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>

$63 CHEAP FLIGHTS from Maine to Chicago

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

...and more

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41,299,237 searches in the past 7 days on KAYAK

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Cheapest round-trip

$125

Overall average: $212

JetBlue

Sat 1/17Sun 1/18

BOS - ORD • Non-stop

Cheapest non-stop

$123

Typical prices: $176-$373

JetBlue

Sat 12/13Sun 12/14

BOS - ORD • Non-stop

Start a new search

KAYAK searches 100s of sites at once to find you the best travel deals.

We hope you love your trip to Chicago!

Flight Deals

Cheap Flights from Maine to Chicago

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Maine to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

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, Jan 17 - Sun, Jan 18

3:35 pm - 5:43 pm

BOS

ORD

3h 08mnonstop

7:45 am - 11:10 am

ORD

BOS

2h 25mnonstop

$125JetBlue

Thu, Jan 22 - Thu, Jan 29

6:00 am - 11:45 am

BOS

MDW

6h 45m1 stop

5:01 pm - 1:13 am

MDW

BOS

7h 12m1 stop

$126Frontier

Sat, Jan 17 - Sun, Jan 18

3:35 pm - 5:43 pm

BOS

ORD

3h 08mnonstop

9:15 am - 3:34 pm

ORD

BOS

5h 19m1 stop

$126JetBlue

Sat, Jan 17 - Sun, Jan 18

4:49 pm - 6:49 pm

BOS

ORD

3h 00mnonstop

11:05 am - 2:29 pm

ORD

BOS

2h 24mnonstop

$127United Airlines

Fri, Jan 23 - Sun, Jan 25

6:00 am - 11:45 am

BOS

MDW

6h 45m1 stop

5:01 pm - 1:13 am

MDW

BOS

7h 12m1 stop

$128Frontier

Tue, Jan 20 - Thu, Jan 29

4:10 pm - 6:19 pm

BOS

ORD

3h 09mnonstop

10:40 am - 2:13 pm

ORD

BOS

2h 33mnonstop

$132Delta

Sat, Jan 17 - Sun, Jan 18

5:30 am - 7:20 am

BOS

MDW

2h 50mnonstop

5:35 pm - 8:50 pm

MDW

BOS

2h 15mnonstop

$137Southwest

Wed, Jan 14 - Sat, Jan 17

2:40 pm - 4:30 pm

BOS

MDW

2h 50mnonstop

10:15 am - 1:30 pm

MDW

BOS

2h 15mnonstop

$142Southwest

Wed, Dec 24 - Thu, Dec 25

7:30 pm - 11:44 pm

PWM

ORD

5h 14m1 stop

6:21 pm - 11:59 pm

ORD

PWM

4h 38m1 stop

$269United Airlines

Thu, Mar 12 - Sun, Mar 15

5:30 am - 12:29 pm

PWM

MDW

7h 59m2 stops

9:32 am - 4:10 pm

MDW

PWM

5h 38m1 stop

$284Delta

Useful Info

Low season	January
High season	July
Cheapest flight	$63

Best time to beat the crowds with an average 16% drop in price.

Most popular time to fly with an average 2% 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

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 $699

Business Class flights to Chicagofrom $639

Prem Econ Class flights to Chicagofrom $527

Economy Class flights to Chicagofrom $279

$64 Find Cheap Flights from Maine to Chicago

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

Everything you should know

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