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.

$110 CHEAP FLIGHTS from Massachusetts to Chicago (ORD)

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals

Cheap Flights from Massachusetts to O'Hare Intl

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 O'Hare Intl

Tue, Oct 13 - Wed, Oct 14

4:15 pm - 8:43 pmORH Worcester-ORD Chicago O'Hare Intl

5h 28m1 stop New York LaGuardia

7:00 am - 2:58 pmORD Chicago O'Hare Intl-ORH Worcester

6h 58m1 stop New York LaGuardia

$204Delta

Tue, Oct 13 - Wed, Oct 14

4:15 pm - 8:43 pmORH Worcester-ORD Chicago O'Hare Intl

5h 28m1 stop New York LaGuardia

7:00 am - 2:58 pmORD Chicago O'Hare Intl-ORH Worcester

6h 58m2 stops Detroit Metropolitan Wayne County New York LaGuardia

$214Delta

Wed, Oct 21 - Sat, Oct 24

6:55 am - 8:47 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

8:04 pm - 11:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 55mnonstop

$215JetBlue

Mon, Nov 16 - Wed, Nov 18

5:05 pm - 7:17 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 12mnonstop

1:00 pm - 4:49 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 49mnonstop

$215JetBlue

Tue, Nov 3 - Wed, Nov 4

3:01 pm - 5:05 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 04mnonstop

7:00 am - 12:26 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

4h 26m1 stop Newark

$219United Airlines

Wed, Oct 28 - Wed, Nov 4

4:38 pm - 6:42 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 04mnonstop

12:59 pm - 6:34 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

4h 35m1 stop Newark

$219United Airlines

Mon, Nov 16 - Wed, Nov 18

5:43 am - 8:00 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 17mnonstop

1:37 pm - 5:08 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 31mnonstop

$222American Airlines

Wed, Nov 4 - Thu, Nov 5

7:14 am - 9:30 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 16mnonstop

7:13 pm - 10:42 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 29mnonstop

$222American Airlines

Sat, Oct 31 - Tue, Nov 10

11:27 am - 6:16 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

7h 49m1 stop Atlanta Hartsfield-Jackson

1:00 pm - 4:49 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 49mnonstop

$222Multiple Airlines

Mon, Nov 9 - Wed, Nov 11

12:39 pm - 6:45 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

7h 06m1 stop Atlanta Hartsfield-Jackson

1:00 pm - 4:49 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 49mnonstop

$222Multiple Airlines

Recent last minute flight deals from Massachusetts to O'Hare Intl

Fri, Oct 9 - Tue, Oct 13

4:57 pm - 7:00 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 03mnonstop

12:38 pm - 8:49 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

7h 11m1 stop New York John F Kennedy Intl

$269JetBlue

Thu, Oct 8 - Tue, Oct 13

6:55 am - 8:47 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

8:04 pm - 11:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 55mnonstop

$293JetBlue

Mon, Oct 5 - Wed, Oct 7

12:54 pm - 6:23 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 29m1 stop Atlanta Hartsfield-Jackson

3:50 pm - 11:02 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

18h 12m1 stop Orlando

$294Frontier

Tue, Oct 6 - Wed, Oct 7

12:52 pm - 6:23 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 31m1 stop Atlanta Hartsfield-Jackson

