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.

$104 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, Sep 16 - Sat, Sep 19

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

17h 32m1 stop Orlando

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

6h 29m1 stop Atlanta Hartsfield-Jackson

$185Frontier

Fri, Oct 23 - Tue, Oct 27

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

13h 51m1 stop Orlando

12:15 pm - 6:45 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

7h 30m1 stop Atlanta Hartsfield-Jackson

$187Frontier

Thu, Sep 17 - Mon, Sep 21

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

2h 28mnonstop

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

3h 01mnonstop

$197JetBlue

Sat, Sep 12 - Mon, Sep 14

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

2h 45mnonstop

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

3h 01mnonstop

$198JetBlue

Thu, Sep 17 - Thu, Sep 17

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

2h 33mnonstop

8:50 pm - 10:32 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 42mnonstop

$217Delta

Tue, Nov 10 - Thu, Nov 26

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

2h 23mnonstop

7:30 am - 9:38 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 08mnonstop

$217Delta

Wed, Oct 14 - Mon, Oct 19

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

2h 47mnonstop

7:01 am - 9:00 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

$217United Airlines

Wed, Sep 23 - Sat, Sep 26

1:55 pm - 5:36 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 41mnonstop

7:01 am - 9:00 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

$217United Airlines

Wed, Sep 23 - Mon, Sep 28

8:19 pm - 11:54 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

6:00 am - 8:10 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 10mnonstop

$217American Airlines

Thu, Oct 1 - Mon, Oct 5

8:10 pm - 11:45 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

6:16 pm - 8:28 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 12mnonstop

$217American Airlines

Recent last minute flight deals from Illinois to Boston

Sat, Aug 29 - Sat, Sep 12

5:59 pm - 9:09 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

14h 10m1 stop Orlando

11:36 am - 10:59 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

12h 23m1 stop Orlando

$237Frontier

Sat, Aug 29 - Sat, Sep 12

5:59 pm - 9:09 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

14h 10m1 stop Orlando

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

6h 29m1 stop Atlanta Hartsfield-Jackson

$237Frontier

Sat, Aug 29 - Sat, Sep 12

6:05 am - 9:37 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 32mnonstop

10:30 am - 12:32 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

$277American Airlines

Sat, Aug 29 - Sat, Sep 12

4:30 pm - 8:11 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 41mnonstop

1:35 pm - 3:26 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 51mnonstop

$287Delta

Sat, Aug 29 - Sat, Sep 12

6:05 am - 9:37 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 32mnonstop

10:30 am - 12:32 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 02mnonstop

$296American Airlines

Fri, Aug 28 - Sat, Sep 12

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

2h 30mnonstop

6:00 pm - 7:59 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

$296Delta

Fri, Aug 28 - Sat, Sep 12

2:35 pm - 5:55 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

8:40 am - 10:15 amBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

$296Southwest

Mon, Aug 31 - Mon, Sep 7

6:24 pm - 9:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

6:01 am - 8:00 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 59mnonstop

$296United Airlines

Fri, Aug 28 - Sat, Sep 12

9:20 am - 5:05 pmMDW Chicago Midway-BOS Boston Logan Intl

6h 45m1 stop Lambert-St Louis

8:40 am - 10:15 amBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

$306Southwest

Mon, Aug 31 - Sat, Sep 5

6:24 pm - 9:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

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

2h 59mnonstop

$336United Airlines

Recent direct flight deals from Illinois to Boston

Thu, Sep 17 - Mon, Sep 21

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

2h 28mnonstop

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

3h 01mnonstop

$197JetBlue

Sat, Sep 12 - Mon, Sep 14

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

2h 45mnonstop

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

3h 01mnonstop

$198JetBlue

Tue, Oct 6 - Tue, Oct 13

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

2h 35mnonstop

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

2h 54mnonstop

$217Delta

Tue, Oct 6 - Sat, Oct 10

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

2h 35mnonstop

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

2h 51mnonstop

$217Delta

Wed, Sep 23 - Mon, Sep 28

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

2h 35mnonstop

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

2h 59mnonstop

$217United Airlines

Thu, Oct 15 - Tue, Oct 20

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

$217United Airlines

Wed, Oct 21 - Mon, Oct 26

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

2h 37mnonstop

3:31 pm - 5:36 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 05mnonstop

$217American Airlines

Sat, Nov 7 - Tue, Nov 10

8:06 am - 11:41 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 35mnonstop

4:42 pm - 6:55 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 13mnonstop

$217American Airlines

Sat, Sep 12 - Mon, Sep 14

7:40 am - 11:00 amMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

6:40 pm - 8:25 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 45mnonstop

$217Southwest

Thu, Nov 12 - Tue, Nov 17

6:45 pm - 10:00 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 15mnonstop

7:10 am - 8:55 amBOS Boston Logan Intl-MDW Chicago Midway

2h 45mnonstop

$217Southwest

Useful Info

Low season	January
High season	October
Cheapest flight	$104

Best time to beat the crowds with an average 21% drop in price.

Most popular time to fly and prices are also 6% lower on average.

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

Wells

Middletown

Waltham

Plymouth

South Portland

Revere

Brookline

Concord

Woburn

Gloucester

York Beach

Burlington

West Yarmouth

Danvers

Seekonk

Somerville

Everything you need to know for your flight to Boston

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Information on the airport you'll fly into in Boston

Boston (BOS)

BOS

$104 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?

Everything you need to know for your flight to Boston

Information on the airport you'll fly into in Boston

Cabin class types available on flights to Illinois

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

Find direct flights for Boston

Flights to other popular destinations

Flights from domestic origins to Boston

Choose which airport to fly into in Boston

Find deals for your return flight