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.

$180 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.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Maine to Chicago

Tue, Apr 13 - Sat, Apr 17

6:15 pm - 8:44 pmBGR Bangor-ORD Chicago O'Hare Intl

3h 29mnonstop

1:24 pm - 5:05 pmORD Chicago O'Hare Intl-BGR Bangor

2h 41mnonstop

$341American Airlines

Sat, Jan 23 - Sun, Jan 24

9:40 am - 7:48 amPWM Portland-ORD Chicago O'Hare Intl

23h 08m2 stops Washington, D.C. Dulles Intl New York LaGuardia

11:00 am - 2:44 pmORD Chicago O'Hare Intl-PWM Portland

2h 44mnonstop

$347United Airlines

Fri, Feb 26 - Wed, Mar 3

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

Sat, Jan 23 - Sun, Jan 24

4:25 pm - 6:44 pmPWM Portland-ORD Chicago O'Hare Intl

3h 19mnonstop

11:00 am - 2:44 pmORD Chicago O'Hare Intl-PWM Portland

2h 44mnonstop

$349United 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 - 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

$362Multiple Airlines

Sat, Jan 23 - Wed, Jan 27

7:00 am - 4:57 pmBGR Bangor-ORD Chicago O'Hare Intl

10h 57m2 stops New York LaGuardia Minneapolis St Paul

2:45 pm - 11:26 pmORD Chicago O'Hare Intl-BGR Bangor

7h 41m1 stop New York LaGuardia

$366Delta

Tue, Jan 12 - Sun, Jan 17

11:38 am - 6:53 pmPWM Portland-ORD Chicago O'Hare Intl

8h 15m1 stop New York LaGuardia

6:30 am - 2:23 pmORD Chicago O'Hare Intl-PWM Portland

6h 53m1 stop New York John F Kennedy Intl

$369Delta

Mon, Dec 7 - Tue, Dec 8

3:25 pm - 9:30 pmPWM Portland-MDW Chicago Midway

7h 05m1 stop Baltimore/Washington

6:00 am - 12:10 pmMDW Chicago Midway-PWM Portland

5h 10m1 stop Baltimore/Washington

$369Southwest

Fri, Dec 4 - Mon, Dec 7

3:25 pm - 9:30 pmPWM Portland-MDW Chicago Midway

7h 05m1 stop Baltimore/Washington

6:00 am - 12:10 pmMDW Chicago Midway-PWM Portland

5h 10m1 stop Baltimore/Washington

$369Southwest

Recent last minute flight deals from Maine to Chicago

Tue, Nov 17 - Tue, Jan 5

8:47 am - 10:47 amPWM Portland-ORD Chicago O'Hare Intl

3h 00mnonstop

11:00 am - 2:44 pmORD Chicago O'Hare Intl-PWM Portland

2h 44mnonstop

$379United Airlines

Tue, Nov 17 - Tue, Jan 5

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

2h 57mnonstop

12:40 pm - 6:53 pmORD Chicago O'Hare Intl-PWM Portland

5h 13m1 stop Newark

$389United Airlines

Tue, Nov 17 - Tue, Jan 5

12:45 pm - 6:55 pmPWM Portland-MDW Chicago Midway

7h 10m1 stop Baltimore/Washington

6:00 am - 12:10 pmMDW Chicago Midway-PWM Portland

5h 10m1 stop Baltimore/Washington

$399Southwest

Tue, Nov 17 - Tue, Jan 5

12:45 pm - 6:55 pmPWM Portland-MDW Chicago Midway

7h 10m1 stop Baltimore/Washington

9:55 am - 9:50 pmMDW Chicago Midway-PWM Portland

10h 55m2 stops Atlanta Hartsfield-Jackson Baltimore/Washington

$404Southwest

Mon, Nov 16 - Sun, Nov 22

12:50 pm - 3:00 pmPWM Portland-ORD Chicago O'Hare Intl

3h 10mnonstop

8:29 am - 11:56 amORD Chicago O'Hare Intl-PWM Portland

2h 27mnonstop

$409American Airlines

Tue, Nov 17 - Thu, Jan 7

6:00 am - 12:46 pmPWM Portland-ORD Chicago O'Hare Intl

7h 46m1 stop New York John F Kennedy Intl

6:00 pm - 11:55 pmORD Chicago O'Hare Intl-PWM Portland

4h 55m1 stop New York John F Kennedy Intl

$409Delta

Tue, Nov 17 - Tue, Jan 5

6:27 am - 2:49 pmPWM Portland-ORD Chicago O'Hare Intl

9h 22m2 stops New York LaGuardia Atlanta Hartsfield-Jackson

6:00 pm - 11:59 pmORD Chicago O'Hare Intl-PWM Portland

4h 59m1 stop New York John F Kennedy Intl

$414Delta

Mon, Nov 16 - Sun, Nov 22

12:50 pm - 3:00 pmPWM Portland-ORD Chicago O'Hare Intl

3h 10mnonstop

8:45 am - 3:35 pmORD Chicago O'Hare Intl-PWM Portland

5h 50m1 stop Washington, D.C. Reagan-National

$419American Airlines

Tue, Nov 17 - Tue, Jan 5

5:09 pm - 5:07 pmPWM Portland-ORD Chicago O'Hare Intl

24h 58m2 stops Raleigh-Durham Orlando

7:52 pm - 5:51 pmORD Chicago O'Hare Intl-PWM Portland

20h 59m1 stop Tampa

$492Multiple Airlines

Tue, Nov 17 - Tue, Jan 5

5:09 pm - 5:07 pmPWM Portland-ORD Chicago O'Hare Intl

24h 58m2 stops Raleigh-Durham Orlando

7:52 pm - 5:51 pmORD Chicago O'Hare Intl-PWM Portland

20h 59m1 stop Tampa

$493Multiple Airlines

Useful Info

Low season	January
High season	June
Cheapest flight	$180

Best time to beat the crowds with an average 13% drop in price.

Most popular time to fly and prices are also 8% 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

Chesterton

Munster

Schererville

Porter

Monticello

Saint John

Griffith

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$180 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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