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.

$103 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

Mon, Sep 14 - Mon, Oct 12

5:15 am - 9:58 am

BOS

ORD

5h 43m

1 stop

9:38 am - 1:06 pm

ORD

BOS

2h 28mnonstop

$204JetBlue

Sat, Sep 12 - Sun, Sep 13

5:00 pm - 7:01 pm

BOS

ORD

3h 01mnonstop

7:00 am - 3:14 pm

ORD

BOS

7h 14m

1 stop

$210JetBlue

Wed, Sep 9 - Wed, Sep 16

7:30 am - 9:24 am

BOS

ORD

2h 54mnonstop

10:29 am - 2:05 pm

ORD

BOS

2h 36mnonstop

$217Delta

Tue, Sep 22 - Sat, Sep 26

7:30 am - 9:24 am

BOS

ORD

2h 54mnonstop

11:30 am - 3:15 pm

ORD

BOS

2h 45mnonstop

$217Delta

Wed, Oct 21 - Sat, Oct 24

8:00 am - 9:56 am

BOS

ORD

2h 56mnonstop

9:24 pm - 12:54 am

ORD

BOS

2h 30mnonstop

$217United Airlines

Sat, Oct 3 - Sat, Oct 10

6:43 pm - 8:40 pm

BOS

ORD

2h 57mnonstop

9:24 pm - 12:54 am

ORD

BOS

2h 30mnonstop

$217United Airlines

Sat, Oct 10 - Tue, Oct 13

6:00 pm - 8:12 pm

BOS

ORD

3h 12mnonstop

7:00 am - 10:33 am

ORD

BOS

2h 33mnonstop

$217American Airlines

Wed, Sep 16 - Sat, Sep 19

1:34 pm - 3:35 pm

BOS

ORD

3h 01mnonstop

6:50 am - 10:29 am

ORD

BOS

2h 39mnonstop

$217American Airlines

Tue, Sep 15 - Sat, Sep 19

7:30 am - 9:05 am

BOS

MDW

2h 35mnonstop

7:40 am - 11:00 am

MDW

BOS

2h 20mnonstop

$217Southwest

Wed, Sep 9 - Wed, Sep 16

3:20 pm - 4:55 pm

BOS

MDW

2h 35mnonstop

8:45 am - 12:15 pm

MDW

BOS

2h 30mnonstop

$217Southwest

Useful Info

Low season	January
High season	October
Cheapest flight	$103

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

Most popular time to fly with an average 17% 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

Saint Joseph

Hammond

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

Direct Flights

Flights to other cities

Origins

Other airports

Return flight deals

Cabin class types available on flights to Maine

First Class flights to Chicagofrom $701

Business Class flights to Chicagofrom $929

Premium Economy Class flights to Chicagofrom $885

Economy Class flights to Chicagofrom $291

$103 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

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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