How does KAYAK find such low prices on flights from Maine to Chicago?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Maine to Chicago.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Maine to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Maine is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights from Maine to Chicago?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Maine with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Maine to Chicago?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Maine up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

$145 CHEAP FLIGHTS from Maine to Chicago

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Cheap Flights from Maine to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

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Last minute

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Recent round-trip flight deals from Maine to Chicago

Wed, Dec 2 - Fri, Dec 11

10:07 am - 9:34 pmBGR Bangor-ORD Chicago O'Hare Intl

36h 27m2 stops Tampa Atlanta Hartsfield-Jackson

7:59 am - 9:27 amORD Chicago O'Hare Intl-BGR Bangor

24h 28m1 stop Tampa

$343Multiple Airlines

Fri, Dec 4 - Sun, Dec 6

12:44 pm - 3:00 pmPWM Portland-ORD Chicago O'Hare Intl

3h 16mnonstop

8:30 am - 12:02 pmORD Chicago O'Hare Intl-PWM Portland

2h 32mnonstop

$349American Airlines

Thu, Dec 3 - Thu, Dec 10

6:00 am - 4:43 pmPWM Portland-ORD Chicago O'Hare Intl

11h 43m2 stops Atlanta Hartsfield-Jackson Minneapolis St Paul

2:39 pm - 11:20 pmORD Chicago O'Hare Intl-PWM Portland

7h 41m1 stop New York LaGuardia

$349Delta

Wed, Jan 13 - Sun, Jan 17

6:17 am - 3:57 pmPWM Portland-ORD Chicago O'Hare Intl

10h 40m2 stops New York LaGuardia Atlanta Hartsfield-Jackson

2:40 pm - 11:10 pmORD Chicago O'Hare Intl-PWM Portland

7h 30m1 stop New York LaGuardia

$349Delta

Fri, Feb 19 - Sat, Feb 27

4:40 pm - 6:58 pmPWM Portland-ORD Chicago O'Hare Intl

3h 18mnonstop

5:45 pm - 9:16 pmORD Chicago O'Hare Intl-PWM Portland

2h 31mnonstop

$349United Airlines

Sun, Dec 20 - Mon, Jan 4

5:15 am - 11:37 amPWM Portland-ORD Chicago O'Hare Intl

7h 22m1 stop Washington, D.C. Dulles Intl

6:50 pm - 10:45 pmORD Chicago O'Hare Intl-PWM Portland

2h 55mnonstop

$349United Airlines

Fri, Feb 19 - Sat, Feb 27

12:15 pm - 2:31 pmPWM Portland-ORD Chicago O'Hare Intl

3h 16mnonstop

8:10 am - 11:45 amORD Chicago O'Hare Intl-PWM Portland

2h 35mnonstop

$349American Airlines

Wed, Jan 13 - Mon, Jan 18

12:28 pm - 12:50 amPWM Portland-ORD Chicago O'Hare Intl

13h 22m2 stops Raleigh-Durham Fort Lauderdale

4:22 pm - 9:21 amORD Chicago O'Hare Intl-PWM Portland

15h 59m1 stop Fort Myers SW Florida Intl

$350Multiple Airlines

Wed, Jan 13 - Sun, Jan 17

12:55 pm - 6:20 pmPWM Portland-MDW Chicago Midway

6h 25m1 stop Baltimore/Washington

8:45 am - 2:50 pmMDW Chicago Midway-PWM Portland

5h 05m1 stop Baltimore/Washington

$354Southwest

Wed, Jan 13 - Sun, Jan 17

12:55 pm - 6:35 pmPWM Portland-MDW Chicago Midway

6h 40m2 stops Baltimore/Washington Greater Rochester Intl

6:35 am - 2:50 pmMDW Chicago Midway-PWM Portland

7h 15m1 stop Baltimore/Washington

$359Southwest

Recent last minute flight deals from Maine to Chicago

Thu, Nov 12 - Wed, Dec 9

5:08 pm - 7:05 pmPWM Portland-ORD Chicago O'Hare Intl

2h 57mnonstop

11:59 am - 3:38 pmORD Chicago O'Hare Intl-PWM Portland

2h 39mnonstop

$354United Airlines

Thu, Nov 12 - Tue, Dec 8

5:08 pm - 7:05 pmPWM Portland-ORD Chicago O'Hare Intl

2h 57mnonstop

11:59 am - 3:38 pmORD Chicago O'Hare Intl-PWM Portland

2h 39mnonstop

$354United Airlines

Thu, Nov 12 - Tue, Dec 8

