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Cheap flights from Maine to Chicago 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 Maine to Chicago departing on 2/5. 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 Maine to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Maine to Chicago 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 Maine to Chicago.

Cheap last minute flights

Planning a quick getaway from Maine to Chicago? 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 Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Maine to Chicago

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

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
6:25 am - 4:10 pmBOS-ORD
10h 45m1 stop
3:14 pm - 11:47 pmORD-BOS
7h 33m1 stop
$92Spirit Airlines
Find Deal
Wed, Feb 5 - Wed, Feb 12
6:25 am - 4:10 pmBOS-ORD
10h 45m1 stop
3:14 pm - 11:47 pmORD-BOS
7h 33m1 stop
$93Spirit Airlines
Find Deal
Wed, Feb 5 - Wed, Feb 12
6:00 am - 2:25 pmBOS-ORD
9h 25m1 stop
5:45 am - 9:03 amORD-BOS
2h 18mnonstop
Wed, Feb 26 - Wed, Mar 5
11:31 am - 11:32 pmBOS-ORD
13h 01m1 stop
4:41 pm - 12:39 amORD-BOS
6h 58m1 stop
Wed, Feb 5 - Mon, Feb 10
6:00 am - 10:02 amBOS-MDW
29h 02m1 stop
5:31 pm - 12:39 amMDW-BOS
6h 08m1 stop
$108Frontier
Find Deal
Sat, Jan 25 - Tue, Jan 28
6:00 am - 4:16 pmBOS-MDW
11h 16m1 stop
5:31 pm - 12:39 amMDW-BOS
6h 08m1 stop
$109Frontier
Find Deal
Tue, Feb 4 - Tue, Feb 11
5:40 pm - 7:30 pmBOS-MDW
2h 50mnonstop
10:05 am - 1:20 pmMDW-BOS
2h 15mnonstop
$137Southwest
Find Deal
Mon, Jan 27 - Thu, Jan 30
8:20 pm - 10:19 pmBOS-ORD
2h 59mnonstop
7:10 am - 10:43 amORD-BOS
2h 33mnonstop
$137Delta
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Wed, Feb 26 - Wed, Mar 5
5:40 pm - 7:30 pmBOS-MDW
2h 50mnonstop
6:25 pm - 9:40 pmMDW-BOS
2h 15mnonstop
$147Southwest
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Fri, Jan 31 - Mon, Feb 3
11:45 am - 1:46 pmBOS-ORD
3h 01mnonstop
7:10 am - 10:43 amORD-BOS
2h 33mnonstop
$147Delta
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Fri, Feb 7 - Mon, Feb 10
11:31 am - 8:13 pmBOS-ORD
9h 42m1 stop
$45Spirit Airlines
Find Deal
Wed, Feb 5
11:31 am - 8:13 pmBOS-ORD
9h 42m1 stop
$46Spirit Airlines
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Tue, Feb 11
5:10 am - 11:34 amBOS-MDW
7h 24m1 stop
$55Frontier
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Mon, Mar 10
6:00 am - 1:34 pmBOS-ORD
8h 34m1 stop
$55Frontier
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Tue, Jan 14
5:50 am - 7:30 amBOS-MDW
2h 40mnonstop
$69Southwest
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Tue, Apr 8
6:10 am - 8:14 amBOS-ORD
3h 04mnonstop
$69JetBlue
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Wed, Jan 15
8:20 pm - 10:23 pmBOS-ORD
3h 03mnonstop
$78Delta
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Mon, Jan 13
7:00 am - 8:55 amBOS-MDW
2h 55mnonstop
$79Southwest
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Fri, Feb 7
