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Cheap flights from Chicago to Maine from $49

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 2/26. 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 to Maine

The cheapest plane tickets to Maine found on KAYAK recently.
4:20 pm - 12:31 amMDW-BOS
7h 11m1 stop
6:00 am - 3:12 pmBOS-MDW
10h 12m1 stop
$97Frontier
Find Deal
Wed, Feb 12 - Tue, Feb 25
4:20 pm - 12:31 amMDW-BOS
7h 11m1 stop
6:00 am - 3:12 pmBOS-MDW
10h 12m1 stop
$101Frontier
Find Deal
Wed, Feb 12 - Tue, Feb 25
7:10 am - 10:47 amORD-BOS
2h 37mnonstop
3:30 pm - 5:36 pmBOS-ORD
3h 06mnonstop
$155Delta
Find Deal
Sun, Jan 26 - Fri, Jan 31
7:10 am - 10:47 amORD-BOS
2h 37mnonstop
7:15 am - 9:25 amBOS-ORD
3h 10mnonstop
$157Delta
Find Deal
Thu, Jan 23 - Sun, Jan 26
7:00 pm - 10:15 pmMDW-BOS
2h 15mnonstop
5:40 pm - 7:30 pmBOS-MDW
2h 50mnonstop
$158Southwest
Find Deal
Thu, Jan 16 - Sun, Jan 19
10:05 am - 1:20 pmMDW-BOS
2h 15mnonstop
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
$168Southwest
Find Deal
Thu, Jan 9 - Tue, Jan 21
4:08 pm - 9:36 pmORD-BOS
4h 28m1 stop
6:00 am - 10:44 amBOS-ORD
5h 44m1 stop
$176United Airlines
Find Deal
Sat, Jan 18 - Sun, Jan 19
6:45 pm - 10:12 pmORD-BOS
2h 27mnonstop
6:34 am - 8:39 amBOS-ORD
3h 05mnonstop
$181American Airlines
Find Deal
Mon, Feb 10 - Mon, Feb 17
7:40 am - 11:00 amORD-BOS
2h 20mnonstop
3:00 pm - 5:04 pmBOS-ORD
3h 04mnonstop
$183American Airlines
Find Deal
Sat, Feb 15 - Tue, Feb 18
6:00 am - 2:07 pmORD-BOS
7h 07m1 stop
7:28 pm - 11:15 pmBOS-ORD
4h 47m1 stop
$196United Airlines
Find Deal
Wed, Jan 8 - Wed, Jan 8
4:20 pm - 12:31 amMDW-BOS
7h 11m1 stop
$49Frontier
Find Deal
Wed, Feb 26
5:31 pm - 12:39 amMDW-BOS
6h 08m1 stop
$52Frontier
Find Deal
Tue, Feb 11
9:00 am - 12:15 pmMDW-BOS
2h 15mnonstop
$79Southwest
Find Deal
Sat, Jan 18
4:08 pm - 9:36 pmORD-BOS
4h 28m1 stop
$88United Airlines
Find Deal
Sat, Jan 18
7:00 am - 10:25 amORD-BOS
2h 25mnonstop
$89Delta
Find Deal
Tue, Mar 25
6:25 pm - 9:40 pmMDW-BOS
2h 15mnonstop
$89Southwest
Find Deal
Tue, Feb 25
6:18 pm - 11:50 pmORD-BOS
4h 32m1 stop
$98United Airlines
Find Deal
Fri, Mar 7
7:10 am - 10:43 amORD-BOS
2h 33mnonstop
$109Delta
Find Deal
Mon, Feb 24
6:39 pm - 12:38 amORD-BOS
4h 59m1 stop
$133American Airlines
Find Deal
Fri, Jan 3
6:07 am - 2:03 pmORD-PWM
6h 56m1 stop
$139American Airlines
Find Deal
Thu, Apr 10
2:00 pm - 9:12 pmORD-BOS
6h 12m1 stop
6:45 am - 8:49 amBOS-ORD
3h 04mnonstop
$228American Airlines
Find Deal
Sun, Dec 29 - Wed, Jan 1
4:20 pm - 9:12 pmORD-BOS
3h 52m1 stop
5:15 am - 7:19 amBOS-ORD
3h 04mnonstop
$257American Airlines
Find Deal
Sun, Dec 29 - Thu, Jan 2
7:35 am - 11:03 amORD-BOS
2h 28mnonstop
11:45 am - 1:50 pmBOS-ORD
3h 05mnonstop
$287Delta
Find Deal
Wed, Dec 25 - Tue, Jan 7
10:15 pm - 7:33 amORD-BOS
8h 18m1 stop
12:59 pm - 10:47 pmBOS-ORD
10h 48m1 stop
$308Frontier
Find Deal
Thu, Dec 26 - Wed, Jan 1
9:30 pm - 12:54 amORD-BOS
2h 24mnonstop
6:02 am - 8:05 amBOS-ORD
3h 03mnonstop
$314United Airlines
Find Deal
Wed, Dec 25 - Tue, Dec 31
9:30 pm - 12:54 amORD-BOS
2h 24mnonstop
6:02 am - 8:00 amBOS-ORD
2h 58mnonstop
$321United Airlines
Find Deal
Thu, Dec 26 - Sun, Dec 29
7:35 am - 11:03 amORD-BOS
2h 28mnonstop
7:40 pm - 9:41 pmBOS-ORD
3h 01mnonstop
$322Delta
Find Deal
Wed, Dec 25 - Thu, Jan 2
6:50 pm - 12:25 amMDW-BOS
4h 35m1 stop
6:25 am - 8:15 amBOS-MDW
2h 50mnonstop
$322Southwest
Find Deal
Sat, Dec 28 - Thu, Jan 2
6:25 am - 9:40 amMDW-BOS
2h 15mnonstop
7:55 pm - 9:40 pmBOS-MDW
2h 45mnonstop
$323Southwest
Find Deal
Thu, Dec 26 - Fri, Jan 3
10:14 pm - 7:33 amORD-BOS
8h 19m1 stop
12:59 pm - 10:47 pmBOS-ORD
10h 48m1 stop
$393Frontier
Find Deal
Sun, Dec 29 - Wed, Jan 1
7:10 am - 10:47 amORD-BOS
2h 37mnonstop
3:30 pm - 5:36 pmBOS-ORD
3h 06mnonstop
$155Delta
Find Deal
Sun, Jan 26 - Fri, Jan 31
2:51 pm - 6:17 pmORD-BOS
2h 26mnonstop
7:47 pm - 9:56 pmBOS-ORD
3h 09mnonstop
$156American Airlines
Find Deal
Tue, Feb 4 - Tue, Feb 11
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
3:52 pm - 5:55 pmBOS-ORD
3h 03mnonstop
$157JetBlue
Find Deal
Tue, Feb 4 - Mon, Feb 10
7:00 pm - 10:15 pmMDW-BOS
2h 15mnonstop
5:40 pm - 7:30 pmBOS-MDW
2h 50mnonstop
$158Southwest
Find Deal
Thu, Jan 16 - Sun, Jan 19
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
6:10 am - 8:14 amBOS-ORD
3h 04mnonstop
$158JetBlue
Find Deal
Thu, Jan 16 - Sun, Jan 19
6:30 am - 10:03 amORD-BOS
2h 33mnonstop
6:00 am - 8:08 amBOS-ORD
3h 08mnonstop
$159American Airlines
Find Deal
Thu, Jan 16 - Sun, Jan 19
7:10 am - 10:47 amORD-BOS
2h 37mnonstop
7:15 am - 9:25 amBOS-ORD
3h 10mnonstop
$165Delta
Find Deal
Sun, Jan 12 - Thu, Jan 16
10:05 am - 1:20 pmMDW-BOS
2h 15mnonstop
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
$168Southwest
Find Deal
Thu, Jan 9 - Tue, Jan 21
7:30 am - 10:56 amORD-BOS
2h 26mnonstop
12:12 pm - 2:10 pmBOS-ORD
2h 58mnonstop
$191United Airlines
Find Deal
Mon, Jan 20 - Mon, Jan 27
9:37 pm - 1:09 amORD-BOS
2h 32mnonstop
9:31 pm - 11:15 pmBOS-ORD
2h 44mnonstop
$222United Airlines
Find Deal
Fri, May 23 - Tue, May 27

