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>

$86 CHEAP FLIGHTS from Massachusetts 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.

Flight Deals

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

Tue, Jun 2 - Tue, Jun 9

6:00 am - 8:00 am

BOS

ORD

3h 00mnonstop

8:30 pm - 11:59 pm

ORD

BOS

2h 29mnonstop

$173JetBlue

Sat, Jun 6 - Tue, Jun 9

5:20 am - 6:55 am

BOS

MDW

2h 35mnonstop

2:40 pm - 6:00 pm

MDW

BOS

2h 20mnonstop

$176Southwest

Tue, Jun 2 - Tue, Jun 9

3:00 pm - 5:06 pm

BOS

ORD

3h 06mnonstop

1:57 pm - 5:32 pm

ORD

BOS

2h 35mnonstop

$186American Airlines

Tue, Jun 2 - Wed, Jun 10

8:40 pm - 10:35 pm

BOS

ORD

2h 55mnonstop

7:10 am - 10:46 am

ORD

BOS

2h 36mnonstop

$187Delta

Tue, Jun 16 - Tue, Jun 23

9:10 am - 7:50 pm

BOS

ORD

11h 40m

1 stop

1:29 pm - 1:27 am

ORD

BOS

10h 58m

1 stop

$189Frontier

Wed, Jul 29 - Tue, Aug 4

12:04 pm - 10:08 pm

BOS

MDW

11h 04m

1 stop

12:11 pm - 1:23 am

MDW

BOS

12h 12m

1 stop

$190Frontier

Tue, Jun 30 - Tue, Jul 7

5:18 pm - 11:00 am

ORH

ORD

18h 42m

1 stop

8:30 am - 4:51 pm

ORD

ORH

7h 21m

1 stop

$219American Airlines

Fri, Jul 3 - Sun, Jul 12

12:37 pm - 8:15 am

BOS

RFD

20h 38m

1 stop

11:27 am - 7:46 am

RFD

BOS

19h 19m

2 stops

$325Multiple Airlines

Fri, Jul 17 - Thu, Jul 23

7:53 pm - 10:08 pm

ALB

MDW

27h 15m

2 stops

9:08 am - 11:33 am

MDW

ALB

25h 25m

1 stop

$331Multiple Airlines

Wed, Sep 16 - Mon, Sep 21

6:00 am - 8:42 am

ALB

MDW

3h 42m

1 stop

5:59 pm - 11:06 pm

MDW

ALB

4h 07m

1 stop

$332Delta

Useful Info

Low season	January
High season	October
Cheapest flight	$86

Best time to beat the crowds with an average 13% 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 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

Schererville

Chesterton

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 $410

Business Class flights to Chicagofrom $490

Premium Economy Class flights to Chicagofrom $555

Economy Class flights to Chicagofrom $168

$86 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