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Cheap flights from Chicago to Maine from $45

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Maine departing on 3/4. 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 Chicago to Maine

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Maine that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Maine.

Cheap last minute flights

Planning a quick getaway from Chicago to Maine? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Maine, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Maine

Find recent round-trip train or bus tickets from Chicago to Maine.

All round-trip flight deals from Chicago to Maine

The cheapest plane tickets from Chicago to Maine found on KAYAK recently.
2:59 pm - 12:39 amORD-BOS
8h 40m1 stop
6:00 am - 12:45 pmBOS-ORD
7h 45m1 stop
$109Frontier
Find Deal
Tue, Feb 4 - Wed, Feb 5
11:33 am - 12:27 amMDW-BOS
11h 54m1 stop
6:00 am - 4:16 pmBOS-MDW
11h 16m1 stop
$109Frontier
Find Deal
Mon, Feb 10 - Tue, Feb 11
7:10 am - 10:43 amORD-BOS
2h 33mnonstop
3:30 pm - 5:32 pmBOS-ORD
3h 02mnonstop
$157Delta
Find Deal
Thu, Feb 20 - Tue, Feb 25
8:05 am - 11:20 amMDW-BOS
2h 15mnonstop
6:50 am - 8:45 amBOS-MDW
2h 55mnonstop
$157Southwest
Find Deal
Sun, Feb 16 - Sun, Feb 23
7:10 am - 10:43 amORD-BOS
2h 33mnonstop
3:20 pm - 5:19 pmBOS-ORD
2h 59mnonstop
$167Delta
Find Deal
Wed, Feb 26 - Wed, Apr 2
7:40 am - 11:00 amORD-BOS
2h 20mnonstop
5:15 am - 7:14 amBOS-ORD
2h 59mnonstop
$176American Airlines
Find Deal
Sat, Mar 1 - Mon, Mar 10
8:35 pm - 11:50 pmMDW-BOS
2h 15mnonstop
6:00 am - 7:50 amBOS-MDW
2h 50mnonstop
$177Southwest
Find Deal
Fri, Mar 7 - Sun, Mar 9
8:09 am - 11:22 amORD-BOS
2h 13mnonstop
1:40 pm - 3:40 pmBOS-ORD
3h 00mnonstop
$179American Airlines
Find Deal
Sat, Mar 8 - Sat, Mar 15
7:30 am - 10:56 amORD-BOS
2h 26mnonstop
6:00 am - 8:03 amBOS-ORD
3h 03mnonstop
$212United Airlines
Find Deal
Tue, Feb 4 - Sun, Feb 9
11:10 am - 2:42 pmORD-PWM
2h 32mnonstop
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
$219United Airlines
Find Deal
Wed, Feb 5 - Wed, Feb 12
7:10 am - 3:46 pmORD-BOS
7h 36m1 stop
$45Spirit Airlines
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Tue, Mar 4
4:40 pm - 12:47 amMDW-BOS
7h 07m1 stop
$50Frontier
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Tue, Apr 15
7:10 am - 10:43 amORD-BOS
2h 33mnonstop
$79Delta
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Mon, Feb 17
8:05 am - 11:20 amMDW-BOS
2h 15mnonstop
$79Southwest
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Sun, Feb 16
6:55 pm - 10:26 pmORD-BOS
2h 31mnonstop
$89Delta
Find Deal
Fri, Apr 4
8:40 am - 11:55 amMDW-BOS
2h 15mnonstop
$89Southwest
Find Deal
Mon, Mar 3
9:20 pm - 12:45 amORD-BOS
2h 25mnonstop
$100United Airlines
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Fri, May 2
7:00 am - 10:20 amORD-BOS
2h 20mnonstop
$109American Airlines
