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.

$129 CHEAP FLIGHTS from Maine to Chicago

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Cheap Flights from Maine to Chicago

Cheap flights from Maine to Chicago with top airlines, updated regularly. Compare round-trip, one-way, direct and last-minute deals.

Round-trip

One-way

Last minute

Direct

Wed, Jan 13 - Tue, Jan 19

10:07 am - 4:14 pmBGR Bangor-ORD Chicago O'Hare Intl

31h 07m2 stops Tampa Fort Lauderdale

10:18 am - 9:27 amORD Chicago O'Hare Intl-BGR Bangor

22h 09m1 stop Tampa

$291Multiple Airlines

Wed, Jan 13 - Tue, Jan 19

10:07 am - 9:13 amBGR Bangor-ORD Chicago O'Hare Intl

24h 06m1 stop Tampa

10:18 am - 9:27 amORD Chicago O'Hare Intl-BGR Bangor

22h 09m1 stop Tampa

$335Multiple Airlines

Mon, Nov 9 - Sat, Nov 14

8:49 am - 1:54 pmPWM Portland-ORD Chicago O'Hare Intl

6h 05m1 stop Newark

5:30 pm - 11:21 pmORD Chicago O'Hare Intl-PWM Portland

4h 51m1 stop Newark

$341United Airlines

Tue, Nov 17 - Sat, Nov 21

2:05 pm - 6:54 pmPWM Portland-ORD Chicago O'Hare Intl

5h 49m1 stop Washington, D.C. Dulles Intl

6:15 pm - 9:48 pmORD Chicago O'Hare Intl-PWM Portland

2h 33mnonstop

$343United Airlines

Mon, Nov 9 - Sat, Nov 14

5:20 am - 4:00 pmPWM Portland-MDW Chicago Midway

11h 40m1 stop Baltimore/Washington

7:35 am - 2:45 pmMDW Chicago Midway-PWM Portland

6h 10m1 stop Baltimore/Washington

$346Southwest

Tue, Jan 26 - Sat, Jan 30

5:46 pm - 11:30 pmBGR Bangor-ORD Chicago O'Hare Intl

6h 44m1 stop Washington, D.C. Reagan-National

3:21 pm - 11:05 pmORD Chicago O'Hare Intl-BGR Bangor

6h 44m1 stop Philadelphia

$351American Airlines

Tue, Jan 26 - Sat, Jan 30

12:36 pm - 5:26 pmBGR Bangor-ORD Chicago O'Hare Intl

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

3:21 pm - 11:05 pmORD Chicago O'Hare Intl-BGR Bangor

6h 44m1 stop Philadelphia

$351American Airlines

Mon, Nov 9 - Sat, Nov 14

5:20 am - 4:00 pmPWM Portland-MDW Chicago Midway

11h 40m1 stop Baltimore/Washington

7:45 am - 2:45 pmMDW Chicago Midway-PWM Portland

6h 00m2 stops Greater Rochester Intl Baltimore/Washington

$352Southwest

Wed, Dec 16 - Sat, Dec 19

12:49 pm - 6:01 pmPWM Portland-MDW Chicago Midway

6h 12m1 stop Detroit Metropolitan Wayne County

9:30 am - 3:58 pmMDW Chicago Midway-PWM Portland

5h 28m1 stop Detroit Metropolitan Wayne County

$353Delta

Wed, Dec 16 - Sat, Dec 19

5:19 pm - 10:13 pmPWM Portland-ORD Chicago O'Hare Intl

5h 54m1 stop New York LaGuardia

5:00 pm - 11:06 pmORD Chicago O'Hare Intl-PWM Portland

5h 06m1 stop New York LaGuardia

$353Delta

Wed, Oct 21 - Sat, Oct 24

1:05 pm - 3:07 pmPWM Portland-ORD Chicago O'Hare Intl

3h 02mnonstop

7:59 pm - 11:43 pmORD Chicago O'Hare Intl-PWM Portland

2h 44mnonstop

$425American Airlines

Sat, Oct 24 - Tue, Oct 27

5:45 pm - 7:55 pmPWM Portland-ORD Chicago O'Hare Intl

3h 10mnonstop

1:29 pm - 5:04 pmORD Chicago O'Hare Intl-PWM Portland

2h 35mnonstop

$425American Airlines

Wed, Oct 21 - Sat, Oct 24

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

2h 35mnonstop

4:10 pm - 7:25 pmMDW Chicago Midway-PWM Portland

2h 15mnonstop

$433Southwest

Wed, Oct 21 - Sat, Oct 24

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

2h 35mnonstop

4:10 pm - 7:25 pmMDW Chicago Midway-PWM Portland

2h 15mnonstop

$435Southwest

Wed, Oct 21 - Sat, Oct 24

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

2h 57mnonstop

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

2h 34mnonstop

$435United Airlines

Sat, Oct 24 - Wed, Oct 28

11:55 am - 4:47 pmPWM Portland-MDW Chicago Midway

5h 52m1 stop Minneapolis St Paul

9:29 am - 4:02 pmMDW Chicago Midway-PWM Portland

5h 33m1 stop Detroit Metropolitan Wayne County

$455Delta

Sat, Oct 24 - Sat, Oct 31

6:01 am - 12:13 pmPWM Portland-ORD Chicago O'Hare Intl

7h 12m1 stop Atlanta Hartsfield-Jackson

5:27 am - 1:03 pmORD Chicago O'Hare Intl-PWM Portland

6h 36m1 stop Atlanta Hartsfield-Jackson

$455Delta

Thu, Oct 22 - Sat, Oct 24

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

2h 57mnonstop

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

2h 34mnonstop

$486United Airlines

Sat, Oct 24 - Thu, Oct 29

5:09 pm - 7:31 amPWM Portland-ORD Chicago O'Hare Intl

15h 22m2 stops Raleigh-Durham Orlando

9:51 am - 9:08 amORD Chicago O'Hare Intl-PWM Portland

22h 17m1 stop Orlando

$577Multiple Airlines

Sat, Oct 24 - Mon, Oct 26

9:48 am - 7:31 amPWM Portland-ORD Chicago O'Hare Intl

22h 43m1 stop Orlando

8:36 am - 4:24 pmORD Chicago O'Hare Intl-PWM Portland

30h 48m2 stops Orlando Raleigh-Durham

$615Multiple Airlines

Low season	January
High season	October
Cheapest flight	$129

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

Most popular time to fly with an average 7% increase in price.

Flight from Portland to Chicago Midway 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.