6:10 am - 12:27 pmPWM-ORD
7h 17m1 stop
$82JetBlue
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Tue, Apr 8
5:27 am - 9:55 amPWM-ORD
5h 28m1 stop
$115Delta
Find Deal
Mon, Feb 10
6:00 am - 9:55 amBOS-MDW
28h 55m1 stop
5:31 pm - 12:39 amMDW-BOS
6h 08m1 stop
$111Frontier
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Sat, Jan 11 - Tue, Feb 11
6:00 am - 9:54 amBOS-ORD
28h 54m1 stop
2:59 pm - 12:39 amORD-BOS
8h 40m1 stop
$112Frontier
Find Deal
Sat, Jan 11 - Tue, Feb 11
6:00 am - 9:54 amBOS-ORD
28h 54m1 stop
12:25 pm - 10:00 pmORD-BOS
8h 35m1 stop
Sat, Jan 11 - Sat, Jan 25
3:52 pm - 5:59 pmBOS-ORD
3h 07mnonstop
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
$137JetBlue
Find Deal
Sat, Jan 11 - Mon, Jan 13
7:00 am - 9:00 amBOS-ORD
3h 00mnonstop
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
$138JetBlue
Find Deal
Sat, Jan 11 - Mon, Jan 13
6:00 am - 9:54 amBOS-ORD
28h 54m1 stop
12:25 pm - 11:35 pmORD-BOS
10h 10m1 stop
Sat, Jan 11 - Mon, Jan 13
9:30 am - 11:28 amBOS-ORD
2h 58mnonstop
9:10 am - 3:41 pmORD-BOS
5h 31m1 stop
$157United Airlines
Find Deal
Sat, Jan 11 - Tue, Feb 11
5:01 pm - 6:55 pmBOS-ORD
2h 54mnonstop
3:35 pm - 11:59 pmORD-BOS
7h 24m1 stop
$167United Airlines
Find Deal
Sat, Jan 11 - Sat, Jan 25
6:00 am - 8:08 amBOS-ORD
3h 08mnonstop
11:06 am - 4:49 pmORD-BOS
4h 43m1 stop
$202American Airlines
Find Deal
Sat, Jan 11 - Tue, Jan 14
3:40 pm - 7:24 pmBOS-ORD
4h 44m1 stop
6:45 pm - 10:12 pmORD-BOS
2h 27mnonstop
$204American Airlines
Find Deal
Sat, Jan 11 - Mon, Jan 13
8:10 am - 10:05 amBOS-MDW
2h 55mnonstop
10:05 am - 1:20 pmMDW-BOS
2h 15mnonstop
$137Southwest
Find Deal
Mon, Jan 27 - Thu, Jan 30
3:30 pm - 5:32 pmBOS-ORD
3h 02mnonstop
10:40 am - 2:09 pmORD-BOS
2h 29mnonstop
$137Delta
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Thu, Feb 6 - Sat, Feb 8
7:15 am - 9:25 amBOS-ORD
3h 10mnonstop
7:10 am - 10:47 amORD-BOS
2h 37mnonstop
$145Delta
Find Deal
Mon, Jan 20 - Thu, Jan 23
5:40 pm - 7:30 pmBOS-MDW
2h 50mnonstop
6:25 pm - 9:40 pmMDW-BOS
2h 15mnonstop
$147Southwest
Find Deal
Fri, Jan 31 - Mon, Feb 3
6:10 am - 8:14 amBOS-ORD
3h 04mnonstop
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
$148JetBlue
Find Deal
Thu, Jan 30 - Sun, Feb 2
8:10 am - 10:12 amBOS-ORD
3h 02mnonstop
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
$163JetBlue
Find Deal
Sun, Jan 19 - Wed, Jan 22
6:00 am - 8:08 amBOS-ORD
3h 08mnonstop
8:05 am - 11:26 amORD-BOS
2h 21mnonstop
$167American Airlines
Find Deal
Sat, Jan 18 - Mon, Jan 20
9:20 am - 11:22 amBOS-ORD
3h 02mnonstop
9:30 pm - 12:50 amORD-BOS
2h 20mnonstop
$176United Airlines
Find Deal
Thu, Mar 20 - Mon, Mar 24
12:18 pm - 2:20 pmBOS-ORD
3h 02mnonstop
9:30 pm - 12:50 amORD-BOS
2h 20mnonstop
$185United Airlines
Find Deal
Fri, Mar 21 - Mon, Mar 24
5:14 am - 7:15 amBOS-ORD
3h 01mnonstop
8:05 am - 11:19 amORD-BOS
2h 14mnonstop
$189American Airlines
Find Deal
Fri, Feb 21 - Fri, Feb 28

