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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 12/10. 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.
6:00 am - 11:42 amBOS-MDW
6h 42m1 stop
2:20 pm - 12:30 amMDW-BOS
9h 10m1 stop
$103Frontier
Find Deal
Wed, Dec 11 - Wed, Dec 18
5:00 am - 4:06 pmBOS-ORD
12h 06m1 stop
5:38 pm - 12:35 amORD-BOS
5h 57m1 stop
Tue, Dec 10 - Tue, Dec 17
12:38 pm - 9:02 pmBOS-MDW
9h 24m1 stop
12:57 pm - 12:30 amMDW-BOS
10h 33m1 stop
$104Frontier
Find Deal
Mon, Dec 9 - Tue, Dec 10
8:54 am - 3:43 pmBOS-ORD
7h 49m1 stop
9:58 am - 12:38 amORD-BOS
13h 40m1 stop
Mon, Dec 9 - Tue, Dec 10
8:10 am - 10:21 amBOS-ORD
3h 11mnonstop
9:58 am - 12:38 amORD-BOS
13h 40m1 stop
$126Spirit Airlines
Find Deal
Tue, Dec 3 - Tue, Dec 10
10:34 am - 9:07 pmBOS-ORD
11h 33m1 stop
8:20 am - 11:42 pmORD-BOS
14h 22m1 stop
$129Spirit Airlines
Find Deal
Tue, Dec 10 - Sat, Dec 14
6:28 pm - 8:24 pmBOS-ORD
2h 56mnonstop
9:20 am - 12:45 pmORD-BOS
2h 25mnonstop
$157United Airlines
Find Deal
Fri, Dec 6 - Sun, Dec 8
6:00 pm - 7:45 pmBOS-MDW
2h 45mnonstop
8:30 am - 11:45 amMDW-BOS
2h 15mnonstop
$158Southwest
Find Deal
Fri, Dec 6 - Wed, Dec 11
7:38 pm - 11:20 pmBOS-ORD
4h 42m1 stop
9:20 am - 12:45 pmORD-BOS
2h 25mnonstop
$167United Airlines
Find Deal
Fri, Dec 6 - Sun, Dec 8
6:40 am - 8:25 amBOS-MDW
2h 45mnonstop
6:25 pm - 9:35 pmMDW-BOS
2h 10mnonstop
$174Southwest
Find Deal
Sun, Nov 24 - Wed, Dec 4
5:00 am - 4:06 pmBOS-ORD
12h 06m1 stop
$45Spirit Airlines
Find Deal
Tue, Dec 10
5:00 am - 4:06 pmBOS-ORD
12h 06m1 stop
$46Spirit Airlines
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Tue, Dec 10
6:00 am - 11:42 amBOS-MDW
6h 42m1 stop
$49Frontier
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Wed, Dec 11
6:00 am - 10:55 amBOS-MDW
5h 55m1 stop
$52Frontier
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Wed, Feb 26
5:40 pm - 7:30 pmBOS-MDW
2h 50mnonstop
$79Southwest
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Wed, Feb 5
7:45 pm - 9:43 pmBOS-ORD
2h 58mnonstop
$79Delta
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Sat, Dec 14
4:50 pm - 10:04 pmPWM-ORD
6h 14m1 stop
$84American Airlines
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Tue, Jan 7
5:10 am - 7:00 amBOS-MDW
2h 50mnonstop
$95Southwest
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Sat, Nov 23
3:45 pm - 5:46 pmBOS-ORD
3h 01mnonstop
$95Delta
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Thu, Nov 21
5:50 am - 12:20 pmPWM-ORD
7h 30m1 stop
$99American Airlines
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Sat, Dec 14
10:55 am - 9:45 pmBOS-ORD
11h 50m1 stop
2:15 pm - 12:29 amORD-BOS
9h 14m1 stop
$124Frontier
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Sat, Nov 16 - Wed, Nov 20
7:40 am - 9:50 amBOS-ORD
3h 10mnonstop
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
$130Spirit Airlines
Find Deal
Tue, Nov 19 - Sun, Nov 24
11:24 am - 12:38 amBOS-ORD
14h 14m1 stop
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
Mon, Nov 18 - Sat, Nov 23
11:24 am - 12:38 amBOS-ORD
14h 14m1 stop
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
Mon, Nov 18 - Thu, Nov 21
2:30 pm - 4:26 pmBOS-ORD
2h 56mnonstop
6:40 am - 10:00 amORD-BOS
2h 20mnonstop
$268Delta
Find Deal
Sat, Nov 16 - Thu, Nov 21
11:15 am - 4:52 pmBOS-ORD
6h 37m1 stop
7:15 am - 10:40 amORD-BOS
2h 25mnonstop
$278Delta
Find Deal
Tue, Nov 19 - Sat, Nov 23
7:55 pm - 9:40 pmBOS-MDW
2h 45mnonstop
8:30 am - 11:45 amMDW-BOS
2h 15mnonstop
$282Southwest
Find Deal
Mon, Nov 18 - Wed, Nov 20
7:45 pm - 11:55 pmBOS-MDW
5h 10m1 stop
8:30 am - 11:45 amMDW-BOS
2h 15mnonstop
$292Southwest
Find Deal
Mon, Nov 18 - Wed, Nov 20
6:28 pm - 8:24 pmBOS-ORD
2h 56mnonstop
9:25 am - 12:50 pmORD-BOS
2h 25mnonstop
$297United Airlines
Find Deal
Sat, Nov 16 - Wed, Nov 20
4:30 pm - 6:42 pmPWM-ORD
3h 12mnonstop
6:14 pm - 11:59 pmORD-PWM
4h 45m1 stop
$479United Airlines
Find Deal
Sat, Nov 16 - Mon, Nov 18
5:30 am - 7:37 amBOS-ORD
3h 07mnonstop
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
$139Spirit Airlines
Find Deal
Mon, Nov 25 - Thu, Nov 28
5:30 am - 7:37 amBOS-ORD
3h 07mnonstop
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
$148Spirit Airlines
Find Deal
Sun, Nov 24 - Thu, Nov 28
7:25 am - 9:28 amBOS-ORD
3h 03mnonstop
10:30 am - 1:52 pmORD-BOS
2h 22mnonstop
$155Delta
Find Deal
Mon, Dec 9 - Wed, Dec 11
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
8:51 am - 12:13 pmORD-BOS
2h 22mnonstop
$156JetBlue
Find Deal
Mon, Dec 9 - Mon, Dec 16
7:50 pm - 9:51 pmBOS-ORD
3h 01mnonstop
2:05 pm - 5:34 pmORD-BOS
2h 29mnonstop
$157Delta
Find Deal
Wed, Dec 4 - Fri, Dec 13
6:00 pm - 7:45 pmBOS-MDW
2h 45mnonstop
6:25 pm - 9:35 pmMDW-BOS
2h 10mnonstop
$158Southwest
Find Deal
Fri, Dec 6 - Mon, Dec 9
5:10 am - 7:16 amBOS-ORD
3h 06mnonstop
8:12 am - 11:27 amORD-BOS
2h 15mnonstop
$160American Airlines
Find Deal
Sat, Dec 7 - Mon, Dec 9
2:41 pm - 4:41 pmBOS-ORD
3h 00mnonstop
7:00 am - 10:28 amORD-BOS
2h 28mnonstop
$162American Airlines
Find Deal
Wed, Dec 4 - Sun, Dec 8
3:50 pm - 5:53 pmBOS-ORD
3h 03mnonstop
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
$167JetBlue
Find Deal
Wed, Jan 8 - Mon, Jan 13
6:40 am - 8:25 amBOS-MDW
2h 45mnonstop
6:25 pm - 9:35 pmMDW-BOS
2h 10mnonstop
$174Southwest
Find Deal
Sun, Nov 24 - Wed, Dec 4