3:50 pm - 11:02 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

18h 12m1 stop Orlando

$294Frontier

Thu, Oct 8 - Tue, Oct 13

7:00 am - 9:05 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 05mnonstop

7:03 pm - 10:37 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 34mnonstop

$303American Airlines

Thu, Oct 8 - Tue, Oct 13

7:00 am - 9:05 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 05mnonstop

8:00 pm - 11:36 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 36mnonstop

$303American Airlines

Mon, Oct 5 - Wed, Oct 14

8:50 pm - 10:32 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 42mnonstop

10:24 am - 1:54 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 30mnonstop

$303Delta

Tue, Oct 6 - Wed, Oct 14

4:25 pm - 6:20 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 55mnonstop

10:24 am - 1:54 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 30mnonstop

$303Delta

Tue, Oct 6 - Wed, Oct 14

6:43 pm - 8:40 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 57mnonstop

6:00 am - 11:24 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

4h 24m1 stop Newark

$313United Airlines

Thu, Oct 8 - Mon, Nov 9

8:05 am - 10:00 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 55mnonstop

9:13 am - 12:46 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 33mnonstop

$316United Airlines

Recent direct flight deals from Massachusetts to O'Hare Intl

Wed, Oct 21 - Sat, Oct 24

6:55 am - 8:47 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

8:04 pm - 11:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 55mnonstop

$215JetBlue

Mon, Nov 16 - Wed, Nov 18

5:05 pm - 7:17 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 12mnonstop

1:00 pm - 4:49 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 49mnonstop

$215JetBlue

Wed, Nov 11 - Mon, Nov 16

9:59 am - 12:00 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 01mnonstop

1:00 pm - 4:49 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 49mnonstop

$215JetBlue

Mon, Nov 16 - Wed, Nov 18

5:43 am - 8:00 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 17mnonstop

1:37 pm - 5:08 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 31mnonstop

$222American Airlines

Wed, Nov 4 - Thu, Nov 5

7:14 am - 9:30 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 16mnonstop

7:13 pm - 10:42 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 29mnonstop

$222American Airlines

Mon, Nov 9 - Wed, Nov 11

8:40 pm - 10:36 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

7:05 am - 10:32 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 27mnonstop

$222Delta

Tue, Oct 27 - Sat, Oct 31

7:30 am - 9:24 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

12:00 pm - 3:32 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 32mnonstop

$222Delta

Sat, Oct 24 - Tue, Oct 27

6:00 am - 7:59 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

12:33 pm - 3:58 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 25mnonstop

$222United Airlines

Mon, Nov 16 - Wed, Nov 18

6:00 am - 8:00 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 00mnonstop

9:20 pm - 12:46 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 26mnonstop

$222United Airlines

Thu, Oct 15 - Tue, Oct 20

7:00 am - 9:05 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 05mnonstop

3:48 pm - 7:33 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 45mnonstop

$222American Airlines

Useful Info

Low season	January
High season	July
Cheapest flight	$110

Best time to beat the crowds with an average 16% drop in price.

Most popular time to fly with an average 13% 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

Gurnee

South Haven

Oak Brook

Tinley Park

Hammond

Saint Joseph

Des Plaines

Elk Grove Village

Hoffman Estates

Oakbrook Terrace

Portage

South Holland

Willowbrook

Lansing

Lisle

Alsip

Delavan

Valparaiso

Northbrook

More options for your flight to O'Hare Intl

Add a hotel or car rental

Airports

Cabin class

Direct Flights

Origins

Other destinations

Return flight

Complete your trip to O'Hare Intl with a hotel stay or car rental

Car rentals in Chicago

ORD

$110 Find Cheap Flights from Massachusetts to Chicago - Compare and Save

Cheap Flights from Massachusetts to O'Hare Intl

Recent round-trip flight deals from Massachusetts to O'Hare Intl

Recent one-way flight deals from Massachusetts to O'Hare Intl

Recent last minute flight deals from Massachusetts to O'Hare Intl

Recent direct flight deals from Massachusetts to O'Hare Intl

Good to know

Low season

High season

Cheapest flight

FAQs for booking Massachusetts to Chicago flights

Traveling to a place near O'Hare Intl?

More options for your flight to O'Hare Intl

Complete your trip to O'Hare Intl with a hotel stay or car rental

Information on your arrival and departure airports

Cabin class types available on flights to O'Hare Intl

Find direct flights for O'Hare Intl

Flights from domestic origins to Massachusetts

Flights to other popular destinations

Find deals for your return flight