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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Flight Deals

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

Thu, Oct 29 - Mon, Nov 2

8:29 am - 4:15 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

6h 46m1 stop Detroit Metropolitan Wayne County

6:25 pm - 11:57 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 32m1 stop Atlanta Hartsfield-Jackson

$220Delta

Fri, Nov 13 - Tue, Nov 17

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

2h 44mnonstop

12:15 pm - 6:30 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

7h 15m1 stop Atlanta Hartsfield-Jackson

$220Multiple Airlines

Fri, Nov 13 - Sat, Nov 14

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

2h 49mnonstop

11:27 am - 6:30 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

8h 03m1 stop Atlanta Hartsfield-Jackson

$220Multiple Airlines

Sat, Jan 16 - Tue, Jan 19

7:05 am - 12:21 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

4h 16m1 stop Newark

8:50 am - 1:09 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 19m1 stop Newark

$221United Airlines

Sat, Jan 23 - Wed, Jan 27

2:26 pm - 7:50 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

4h 24m1 stop Newark

2:25 pm - 6:40 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 15m1 stop Washington, D.C. Dulles Intl

$221United Airlines

Thu, Nov 5 - Thu, Nov 12

6:10 pm - 11:55 pmMDW Chicago Midway-BOS Boston Logan Intl

4h 45m1 stop Baltimore/Washington

2:30 pm - 10:00 pmBOS Boston Logan Intl-MDW Chicago Midway

8h 30m1 stop Kansas City

$221Southwest

Mon, Oct 26 - Tue, Oct 27

4:30 pm - 11:55 pmMDW Chicago Midway-BOS Boston Logan Intl

6h 25m1 stop Nashville Intl

3:50 pm - 7:25 pmBOS Boston Logan Intl-MDW Chicago Midway

4h 35m1 stop Baltimore/Washington

$221Southwest

Sat, Nov 7 - Mon, Nov 9

9:59 am - 5:11 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

6h 12m1 stop Minneapolis St Paul

2:55 pm - 8:49 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 54m1 stop Atlanta Hartsfield-Jackson

$221Delta

Mon, Oct 26 - Fri, Oct 30

8:24 pm - 12:08 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 44mnonstop

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

3h 14mnonstop

$223JetBlue

Fri, Oct 23 - Mon, Oct 26

6:10 am - 2:29 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

7h 19m1 stop New York John F Kennedy Intl

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

3h 14mnonstop

$225JetBlue

Recent last minute flight deals from Illinois to Boston

Wed, Oct 14 - Sat, Oct 24

8:46 am - 11:02 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

25h 16m1 stop Orlando

11:42 am - 6:31 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

7h 49m1 stop Atlanta Hartsfield-Jackson

$256Frontier

Wed, Oct 14 - Wed, Oct 21

8:46 am - 11:02 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

25h 16m1 stop Orlando

12:57 pm - 6:31 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 34m1 stop Atlanta Hartsfield-Jackson

$256Frontier

Sat, Oct 10 - 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

$347JetBlue

Wed, Oct 14 - Tue, Oct 20

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

2h 28mnonstop

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

2h 52mnonstop

$347JetBlue

Wed, Oct 14 - Tue, Oct 20

8:00 pm - 11:36 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 36mnonstop

4:48 pm - 7:00 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 12mnonstop

$355American Airlines

Wed, Oct 14 - Tue, Oct 20

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

2h 30mnonstop

4:25 pm - 6:20 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 55mnonstop

$356Delta

Wed, Oct 14 - Sat, Oct 17

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

2h 35mnonstop

7:50 am - 9:48 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 58mnonstop

$356Delta

Tue, Oct 13 - Fri, Oct 23

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

2h 23mnonstop

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

2h 59mnonstop

$356United Airlines

Wed, Oct 14 - Tue, Oct 20

6:50 am - 12:44 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

4h 54m1 stop New York LaGuardia

1:33 pm - 3:37 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 04mnonstop

$365American Airlines

Sat, Oct 10 - Wed, Oct 14

7:50 pm - 11:25 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

8:05 am - 10:00 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 55mnonstop

$397United Airlines

Recent direct flight deals from Illinois to Boston

Mon, Oct 26 - Fri, Oct 30

8:24 pm - 12:08 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 44mnonstop

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

3h 14mnonstop

$223JetBlue

Sat, Oct 31 - Sat, Oct 31

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

2h 37mnonstop

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

3h 06mnonstop

$225American Airlines

Tue, Feb 9 - Thu, Feb 11

10:30 am - 1:55 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 25mnonstop

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

3h 00mnonstop

$225United Airlines

Fri, Oct 30 - Mon, Nov 2

8:24 pm - 12:08 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 44mnonstop

5:05 pm - 7:17 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 12mnonstop

$226JetBlue

Fri, Oct 30 - Mon, Nov 2

6:00 pm - 9:30 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 30mnonstop

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

3h 04mnonstop

$229United Airlines

Fri, Nov 13 - Mon, Nov 16

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

2h 27mnonstop

4:35 pm - 6:44 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 09mnonstop

$229Delta

Fri, Nov 27 - Tue, Dec 15

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

2h 27mnonstop

8:59 pm - 10:57 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 58mnonstop

$229Delta

Fri, Oct 30 - Sat, Oct 31

12:45 pm - 4:05 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

1:40 pm - 3:15 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

$229Southwest

Fri, Jan 8 - Mon, Jan 11

1:25 pm - 4:35 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 10mnonstop

7:10 am - 9:10 amBOS Boston Logan Intl-MDW Chicago Midway

3h 00mnonstop

$229Southwest

Tue, Nov 24 - Fri, Nov 27

12:00 pm - 3:26 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 26mnonstop

6:48 am - 9:10 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 22mnonstop

$229American Airlines

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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$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