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.

$118 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, Dec 22 - Sat, Jan 9

10:25 am - 12:56 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

15h 31m1 stop Orlando

5:01 am - 9:06 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

27h 05m1 stop Orlando

$218Frontier

Sat, Dec 12 - Wed, Dec 16

11:34 am - 10:00 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

11h 26m1 stop Atlanta Hartsfield-Jackson

5:24 pm - 9:30 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

15h 06m1 stop Orlando

$218Frontier

Thu, Dec 10 - Mon, Dec 14

1:05 pm - 4:17 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

4h 12m1 stop Detroit Metropolitan Wayne County

3:05 pm - 6:36 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 31mnonstop

$222Delta

Wed, Dec 9 - Wed, Dec 16

12:04 pm - 2:05 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 01mnonstop

2:41 pm - 7:57 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

4h 16m1 stop Detroit Metropolitan Wayne County

$222Delta

Tue, Dec 15 - Wed, Dec 16

2:40 pm - 4:42 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

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

2h 28mnonstop

$245JetBlue

Thu, Dec 10 - Mon, Dec 14

2:40 pm - 4:42 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

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

2h 28mnonstop

$245JetBlue

Thu, Dec 3 - Tue, Dec 8

12:08 pm - 2:20 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 12mnonstop

1:30 pm - 5:03 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 33mnonstop

$246American Airlines

Mon, Dec 7 - Wed, Dec 9

5:56 pm - 8:12 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 16mnonstop

4:52 pm - 8:28 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 36mnonstop

$247American Airlines

Sat, Jan 16 - Wed, Jan 20

4:54 pm - 7:00 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 06mnonstop

6:18 pm - 9:53 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

$247United Airlines

Sat, Nov 21 - Thu, Dec 3

4:56 pm - 6:58 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

9:10 am - 12:43 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 33mnonstop

$247United Airlines

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

Wed, Nov 4 - Wed, Nov 11

12:39 pm - 6:30 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 51m1 stop Atlanta Hartsfield-Jackson

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

2h 49mnonstop

$307Multiple Airlines

Wed, Nov 4 - Thu, Nov 12

12:39 pm - 6:30 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 51m1 stop Atlanta Hartsfield-Jackson

8:15 pm - 11:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 44mnonstop

$317Multiple Airlines

Thu, Nov 5 - Wed, Nov 11

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

2h 54mnonstop

3:05 pm - 6:29 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 24mnonstop

$340Delta

Wed, Nov 4 - Wed, Nov 11

1:35 pm - 3:27 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

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

2h 27mnonstop

$340Delta

Thu, Nov 5 - Sat, Nov 7

12:12 pm - 2:18 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 06mnonstop

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

2h 31mnonstop

$359American Airlines

Tue, Nov 3 - Thu, Nov 5

7:40 pm - 9:54 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 14mnonstop

8:00 pm - 11:31 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 31mnonstop

$359American Airlines

Mon, Nov 2 - Wed, Nov 4

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

3h 04mnonstop

3:44 pm - 7:14 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 30mnonstop

$359United Airlines

Tue, Nov 3 - Thu, Nov 5

11:55 am - 1:59 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 04mnonstop

7:00 am - 10:19 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 19mnonstop

$359United Airlines

Wed, Nov 4 - Thu, Nov 5

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

3h 01mnonstop

8:15 pm - 11:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 44mnonstop

$366JetBlue

Mon, Nov 2 - Wed, Nov 4

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

3h 01mnonstop

1:00 pm - 4:48 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 48mnonstop

$366JetBlue

Recent direct flight deals from Massachusetts to O'Hare Intl

Tue, Dec 15 - Wed, Dec 16

2:40 pm - 4:42 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

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

2h 28mnonstop

$245JetBlue

Thu, Dec 10 - Mon, Dec 14

2:40 pm - 4:42 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

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

2h 28mnonstop

$245JetBlue

Sat, Dec 12 - Wed, Dec 16

2:45 pm - 4:47 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

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

2h 28mnonstop

$245JetBlue

Thu, Dec 3 - Tue, Dec 8

12:08 pm - 2:20 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 12mnonstop

1:30 pm - 5:03 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 33mnonstop

$246American Airlines

Mon, Dec 7 - Wed, Dec 9

5:56 pm - 8:12 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 16mnonstop

4:52 pm - 8:28 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 36mnonstop

$247American Airlines

Sat, Dec 12 - Sat, Dec 12

7:40 am - 9:51 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 11mnonstop

4:40 pm - 8:10 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 30mnonstop

$247Delta

Thu, Dec 3 - Mon, Dec 7

12:04 pm - 2:05 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 01mnonstop

10:38 am - 2:15 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 37mnonstop

$247Delta

Sat, Jan 16 - Wed, Jan 20

4:54 pm - 7:00 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 06mnonstop

6:18 pm - 9:53 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

$247United Airlines

Sat, Nov 21 - Thu, Dec 3

4:56 pm - 6:58 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

9:10 am - 12:43 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 33mnonstop

$247United Airlines

Thu, Dec 3 - Tue, Dec 8

12:08 pm - 2:20 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 12mnonstop

1:30 pm - 5:03 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 33mnonstop

$247American Airlines

Useful Info

Low season	January
High season	July
Cheapest flight	$118

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

Most popular time to fly with an average 9% increase in price.

Flight from Boston to Chicago O'Hare Airport

WeiFlew with United Airlines-Oct 2026

This flight usually departs from gate B28. Enjoy a quick meal at Legal’s or Stephanie’s, refill your water bottle at the water station nearby, and enjoy the very quick boarding process implemented!

GailFlew with JetBlue-Jul 2024

Prepare for a long wait after you actually touch down. Ohare Airport is HUGE and you can taxi for a long time.

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

Hammond

Saint Joseph

Des Plaines

Elk Grove Village

Hoffman Estates

Oakbrook Terrace

Portage

South Holland

Willowbrook

Lansing

Lisle

Alsip

Valparaiso

Northbrook

Delavan

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$118 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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Flights from Massachusetts to O'Hare Intl: the best tips from KAYAK users

FAQs for booking Massachusetts to Chicago flights

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

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