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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 4/11. 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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Find the cheapest flights from Chicago to Maine

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Maine.
United Airlines Logo
7:10 am - 10:38 amORD-BOS
2h 28mnonstop
United Airlines Logo
7:43 am - 9:40 amBOS-ORD
2h 57mnonstop
$97United Airlines
Find Deal
Mon, Apr 14 - Wed, Apr 16
United Airlines Logo
9:31 pm - 12:59 amORD-BOS
2h 28mnonstop
United Airlines Logo
9:54 am - 11:51 amBOS-ORD
2h 57mnonstop
$107United Airlines
Find Deal
Sun, Apr 20 - Wed, May 7
American Airlines Logo
11:50 am - 3:22 pmORD-BOS
2h 32mnonstop
American Airlines Logo
5:38 pm - 7:36 pmBOS-ORD
2h 58mnonstop
$113American Airlines
Find Deal
Sat, May 10 - Sat, May 10
Southwest Logo
6:25 pm - 9:45 pmMDW-BOS
2h 20mnonstop
Southwest Logo
7:40 am - 9:15 amBOS-MDW
2h 35mnonstop
$117Southwest
Find Deal
Tue, May 6 - Sun, May 11
American Airlines Logo
8:21 am - 11:43 amORD-BOS
2h 22mnonstop
American Airlines Logo
8:51 pm - 10:52 pmBOS-ORD
3h 01mnonstop
$118American Airlines
Find Deal
Tue, May 13 - Sat, May 17
Southwest Logo
2:40 pm - 10:30 pmMDW-BOS
6h 50m1 stop
Southwest Logo
5:00 am - 10:35 amBOS-MDW
6h 35m1 stop
$126Southwest
Find Deal
Tue, Apr 22 - Thu, Apr 24
Delta Logo
7:05 am - 10:34 amORD-BOS
2h 29mnonstop
Delta Logo
7:00 am - 8:59 amBOS-ORD
2h 59mnonstop
$177Delta
Find Deal
Sat, Jul 5 - Wed, Jul 16
Frontier Logo
4:15 pm - 8:40 pmORD-PWM
27h 25m1 stop
Frontier Logo
7:30 pm - 11:32 pmPWM-ORD
29h 02m1 stop
$200Frontier
Find Deal
Sun, May 4 - Sat, May 10
Frontier Logo
4:00 pm - 9:34 amMDW-BOS
16h 34m1 stop
Frontier Logo
12:58 pm - 11:47 pmBOS-MDW
11h 49m1 stop
$200Frontier
Find Deal
Thu, May 8 - Mon, May 12
Delta Logo
1:45 pm - 11:21 pmORD-PWM
8h 36m2 stops
Delta Logo
1:30 pm - 9:20 pmPWM-ORD
8h 50m1 stop
$222Delta
Find Deal
Wed, May 28 - Fri, May 30

United Airlines flights from Chicago to Maine

Our best United Airlines deals on Chicago to Maine flight tickets
United Airlines
Apr 14
ORD7:10 amChicago O'Hare Intl
2h 28m
BOS10:38 amBoston Logan Intl
Apr 16
BOS7:43 amBoston Logan Intl
2h 57m
ORD9:40 amChicago O'Hare Intl
United Airlines
Apr 20
ORD9:31 pmChicago O'Hare Intl
2h 28m
BOS12:59 amBoston Logan Intl
May 7
BOS9:54 amBoston Logan Intl
2h 57m
ORD11:51 amChicago O'Hare Intl
United Airlines
Sep 4
ORD7:35 amChicago O'Hare Intl
2h 31m
BOS11:06 amBoston Logan Intl
Sep 8
BOS7:30 pmBoston Logan Intl
5h 12m
1 stop
ORD11:42 pmChicago O'Hare Intl

JetBlue flights from Chicago to Maine

Our best JetBlue deals on Chicago to Maine flight tickets
JetBlue
May 6
ORD7:31 pmChicago O'Hare Intl
2h 29m
BOS11:00 pmBoston Logan Intl
May 8
BOS6:00 amBoston Logan Intl
3h 00m
ORD8:00 amChicago O'Hare Intl
JetBlue
Apr 12
ORD8:29 pmChicago O'Hare Intl
2h 29m
BOS11:58 pmBoston Logan Intl
Apr 14
BOS5:15 pmBoston Logan Intl
3h 12m
ORD7:27 pmChicago O'Hare Intl
JetBlue
May 13
ORD6:15 amChicago O'Hare Intl
5h 56m
1 stop
BOS1:11 pmBoston Logan Intl
May 13
BOS4:30 pmBoston Logan Intl
3h 06m
ORD6:36 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 February. Flight prices, which tend to average around $285, 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 February, then flying in June is also cheap. Prices for this month can be found on momondo for an average of $301.

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 $192. Flights from Chicago to Maine on a Friday will generally be more expensive and average around $395. 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 $208. Flights in the morning are often more expensive with an average ticket price of $381.

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?

You are more likely to see cheaper flights to Maine from Chicago when booking 7 weeks ahead of your departure date. In general, you can expect to find flights to Maine for around $390 when searching 7 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 $239 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

$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
5.9
3,276 reviews
Search Frontier flights
American AirlinesPriceFrom $179Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $191Free CancellationRating
8.0
4,276 reviews
Search Southwest flights
DeltaPriceFrom $217Free CancellationRating
8.0
7,897 reviews
Search Delta flights
United AirlinesPriceFrom $218Free CancellationRating
7.4
8,619 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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Wed 4/9
Wed 4/16

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Popular cities in Maine

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