Find Deal
Sun, Mar 2
6:00 am - 12:45 pmORD-BOS
5h 45m1 stop
$114United Airlines
Find Deal
Fri, Mar 14
8:05 am - 11:26 amORD-BOS
2h 21mnonstop
$120American Airlines
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Sun, May 4
2:59 pm - 12:39 amORD-BOS
8h 40m1 stop
6:00 am - 9:52 amBOS-ORD
28h 52m1 stop
$120Frontier
Find Deal
Tue, Jan 28 - Sat, Feb 1
12:25 pm - 11:35 pmORD-BOS
10h 10m1 stop
6:00 am - 12:45 pmBOS-ORD
7h 45m1 stop
Fri, Jan 24 - Wed, Jan 29
6:25 pm - 9:40 pmMDW-BOS
2h 15mnonstop
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
$273Southwest
Find Deal
Mon, Jan 27 - Thu, Jan 30
10:00 am - 5:50 pmMDW-BOS
6h 50m2 stops
5:40 pm - 7:30 pmBOS-MDW
2h 50mnonstop
$275Southwest
Find Deal
Sun, Jan 26 - Wed, Jan 29
6:35 pm - 12:58 amORD-BOS
5h 23m1 stop
7:15 am - 9:25 amBOS-ORD
3h 10mnonstop
$332Delta
Find Deal
Fri, Jan 24 - Sun, Feb 2
3:00 pm - 6:35 pmORD-BOS
2h 35mnonstop
7:15 am - 9:25 amBOS-ORD
3h 10mnonstop
$347Delta
Find Deal
Sat, Jan 25 - Sun, Jan 26
6:00 am - 12:29 pmORD-BOS
5h 29m1 stop
9:26 am - 2:15 pmBOS-ORD
5h 49m1 stop
$354American Airlines
Find Deal
Mon, Jan 27 - Wed, Jan 29
2:20 pm - 10:30 pmORD-PWM
7h 10m1 stop
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
$419United Airlines
Find Deal
Sat, Jan 25 - Mon, Jan 27
3:15 pm - 10:30 pmORD-PWM
6h 15m1 stop
4:10 pm - 6:24 pmPWM-ORD
3h 14mnonstop
$529United Airlines
Find Deal
Fri, Jan 24 - Sun, Feb 2
6:00 am - 12:05 pmORD-BGR
5h 05m1 stop
5:08 am - 10:47 amBGR-ORD
6h 39m1 stop
$753American Airlines
Find Deal
Sun, Jan 26 - Wed, Jan 29
7:10 am - 10:43 amORD-BOS
2h 33mnonstop
3:30 pm - 5:32 pmBOS-ORD
3h 02mnonstop
$157Delta
Find Deal
Thu, Feb 20 - Tue, Feb 25
8:05 am - 11:20 amMDW-BOS
2h 15mnonstop
6:50 am - 8:45 amBOS-MDW
2h 55mnonstop
$157Southwest
Find Deal
Sun, Feb 16 - Sun, Feb 23
7:00 am - 10:20 amORD-BOS
2h 20mnonstop
1:15 pm - 3:17 pmBOS-ORD
3h 02mnonstop
$158American Airlines
Find Deal
Thu, Feb 20 - Sun, Feb 23
7:00 am - 10:20 amORD-BOS
2h 20mnonstop
6:34 am - 8:39 amBOS-ORD
3h 05mnonstop
$159American Airlines
Find Deal
Thu, Feb 20 - Sun, Feb 23
12:50 pm - 4:13 pmORD-BOS
2h 23mnonstop
2:00 pm - 4:05 pmBOS-ORD
3h 05mnonstop
$167JetBlue
Find Deal
Fri, Feb 28 - Sat, Mar 1
8:05 am - 11:19 amORD-BOS
2h 14mnonstop
5:14 am - 7:15 amBOS-ORD
3h 01mnonstop
$168American Airlines
Find Deal
Thu, Feb 20 - Sun, Feb 23
7:40 am - 11:00 amORD-BOS
2h 20mnonstop
5:15 am - 7:14 amBOS-ORD
2h 59mnonstop
$176American Airlines
Find Deal
Sat, Mar 1 - Mon, Mar 10
6:13 pm - 9:37 pmORD-BOS
2h 24mnonstop
6:00 am - 8:04 amBOS-ORD
3h 04mnonstop
$188United Airlines
Find Deal
Wed, Mar 12 - Sun, Mar 16
1:15 pm - 4:39 pmORD-BOS
2h 24mnonstop
10:05 am - 12:05 pmBOS-ORD
3h 00mnonstop
$192JetBlue
Find Deal
Thu, Mar 13 - Mon, Mar 17
6:30 pm - 9:59 pmORD-BOS
2h 29mnonstop
4:23 pm - 6:25 pmBOS-ORD
3h 02mnonstop
$202United Airlines
Find Deal
Tue, Feb 4 - Thu, Feb 20

