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.

$94 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

Wed, Sep 2 - Sat, Sep 5

7:44 pm - 9:09 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

12h 25m1 stop Orlando

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

8h 23m1 stop Atlanta Hartsfield-Jackson

$176Frontier

Wed, Sep 9 - Sat, Sep 12

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

$183Frontier

Fri, Oct 2 - Wed, Oct 7

6:30 am - 2:40 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

7h 10m1 stop New York John F Kennedy Intl

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

2h 51mnonstop

$195JetBlue

Fri, Oct 2 - Wed, Oct 7

6:30 am - 2:40 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

7h 10m1 stop New York John F Kennedy Intl

6:55 am - 11:47 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 52m1 stop New York John F Kennedy Intl

$197JetBlue

Wed, Nov 4 - Sat, Nov 7

8:30 am - 12:00 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 30mnonstop

3:10 pm - 4:55 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 45mnonstop

$255Southwest

Mon, Dec 21 - Mon, Jan 11

7:45 am - 11:00 amMDW Chicago Midway-BOS Boston Logan Intl

2h 15mnonstop

1:10 pm - 2:55 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 45mnonstop

$255Southwest

Tue, Jan 26 - Tue, Feb 23

4:10 pm - 7:38 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 28mnonstop

6:33 pm - 8:25 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 52mnonstop

$255United Airlines

Thu, Oct 1 - Sun, Oct 4

9:24 pm - 12:54 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 30mnonstop

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

2h 59mnonstop

$255United Airlines

Mon, Nov 16 - Fri, Nov 20

10:35 am - 1:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 24mnonstop

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

3h 05mnonstop

$255Delta

Fri, Sep 25 - Mon, Sep 28

7:30 pm - 11:09 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 39mnonstop

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

2h 42mnonstop

$255Delta

Recent last minute flight deals from Illinois to Boston

Sat, Aug 22 - Tue, Sep 1

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

14h 10m1 stop Orlando

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

8h 23m1 stop Atlanta Hartsfield-Jackson

$207Frontier

Sat, Aug 22 - Wed, Sep 2

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

14h 10m1 stop Orlando

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

8h 23m1 stop Atlanta Hartsfield-Jackson

$207Frontier

Tue, Aug 25 - Mon, Aug 31

8:20 pm - 11:51 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 31mnonstop

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

3h 06mnonstop

$283JetBlue

Sat, Aug 22 - Tue, Sep 1

1:55 pm - 5:31 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 36mnonstop

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

3h 06mnonstop

$284JetBlue

Mon, Aug 24 - Mon, Aug 31

10:30 am - 1:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 29mnonstop

4:16 pm - 6:20 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 04mnonstop

$286Delta

Mon, Aug 24 - Wed, Sep 2

10:30 am - 1:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 29mnonstop

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

2h 56mnonstop

$286Delta

Tue, Aug 25 - Mon, Aug 31

3:00 pm - 6:40 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 40mnonstop

8:27 am - 10:30 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 03mnonstop

$286American Airlines

Sun, Aug 23 - Mon, Aug 31

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

2h 32mnonstop

3:53 pm - 6:04 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 11mnonstop

$286American Airlines

Mon, Aug 24 - Thu, Aug 27

5:45 am - 9:00 amMDW Chicago Midway-BOS Boston Logan Intl

2h 15mnonstop

3:55 pm - 5:30 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

$300Southwest

Tue, Aug 25 - Wed, Aug 26

12:50 pm - 4:10 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

7:15 pm - 8:50 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 35mnonstop

$300Southwest

Recent direct flight deals from Illinois to Boston

Fri, Oct 2 - Wed, Oct 7

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

2h 28mnonstop

5:00 pm - 7:22 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 22mnonstop

$203JetBlue

Wed, Sep 2 - Wed, Sep 9

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

2h 30mnonstop

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

2h 42mnonstop

$214JetBlue

Sun, Oct 25 - Mon, Oct 26

6:00 am - 9:17 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 17mnonstop

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

3h 04mnonstop

$255United Airlines

Wed, Oct 21 - Mon, Oct 26

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

$255United Airlines

Wed, Nov 25 - Wed, Dec 2

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

2h 27mnonstop

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

3h 00mnonstop

$255Delta

Fri, Nov 20 - Wed, Dec 2

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

2h 23mnonstop

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

3h 00mnonstop

$255Delta

Mon, Oct 5 - Sat, Oct 10

8:29 am - 12:06 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 37mnonstop

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

3h 12mnonstop

$255American Airlines

Fri, Oct 16 - Mon, Oct 19

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

2h 36mnonstop

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

3h 06mnonstop

$255American Airlines

Wed, Nov 4 - Sat, Nov 7

8:30 am - 12:00 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 30mnonstop

3:10 pm - 4:55 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 45mnonstop

$255Southwest

Mon, Dec 21 - Mon, Jan 11

7:45 am - 11:00 amMDW Chicago Midway-BOS Boston Logan Intl

2h 15mnonstop

1:10 pm - 2:55 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 45mnonstop

$255Southwest

Useful Info

Low season	January
High season	October
Cheapest flight	$94

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

Most popular time to fly and prices are also 7% 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

Brookline

Revere

Concord

Gloucester

Woburn

York Beach

Burlington

West Yarmouth

Danvers

Seekonk

Braintree

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

$94 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