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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 12/17. 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.
9:58 am - 12:38 amORD-BOS
13h 40m1 stop
5:00 am - 4:06 pmBOS-ORD
12h 06m1 stop
$101Spirit Airlines
Find Deal
Tue, Dec 10 - Wed, Dec 11
12:57 pm - 12:30 amMDW-BOS
10h 33m1 stop
5:45 am - 1:24 pmBOS-MDW
8h 39m1 stop
$103Frontier
Find Deal
Wed, Dec 11 - Wed, Dec 18
2:05 pm - 5:34 pmORD-BOS
2h 29mnonstop
7:25 am - 9:28 amBOS-ORD
3h 03mnonstop
$155Delta
Find Deal
Tue, Dec 10 - Thu, Dec 12
8:30 pm - 11:40 pmMDW-BOS
2h 10mnonstop
6:40 am - 8:25 amBOS-MDW
2h 45mnonstop
$158Southwest
Find Deal
Fri, Dec 13 - Sun, Dec 15
1:55 pm - 5:16 pmORD-BOS
2h 21mnonstop
5:45 am - 9:34 amBOS-ORD
4h 49m1 stop
$167United Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
7:35 am - 11:03 amORD-BOS
2h 28mnonstop
3:30 pm - 5:36 pmBOS-ORD
3h 06mnonstop
$173Delta
Find Deal
Wed, Dec 25 - Tue, Jan 7
8:30 pm - 11:40 pmMDW-BOS
2h 10mnonstop
8:15 pm - 10:00 pmBOS-MDW
2h 45mnonstop
$179Southwest
Find Deal
Fri, Dec 13 - Sat, Jan 4
8:30 pm - 12:15 amORD-BOS
2h 45mnonstop
6:00 am - 8:08 amBOS-ORD
3h 08mnonstop
$182American Airlines
Find Deal
Sun, Jan 5 - Fri, Jan 10
8:30 pm - 12:15 amORD-BOS
2h 45mnonstop
2:52 pm - 4:52 pmBOS-ORD
3h 00mnonstop
$183American Airlines
Find Deal
Sun, Jan 5 - Sun, Jan 12
10:55 am - 2:22 pmORD-BOS
2h 27mnonstop
6:02 am - 8:05 amBOS-ORD
3h 03mnonstop
$218United Airlines
Find Deal
Wed, Dec 25 - Sat, Dec 28
9:58 am - 12:38 amORD-BOS
13h 40m1 stop
$45Spirit Airlines
Find Deal
Tue, Dec 17
5:24 pm - 12:30 amMDW-BOS
6h 06m1 stop
$52Frontier
Find Deal
Tue, Jan 14
2:35 pm - 6:10 pmORD-BOS
2h 35mnonstop
$79Delta
Find Deal
Mon, Feb 3
10:05 am - 1:20 pmMDW-BOS
2h 15mnonstop
$79Southwest
Find Deal
Mon, Feb 3
11:53 am - 5:28 pmORD-BOS
4h 35m1 stop
$88United Airlines
Find Deal
Sun, Feb 16
9:30 pm - 12:54 amORD-BOS
2h 24mnonstop
$95United Airlines
Find Deal
Wed, Dec 25
5:40 am - 8:55 amMDW-BOS
2h 15mnonstop
$95Southwest
Find Deal
Thu, Nov 28
2:35 pm - 6:10 pmORD-BOS
2h 35mnonstop
$100Delta
Find Deal
Mon, Jan 6
1:39 pm - 8:32 pmORD-BOS
5h 53m1 stop
$128American Airlines
Find Deal
Fri, Feb 21
5:42 pm - 10:52 pmORD-BOS
4h 10m1 stop
$133American Airlines
Find Deal
Mon, Dec 23
11:51 am - 7:29 pmORD-BOS
6h 38m1 stop
8:54 am - 3:43 pmBOS-ORD
7h 49m1 stop
Tue, Nov 26 - Mon, Dec 9
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
8:54 am - 11:19 pmBOS-ORD
15h 25m1 stop
Mon, Nov 25 - Fri, Dec 6
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
8:10 am - 10:21 amBOS-ORD
3h 11mnonstop
$200Spirit Airlines
Find Deal
Mon, Nov 25 - Tue, Dec 3
11:51 am - 7:29 pmORD-BOS
6h 38m1 stop
8:10 am - 10:21 amBOS-ORD
3h 11mnonstop
$207Spirit Airlines
Find Deal
Tue, Nov 26 - Tue, Dec 3
6:48 pm - 12:31 amMDW-BOS
4h 43m1 stop
6:00 am - 11:42 amBOS-MDW
6h 42m1 stop
$208Frontier
Find Deal
Tue, Nov 26 - Tue, Dec 10
6:48 pm - 12:31 amMDW-BOS
4h 43m1 stop
12:38 pm - 9:02 pmBOS-MDW
9h 24m1 stop
$218Frontier
Find Deal
Tue, Nov 26 - Fri, Dec 6
9:45 am - 1:08 pmORD-BOS
2h 23mnonstop
6:45 am - 8:49 amBOS-ORD
3h 04mnonstop
$277American Airlines
Find Deal
Mon, Nov 25 - Mon, Dec 30
1:25 pm - 4:38 pmORD-BOS
2h 13mnonstop
8:00 am - 12:25 pmBOS-ORD
5h 25m1 stop
$307American Airlines
Find Deal
Sun, Nov 24 - Wed, Nov 27
10:35 am - 2:00 pmORD-BOS
2h 25mnonstop
10:45 am - 12:41 pmBOS-ORD
2h 56mnonstop
$318United Airlines
Find Deal
Tue, Nov 26 - Fri, Nov 29
11:05 am - 2:35 pmORD-PWM
2h 30mnonstop
5:30 am - 9:49 amPWM-ORD
5h 19m1 stop
$419United Airlines
Find Deal
Mon, Nov 25 - Thu, Nov 28
6:30 am - 10:00 amORD-BOS
2h 30mnonstop
11:05 am - 1:00 pmBOS-ORD
2h 55mnonstop
$155Delta
Find Deal
Mon, Dec 9 - Wed, Dec 11
8:50 am - 12:12 pmORD-BOS
2h 22mnonstop
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
$157JetBlue
Find Deal
Thu, Dec 5 - Thu, Dec 12
8:05 am - 11:20 amMDW-BOS
2h 15mnonstop
7:00 am - 8:45 amBOS-MDW
2h 45mnonstop
$158Southwest
Find Deal
Sat, Dec 7 - Thu, Dec 12
6:40 am - 10:00 amORD-BOS
2h 20mnonstop
7:25 am - 9:28 amBOS-ORD
3h 03mnonstop
$158Delta
Find Deal
Thu, Dec 5 - Sun, Dec 8
8:30 pm - 11:40 pmMDW-BOS
2h 10mnonstop
8:15 pm - 10:00 pmBOS-MDW
2h 45mnonstop
$179Southwest
Find Deal
Fri, Dec 13 - Sat, Jan 4
8:30 pm - 12:15 amORD-BOS
2h 45mnonstop
2:52 pm - 4:52 pmBOS-ORD
3h 00mnonstop
$183American Airlines
Find Deal
Sun, Jan 5 - Sun, Jan 12
7:25 am - 10:59 amORD-BOS
2h 34mnonstop
6:45 am - 8:49 amBOS-ORD
3h 04mnonstop
$189American Airlines
Find Deal
Wed, Dec 25 - Wed, Jan 1
1:55 pm - 5:16 pmORD-BOS
2h 21mnonstop
6:02 am - 8:05 amBOS-ORD
3h 03mnonstop
$197United Airlines
Find Deal
Sat, Dec 14 - Sat, Jan 4
9:37 pm - 1:09 amORD-BOS
2h 32mnonstop
6:00 am - 7:50 amBOS-ORD
2h 50mnonstop
$207United Airlines
Find Deal
Mon, Mar 31 - Sun, Apr 6
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
8:10 am - 10:21 amBOS-ORD
3h 11mnonstop
$284Spirit Airlines
Find Deal
Mon, Dec 2 - Tue, Dec 3

