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.

$106 CHEAP FLIGHTS from Massachusetts to Chicago (ORD)

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Cheap Flights from Massachusetts to O'Hare Intl

Cheap flights from Massachusetts to O'Hare Intl with top airlines, updated regularly. Compare round-trip, one-way, direct and last-minute deals.

Round-trip

One-way

Last minute

Direct

Mon, Nov 16 - Thu, Nov 19

9:15 am - 1:59 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 44m1 stop Detroit Metropolitan Wayne County

10:35 am - 1:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 24mnonstop

$211Delta

Sat, Nov 14 - Tue, Nov 17

7:55 pm - 9:51 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

8:45 am - 2:21 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

4h 36m1 stop New York LaGuardia

$211Delta

Tue, Oct 27 - Sat, Oct 31

9:12 am - 11:15 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 03mnonstop

6:59 am - 12:26 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

4h 27m1 stop Newark

$211United Airlines

Wed, Oct 28 - Sat, Oct 31

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

3h 04mnonstop

8:50 am - 2:32 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

4h 42m1 stop Washington, D.C. Dulles Intl

$211United Airlines

Thu, Dec 3 - Thu, Dec 10

11:34 am - 9:40 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

11h 06m1 stop Atlanta Hartsfield-Jackson

10:37 pm - 10:39 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

11h 02m1 stop Atlanta Hartsfield-Jackson

$212Frontier

Fri, Dec 11 - Tue, Dec 15

11:08 am - 1:01 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

14h 53m1 stop Orlando

5:46 pm - 9:14 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 28mnonstop

$215Multiple Airlines

Mon, Oct 26 - Wed, Oct 28

5:16 pm - 10:30 pmORH Worcester-ORD Chicago O'Hare Intl

6h 14m1 stop Philadelphia

6:29 am - 4:49 pmORD Chicago O'Hare Intl-ORH Worcester

9h 20m1 stop Philadelphia

$216American Airlines

Fri, Jan 15 - Mon, Jan 18

11:45 am - 1:49 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 04mnonstop

2:55 pm - 6:17 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 22mnonstop

$222JetBlue

Fri, Jan 15 - Mon, Jan 18

2:40 pm - 4:45 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 05mnonstop

5:46 pm - 9:10 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 24mnonstop

$222JetBlue

Tue, Nov 24 - Fri, Nov 27

5:39 am - 8:00 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 21mnonstop

12:00 pm - 3:26 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 26mnonstop

$229American Airlines

Sun, Oct 11 - Thu, Nov 12

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

2h 52mnonstop

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

2h 49mnonstop

$290JetBlue

Thu, Oct 15 - Sun, Oct 18

11:47 am - 7:31 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

20h 44m1 stop Orlando

6:58 pm - 11:02 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

15h 04m1 stop Orlando

$294Frontier

Wed, Oct 14 - Fri, Oct 16

12:57 pm - 6:31 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 34m1 stop Atlanta Hartsfield-Jackson

8:11 pm - 11:02 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

13h 51m1 stop Orlando

$294Frontier

Sun, Oct 11 - Mon, Oct 26

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

2h 52mnonstop

8:24 pm - 12:08 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 44mnonstop

$299JetBlue

Sun, Oct 11 - Wed, Oct 14

4:15 pm - 10:17 pmORH Worcester-ORD Chicago O'Hare Intl

7h 02m1 stop New York LaGuardia

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

6h 58m1 stop New York LaGuardia

$342Delta

Sun, Oct 11 - Tue, Oct 13

4:15 pm - 10:17 pmORH Worcester-ORD Chicago O'Hare Intl

7h 02m1 stop New York LaGuardia

5:27 am - 2:58 pmORD Chicago O'Hare Intl-ORH Worcester

8h 31m2 stops Atlanta Hartsfield-Jackson New York LaGuardia

$352Delta

Sat, Oct 10 - Thu, Oct 22

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

2h 57mnonstop

6:10 am - 9:33 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 23mnonstop

$356United Airlines

Thu, Oct 15 - Tue, Oct 20

12:45 pm - 2:37 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

9:05 am - 12:48 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 43mnonstop

$356United Airlines

Sat, Oct 10 - Sat, Oct 24

6:53 pm - 11:44 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 51m1 stop Washington, D.C. Reagan-National

1:22 pm - 6:55 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

4h 33m1 stop Philadelphia

$376American Airlines

Sat, Oct 10 - Thu, Oct 22

6:53 pm - 11:44 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 51m1 stop Washington, D.C. Reagan-National

5:29 pm - 11:39 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

5h 10m1 stop Philadelphia

$376American Airlines

Fri, Jan 15 - Mon, Jan 18

11:45 am - 1:49 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 04mnonstop

2:55 pm - 6:17 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 22mnonstop

$222JetBlue

Fri, Jan 15 - Mon, Jan 18

2:40 pm - 4:45 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 05mnonstop

5:46 pm - 9:10 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 24mnonstop

$222JetBlue

Fri, Jan 15 - Tue, Jan 19

2:40 pm - 4:45 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 05mnonstop

5:46 pm - 9:10 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 24mnonstop

$222JetBlue

Tue, Nov 24 - Fri, Nov 27

5:39 am - 8:00 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 21mnonstop

12:00 pm - 3:26 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 26mnonstop

$229American Airlines

Fri, Feb 26 - Sat, Feb 27

5:42 pm - 8:05 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 23mnonstop

1:34 pm - 5:02 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 28mnonstop

$229American Airlines

Mon, Nov 9 - Fri, Nov 13

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

2h 56mnonstop

7:45 pm - 11:08 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 23mnonstop

$229Delta

Fri, Nov 13 - Sat, Nov 14

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

$229Delta

Fri, Feb 19 - Mon, Feb 22

3:00 pm - 5:05 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 05mnonstop

9:10 am - 12:36 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 26mnonstop

$229United Airlines

Fri, Nov 6 - Mon, Nov 9

7:31 am - 9:34 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 03mnonstop

6:05 am - 9:23 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 18mnonstop

$229United Airlines

Fri, Feb 26 - Sat, Feb 27

5:42 pm - 8:05 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 23mnonstop

1:34 pm - 5:02 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 28mnonstop

$229American Airlines

Low season	January
High season	July
Cheapest flight	$106

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

Most popular time to fly with an average 11% increase in price.

Flight from Worcester 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.

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

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$106 Find Cheap Flights from Massachusetts to Chicago - Compare and Save

Cheap Flights from Massachusetts to O'Hare Intl

Cheap flights from Massachusetts to O'Hare Intl with top airlines, updated regularly. Compare round-trip, one-way, direct and last-minute deals.

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

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Find direct flights for O'Hare Intl

Flights from domestic origins to Massachusetts

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