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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

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. Visit our flight page for the latest deals!>/a>

$70 CHEAP FLIGHTS from Maine to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights 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

Tue, Apr 14 - Wed, Apr 15

12:40 pm - 7:31 pm

BOS

MDW

7h 51m

1 stop

2:15 pm - 1:31 am

MDW

BOS

10h 16m

1 stop

$140Frontier

Mon, Apr 13 - Tue, Apr 14

12:45 pm - 6:30 pm

BOS

ORD

6h 45m

1 stop

6:08 pm - 1:31 am

ORD

BOS

6h 23m

1 stop

$140Frontier

Sat, Apr 11 - Sun, Apr 12

6:05 am - 8:08 am

BOS

ORD

3h 03mnonstop

8:58 am - 12:28 pm

ORD

BOS

2h 30mnonstop

$142JetBlue

Wed, May 27 - Sat, May 30

6:00 am - 8:00 am

BOS

ORD

3h 00mnonstop

1:55 pm - 5:24 pm

ORD

BOS

2h 29mnonstop

$152JetBlue

Sat, Apr 11 - Sun, Apr 12

7:40 pm - 9:50 pm

BOS

ORD

3h 10mnonstop

6:00 am - 9:27 am

ORD

BOS

2h 27mnonstop

$156American Airlines

Sat, Apr 11 - Tue, Apr 14

9:25 am - 11:05 am

BOS

MDW

2h 40mnonstop

12:45 pm - 4:05 pm

MDW

BOS

2h 20mnonstop

$157Southwest

Wed, Apr 15 - Wed, Apr 22

6:00 am - 7:59 am

BOS

ORD

2h 59mnonstop

9:15 am - 12:46 pm

ORD

BOS

2h 31mnonstop

$157United Airlines

Sat, Apr 11 - Sun, Apr 12

3:16 pm - 5:30 pm

BOS

ORD

3h 14mnonstop

6:00 am - 9:27 am

ORD

BOS

2h 27mnonstop

$158American Airlines

Sat, Apr 11 - Tue, Apr 14

7:15 am - 9:05 am

BOS

MDW

2h 50mnonstop

3:00 pm - 10:30 pm

MDW

BOS

6h 30m

1 stop

$167Southwest

Tue, Jun 2 - Sat, Jun 6

6:00 am - 8:00 am

BGR

ORD

3h 00mnonstop

6:08 pm - 9:56 pm

ORD

BGR

2h 48mnonstop

$267United Airlines

Useful Info

Low season	January
High season	May
Cheapest flight	$70

Best time to beat the crowds with an average 6% drop in price.

Most popular time to fly and prices are also 8% lower on average.

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

Saint Joseph

Hammond

Portage

Lansing

Valparaiso

Chesterton

Schererville

Munster

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

Cabin class

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 $601

Business Class flights to Chicagofrom $954

Premium Economy Class flights to Chicagofrom $479

Economy Class flights to Chicagofrom $246

$70 Find Cheap Flights from Maine to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

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

FAQs for booking flights from Maine to Chicago

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.

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