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Cheap flights from Maine to Chicago from $64

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 2/18. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:00 am - 10:44 pm
BOS
-
ORD
17h 44m1 stop
Multiple Airlines Logo
9:23 am - 4:19 pm
ORD
-
BOS
29h 56m1 stop
$124Multiple Airlines
Sat, Jan 24 - Tue, Jan 27
Multiple Airlines Logo
5:23 pm - 8:18 am
BOS
-
ORD
15h 55m1 stop
Multiple Airlines Logo
4:41 pm - 1:13 am
ORD
-
BOS
7h 32m1 stop
$125Multiple Airlines
Mon, Jan 12 - Sat, Jan 17
Spirit Airlines Logo
7:00 am - 7:41 pm
BOS
-
ORD
13h 41m1 stop
Spirit Airlines Logo
12:44 pm - 11:19 pm
ORD
-
BOS
9h 35m1 stop
$126Spirit Airlines
Sat, Jan 31 - Mon, Feb 2
JetBlue Logo
3:35 pm - 5:43 pm
BOS
-
ORD
3h 08mnonstop
JetBlue Logo
7:45 am - 11:10 am
ORD
-
BOS
2h 25mnonstop
$128JetBlue
Wed, Jan 28 - Sun, Feb 1
Spirit Airlines Logo
7:00 am - 7:41 pm
BOS
-
ORD
13h 41m1 stop
Spirit Airlines Logo
5:15 am - 4:28 pm
ORD
-
BOS
10h 13m1 stop
$129Spirit Airlines
Mon, Jan 12 - Thu, Jan 15
JetBlue Logo
3:35 pm - 5:43 pm
BOS
-
ORD
3h 08mnonstop
JetBlue Logo
7:45 am - 11:10 am
ORD
-
BOS
2h 25mnonstop
$130JetBlue
Tue, Jan 13 - Tue, Jan 20
Delta Logo
1:07 pm - 5:45 pm
BGR
-
ORD
5h 38m1 stop
Delta Logo
5:20 pm - 11:25 pm
ORD
-
BGR
5h 05m1 stop
$249Delta
Mon, Jan 12 - Tue, Jan 20
United Airlines Logo
6:46 pm - 11:35 pm
PWM
-
ORD
5h 49m1 stop
United Airlines Logo
11:00 am - 2:39 pm
ORD
-
PWM
2h 39mnonstop
$255United Airlines
Fri, Jan 2 - Wed, Jan 7
Delta Logo
5:04 am - 1:08 pm
BGR
-
ORD
9h 04m2 stops
Delta Logo
1:58 pm - 11:25 pm
ORD
-
BGR
8h 27m2 stops
$259Delta
Mon, Jan 12 - Tue, Jan 20
United Airlines Logo
6:46 pm - 11:35 pm
PWM
-
ORD
5h 49m1 stop
United Airlines Logo
6:00 am - 2:31 pm
ORD
-
PWM
7h 31m1 stop
$265United Airlines
Fri, Jan 2 - Wed, Jan 7

JetBlue flights from Maine to Chicago O'Hare Intl Airport

Our best JetBlue deals on Maine to Chicago O'Hare Intl Airport flight tickets
JetBlue
Jan 28
BOS3:35 pmBoston Logan Intl
3h 08m
ORD5:43 pmChicago O'Hare Intl
Feb 1
ORD7:45 amChicago O'Hare Intl
2h 25m
BOS11:10 amBoston Logan Intl
$128
Find similar
JetBlue
Jan 13
BOS3:35 pmBoston Logan Intl
3h 08m
ORD5:43 pmChicago O'Hare Intl
Jan 20
ORD7:45 amChicago O'Hare Intl
2h 25m
BOS11:10 amBoston Logan Intl
$130
Find similar
JetBlue
Jan 13
BOS3:35 pmBoston Logan Intl
3h 08m
ORD5:43 pmChicago O'Hare Intl
Jan 20
ORD7:45 amChicago O'Hare Intl
2h 25m
BOS11:10 amBoston Logan Intl
$132
Find similar

