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>

$55 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 20% 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.

Flights 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

Tue, Jul 8 - Wed, Jul 9

4:44 pm - 11:45 pmBOS-ORD

8h 01m1 stop

10:00 am - 7:30 pmORD-BOS

8h 30m1 stop

$121Spirit Airlines

Find Deal

Tue, Jul 1 - Sat, Jul 12

6:50 pm - 8:35 pmBOS-MDW

2h 45mnonstop

7:00 pm - 10:15 pmMDW-BOS

2h 15mnonstop

$123Southwest

Find Deal

Fri, Sep 5 - Mon, Sep 8

7:00 am - 8:57 amBOS-ORD

2h 57mnonstop

9:42 am - 1:10 pmORD-BOS

2h 28mnonstop

$125JetBlue

Find Deal

Sat, Sep 13 - Thu, Sep 25

7:00 am - 8:57 amBOS-ORD

2h 57mnonstop

6:50 pm - 10:23 pmORD-BOS

2h 33mnonstop

$131JetBlue

Find Deal

Tue, Jul 1 - Fri, Jul 4

7:04 pm - 11:37 pmBOS-ORD

5h 33m1 stop

3:48 pm - 7:18 pmORD-BOS

2h 30mnonstop

$143United Airlines

Find Deal

Thu, Jul 3 - Mon, Jul 7

6:07 am - 8:05 amBOS-ORD

2h 58mnonstop

6:00 am - 9:26 amORD-BOS

2h 26mnonstop

$155United Airlines

Find Deal

Thu, Oct 30 - Sun, Nov 2

5:00 am - 6:58 amBOS-ORD

2h 58mnonstop

7:00 am - 10:19 amORD-BOS

2h 19mnonstop

$156American Airlines

Find Deal

Tue, Jul 1 - Sat, Jul 5

7:20 am - 9:18 amBOS-ORD

2h 58mnonstop

7:00 am - 10:31 amORD-BOS

2h 31mnonstop

$160Delta

Find Deal

Mon, Jul 14 - Mon, Jul 21

5:00 am - 6:58 amBOS-ORD

2h 58mnonstop

8:30 pm - 12:14 amORD-BOS

2h 44mnonstop

$173American Airlines

Find Deal

Mon, Jun 30 - Thu, Jul 24

7:20 am - 9:18 amBOS-ORD

2h 58mnonstop

7:00 am - 10:31 amORD-BOS

2h 31mnonstop

$188Delta

Find Deal

Useful Info

Low season	January
High season	August
Cheapest flight	$55

Best time to beat the crowds with an average 10% drop in price.

Most popular time to fly and prices are also 11% lower on average.

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.

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 $463

Business Class flights to Chicagofrom $759

Prem Econ Class flights to Chicagofrom $756

Economy Class flights to Chicagofrom $211

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

$55 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.

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