Spirit Airlines flights from Chicago to Maine

Our best Spirit Airlines deals on Chicago to Maine flight tickets
Spirit Airlines
Dec 10
ORD9:58 amChicago O'Hare Intl
13h 40m
1 stop
BOS12:38 amBoston Logan Intl
Dec 11
BOS5:00 amBoston Logan Intl
12h 06m
1 stop
ORD4:06 pmChicago O'Hare Intl
Spirit Airlines
Dec 10
ORD9:58 amChicago O'Hare Intl
13h 40m
1 stop
BOS12:38 amBoston Logan Intl
Dec 17
BOS9:57 amBoston Logan Intl
11h 18m
1 stop
ORD8:15 pmChicago O'Hare Intl
Spirit Airlines
Dec 6
ORD11:45 amChicago O'Hare Intl
11h 53m
1 stop
BOS12:38 amBoston Logan Intl
Dec 10
BOS5:00 amBoston Logan Intl
12h 06m
1 stop
ORD4:06 pmChicago O'Hare Intl

Frontier flights from Chicago to Maine

Our best Frontier deals on Chicago to Maine flight tickets
Frontier
Dec 11
MDW12:57 pmChicago Midway
10h 33m
1 stop
BOS12:30 amBoston Logan Intl
Dec 18
BOS5:45 amBoston Logan Intl
8h 39m
1 stop
MDW1:24 pmChicago Midway
Frontier
Dec 10
MDW12:57 pmChicago Midway
10h 33m
1 stop
BOS12:30 amBoston Logan Intl
Dec 11
BOS6:00 amBoston Logan Intl
6h 42m
1 stop
MDW11:42 amChicago Midway
Frontier
Jan 21
MDW5:31 pmChicago Midway
6h 08m
1 stop
BOS12:39 amBoston Logan Intl
Jan 28
BOS6:00 amBoston Logan Intl
11h 16m
1 stop
MDW4:16 pmChicago Midway

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 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 $218. 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 Chicago to Maine flight route?

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

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 38% 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

$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 $101.
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
3,536 reviews
Search Frontier flights
American AirlinesPriceFrom $184Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $196Free CancellationRating
8.0
8,755 reviews
Search Delta flights
United AirlinesPriceFrom $217Free CancellationRating
7.4
9,172 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 flights according to clicks in the last 7 days on momondo