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.

$109 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

Sat, Oct 17 - Tue, Oct 20

4:11 pm - 10:10 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 59m1 stop New York John F Kennedy Intl

6:10 am - 2:29 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

7h 19m1 stop New York John F Kennedy Intl

$210JetBlue

Tue, Oct 20 - Wed, Oct 21

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

5h 29m1 stop New York John F Kennedy Intl

12:38 pm - 8:49 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

7h 11m1 stop New York John F Kennedy Intl

$217JetBlue

Tue, Sep 29 - Wed, Sep 30

12:52 pm - 6:23 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 31m1 stop Atlanta Hartsfield-Jackson

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

17h 32m1 stop Orlando

$228Frontier

Tue, Sep 29 - Wed, Sep 30

12:52 pm - 6:23 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 31m1 stop Atlanta Hartsfield-Jackson

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

17h 32m1 stop Orlando

$232Frontier

Tue, Oct 13 - Sun, Oct 18

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

$274American Airlines

Sat, Oct 24 - Wed, Oct 28

4:48 pm - 7:00 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 12mnonstop

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

2h 45mnonstop

$274American Airlines

Mon, Oct 26 - Wed, Oct 28

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

$275Delta

Tue, Oct 13 - Wed, Oct 21

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

$275Delta

Fri, Oct 2 - Sun, Oct 4

6:43 pm - 8:40 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 57mnonstop

6:10 am - 9:33 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 23mnonstop

$275United Airlines

Fri, Oct 23 - Mon, Oct 26

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

2h 52mnonstop

6:59 am - 10:18 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 19mnonstop

$275United Airlines

Recent last minute flight deals from Maine to Chicago

Tue, Sep 15 - Wed, Sep 30

12:52 pm - 6:23 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 31m1 stop Atlanta Hartsfield-Jackson

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

17h 32m1 stop Orlando

$260Frontier

Tue, Sep 15 - Wed, Sep 23

12:52 pm - 6:23 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 31m1 stop Atlanta Hartsfield-Jackson

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

17h 32m1 stop Orlando

$271Frontier

Tue, Sep 15 - Wed, Sep 30

5:00 pm - 7:01 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 01mnonstop

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

2h 45mnonstop

$313JetBlue

Sun, Sep 13 - Sat, Sep 19

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

$313JetBlue

Tue, Sep 15 - Tue, Sep 22

3:20 pm - 4:55 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

6:40 am - 9:55 amMDW Chicago Midway-BOS Boston Logan Intl

2h 15mnonstop

$316Southwest

Tue, Sep 15 - Wed, Oct 14

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

2h 35mnonstop

6:10 pm - 9:30 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

$316Southwest

Sat, Sep 12 - Wed, Oct 7

5:45 pm - 8:05 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 20mnonstop

8:00 pm - 11:36 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 36mnonstop

$316American Airlines

Tue, Sep 15 - Wed, Oct 14

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

3h 01mnonstop

2:00 pm - 5:45 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 45mnonstop

$316American Airlines

Sun, Sep 13 - Tue, Sep 22

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

$336Delta

Sun, Sep 13 - Mon, Sep 21

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

$336Delta

Recent direct flight deals from Maine to Chicago

Sat, Oct 3 - Mon, Oct 5

5:00 pm - 7:01 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 01mnonstop

8:24 pm - 12:23 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 59mnonstop

$265JetBlue

Tue, Oct 27 - Sat, Oct 31

9:59 am - 11:59 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 00mnonstop

1:00 pm - 4:48 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 48mnonstop

$266JetBlue

Tue, Oct 13 - Sun, Oct 18

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

$274American Airlines

Sat, Oct 24 - Wed, Oct 28

4:48 pm - 7:00 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 12mnonstop

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

2h 45mnonstop

$274American Airlines

Mon, Oct 26 - Wed, Oct 28

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

$275Delta

Tue, Oct 13 - Wed, Oct 21

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

$275Delta

Fri, Oct 2 - Sun, Oct 4

6:43 pm - 8:40 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 57mnonstop

6:10 am - 9:33 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 23mnonstop

$275United Airlines

Fri, Oct 23 - Mon, Oct 26

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

2h 52mnonstop

6:59 am - 10:18 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 19mnonstop

$275United Airlines

Thu, Nov 12 - Sun, Nov 15

6:30 pm - 8:15 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 45mnonstop

7:50 am - 11:10 amMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

$275Southwest

Thu, Nov 12 - Sun, Nov 15

6:30 pm - 8:15 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 45mnonstop

7:50 am - 11:10 amMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

$275Southwest

Useful Info

Low season	January
High season	October
Cheapest flight	$109

Best time to beat the crowds with an average 10% 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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$109 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

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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