American Airlines flights from Maine to Chicago O'Hare Intl Airport

Our best American Airlines deals on Maine to Chicago O'Hare Intl Airport flight tickets
American Airlines
Jan 5
BOS4:36 pmBoston Logan Intl
3h 27m
ORD7:03 pmChicago O'Hare Intl
Jan 7
ORD8:45 amChicago O'Hare Intl
2h 25m
BOS12:10 pmBoston Logan Intl
$142
Find similar
American Airlines
Jan 1
BOS6:36 amBoston Logan Intl
3h 11m
ORD8:47 amChicago O'Hare Intl
Jan 20
ORD7:00 amChicago O'Hare Intl
2h 23m
BOS10:23 amBoston Logan Intl
$152
Find similar
American Airlines
Jan 1
BOS6:36 amBoston Logan Intl
3h 11m
ORD8:47 amChicago O'Hare Intl
Jan 5
ORD8:20 pmChicago O'Hare Intl
2h 31m
BOS11:51 pmBoston Logan Intl
$154
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Maine to Chicago O'Hare Intl 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 December 18, 2025.
Use the filters below to find and compare flights from Maine to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 1/24

6:00 am-10:44 pm

1 stop17h 44m

Chicago O'Hare Intl

Tue 1/27

9:23 am-4:19 pm

1 stop29h 56m

$124

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 1/12

5:23 pm-8:18 am

1 stop15h 55m

Chicago O'Hare Intl

Sat 1/17

4:41 pm-1:13 am

1 stop7h 32m

$125

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 1/31

7:00 am-7:41 pm

1 stop13h 41m

Chicago O'Hare Intl

Mon 2/2

12:44 pm-11:19 pm

1 stop9h 35m

$126

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/28

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Sun 2/1

7:45 am-11:10 am

Nonstop2h 25m

$128

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 1/12

7:00 am-7:41 pm

1 stop13h 41m

Chicago O'Hare Intl

Thu 1/15

5:15 am-4:28 pm

1 stop10h 13m

$129

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 1/13

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Tue 1/20

7:45 am-11:10 am

Nonstop2h 25m

$130

BangorChicago

BGR - ORD

BGRORD

Bangor

Mon 1/12

1:07 pm-5:45 pm

1 stop5h 38m

Chicago O'Hare Intl

Tue 1/20

5:20 pm-11:25 pm

1 stop5h 05m

$249

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 1/2

6:46 pm-11:35 pm

1 stop5h 49m

Chicago O'Hare Intl

Wed 1/7

11:00 am-2:39 pm

Nonstop2h 39m

$255

BangorChicago

BGR - ORD

BGRORD

Bangor

Mon 1/12

5:04 am-1:08 pm

2 stops9h 04m

Chicago O'Hare Intl

Tue 1/20

1:58 pm-11:25 pm

2 stops8h 27m

$259

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 1/2

6:46 pm-11:35 pm

1 stop5h 49m

Chicago O'Hare Intl

Wed 1/7

6:00 am-2:31 pm

1 stop7h 31m

$265

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 O'Hare Intl 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 O'Hare Intl Airport?

The month of January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Maine averaging around $214.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $321. This is often the case because there is less demand to fly during this day of the week. 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 $421.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Maine in the evening is the least expensive time of day to depart. momondo users have found prices as low as $271 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $363. 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 O'Hare Intl flight route?

Fly from Portland to Chicago O'Hare Intl for the best Maine - Chicago O'Hare Intl flight prices

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Maine when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $250 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Maine for as low as $207 on momondo.

What cabin class options are available on Maine to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Maine to Chicago O'Hare Intl 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 O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Maine to Chicago O'Hare Intl Airport.

Cheap Maine to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Maine to Chicago O'Hare Intl Airport

Best Price Found

$298

Fastest flight time

2h 44m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Maine in the past 72 hours is $298. The best round-trip flight deal from Maine to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $400.
The fastest flight from Maine to Chicago O'Hare Intl Airport takes 2h 44m
Direct flights go from Maine to Chicago O'Hare Intl Airport every day.
Search flight deals

  • When did momondo last update prices for flights from Maine to Chicago O'Hare Intl Airport?

    Prices for flights from Maine to Chicago O'Hare Intl Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Maine to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Maine to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Maine to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Maine to Chicago O'Hare Intl Airport?

Best airlines flying from Maine to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Maine to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $124Free CancellationRating
7.9
8,005 reviews
Search Delta flights
American AirlinesPriceFrom $209Free CancellationRating
7.2
11,054 reviews
Search American Airlines flights
United AirlinesPriceFrom $229Free CancellationRating
7.4
9,091 reviews
Search United Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Aurora
Elgin
Benton Harbor

Why use momondo?

Why should I use momondo to find a flight deal from Maine to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Maine to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Maine to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Maine which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Maine to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Maine.

I’m not ready to book a flight from Maine to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Maine to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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