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.

$103 CHEAP FLIGHTS from Massachusetts to Chicago (ORD)

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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

Wed, Oct 21 - Fri, Oct 23

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

$176Frontier

Wed, Sep 2 - Sat, Sep 5

12:45 pm - 8:08 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

8h 23m1 stop Atlanta Hartsfield-Jackson

7:44 pm - 9:09 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

12h 25m1 stop Orlando

$176Frontier

Tue, Jan 5 - Mon, Jan 11

8:10 pm - 10:04 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

6:50 pm - 10:25 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

$214JetBlue

Tue, Nov 24 - Mon, Nov 30

7:00 am - 10:54 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

4h 54m1 stop New York LaGuardia

12:59 pm - 8:08 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

6h 09m1 stop Philadelphia

$233American Airlines

Wed, Nov 4 - Tue, Nov 10

5:00 pm - 7:12 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 12mnonstop

2:15 pm - 5:45 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 30mnonstop

$236JetBlue

Wed, Sep 23 - Wed, Sep 23

10:30 am - 12:32 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

3:50 pm - 7:30 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 40mnonstop

$250American Airlines

Sat, Oct 10 - Tue, Oct 13

7:40 pm - 9:31 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 51mnonstop

7:10 pm - 10:53 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 43mnonstop

$255Delta

Sat, Nov 21 - Fri, Nov 27

7:40 pm - 9:36 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

4:40 pm - 8:03 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 23mnonstop

$255Delta

Sat, Nov 21 - Sun, Nov 22

6:36 pm - 8:40 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 04mnonstop

6:15 am - 9:34 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 19mnonstop

$255United Airlines

Fri, Sep 4 - Sat, Sep 5

3:30 pm - 5:22 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

7:45 am - 11:19 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 34mnonstop

$255United Airlines

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

Fri, Aug 21 - Sat, Aug 29

9:36 am - 7:59 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

11h 23m1 stop Atlanta Hartsfield-Jackson

5:59 pm - 9:09 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

14h 10m1 stop Orlando

$207Frontier

Mon, Aug 24 - Sat, Aug 29

9:36 am - 7:59 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

11h 23m1 stop Atlanta Hartsfield-Jackson

5:59 pm - 9:09 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

14h 10m1 stop Orlando

$207Frontier

Sat, Aug 22 - Sat, Sep 12

11:05 am - 12:59 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

8:24 pm - 12:09 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 45mnonstop

$283JetBlue

Tue, Aug 25 - Sat, Sep 12

5:21 pm - 7:27 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 06mnonstop

9:38 am - 1:06 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 28mnonstop

$283JetBlue

Mon, Aug 24 - Mon, Aug 31

8:50 pm - 10:44 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

7:55 am - 11:24 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 29mnonstop

$286Delta

Sun, Aug 23 - Sat, Aug 29

7:30 am - 9:26 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

7:30 am - 10:59 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 29mnonstop

$286Delta

Sat, Aug 22 - Mon, Aug 31

11:58 am - 1:59 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 01mnonstop

7:00 am - 10:32 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 32mnonstop

$286American Airlines

Sat, Aug 22 - Sun, Aug 30

6:19 pm - 8:38 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 19mnonstop

6:05 am - 9:37 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 32mnonstop

$286American Airlines

Sun, Aug 23 - Sun, Aug 30

6:01 am - 8:00 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

6:24 pm - 9:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

$286United Airlines

Sat, Aug 22 - Wed, Sep 2

12:27 pm - 2:20 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 53mnonstop

7:45 am - 11:19 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 34mnonstop

$286United Airlines

Recent direct flight deals from Massachusetts to O'Hare Intl

Tue, Jan 5 - Mon, Jan 11

8:10 pm - 10:04 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

6:50 pm - 10:25 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

$214JetBlue

Wed, Nov 4 - Tue, Nov 10

5:00 pm - 7:12 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 12mnonstop

2:15 pm - 5:45 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 30mnonstop

$236JetBlue

Sat, Sep 5 - Mon, Sep 7

11:00 am - 12:54 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

8:20 pm - 12:16 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 56mnonstop

$242JetBlue

Wed, Sep 23 - Wed, Sep 23

10:30 am - 12:32 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

3:50 pm - 7:30 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 40mnonstop

$250American Airlines

Tue, Oct 13 - Sun, Oct 18

5:54 am - 8:00 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 06mnonstop

7:00 am - 10:33 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 33mnonstop

$253American Airlines

Tue, Sep 22 - Sat, Sep 26

5:45 pm - 8:05 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 20mnonstop

6:00 am - 9:39 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 39mnonstop

$253American Airlines

Thu, Sep 17 - Sun, Sep 27

4:30 pm - 6:28 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 58mnonstop

7:35 am - 11:08 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 33mnonstop

$255Delta

Wed, Sep 16 - Fri, Oct 2

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

2h 42mnonstop

7:30 pm - 11:09 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 39mnonstop

$255Delta

Sat, Sep 26 - Tue, Sep 29

9:23 am - 11:15 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

10:25 am - 2:07 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 42mnonstop

$255United Airlines

Thu, Oct 22 - Sat, Oct 24

7:55 am - 9:51 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

10:25 am - 2:07 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 42mnonstop

$255United Airlines

Useful Info

Low season	January
High season	July
Cheapest flight	$103

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

Most popular time to fly with an average 19% 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.

Gurnee

Merrillville

South Haven

Oak Brook

Saint Joseph

Tinley Park

Hammond

Elk Grove Village

Des Plaines

Hoffman Estates

South Holland

Portage

Oakbrook Terrace

Willowbrook

Lansing

Delavan

Alsip

Northbrook

Lisle

Valparaiso

Everything you need to know for your flight to O'Hare Intl

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Chicago (ORD)

ORD

$103 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

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Cheapest flight

FAQs for booking Massachusetts to Chicago flights

Traveling to a place near O'Hare Intl?

Everything you need to know for your flight to O'Hare Intl

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Cabin class types available on flights to O'Hare Intl

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

Find direct flights for O'Hare Intl

Flights to other popular destinations

Flights from domestic origins to Massachusetts

Choose which airport to fly into in Chicago

Find deals for your return flight