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.

$107 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 1 - Sat, Oct 3

11:17 am - 10:59 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

12h 42m1 stop Orlando

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

18h 08m1 stop Orlando

$188Frontier

Thu, Oct 1 - Sat, Oct 3

11:17 am - 10:59 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

12h 42m1 stop Orlando

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

18h 08m1 stop Orlando

$192Frontier

Thu, Sep 17 - Mon, Sep 21

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

2h 48mnonstop

9:38 am - 1:06 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 28mnonstop

$198JetBlue

Thu, Sep 24 - Tue, Sep 29

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

$211JetBlue

Thu, Nov 5 - Thu, Nov 5

12:12 pm - 2:18 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 06mnonstop

5:17 pm - 8:51 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 34mnonstop

$213American Airlines

Mon, Sep 28 - Tue, Sep 29

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

3h 06mnonstop

1:54 pm - 5:35 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 41mnonstop

$217American Airlines

Thu, Sep 24 - Mon, Sep 28

8:50 pm - 10:32 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 42mnonstop

7:35 am - 11:08 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 33mnonstop

$217Delta

Wed, Oct 28 - Tue, Nov 3

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

2h 51mnonstop

12:00 pm - 3:32 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 32mnonstop

$217Delta

Sat, Sep 19 - Mon, Sep 21

3:16 pm - 5:05 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 49mnonstop

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

2h 23mnonstop

$217United Airlines

Tue, Oct 6 - Wed, Oct 7

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

2h 59mnonstop

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

2h 23mnonstop

$217United Airlines

Recent last minute flight deals from Maine to Chicago

Sat, Sep 5 - Fri, Sep 11

12:45 pm - 8:08 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

8h 23m1 stop Atlanta Hartsfield-Jackson

3:50 pm - 10:51 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

18h 01m1 stop Orlando

$263Frontier

Fri, Sep 4 - Sat, Sep 19

12:45 pm - 7:59 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

8h 14m1 stop Atlanta Hartsfield-Jackson

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

18h 08m1 stop Orlando

$263Frontier

Sun, Sep 6 - Thu, Sep 17

5:20 pm - 7:25 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 05mnonstop

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

2h 45mnonstop

$266JetBlue

Sun, Sep 6 - Sat, Sep 19

5:15 pm - 7:27 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 12mnonstop

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

2h 31mnonstop

$266Delta

Sun, Sep 6 - Fri, Sep 18

8:10 am - 10:06 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

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

2h 45mnonstop

$275JetBlue

Sun, Sep 6 - Sat, Sep 19

4:00 pm - 10:24 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

7h 24m1 stop New York LaGuardia

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

2h 31mnonstop

$276Delta

Sat, Sep 5 - Fri, Sep 11

1:00 pm - 2:35 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

5:45 am - 9:00 amMDW Chicago Midway-BOS Boston Logan Intl

2h 15mnonstop

$295Southwest

Sat, Sep 5 - Sat, Sep 12

3:25 pm - 5:00 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

3:10 pm - 6:35 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 25mnonstop

$295Southwest

Sat, Sep 5 - Fri, Sep 11

7:17 pm - 9:35 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 18mnonstop

11:59 am - 3:38 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 39mnonstop

$295American Airlines

Sat, Sep 5 - Sat, Sep 12

11:58 am - 1:59 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

$295American Airlines

Recent direct flight deals from Maine to Chicago

Thu, Sep 17 - Mon, Sep 21

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

2h 48mnonstop

9:38 am - 1:06 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 28mnonstop

$198JetBlue

Thu, Sep 24 - Tue, Sep 29

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

$211JetBlue

Thu, Nov 5 - Thu, Nov 5

12:12 pm - 2:18 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 06mnonstop

5:17 pm - 8:51 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 34mnonstop

$213American Airlines

Mon, Sep 28 - Tue, Sep 29

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

3h 06mnonstop

1:54 pm - 5:35 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 41mnonstop

$217American Airlines

Thu, Sep 24 - Mon, Sep 28

8:50 pm - 10:32 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 42mnonstop

7:35 am - 11:08 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 33mnonstop

$217Delta

Wed, Oct 28 - Tue, Nov 3

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

2h 51mnonstop

12:00 pm - 3:32 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 32mnonstop

$217Delta

Sat, Sep 19 - Mon, Sep 21

3:16 pm - 5:05 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 49mnonstop

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

2h 23mnonstop

$217United Airlines

Tue, Oct 6 - Wed, Oct 7

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

2h 59mnonstop

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

2h 23mnonstop

$217United Airlines

Tue, Feb 23 - Sat, Feb 27

4:55 pm - 6:45 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 50mnonstop

1:10 pm - 4:20 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 10mnonstop

$217Southwest

Wed, Oct 14 - Mon, Oct 19

10:55 am - 12:30 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

6:45 pm - 10:05 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

$217Southwest

Useful Info

Low season	January
High season	October
Cheapest flight	$107

Best time to beat the crowds with an average 10% drop in price.

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

Flight from Boston 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

Schererville

Chesterton

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

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Complete your trip

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Flights to other cities

Origins

Other airports

Return flight deals

Cabin class types available on flights to Maine

First Class flights to Chicagofrom $562

Business Class flights to Chicagofrom $837

Premium Economy Class flights to Chicagofrom $885

Economy Class flights to Chicagofrom $299

$107 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?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Maine

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

Find direct flights for Chicago

Flights to other popular destinations

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Find deals for your return flight