12:45 pm - 6:04 pmPWM Portland-MDW Chicago Midway

6h 19m1 stop Detroit Metropolitan Wayne County

5:12 pm - 11:33 pmMDW Chicago Midway-PWM Portland

5h 21m1 stop Atlanta Hartsfield-Jackson

$374Delta

Thu, Nov 12 - Tue, Dec 8

4:50 pm - 11:54 pmPWM Portland-ORD Chicago O'Hare Intl

8h 04m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson

2:39 pm - 11:20 pmORD Chicago O'Hare Intl-PWM Portland

7h 41m1 stop New York LaGuardia

$379Delta

Fri, Nov 13 - Mon, Nov 16

4:10 pm - 9:29 pmPWM Portland-ORD Chicago O'Hare Intl

6h 19m1 stop Washington, D.C. Reagan-National

8:25 am - 11:53 amORD Chicago O'Hare Intl-PWM Portland

2h 28mnonstop

$409American Airlines

Thu, Nov 12 - Tue, Dec 8

11:10 am - 6:55 pmPWM Portland-MDW Chicago Midway

8h 45m2 stops Baltimore/Washington Orlando

1:15 pm - 9:50 pmMDW Chicago Midway-PWM Portland

7h 35m2 stops Richmond Byrd Intl Baltimore/Washington

$410Southwest

Fri, Nov 13 - Mon, Nov 16

4:10 pm - 9:29 pmPWM Portland-ORD Chicago O'Hare Intl

6h 19m1 stop Washington, D.C. Reagan-National

4:51 pm - 10:29 pmORD Chicago O'Hare Intl-PWM Portland

4h 38m1 stop Washington, D.C. Reagan-National

$419American Airlines

Tue, Nov 10 - Wed, Nov 11

5:15 am - 9:00 amPWM Portland-MDW Chicago Midway

4h 45m1 stop Baltimore/Washington

8:50 am - 2:45 pmMDW Chicago Midway-PWM Portland

4h 55m1 stop Baltimore/Washington

$439Southwest

Thu, Nov 12 - Sun, Nov 15

11:06 am - 3:32 pmAUG Augusta-ORD Chicago O'Hare Intl

5h 26m1 stop Boston Logan Intl

7:00 am - 2:27 pmORD Chicago O'Hare Intl-AUG Augusta

6h 27m1 stop Boston Logan Intl

$654Multiple Airlines

Thu, Nov 12 - Sun, Nov 15

3:37 pm - 11:15 amAUG Augusta-ORD Chicago O'Hare Intl

20h 38m1 stop Boston Logan Intl

5:55 am - 7:05 pmORD Chicago O'Hare Intl-AUG Augusta

12h 10m2 stops Newark Boston Logan Intl

$664Multiple Airlines

Useful Info

Low season	January
High season	June
Cheapest flight	$145

Best time to beat the crowds with an average 11% drop in price.

Most popular time to fly and prices are also 6% lower on average.

Flight from Portland to Chicago O'Hare Airport

How does KAYAK find such low prices on flights from Maine to Chicago?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Maine to Chicago.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Maine to Chicago?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Maine is likely to change within 7 days, so travelers know whether to wait or book now.
What is the Hacker Fare option on flights from Maine to Chicago?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Maine with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Maine to Chicago?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Maine up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Merrillville

Hammond

Saint Joseph

Portage

Lansing

Valparaiso

Munster

Chesterton

Schererville

Porter

Monticello

Saint John

Griffith

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$145 Find Cheap Flights from Maine to Chicago - Compare and Save

Cheap Flights from Maine to Chicago

Recent round-trip flight deals from Maine to Chicago

Recent one-way flight deals from Maine to Chicago

Recent last minute flight deals from Maine to Chicago

Recent direct flight deals from Maine to Chicago

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High season

Cheapest flight

FAQs for booking flights from Maine to Chicago

Traveling to a place near Chicago?

More options for your flight to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Cabin class types available on flights to Maine

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