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.

$94 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

Thu, Oct 1 - Mon, Oct 5

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

12h 42m1 stop Orlando

8:24 pm - 12:23 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 59mnonstop

$162Multiple Airlines

Sat, Sep 26 - Sat, Oct 3

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

6h 29m1 stop Atlanta Hartsfield-Jackson

8:05 am - 4:29 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

7h 24m1 stop Atlanta Hartsfield-Jackson

$162Frontier

Sat, Oct 24 - Mon, Oct 26

6:55 am - 8:46 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 51mnonstop

8:24 pm - 11:56 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 32mnonstop

$163JetBlue

Wed, Sep 2 - Wed, Sep 9

5:20 pm - 7:26 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 06mnonstop

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

2h 45mnonstop

$163JetBlue

Thu, Oct 8 - Sun, Oct 11

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

$165American Airlines

Mon, Oct 12 - Sun, Oct 18

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

3h 05mnonstop

6:00 am - 9:37 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 37mnonstop

$165American Airlines

Mon, Aug 31 - Tue, Sep 1

12:25 pm - 2:19 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 54mnonstop

7:30 pm - 11:00 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 30mnonstop

$165Delta

Tue, Oct 13 - Wed, Oct 14

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

2h 54mnonstop

3:05 pm - 6:44 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 39mnonstop

$165Delta

Sun, Sep 20 - Mon, Sep 21

7:05 am - 9:03 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 58mnonstop

7:55 pm - 11:30 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

$165United Airlines

Fri, Oct 9 - Sun, Oct 11

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

2h 57mnonstop

7:30 am - 11:01 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 31mnonstop

$165United Airlines

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

Tue, Aug 18 - 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

$197Frontier

Tue, Aug 18 - Tue, Sep 15

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

8h 23m1 stop Atlanta Hartsfield-Jackson

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

2h 45mnonstop

$207Multiple Airlines

Tue, Aug 18 - Wed, Sep 2

8:15 am - 10:11 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

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

2h 56mnonstop

$224JetBlue

Tue, Aug 18 - Tue, Sep 15

8:15 am - 10:11 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

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

2h 45mnonstop

$240JetBlue

Sat, Aug 15 - Tue, Sep 1

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

2h 56mnonstop

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

2h 29mnonstop

$241Delta

Tue, Aug 18 - Sat, Sep 5

6:14 am - 8:20 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 06mnonstop

3:01 pm - 6:41 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 40mnonstop

$241American Airlines

Tue, Aug 18 - Wed, Sep 2

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

2h 59mnonstop

3:35 pm - 7:19 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 44mnonstop

$241United Airlines

Tue, Aug 18 - Sat, Sep 5

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

2h 59mnonstop

7:59 pm - 11:34 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

$241United Airlines

Sat, Aug 15 - Tue, Sep 1

8:15 am - 3:30 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

8h 15m1 stop Minneapolis St Paul

7:30 pm - 11:00 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 30mnonstop

$251Delta

Tue, Aug 18 - Sat, Sep 5

6:14 am - 8:20 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 06mnonstop

1:54 pm - 5:34 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 40mnonstop

$251American Airlines

Recent direct flight deals from Massachusetts to O'Hare Intl

Wed, Oct 21 - Sat, Oct 24

6:55 am - 8:46 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 51mnonstop

8:24 pm - 11:58 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 34mnonstop

$163JetBlue

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

$163JetBlue

Thu, Oct 22 - Tue, Oct 27

6:55 am - 8:46 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 51mnonstop

8:24 pm - 11:56 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 32mnonstop

$163JetBlue

Sat, Sep 26 - Sat, Oct 3

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

2h 54mnonstop

7:30 am - 11:01 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 31mnonstop

$165Delta

Sat, Nov 14 - Mon, Nov 16

7:30 am - 9:35 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

$165Delta

Wed, Sep 9 - Wed, Sep 16

11:57 am - 1:59 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

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

2h 39mnonstop

$165American Airlines

Wed, Sep 9 - Wed, Sep 16

11:57 am - 1:59 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

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

2h 39mnonstop

$165American Airlines

Tue, Sep 29 - Wed, Sep 30

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

2h 56mnonstop

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

2h 23mnonstop

$165United Airlines

Mon, Sep 7 - Mon, Sep 14

7:05 am - 9:04 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

7:55 pm - 11:30 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

$165United Airlines

Wed, Sep 9 - Wed, Sep 16

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

2h 54mnonstop

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

2h 33mnonstop

$165Delta

Useful Info

Low season	January
High season	July
Cheapest flight	$94

Best time to beat the crowds with an average 12% drop in price.

Most popular time to fly with an average 17% 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

Saint Joseph

Tinley Park

Hammond

Elk Grove Village

Des Plaines

Hoffman Estates

Portage

South Holland

Willowbrook

Oakbrook Terrace

Lansing

Delavan

Alsip

Northbrook

Lisle

Elmhurst

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

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Chicago (ORD)

ORD

$94 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

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