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.

$117 CHEAP FLIGHTS from Maine to Chicago

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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

Fri, Dec 11 - Tue, Dec 15

12:45 pm - 2:30 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 45mnonstop

6:25 pm - 9:40 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 15mnonstop

$216Southwest

Thu, Nov 12 - Mon, Nov 16

7:05 am - 8:50 amBOS Boston Logan Intl-MDW Chicago Midway

2h 45mnonstop

6:25 pm - 9:45 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

$216Southwest

Thu, Oct 8 - Tue, Oct 13

6:55 am - 11:24 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 29m1 stop New York John F Kennedy Intl

8:04 pm - 11:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 55mnonstop

$217JetBlue

Sat, Oct 24 - Mon, Oct 26

11:42 am - 6:31 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

7h 49m1 stop Atlanta Hartsfield-Jackson

7:44 pm - 10:17 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

13h 33m1 stop Atlanta Hartsfield-Jackson

$218Frontier

Sat, Oct 24 - Mon, Oct 26

11:42 am - 6:31 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

7h 49m1 stop Atlanta Hartsfield-Jackson

7:44 pm - 10:17 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

13h 33m1 stop Atlanta Hartsfield-Jackson

$222Frontier

Thu, Oct 22 - Thu, Oct 22

6:55 am - 8:47 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

8:04 pm - 11:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 55mnonstop

$234JetBlue

Wed, Oct 21 - Sun, Oct 25

7:00 am - 9:05 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 05mnonstop

6:00 am - 9:37 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 37mnonstop

$249American Airlines

Thu, Oct 15 - Tue, Oct 20

7:00 am - 9:05 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 05mnonstop

3:48 pm - 7:33 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 45mnonstop

$249American Airlines

Sat, Oct 17 - Tue, Oct 20

7:40 pm - 9:31 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 51mnonstop

7:10 pm - 10:53 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 43mnonstop

$249Delta

Wed, Sep 30 - Wed, Oct 7

7:30 am - 9:24 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

10:24 am - 1:54 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 30mnonstop

$249Delta

Recent last minute flight deals from Maine to Chicago

Sat, Sep 19 - Wed, Sep 30

12:54 pm - 6:23 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 29m1 stop Atlanta Hartsfield-Jackson

3:50 pm - 10:22 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

17h 32m1 stop Orlando

$272Frontier

Thu, Sep 17 - Sat, Sep 19

12:54 pm - 6:23 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 29m1 stop Atlanta Hartsfield-Jackson

3:50 pm - 10:58 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

18h 08m1 stop Orlando

$284Frontier

Sun, Sep 20 - Sat, Sep 26

1:34 pm - 3:35 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 01mnonstop

5:18 pm - 9:00 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 42mnonstop

$303American Airlines

Sun, Sep 20 - Fri, Oct 2

7:30 am - 9:24 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

7:30 pm - 11:09 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 39mnonstop

$303Delta

Sun, Sep 20 - Sat, Sep 26

12:15 pm - 2:04 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 49mnonstop

4:35 pm - 8:20 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 45mnonstop

$303Delta

Thu, Sep 17 - Sat, Oct 3

7:30 am - 9:05 amBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

8:00 am - 11:20 amMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

$303Southwest

Sun, Sep 20 - Fri, Sep 25

7:00 am - 9:06 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 06mnonstop

4:40 pm - 10:40 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

5h 00m1 stop New York LaGuardia

$313American Airlines

Thu, Sep 17 - Sat, Oct 3

9:40 am - 4:15 pmBOS Boston Logan Intl-MDW Chicago Midway

7h 35m1 stop Baltimore/Washington

8:00 am - 11:20 amMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

$313Southwest

Tue, Sep 15 - Tue, Sep 22

5:15 am - 9:58 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 43m1 stop New York John F Kennedy Intl

7:05 am - 2:27 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

6h 22m1 stop New York John F Kennedy Intl

$316JetBlue

Tue, Sep 15 - Wed, Sep 23

5:15 am - 9:58 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 43m1 stop New York John F Kennedy Intl

10:59 am - 5:21 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

5h 22m1 stop New York John F Kennedy Intl

$316JetBlue

Recent direct flight deals from Maine to Chicago

Fri, Dec 11 - Tue, Dec 15

12:45 pm - 2:30 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 45mnonstop

6:25 pm - 9:40 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 15mnonstop

$216Southwest

Thu, Nov 12 - Mon, Nov 16

7:05 am - 8:50 amBOS Boston Logan Intl-MDW Chicago Midway

2h 45mnonstop

6:25 pm - 9:45 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

$216Southwest

Thu, Oct 22 - Thu, Oct 22

6:55 am - 8:47 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

8:04 pm - 11:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 55mnonstop

$234JetBlue

Tue, Sep 29 - Fri, Oct 2

7:00 am - 8:48 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 48mnonstop

8:24 pm - 12:09 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 45mnonstop

$240JetBlue

Thu, Oct 15 - Tue, Oct 20

7:00 am - 9:05 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 05mnonstop

3:48 pm - 7:33 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 45mnonstop

$249American Airlines

Wed, Oct 21 - Sat, Oct 24

5:54 am - 8:00 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 06mnonstop

8:29 am - 12:06 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 37mnonstop

$249American Airlines

Sat, Oct 17 - Tue, Oct 20

7:40 pm - 9:31 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 51mnonstop

7:10 pm - 10:53 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 43mnonstop

$249Delta

Wed, Sep 30 - Wed, Oct 7

7:30 am - 9:24 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

10:24 am - 1:54 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 30mnonstop

$249Delta

Sat, Sep 26 - Sun, Sep 27

7:01 am - 9:00 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

7:30 am - 11:01 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 31mnonstop

$249United Airlines

Sat, Oct 24 - Sun, Oct 25

3:13 pm - 5:05 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

6:00 am - 9:17 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 17mnonstop

$249United Airlines

Useful Info

Low season	January
High season	October
Cheapest flight	$117

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

Most popular time to fly with an average 9% increase in price.

Flight from Boston 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.

Merrillville

Hammond

Saint Joseph

Portage

Lansing

Valparaiso

Munster

Schererville

Chesterton

Porter

Monticello

Saint John

Griffith

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Car rentals in Chicago

$117 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