Spirit Airlines flights from Maine to Chicago

Our best Spirit Airlines deals on Maine to Chicago flight tickets
Spirit Airlines
Feb 5
BOS6:25 amBoston Logan Intl
10h 45m
1 stop
ORD4:10 pmChicago O'Hare Intl
Feb 12
ORD3:14 pmChicago O'Hare Intl
7h 33m
1 stop
BOS11:47 pmBoston Logan Intl
Spirit Airlines
Feb 5
BOS6:25 amBoston Logan Intl
10h 45m
1 stop
ORD4:10 pmChicago O'Hare Intl
Feb 12
ORD3:14 pmChicago O'Hare Intl
7h 33m
1 stop
BOS11:47 pmBoston Logan Intl
Spirit Airlines
Feb 5
BOS11:31 amBoston Logan Intl
13h 01m
1 stop
ORD11:32 pmChicago O'Hare Intl
Feb 11
ORD8:00 amChicago O'Hare Intl
9h 03m
1 stop
BOS6:03 pmBoston Logan Intl

Delta flights from Maine to Chicago

Our best Delta deals on Maine to Chicago flight tickets
Delta
Feb 26
BOS8:20 pmBoston Logan Intl
2h 59m
ORD10:19 pmChicago O'Hare Intl
Mar 5
ORD7:10 amChicago O'Hare Intl
2h 33m
BOS10:43 amBoston Logan Intl
Delta
Feb 7
BOS11:45 amBoston Logan Intl
3h 01m
ORD1:46 pmChicago O'Hare Intl
Feb 10
ORD7:10 amChicago O'Hare Intl
2h 33m
BOS10:43 amBoston Logan Intl
Delta
Jan 28
BOS3:30 pmBoston Logan Intl
3h 06m
ORD5:36 pmChicago O'Hare Intl
Jan 29
ORD2:35 pmChicago O'Hare Intl
2h 35m
BOS6:10 pmBoston Logan Intl

See travel insights to Chicago from

How to get the cheapest flight ticket from Maine to Chicago

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?

The month of September is, on average, the cheapest month to fly to Chicago from Maine, with most prices found around $291. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Maine to Chicago during August average around $309.

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

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $322. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Maine to Chicago for around $441.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Maine to Chicago during this time can be as low as $128. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $361.

What is the cheapest Maine to Chicago flight route?

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

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

The best time to book a flight to Chicago from Maine is 57 days out, which is when prices tend to be around $399. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $94.

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

There are 4 cabin classes available to choose from on Maine to Chicago 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 flights?

You could potentially save up to 34% on your flight if you consider stops on a Maine to Chicago flight.

Cheap Maine to Chicago flight deals and tips

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

Best Price Found

$45

Fastest flight time

2h 35m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Maine in the past 72 hours is $45. The best round-trip flight deal from Maine to Chicago found on momondo in the last 72 hours is $92.
The fastest flight from Maine to Chicago takes 2h 35m
Direct flights go from Maine to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

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

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

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

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

    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 Maine to Chicago.

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

    The travel and health documents required for your trip to Chicago 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 Chicago. 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 Maine to Chicago?


Best airlines flying from Maine to Chicago

Compare and see reviews for airlines that fly from Maine to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $38Free CancellationRating
6.0
3,429 reviews
Search Frontier flights
American AirlinesPriceFrom $158Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $201Free CancellationRating
8.0
8,503 reviews
Search Delta flights
United AirlinesPriceFrom $208Free CancellationRating
7.4
8,934 reviews
Search United Airlines flights
SouthwestPriceFrom $281Free CancellationRating
8.1
4,652 reviews
Search Southwest flights

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Maine to Chicago. momondo saves you time and could save you money on your trip.

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?

momondo provides multiple filters to help you find the best flight to Chicago from Maine. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Maine and alert you when they change.


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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago