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.

$135 CHEAP FLIGHTS from Maine to Chicago

Save 25% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals

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

Wed, Dec 2 - Fri, Dec 4

10:07 am - 7:17 amBGR Bangor-ORD Chicago O'Hare Intl

22h 10m2 stops Tampa Atlanta Hartsfield-Jackson

8:00 am - 9:27 amORD Chicago O'Hare Intl-BGR Bangor

24h 27m1 stop Tampa

$329Multiple Airlines

Thu, Jan 28 - Sun, Jan 31

6:17 am - 3:53 pmPWM Portland-ORD Chicago O'Hare Intl

10h 36m2 stops New York LaGuardia Atlanta Hartsfield-Jackson

9:50 am - 11:10 pmORD Chicago O'Hare Intl-PWM Portland

12h 20m2 stops Atlanta Hartsfield-Jackson New York LaGuardia

$344Delta

Thu, Apr 8 - Tue, Apr 13

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

$345American Airlines

Tue, Nov 24 - Tue, Dec 1

6:27 am - 1:59 pmPWM Portland-ORD Chicago O'Hare Intl

8h 32m2 stops New York LaGuardia Detroit Metropolitan Wayne County

8:50 am - 4:39 pmORD Chicago O'Hare Intl-PWM Portland

6h 49m1 stop New York LaGuardia

$348Delta

Wed, Dec 16 - Sat, Dec 19

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

3h 16mnonstop

5:54 pm - 11:42 pmORD Chicago O'Hare Intl-PWM Portland

4h 48m1 stop Washington, D.C. Reagan-National

$349American Airlines

Tue, Nov 24 - Fri, Nov 27

5:50 am - 11:47 amPWM Portland-ORD Chicago O'Hare Intl

6h 57m1 stop Newark

6:18 pm - 9:52 pmORD Chicago O'Hare Intl-PWM Portland

2h 34mnonstop

$353United Airlines

Thu, Mar 18 - Sat, Mar 20

6:00 am - 1:09 pmPWM Portland-ORD Chicago O'Hare Intl

8h 09m1 stop Newark

6:59 pm - 10:38 pmORD Chicago O'Hare Intl-PWM Portland

2h 39mnonstop

$353United Airlines

Mon, Nov 16 - Mon, Nov 23

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

7h 05m1 stop Baltimore/Washington

6:10 pm - 11:55 pmMDW Chicago Midway-PWM Portland

4h 45m1 stop Baltimore/Washington

$355Southwest

Tue, Nov 24 - Tue, Dec 1

10:07 am - 12:43 amBGR Bangor-ORD Chicago O'Hare Intl

15h 36m1 stop Tampa

8:15 am - 9:27 amORD Chicago O'Hare Intl-BGR Bangor

24h 12m2 stops Atlanta Hartsfield-Jackson Tampa

$355Multiple Airlines

Tue, Nov 17 - Tue, Dec 1

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

7h 05m1 stop Baltimore/Washington

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

7h 35m2 stops Cincinnati Cinci./N. Kentucky Baltimore/Washington

$359Southwest

Recent last minute flight deals from Maine to Chicago

Wed, Nov 4 - Wed, Nov 11

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

$399United Airlines

Thu, Nov 5 - Thu, Nov 12

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

2h 57mnonstop

10:50 am - 2:16 pmORD Chicago O'Hare Intl-PWM Portland

2h 26mnonstop

$399United Airlines

Sat, Oct 31 - Tue, Nov 3

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

3h 02mnonstop

8:00 am - 11:28 amORD Chicago O'Hare Intl-PWM Portland

2h 28mnonstop

$419American Airlines

Wed, Nov 4 - Wed, Nov 11

1:52 pm - 7:20 pmPWM Portland-ORD Chicago O'Hare Intl

6h 28m1 stop New York LaGuardia

6:00 pm - 12:19 amORD Chicago O'Hare Intl-PWM Portland

5h 19m1 stop New York John F Kennedy Intl

$419Delta

Wed, Nov 4 - Wed, Nov 11

12:42 pm - 6:00 pmPWM Portland-MDW Chicago Midway

6h 18m1 stop Detroit Metropolitan Wayne County

6:00 am - 1:01 pmMDW Chicago Midway-PWM Portland

6h 01m1 stop Atlanta Hartsfield-Jackson

$419Delta

Thu, Nov 5 - Thu, Nov 12

5:10 pm - 11:15 pmPWM Portland-MDW Chicago Midway

7h 05m1 stop Baltimore/Washington

5:05 am - 10:30 amMDW Chicago Midway-PWM Portland

4h 25m1 stop Baltimore/Washington

$434Southwest

Mon, Nov 2 - Thu, Nov 5

5:10 pm - 11:05 pmPWM Portland-MDW Chicago Midway

6h 55m1 stop Baltimore/Washington

5:05 am - 10:30 amMDW Chicago Midway-PWM Portland

4h 25m1 stop Baltimore/Washington

$439Southwest

Wed, Nov 4 - Sun, Nov 8

6:47 pm - 11:30 pmPWM Portland-ORD Chicago O'Hare Intl

5h 43m1 stop Philadelphia

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

2h 28mnonstop

$488American Airlines

Sat, Oct 31 - Tue, Nov 3

5:09 pm - 9:46 amPWM Portland-ORD Chicago O'Hare Intl

17h 37m2 stops Raleigh-Durham Orlando

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

22h 17m1 stop Orlando

$559Multiple Airlines

Wed, Nov 4 - Sun, Nov 8

5:09 pm - 8:46 amPWM Portland-ORD Chicago O'Hare Intl

16h 37m2 stops Raleigh-Durham Orlando

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

22h 17m1 stop Orlando

$683Multiple Airlines

Useful Info

Low season	January
High season	October
Cheapest flight	$135

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 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

More options for your flight to Chicago

Add a hotel or car rental

Cabin class

Direct Flights

Origins

Other airports

Other destinations

Return flight

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

Car rentals in Chicago

$135 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

Low season

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

Find direct flights for Chicago

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Flights to other popular destinations

Find deals for your return flight