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.

$177 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

Thu, Oct 22 - Wed, Oct 28

5:50 pm - 8:09 pmBGR Bangor-ORD Chicago O'Hare Intl

3h 19mnonstop

7:13 pm - 11:07 pmORD Chicago O'Hare Intl-BGR Bangor

2h 54mnonstop

$325American Airlines

Wed, Dec 23 - Wed, Jan 6

4:32 pm - 9:31 pmBGR Bangor-ORD Chicago O'Hare Intl

5h 59m1 stop Washington, D.C. Reagan-National

5:56 am - 12:06 pmORD Chicago O'Hare Intl-BGR Bangor

5h 10m1 stop Washington, D.C. Reagan-National

$331American Airlines

Wed, Jan 6 - Sat, Jan 9

6:00 am - 4:37 pmBGR Bangor-ORD Chicago O'Hare Intl

11h 37m2 stops New York LaGuardia Atlanta Hartsfield-Jackson

1:30 pm - 10:01 pmORD Chicago O'Hare Intl-BGR Bangor

7h 31m1 stop New York John F Kennedy Intl

$336Delta

Wed, Jan 20 - Sat, Jan 23

2:00 pm - 8:15 pmBGR Bangor-ORD Chicago O'Hare Intl

7h 15m1 stop New York LaGuardia

11:10 am - 10:01 pmORD Chicago O'Hare Intl-BGR Bangor

9h 51m2 stops Atlanta Hartsfield-Jackson New York John F Kennedy Intl

$336Delta

Thu, Oct 22 - Mon, Oct 26

6:30 am - 8:05 amPWM Portland-MDW Chicago Midway

2h 35mnonstop

6:40 pm - 9:55 pmMDW Chicago Midway-PWM Portland

2h 15mnonstop

$353Southwest

Tue, Oct 27 - Thu, Oct 29

6:00 pm - 7:35 pmPWM Portland-MDW Chicago Midway

2h 35mnonstop

6:40 pm - 9:55 pmMDW Chicago Midway-PWM Portland

2h 15mnonstop

$353Southwest

Tue, Oct 20 - Wed, Oct 21

7:58 am - 10:00 amPWM Portland-ORD Chicago O'Hare Intl

3h 02mnonstop

11:04 am - 2:38 pmORD Chicago O'Hare Intl-PWM Portland

2h 34mnonstop

$353United Airlines

Sat, Oct 24 - Mon, Oct 26

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

2h 57mnonstop

6:18 pm - 9:51 pmORD Chicago O'Hare Intl-PWM Portland

2h 33mnonstop

$353United Airlines

Wed, Dec 9 - Tue, Jan 5

12:28 pm - 1:59 pmPWM Portland-ORD Chicago O'Hare Intl

26h 31m2 stops Raleigh-Durham Fort Lauderdale

10:18 am - 5:51 pmORD Chicago O'Hare Intl-PWM Portland

30h 33m1 stop Tampa

$367Multiple Airlines

Sat, Dec 12 - Tue, Jan 5

12:28 pm - 7:20 amPWM Portland-ORD Chicago O'Hare Intl

43h 52m2 stops Raleigh-Durham Atlanta Hartsfield-Jackson

10:18 am - 5:51 pmORD Chicago O'Hare Intl-PWM Portland

30h 33m1 stop Tampa

$372Multiple Airlines

Recent last minute flight deals from Maine to Chicago

Sat, Oct 3 - Sat, Oct 17

5:49 pm - 8:14 pmBGR Bangor-ORD Chicago O'Hare Intl

3h 25mnonstop

9:30 am - 4:14 pmORD Chicago O'Hare Intl-BGR Bangor

5h 44m1 stop Washington, D.C. Reagan-National

$376American Airlines

Sat, Oct 3 - Sat, Oct 17

4:26 pm - 11:50 pmBGR Bangor-ORD Chicago O'Hare Intl

8h 24m1 stop New York LaGuardia

4:50 pm - 11:55 pmORD Chicago O'Hare Intl-BGR Bangor

6h 05m1 stop Philadelphia

$386American Airlines

Sat, Oct 3 - Sat, Oct 17

5:49 pm - 8:14 pmBGR Bangor-ORD Chicago O'Hare Intl

3h 25mnonstop

7:13 pm - 11:07 pmORD Chicago O'Hare Intl-BGR Bangor

2h 54mnonstop

$393American Airlines

Sat, Oct 3 - Sat, Oct 10

7:58 am - 10:00 amPWM Portland-ORD Chicago O'Hare Intl

3h 02mnonstop

6:59 am - 10:40 amORD Chicago O'Hare Intl-PWM Portland

2h 41mnonstop

$417United Airlines

Sat, Oct 3 - Sat, Oct 10

7:58 am - 10:00 amPWM Portland-ORD Chicago O'Hare Intl

3h 02mnonstop

3:00 pm - 6:43 pmORD Chicago O'Hare Intl-PWM Portland

2h 43mnonstop

$417United Airlines

Tue, Sep 29 - Tue, Sep 29

7:45 am - 9:20 amPWM Portland-MDW Chicago Midway

2h 35mnonstop

6:50 pm - 10:10 pmMDW Chicago Midway-PWM Portland

2h 20mnonstop

$417Southwest

Tue, Sep 29 - Wed, Sep 30

7:45 am - 9:20 amPWM Portland-MDW Chicago Midway

2h 35mnonstop

6:50 pm - 10:10 pmMDW Chicago Midway-PWM Portland

2h 20mnonstop

$417Southwest

Sat, Oct 3 - Mon, Oct 19

4:15 pm - 9:37 pmBGR Bangor-ORD Chicago O'Hare Intl

6h 22m1 stop New York John F Kennedy Intl

8:36 am - 4:22 pmORD Chicago O'Hare Intl-BGR Bangor

6h 46m1 stop New York LaGuardia

$434Delta

Fri, Oct 2 - Mon, Oct 19

5:01 pm - 10:18 pmBGR Bangor-ORD Chicago O'Hare Intl

6h 17m1 stop New York LaGuardia

8:36 am - 4:22 pmORD Chicago O'Hare Intl-BGR Bangor

6h 46m1 stop New York LaGuardia

$434Delta

Wed, Sep 30 - Fri, Oct 2

5:09 pm - 10:59 pmPWM Portland-ORD Chicago O'Hare Intl

30h 50m2 stops Raleigh-Durham Orlando

3:50 pm - 9:08 amORD Chicago O'Hare Intl-PWM Portland

16h 18m1 stop Orlando

$644Multiple Airlines

Useful Info

Low season	January
High season	October
Cheapest flight	$177

Best time to beat the crowds with an average 12% drop in price.

Most popular time to fly with an average 12% increase in price.

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

Schererville

Munster

Chesterton

Porter

Monticello

Saint John

Griffith

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$177 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

Good to know

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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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