How does KAYAK find such low prices on flights from Illinois to Boston?

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 Illinois to Boston.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Illinois to Boston?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Illinois 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 Illinois to Boston?

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 Boston with an airline and back to Illinois with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Illinois to Boston?

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 Boston from Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

$111 CHEAP FLIGHTS from Illinois to Boston

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Cheap Flights from Illinois to Boston

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 Illinois to Boston

Wed, Oct 14 - Sat, Oct 17

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

2h 55mnonstop

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

2h 52mnonstop

$217JetBlue

Wed, Oct 14 - Sat, Oct 17

12:38 pm - 8:49 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

7h 11m1 stop New York John F Kennedy Intl

4:11 pm - 10:10 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 59m1 stop New York John F Kennedy Intl

$217JetBlue

Tue, Oct 20 - Tue, Oct 27

6:00 am - 11:24 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

4h 24m1 stop Newark

8:25 pm - 10:29 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 04mnonstop

$219United Airlines

Wed, Nov 11 - Tue, Nov 17

6:59 am - 10:18 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 19mnonstop

6:05 pm - 10:18 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 13m1 stop Newark

$219United Airlines

Tue, Oct 27 - Tue, Nov 3

3:15 pm - 6:35 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

3:30 pm - 9:25 pmBOS Boston Logan Intl-MDW Chicago Midway

6h 55m1 stop Baltimore/Washington

$219Southwest

Wed, Oct 21 - Tue, Oct 27

1:10 pm - 4:30 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

5:35 am - 11:20 amBOS Boston Logan Intl-MDW Chicago Midway

6h 45m1 stop Baltimore/Washington

$219Southwest

Tue, Oct 27 - Thu, Nov 5

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

2h 37mnonstop

1:30 pm - 3:37 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 07mnonstop

$222American Airlines

Mon, Oct 19 - Wed, Oct 21

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

2h 33mnonstop

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

3h 06mnonstop

$222American Airlines

Sat, Nov 7 - Tue, Nov 10

4:40 pm - 8:21 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 41mnonstop

7:30 am - 9:35 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 05mnonstop

$222Delta

Thu, Oct 29 - Wed, Nov 4

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

2h 35mnonstop

7:10 pm - 9:06 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

$222Delta

Recent last minute flight deals from Illinois to Boston

Wed, Oct 7 - Wed, Oct 14

3:50 pm - 11:02 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

18h 12m1 stop Orlando

5:12 pm - 7:14 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

$258Multiple Airlines

Wed, Oct 7 - Tue, Oct 13

3:50 pm - 11:02 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

18h 12m1 stop Orlando

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

2h 52mnonstop

$261Multiple Airlines

Mon, Oct 5 - Thu, Oct 8

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

2h 28mnonstop

6:55 am - 11:24 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 29m1 stop New York John F Kennedy Intl

$273JetBlue

Mon, Oct 5 - Tue, Oct 6

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

2h 28mnonstop

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

2h 54mnonstop

$279JetBlue

Wed, Oct 7 - Wed, Oct 14

2:00 pm - 5:45 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 45mnonstop

7:23 pm - 9:29 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 06mnonstop

$303American Airlines

Tue, Oct 6 - Tue, Oct 13

12:06 pm - 3:49 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 43mnonstop

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

3h 06mnonstop

$303American Airlines

Wed, Oct 7 - Wed, Oct 14

10:24 am - 1:54 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 30mnonstop

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

2h 54mnonstop

$303Delta

Sat, Oct 10 - Tue, Oct 13

12:46 pm - 4:21 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

8:30 pm - 10:29 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

$303United Airlines

Sat, Oct 10 - Wed, Oct 14

3:35 pm - 7:22 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 47mnonstop

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

2h 59mnonstop

$303United Airlines

Fri, Oct 9 - Wed, Oct 14

5:29 pm - 11:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

5h 30m1 stop Detroit Metropolitan Wayne County

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

2h 51mnonstop

$313Delta

Recent direct flight deals from Illinois to Boston

Wed, Oct 14 - Sat, Oct 17

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

2h 55mnonstop

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

2h 52mnonstop

$217JetBlue

Wed, Oct 21 - Mon, Oct 26

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

2h 28mnonstop

5:15 pm - 7:29 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 14mnonstop

$219JetBlue

Wed, Nov 11 - Mon, Nov 16

7:59 pm - 11:27 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 28mnonstop

7:14 am - 9:30 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 16mnonstop

$222American Airlines

Mon, Oct 19 - Tue, Oct 20

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

2h 34mnonstop

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

3h 06mnonstop

$222American Airlines

Tue, Oct 27 - Sat, Oct 31

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

2h 35mnonstop

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

2h 52mnonstop

$222Delta

Mon, Oct 26 - Wed, Nov 4

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

2h 43mnonstop

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

2h 54mnonstop

$222Delta

Thu, Oct 22 - Wed, Oct 28

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

2h 23mnonstop

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

3h 04mnonstop

$222United Airlines

Thu, Oct 22 - Tue, Oct 27

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

2h 23mnonstop

8:25 pm - 10:29 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 04mnonstop

$222United Airlines

Mon, Nov 16 - Wed, Nov 18

6:25 pm - 9:45 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

5:55 pm - 7:40 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 45mnonstop

$222Southwest

Wed, Oct 21 - Thu, Oct 22

7:50 am - 11:10 amMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

10:00 pm - 11:40 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 40mnonstop

$222Southwest

Useful Info

Low season	January
High season	July
Cheapest flight	$111

Best time to beat the crowds with an average 25% drop in price.

Most popular time to fly with an average 12% increase in price.

Flight from Chicago O'Hare Airport to Boston

How does KAYAK find such low prices on flights from Illinois to Boston?
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 Illinois to Boston.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Illinois to Boston?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Illinois 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 Illinois to Boston?
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 Boston with an airline and back to Illinois with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Illinois to Boston?
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 Boston from Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Hampton Beach

Everett

Warwick

Hampton

Revere

Wells

Middletown

South Portland

Waltham

Plymouth

Brookline

Woburn

Concord

Gloucester

Burlington

York Beach

Seekonk

Danvers

West Yarmouth

Somerville

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Complete your trip to Boston with a hotel stay or car rental

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$111 Find Cheap Flights from Illinois to Boston - Compare and Save

Cheap Flights from Illinois to Boston

Recent round-trip flight deals from Illinois to Boston

Recent one-way flight deals from Illinois to Boston

Recent last minute flight deals from Illinois to Boston

Recent direct flight deals from Illinois to Boston

Good to know

Low season

High season

Cheapest flight

FAQs for booking flights from Illinois to Boston

Traveling to a place near Boston?

More options for your flight to Boston

Complete your trip to Boston with a hotel stay or car rental

Information on the airport you'll fly into in Boston

Cabin class types available on flights to Illinois

Find direct flights for Boston

Flights from domestic origins to Boston

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Find deals for your return flight