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>

$76 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

Thu, May 28 - Fri, May 29

7:35 am - 9:27 am

BOS

ORD

2h 52mnonstop

7:16 pm - 10:50 pm

ORD

BOS

2h 34mnonstop

$150Delta

Wed, May 27 - Tue, Jun 23

10:45 am - 12:25 pm

BOS

MDW

2h 40mnonstop

2:40 pm - 6:00 pm

MDW

BOS

2h 20mnonstop

$151Southwest

Sat, May 16 - Tue, May 19

4:32 pm - 6:49 pm

BOS

ORD

3h 17mnonstop

6:00 am - 9:27 am

ORD

BOS

2h 27mnonstop

$151American Airlines

Sun, May 24 - Wed, May 27

6:00 am - 8:00 am

BOS

ORD

3h 00mnonstop

8:30 pm - 11:59 pm

ORD

BOS

2h 29mnonstop

$152JetBlue

Mon, May 11 - Thu, May 14

7:02 am - 8:59 am

BOS

ORD

2h 57mnonstop

7:20 am - 10:46 am

ORD

BOS

2h 26mnonstop

$153JetBlue

Wed, Jun 10 - Sat, Jun 13

7:19 am - 9:17 am

BOS

ORD

2h 58mnonstop

7:40 pm - 11:16 pm

ORD

BOS

2h 36mnonstop

$156United Airlines

Sat, May 16 - Sun, May 24

12:01 pm - 7:51 pm

BOS

ORD

8h 50m

1 stop

8:50 am - 12:20 pm

ORD

BOS

2h 30mnonstop

$159Multiple Airlines

Sat, May 9 - Thu, May 21

5:45 am - 9:47 am

BOS

RFD

29h 02m

1 stop

11:27 am - 11:54 pm

RFD

BOS

11h 27m

1 stop

$211Multiple Airlines

Wed, Jun 10 - Wed, Jun 17

12:20 pm - 2:34 pm

BGR

ORD

3h 14mnonstop

7:14 pm - 11:03 pm

ORD

BGR

2h 49mnonstop

$261American Airlines

Tue, May 19 - Thu, May 21

6:00 am - 7:56 am

PWM

ORD

2h 56mnonstop

4:00 pm - 11:51 pm

ORD

PWM

6h 51m

1 stop

$263United Airlines

Useful Info

Low season	January
High season	May
Cheapest flight	$76

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

Most popular time to fly and prices are also 10% 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 $773

Business Class flights to Chicagofrom $575

Premium Economy Class flights to Chicagofrom $563

Economy Class flights to Chicagofrom $269

$76 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