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>

$70 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

Thu, Apr 2 - Wed, Apr 15

6:52 am - 9:03 am

BOS

ORD

3h 11mnonstop

11:45 am - 3:18 pm

ORD

BOS

2h 33mnonstop

$137American Airlines

Tue, Apr 28 - Tue, May 5

7:35 pm - 9:39 pm

BOS

ORD

3h 04mnonstop

7:21 am - 10:49 am

ORD

BOS

2h 28mnonstop

$138JetBlue

Sun, Apr 26 - Sun, May 3

7:00 am - 9:00 am

BOS

ORD

3h 00mnonstop

6:00 am - 9:15 am

ORD

BOS

2h 15mnonstop

$144JetBlue

Mon, Apr 6 - Wed, Apr 8

6:05 am - 8:08 am

BOS

ORD

3h 03mnonstop

7:17 am - 3:28 pm

ORD

BOS

7h 11m

1 stop

$149Multiple Airlines

Wed, Apr 8 - Sat, Apr 11

6:20 pm - 8:10 pm

BOS

MDW

2h 50mnonstop

6:05 pm - 9:25 pm

MDW

BOS

2h 20mnonstop

$157Southwest

Thu, Jun 4 - Tue, Jun 9

6:45 pm - 8:35 pm

BOS

MDW

2h 50mnonstop

7:50 am - 3:00 pm

MDW

BOS

6h 10m

1 stop

$167Southwest

Fri, Apr 24 - Tue, Apr 28

12:42 pm - 7:31 pm

BOS

MDW

7h 49m

1 stop

2:15 pm - 1:31 am

MDW

BOS

10h 16m

1 stop

$180Frontier

Wed, Jun 3 - Wed, Jun 10

4:02 pm - 8:46 pm

MVY

ORD

5h 44m

1 stop

7:30 am - 2:19 pm

ORD

MVY

5h 49m

1 stop

$264Delta

Wed, Jun 3 - Thu, Jun 11

12:04 pm - 4:34 pm

MVY

ORD

5h 30m

1 stop

7:30 am - 2:19 pm

ORD

MVY

5h 49m

1 stop

$292Delta

Fri, Apr 24 - Mon, Apr 27

3:34 pm - 10:26 pm

BDL

MDW

7h 52m

1 stop

6:00 am - 2:49 pm

MDW

BDL

7h 49m

1 stop

$330Frontier

Useful Info

Low season	January
High season	May
Cheapest flight	$70

Best time to beat the crowds with an average 13% drop in price.

Most popular time to fly with an average 7% increase in price.

Flight from Hartford to Chicago Midway 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

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 Massachusetts

First Class flights to Chicagofrom $514

Business Class flights to Chicagofrom $447

Premium Economy Class flights to Chicagofrom $288

Economy Class flights to Chicagofrom $136

$69 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