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>

$59 CHEAP FLIGHTS from Maine to Chicago

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

...and more

Travelers love KAYAK

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

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Cheapest round-trip

$117

Overall average: $218

Southwest

Fri 12/5Mon 12/8

BOS - MDW • Non-stop

Cheapest non-stop

$117

Typical prices: $158-$373

Southwest

Thu 12/4Sun 12/7

BOS - MDW • 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

Fri, Dec 5 - Mon, Dec 8

5:30 am - 7:15 amBOS-MDW

2h 45mnonstop

6:15 pm - 9:35 pmMDW-BOS

2h 20mnonstop

$117Southwest

Find Deal

Fri, Dec 12 - Sun, Dec 14

7:52 pm - 9:47 pmBOS-ORD

2h 55mnonstop

7:10 am - 10:36 amORD-BOS

2h 26mnonstop

$117Delta

Find Deal

Thu, Dec 4 - Sun, Dec 7

1:45 pm - 3:55 pmBOS-ORD

3h 10mnonstop

7:00 am - 10:29 amORD-BOS

2h 29mnonstop

$118American Airlines

Find Deal

Mon, Dec 15 - Wed, Dec 17

8:30 am - 10:35 amBOS-ORD

3h 05mnonstop

7:00 am - 3:14 pmORD-BOS

7h 14m1 stop

$119JetBlue

Find Deal

Thu, Dec 11 - Thu, Dec 25

11:28 am - 5:27 pmBOS-ORD

6h 59m1 stop

6:00 am - 1:19 amORD-BOS

18h 19m1 stop

$120Frontier

Find Deal

Wed, Dec 3 - Sun, Dec 7

12:50 pm - 2:50 pmBOS-ORD

3h 00mnonstop

7:30 am - 10:49 amORD-BOS

2h 19mnonstop

$122United Airlines

Find Deal

Thu, Dec 4 - Mon, Dec 8

5:29 pm - 7:43 pmBOS-ORD

3h 14mnonstop

8:38 pm - 12:06 amORD-BOS

2h 28mnonstop

$123JetBlue

Find Deal

Mon, Dec 22 - Thu, Dec 25

6:23 pm - 8:25 pmBOS-ORD

3h 02mnonstop

6:11 pm - 9:44 pmORD-BOS

2h 33mnonstop

$124United Airlines

Find Deal

Thu, Dec 11 - Sun, Dec 14

11:28 am - 6:08 pmBOS-MDW

7h 40m1 stop

6:15 am - 10:22 amMDW-BOS

27h 07m1 stop

$129Frontier

Find Deal

Sun, Nov 16 - Wed, Nov 19

6:45 am - 8:52 amBOS-ORD

3h 07mnonstop

7:00 am - 10:25 amORD-BOS

2h 25mnonstop

$152American Airlines

Find Deal

Useful Info

Low season	January
High season	November
Cheapest flight	$59

Best time to beat the crowds with an average 11% drop in price.

Most popular time to fly with an average 2% increase in price.

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 $956

Business Class flights to Chicagofrom $688

Prem Econ Class flights to Chicagofrom $565

Economy Class flights to Chicagofrom $229

$59 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