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>

$67 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

$121

Overall average: $212

JetBlue

Thu 1/22Sun 1/25

BOS - ORD • Non-stop

Cheapest one-way

$67

Typical prices: $109-$256

Frontier

Thu 11/13

BOS - MDW • 1 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

Thu, Jan 22 - Sun, Jan 25

3:35 pm - 5:44 pmBOS-ORD

3h 09mnonstop

10:45 am - 2:09 pmORD-BOS

2h 24mnonstop

$121JetBlue

Find Deal

Thu, Nov 13 - Sat, Nov 15

10:04 am - 10:03 pmBOS-MDW

12h 59m1 stop

1:37 pm - 9:00 amMDW-BOS

18h 23m1 stop

$123Frontier

Find Deal

Thu, Nov 13 - Sat, Nov 15

10:04 am - 12:11 amBOS-ORD

15h 07m1 stop

5:45 pm - 9:00 amORD-BOS

14h 15m1 stop

$123Frontier

Find Deal

Sat, Nov 1 - Sat, Nov 8

5:20 am - 7:00 amBOS-MDW

2h 40mnonstop

4:45 pm - 9:55 pmMDW-BOS

4h 10m1 stop

$127Southwest

Find Deal

Mon, Dec 15 - Thu, Dec 18

4:05 pm - 6:02 pmBOS-ORD

2h 57mnonstop

10:35 am - 1:59 pmORD-BOS

2h 24mnonstop

$127Delta

Find Deal

Sat, Nov 1 - Mon, Nov 3

6:30 am - 4:25 pmBOS-MDW

10h 55m2 stops

6:15 pm - 9:35 pmMDW-BOS

2h 20mnonstop

$132Southwest

Find Deal

Sat, Nov 1 - Mon, Nov 3

4:15 pm - 6:10 pmBOS-ORD

2h 55mnonstop

9:25 pm - 12:45 amORD-BOS

2h 20mnonstop

$133United Airlines

Find Deal

Fri, Oct 31 - Fri, Oct 31

5:00 am - 6:40 amBOS-MDW

2h 40mnonstop

11:45 am - 9:30 pmMDW-BOS

8h 45m1 stop

$133Southwest

Find Deal

Sat, Nov 22 - Tue, Nov 25

8:30 pm - 10:30 pmBOS-ORD

3h 00mnonstop

7:15 am - 10:34 amORD-BOS

2h 19mnonstop

$136United Airlines

Find Deal

Sat, Nov 8 - Tue, Nov 11

4:10 pm - 6:07 pmBOS-ORD

2h 57mnonstop

7:10 am - 10:36 amORD-BOS

2h 26mnonstop

$137Delta

Find Deal

Useful Info

Low season	January
High season	October
Cheapest flight	$67

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

Most popular time to fly with an average 3% 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

Munster

Chesterton

Schererville

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 $508

Business Class flights to Chicagofrom $688

Prem Econ Class flights to Chicagofrom $419

Economy Class flights to Chicagofrom $227

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.

$67 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