Spirit Airlines flights from Maine to Chicago

Our best Spirit Airlines deals on Maine to Chicago flight tickets
Spirit Airlines
Nov 23
BOS5:30 amBoston Logan Intl
3h 07m
ORD7:37 amChicago O'Hare Intl
Nov 28
ORD4:45 pmChicago O'Hare Intl
2h 19m
BOS8:04 pmBoston Logan Intl
Spirit Airlines
Nov 22
BOS5:30 amBoston Logan Intl
3h 07m
ORD7:37 amChicago O'Hare Intl
Dec 3
ORD1:09 pmChicago O'Hare Intl
8h 00m
1 stop
BOS10:09 pmBoston Logan Intl
Spirit Airlines
Dec 3
BOS8:10 amBoston Logan Intl
3h 11m
ORD10:21 amChicago O'Hare Intl
Dec 10
ORD9:58 amChicago O'Hare Intl
13h 40m
1 stop
BOS12:38 amBoston Logan Intl

United Airlines flights from Maine to Chicago

Our best United Airlines deals on Maine to Chicago flight tickets
United Airlines
Dec 6
BOS6:28 pmBoston Logan Intl
2h 56m
ORD8:24 pmChicago O'Hare Intl
Dec 8
ORD9:20 amChicago O'Hare Intl
2h 25m
BOS12:45 pmBoston Logan Intl
United Airlines
Dec 6
BOS7:38 pmBoston Logan Intl
4h 42m
1 stop
ORD11:20 pmChicago O'Hare Intl
Dec 8
ORD9:20 amChicago O'Hare Intl
2h 25m
BOS12:45 pmBoston Logan Intl
United Airlines
Dec 12
BOS6:00 amBoston Logan Intl
5h 53m
1 stop
ORD10:53 amChicago O'Hare Intl
Dec 19
ORD1:55 pmChicago O'Hare Intl
2h 23m
BOS5:18 pmBoston Logan Intl

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 airline that flies to Chicago from Maine?

Frontier. Frontier, Delta, and American Airlines are the most popular carriers operating from Maine to Chicago

What is the cheapest Maine to Chicago flight route?

Boston Logan Intl - Chicago O'Hare Intl. Fly from Boston Logan Intl to Chicago O'Hare Intl for the best Maine - Chicago flight prices

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

There are 3 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 13% 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 45m

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 $103.
The fastest flight from Maine to Chicago takes 2h 45m
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
6.1
3,551 reviews
Search Frontier flights
American AirlinesPriceFrom $158Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $201Free CancellationRating
8.0
8,788 reviews
Search Delta flights
United AirlinesPriceFrom $206Free CancellationRating
7.4
9,194 reviews
Search United Airlines flights
SouthwestPriceFrom $281Free CancellationRating
8.1
5,045 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