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.

$101 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

Tue, Oct 6 - Thu, Oct 8

6:55 am - 8:49 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

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

2h 55mnonstop

$184JetBlue

Sat, Oct 3 - Sat, Oct 10

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

6h 29m1 stop Atlanta Hartsfield-Jackson

9:00 am - 11:02 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

25h 02m1 stop Orlando

$188Frontier

Thu, Oct 1 - Sat, Oct 3

11:17 am - 10:59 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

12h 42m1 stop Orlando

3:50 pm - 10:58 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

18h 08m1 stop Orlando

$188Frontier

Thu, Sep 17 - Mon, Sep 21

7:00 am - 8:48 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 48mnonstop

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

2h 28mnonstop

$198JetBlue

Thu, Oct 22 - Wed, Oct 28

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

2h 51mnonstop

7:25 am - 11:00 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

$217Delta

Thu, Sep 17 - Mon, Sep 21

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

2h 58mnonstop

3:05 pm - 6:52 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 47mnonstop

$217Delta

Wed, Sep 16 - Sat, Sep 19

1:34 pm - 3:35 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 01mnonstop

6:50 am - 10:29 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 39mnonstop

$217American Airlines

Sat, Oct 10 - Tue, Oct 13

7:22 pm - 9:29 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 07mnonstop

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

2h 34mnonstop

$217American Airlines

Sat, Sep 19 - Mon, Sep 21

3:16 pm - 5:05 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 49mnonstop

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

2h 23mnonstop

$217United Airlines

Tue, Oct 6 - Wed, Oct 7

5:01 pm - 7:00 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

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

2h 23mnonstop

$217United Airlines

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

Wed, Sep 2 - Wed, Sep 9

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

8h 23m1 stop Atlanta Hartsfield-Jackson

3:50 pm - 10:22 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

17h 32m1 stop Orlando

$247Frontier

Tue, Sep 1 - Wed, Sep 2

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

$258Frontier

Sat, Sep 5 - Sat, Sep 12

11:00 am - 12:54 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

$286JetBlue

Sat, Sep 5 - Sun, Sep 13

11:00 am - 12:54 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

$286JetBlue

Sat, Sep 5 - Mon, Sep 14

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

2h 56mnonstop

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

2h 39mnonstop

$295Delta

Sat, Sep 5 - Fri, Sep 11

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

2h 56mnonstop

10:29 am - 2:05 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 36mnonstop

$295Delta

Sat, Sep 5 - Fri, Sep 11

7:17 pm - 9:35 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 18mnonstop

11:59 am - 3:38 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 39mnonstop

$295American Airlines

Sat, Sep 5 - Sat, Sep 12

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

3h 01mnonstop

5:18 pm - 9:00 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 42mnonstop

$295American Airlines

Sat, Sep 5 - Sun, Sep 13

9:00 am - 10:59 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

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

2h 23mnonstop

$295United Airlines

Sat, Sep 5 - Sun, Sep 13

9:00 am - 10:59 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

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

2h 23mnonstop

$305United Airlines

Recent direct flight deals from Massachusetts to O'Hare Intl

Tue, Oct 6 - Thu, Oct 8

6:55 am - 8:49 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

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

2h 55mnonstop

$184JetBlue

Thu, Sep 17 - Mon, Sep 21

7:00 am - 8:48 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 48mnonstop

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

2h 28mnonstop

$198JetBlue

Tue, Sep 22 - Tue, Sep 29

5:00 pm - 7:01 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 01mnonstop

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

2h 28mnonstop

$210JetBlue

Thu, Oct 22 - Wed, Oct 28

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

2h 51mnonstop

7:25 am - 11:00 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

$217Delta

Sat, Nov 14 - Mon, Nov 16

7:50 am - 9:55 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 05mnonstop

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

2h 23mnonstop

$217Delta

Wed, Sep 16 - Sat, Sep 19

1:34 pm - 3:35 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 01mnonstop

6:50 am - 10:29 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 39mnonstop

$217American Airlines

Wed, Oct 14 - Sat, Oct 17

8:23 am - 10:30 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 07mnonstop

2:30 pm - 6:09 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 39mnonstop

$217American Airlines

Tue, Oct 6 - Wed, Oct 7

5:01 pm - 7:00 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

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

2h 23mnonstop

$217United Airlines

Sat, Sep 19 - Mon, Sep 21

3:16 pm - 5:05 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 49mnonstop

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

2h 23mnonstop

$217United Airlines

Thu, Sep 17 - Mon, Sep 21

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

2h 58mnonstop

3:05 pm - 6:52 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 47mnonstop

$217Delta

Useful Info

Low season	January
High season	July
Cheapest flight	$101

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

Most popular time to fly with an average 14% increase in price.

Flight from Albany 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

Tinley Park

Saint Joseph

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

$101 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