Frontier flights from Chicago to Maine

Our best Frontier deals on Chicago to Maine flight tickets
Frontier
Feb 4
ORD2:59 pmChicago O'Hare Intl
8h 40m
1 stop
BOS12:39 amBoston Logan Intl
Feb 5
BOS6:00 amBoston Logan Intl
7h 45m
1 stop
ORD12:45 pmChicago O'Hare Intl
Frontier
Feb 5
ORD1:45 pmChicago O'Hare Intl
9h 54m
1 stop
BOS12:39 amBoston Logan Intl
Feb 12
BOS6:00 amBoston Logan Intl
9h 25m
1 stop
ORD2:25 pmChicago O'Hare Intl
Frontier
Jan 29
ORD1:45 pmChicago O'Hare Intl
9h 54m
1 stop
BOS12:39 amBoston Logan Intl
Feb 5
BOS6:00 amBoston Logan Intl
7h 45m
1 stop
ORD12:45 pmChicago O'Hare Intl

Spirit Airlines flights from Chicago to Maine

Our best Spirit Airlines deals on Chicago to Maine flight tickets
Spirit Airlines
Mar 5
ORD6:45 amChicago O'Hare Intl
8h 25m
1 stop
BOS4:10 pmBoston Logan Intl
Mar 11
BOS11:14 amBoston Logan Intl
13h 53m
1 stop
ORD12:07 amChicago O'Hare Intl
Spirit Airlines
May 7
ORD6:15 amChicago O'Hare Intl
10h 25m
1 stop
BOS5:40 pmBoston Logan Intl
May 10
BOS6:00 amBoston Logan Intl
17h 21m
1 stop
ORD10:21 pmChicago O'Hare Intl
Spirit Airlines
Mar 19
ORD7:07 pmChicago O'Hare Intl
21h 07m
1 stop
BOS5:14 pmBoston Logan Intl
Mar 25
BOS6:09 pmBoston Logan Intl
16h 35m
1 stop
ORD9:44 amChicago O'Hare Intl

See travel insights to Maine from

How to get the cheapest flight ticket from Chicago to Maine

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 Maine?

The cheapest month to fly to Maine from Chicago is in June. Flight prices, which tend to average around $293, are often lower during this time because this is during the off-season. If you aren’t able to travel to Maine during the month of June, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $304.

What is the cheapest day to depart on your flight to Maine?

The cheapest day to depart from Chicago to Maine is on a Tuesday. Travelers who choose to depart for Maine on a Tuesday will often find tickets for as low as $199. Flights from Chicago to Maine on a Friday will generally be more expensive and average around $402. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Maine?

The cheapest time of day to fly to Maine is in the afternoon when flights can be purchased for as low as $212. Flights in the morning are often more expensive with an average ticket price of $393.

What is the cheapest Chicago to Maine flight route?

Fly from Chicago Midway to Portland for the best Chicago - Maine flight prices

How far in advance should I book a flight to Maine?

You are more likely to see cheaper flights to Maine from Chicago when booking 13 weeks ahead of your departure date. In general, you can expect to find flights to Maine for around $403 when searching 13 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Maine from Chicago for as low as $203 on momondo.

What cabin class options are available on Chicago to Maine flights?

There are 4 cabin classes available to choose from on Chicago to Maine flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Chicago to Maine flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Maine

Best Price Found

$45

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Maine

2 airports
The best one-way flight to Maine from Chicago in the past 72 hours is $45. The best round-trip flight deal from Chicago to Maine found on momondo in the last 72 hours is $109.
The fastest flight from Chicago to Maine takes 2h 10m
Direct flights go from Chicago to Maine every day.
There are 2 airports near Maine: Boston Logan Intl (BOS), Portland (PWM)

  • When did momondo last update prices for flights from Chicago to Maine?

    Prices for flights from Chicago to Maine were last updated today.

  • How many operators does momondo search for flights from Chicago to Maine?

  • How old do you have to be to fly from Chicago to Maine?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Maine.

  • What documentation or ID do you need to fly to Maine?

    The travel and health documents required for your trip to Maine can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Maine. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Chicago to Maine?


Best airlines flying from Chicago to Maine

Compare and see reviews for airlines that fly from Chicago to Maine with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $38Free CancellationRating
6.0
3,440 reviews
Search Frontier flights
American AirlinesPriceFrom $181Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $191Free CancellationRating
8.1
4,647 reviews
Search Southwest flights
DeltaPriceFrom $196Free CancellationRating
8.0
8,508 reviews
Search Delta flights
United AirlinesPriceFrom $222Free CancellationRating
7.4
8,971 reviews
Search United Airlines flights

Why use momondo?

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

It is quick and easy to find Chicago to Maine flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Maine that suits you.

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

Yes. All flights to Maine from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once all potential Chicago to Maine flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Yes. momondo can track prices for Chicago to Maine flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.


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Popular cities in Maine

Popular flights according to clicks in the last 7 days on momondo