How does KAYAK find such low prices on flights from Massachusetts 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 Massachusetts 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 Massachusetts to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Massachusetts 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 Massachusetts 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 Massachusetts 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 Massachusetts 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 Massachusetts 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>

$68 CHEAP FLIGHTS from Massachusetts to Chicago

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

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Cheap Flights from Massachusetts 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 Massachusetts to Chicago

Sat, May 2 - Tue, May 5

7:35 pm - 9:36 pm

BOS

ORD

3h 01mnonstop

3:31 pm - 11:18 pm

ORD

BOS

6h 47m

1 stop

$129Multiple Airlines

Mon, Apr 6 - Mon, Apr 6

7:00 am - 9:00 am

BOS

ORD

3h 00mnonstop

9:30 pm - 12:59 am

ORD

BOS

2h 29mnonstop

$130United Airlines

Wed, Mar 11 - Sun, Apr 12

5:31 pm - 7:48 pm

BOS

ORD

3h 17mnonstop

6:00 am - 9:27 am

ORD

BOS

2h 27mnonstop

$131American Airlines

Thu, Apr 2 - Thu, Apr 2

11:50 am - 1:40 pm

BOS

MDW

2h 50mnonstop

3:30 pm - 6:45 pm

MDW

BOS

2h 15mnonstop

$132Southwest

Sat, Apr 11 - Mon, Apr 13

7:15 am - 9:05 am

BOS

MDW

2h 50mnonstop

7:00 pm - 10:20 pm

MDW

BOS

2h 20mnonstop

$133Southwest

Thu, Apr 2 - Sun, Apr 5

7:15 am - 9:25 am

BOS

ORD

3h 10mnonstop

6:15 am - 9:40 am

ORD

BOS

2h 25mnonstop

$137Delta

Thu, Apr 2 - Sun, Apr 5

7:15 am - 9:25 am

BOS

ORD

3h 10mnonstop

6:15 am - 9:40 am

ORD

BOS

2h 25mnonstop

$138Delta

Tue, Mar 3 - Wed, Mar 4

7:00 am - 9:10 am

BOS

ORD

3h 10mnonstop

10:00 am - 1:20 pm

ORD

BOS

2h 20mnonstop

$140JetBlue

Thu, Apr 2 - Sun, Apr 5

6:52 am - 9:03 am

BOS

ORD

3h 11mnonstop

8:20 am - 11:38 am

ORD

BOS

2h 18mnonstop

$142American Airlines

Mon, Mar 16 - Wed, Mar 18

12:07 pm - 5:24 pm

HYA

ORD

6h 17m

1 stop

11:00 am - 5:20 pm

ORD

HYA

5h 20m

1 stop

$416JetBlue

Useful Info

Low season	January
High season	May
Cheapest flight	$68

Best time to beat the crowds with an average 14% drop in price.

Most popular time to fly with an average 8% increase in price.

Flight from Boston to Chicago O'Hare Airport

How does KAYAK find such low prices on flights from Massachusetts 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 Massachusetts to Chicago.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Massachusetts to Chicago?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Massachusetts 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 Massachusetts 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 Massachusetts with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Massachusetts 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 Massachusetts 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

Griffith

Saint John

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 Massachusetts

First Class flights to Chicagofrom $377

Business Class flights to Chicagofrom $447

Premium Economy Class flights to Chicagofrom $322

Economy Class flights to Chicagofrom $135

$68 Find Cheap Flights from Massachusetts to Chicago

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

Cheap Flights from Massachusetts to Chicago

Recent round-trip flight deals from Massachusetts to Chicago

Recent one-way flight deals from Massachusetts to Chicago

Recent last minute flight deals from Massachusetts to Chicago

Recent direct flight deals from Massachusetts to Chicago

Good to know

FAQs for booking flights from Massachusetts to Chicago

How does KAYAK find such low prices on flights from Massachusetts 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 Massachusetts to Chicago.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Massachusetts to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Massachusetts 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 Massachusetts 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 Massachusetts with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Massachusetts 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 Massachusetts 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 Massachusetts

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