Delta flights from Chicago to Maine

Our best Delta deals on Chicago to Maine flight tickets
Delta
Jan 26
ORD7:10 amChicago O'Hare Intl
2h 37m
BOS10:47 amBoston Logan Intl
Jan 31
BOS3:30 pmBoston Logan Intl
3h 06m
ORD5:36 pmChicago O'Hare Intl
Delta
Jan 23
ORD7:10 amChicago O'Hare Intl
2h 37m
BOS10:47 amBoston Logan Intl
Jan 26
BOS7:15 amBoston Logan Intl
3h 10m
ORD9:25 amChicago O'Hare Intl
Delta
Jan 9
ORD7:10 amChicago O'Hare Intl
2h 37m
BOS10:47 amBoston Logan Intl
Jan 23
BOS8:20 pmBoston Logan Intl
3h 03m
ORD10:23 pmChicago O'Hare Intl

United Airlines flights from Chicago to Maine

Our best United Airlines deals on Chicago to Maine flight tickets
United Airlines
Jan 18
ORD4:08 pmChicago O'Hare Intl
4h 28m
1 stop
BOS9:36 pmBoston Logan Intl
Jan 19
BOS6:00 amBoston Logan Intl
5h 44m
1 stop
ORD10:44 amChicago O'Hare Intl
United Airlines
Jan 8
ORD6:00 amChicago O'Hare Intl
7h 07m
1 stop
BOS2:07 pmBoston Logan Intl
Jan 8
BOS7:28 pmBoston Logan Intl
4h 47m
1 stop
ORD11:15 pmChicago O'Hare Intl
United Airlines
Feb 12
ORD11:10 amChicago O'Hare Intl
2h 32m
PWM2:42 pmPortland
Feb 19
PWM7:15 pmPortland
5h 24m
1 stop
ORD11:39 pmChicago 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 July. Flight prices, which tend to average around $283, 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 July, then flying in June is also cheap. Prices for this month can be found on momondo for an average of $299.

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 $217. Flights from Chicago to Maine on a Wednesday will generally be more expensive and average around $408. 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 $230. Flights in the morning are often more expensive with an average ticket price of $379.

What is the cheapest Chicago to Maine flight route?

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

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

We recommend purchasing flights from Chicago to Maine 49 days ahead of your departure date because this is when momondo users tend to see the best flight rates. On average, our users have found flights to Maine for $396. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $70.

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.

Can stopping save me money on Chicago to Maine flights?

You could potentially save up to 37% on your flight if you consider stops on a Chicago to Maine flight.

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

$49

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 $49. The best round-trip flight deal from Chicago to Maine found on momondo in the last 72 hours is $97.
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
6.1
3,468 reviews
Search Frontier flights
American AirlinesPriceFrom $184Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $196Free CancellationRating
8.0
8,580 reviews
Search Delta flights
United AirlinesPriceFrom $217Free CancellationRating
7.4
9,009 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