnonstop
$217Southwest
Wed, Nov 4 - Thu, Nov 5
Frontier Logo
11:57 am - 7:02 pmBOS  Boston Logan Intl-MDW Chicago Midway
8h 05m1 stop Orlando
Frontier Logo
8:07 pm - 11:02 amMDW  Chicago Midway-BOS Boston Logan Intl
13h 55m1 stop Orlando
$248Frontier
Fri, Dec 11 - Sun, Dec 13
Frontier Logo
11:57 am - 7:02 pmBOS  Boston Logan Intl-MDW Chicago Midway
8h 05m1 stop Orlando
Frontier Logo
8:07 pm - 11:02 amMDW  Chicago Midway-BOS Boston Logan Intl
13h 55m1 stop Orlando
$251Frontier
Thu, Dec 3 - Sun, Dec 6
Frontier Logo
11:57 am - 7:02 pmBOS  Boston Logan Intl-MDW Chicago Midway
8h 05m1 stop Orlando
Frontier Logo
8:07 pm - 11:02 amMDW  Chicago Midway-BOS Boston Logan Intl
13h 55m1 stop Orlando
$273Frontier
Thu, Dec 10 - Sun, Dec 13
Delta Logo
6:05 am - 6:00 pmBOS  Boston Logan Intl-MDW Chicago Midway
12h 55m2 stops Washington, D.C. Reagan-National Detroit Metropolitan Wayne County
Delta Logo
6:44 pm - 7:38 amMDW  Chicago Midway-BOS Boston Logan Intl
11h 54m2 stops Detroit Metropolitan Wayne County Washington, D.C. Reagan-National
$294Delta
Thu, Nov 5 - Mon, Nov 9
Delta Logo
9:15 am - 12:47 pmBOS  Boston Logan Intl-MDW Chicago Midway
4h 32m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:44 pm - 7:38 amMDW  Chicago Midway-BOS Boston Logan Intl
11h 54m2 stops Detroit Metropolitan Wayne County Washington, D.C. Reagan-National
$304Delta
Sat, Nov 7 - Mon, Nov 9
Delta Logo
5:39 am - 9:17 amBOS  Boston Logan Intl-MDW Chicago Midway
4h 38m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:44 pm - 7:38 amMDW  Chicago Midway-BOS Boston Logan Intl
11h 54m2 stops Detroit Metropolitan Wayne County Washington, D.C. Reagan-National
$304Delta
Thu, Nov 5 - Mon, Nov 9

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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
Sep 17
BOS3:55 pmBoston Logan Intl
2h 35m
MDW5:30 pmChicago Midway
Sep 21
MDW5:45 amChicago Midway
2h 15m
BOS9:00 amBoston Logan Intl
$217
Southwest
Sep 18
BOS6:45 pmBoston Logan Intl
2h 45m
MDW8:30 pmChicago Midway
Sep 21
MDW5:45 amChicago Midway
2h 15m
BOS9:00 amBoston Logan Intl
$226
Southwest
Sep 12
BOS6:00 amBoston Logan Intl
9h 30m
1 stop
MDW2:30 pmChicago Midway
Sep 14
MDW5:45 amChicago Midway
2h 15m
BOS9:00 amBoston Logan Intl
$227

Delta flights from Maine to Chicago Midway Airport

Our best Delta deals on Maine to Chicago Midway Airport flight tickets
Delta
Sep 5
BOS8:55 amBoston Logan Intl
7h 49m
1 stop
MDW3:44 pmChicago Midway
Sep 12
MDW5:37 pmChicago Midway
5h 21m
1 stop
BOS11:58 pmBoston Logan Intl
$315
Delta
Oct 24
PWM6:01 amPortland
5h 36m
1 stop
MDW10:37 amChicago Midway
Oct 27
MDW5:09 pmChicago Midway
5h 26m
1 stop
PWM11:35 pmPortland
$317
Delta
Oct 24
PWM6:04 amPortland
10h 13m
2 stops
MDW3:17 pmChicago Midway
Oct 27
MDW5:09 pmChicago Midway
5h 26m
1 stop
PWM11:35 pmPortland
$322

momondo Fare Finder

 
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 Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Sat 10/24

9:40 am-11:15 am

Nonstop2h 35m

Chicago Midway

Mon 10/26

11:00 am-2:25 pm

Nonstop2h 25m

$217

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Thu 10/15

5:50 am-7:25 am

Nonstop2h 35m

Chicago Midway

Tue 10/20

6:10 pm-9:25 pm

Nonstop2h 15m

$217
Quickest round-trip

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Tue 9/22

10:05 am-11:35 am

Nonstop2h 30m

Chicago Midway

Tue 9/29

6:40 am-9:55 am

Nonstop2h 15m

$217

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Wed 11/4

5:55 pm-7:40 pm

Nonstop2h 45m

Chicago Midway

Thu 11/5

6:45 pm-10:00 pm

Nonstop2h 15m

$217

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Fri 12/11

11:57 am-7:02 pm

1 stop8h 05m

Chicago Midway

Sun 12/13

8:07 pm-11:02 am

1 stop13h 55m

$248

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Thu 12/3

11:57 am-7:02 pm

1 stop8h 05m

Chicago Midway

Sun 12/6

8:07 pm-11:02 am

1 stop13h 55m

$251

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Thu 12/10

11:57 am-7:02 pm

1 stop8h 05m

Chicago Midway

Sun 12/13

8:07 pm-11:02 am

1 stop13h 55m

$273

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Thu 11/5

6:05 am-6:00 pm

2 stops12h 55m

Chicago Midway

Mon 11/9

6:44 pm-7:38 am

2 stops11h 54m

$294

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Sat 11/7

9:15 am-12:47 pm

1 stop4h 32m

Chicago Midway

Mon 11/9

6:44 pm-7:38 am

2 stops11h 54m

$304

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Thu 11/5

5:39 am-9:17 am

1 stop4h 38m

Chicago Midway

Mon 11/9

6:44 pm-7:38 am

2 stops11h 54m

$304

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, Friday is the cheapest day to fly to Chicago Midway Airport from Maine. The lowest ticket price found for a Friday departure recently was $416. 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 $631.

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

Flying to Chicago Midway Airport from Maine at noon is the least expensive time of day to depart. momondo users have found prices as low as $393 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $487. 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?

You could potentially save up to 7% 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

Best Price Found

$104

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 $104. The best round-trip flight deal from Maine to Chicago Midway Airport found on momondo in the last 72 hours is $217.
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
8.0
4,204 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
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
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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