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

Sat, Jan 16 - Mon, Jan 18

8:05 am - 11:25 amMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

5:40 pm - 11:00 pmBOS Boston Logan Intl-MDW Chicago Midway

6h 20m1 stop Nashville Intl

$223Southwest

Thu, Dec 3 - Mon, Dec 7

12:50 pm - 6:50 pmMDW Chicago Midway-BOS Boston Logan Intl

5h 00m1 stop Baltimore/Washington

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

2h 45mnonstop

$223Southwest

Tue, Dec 1 - Sat, Dec 5

7:45 pm - 11:17 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 32mnonstop

12:20 pm - 7:09 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

7h 49m1 stop Atlanta Hartsfield-Jackson

$223Delta

Wed, Nov 25 - Thu, Dec 3

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

2h 23mnonstop

1:00 pm - 5:04 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 04m1 stop New York LaGuardia

$223Delta

Mon, Nov 16 - Mon, Nov 16

5:00 am - 10:51 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

4h 51m1 stop Newark

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

3h 01mnonstop

$223United Airlines

Wed, Nov 11 - Mon, Nov 16

7:00 am - 12:26 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

4h 26m1 stop Newark

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

3h 01mnonstop

$223United Airlines

Tue, Nov 24 - Sun, Dec 6

8:42 pm - 10:11 amMDW Chicago Midway-BOS Boston Logan Intl

12h 29m1 stop Orlando

11:08 am - 7:42 pmBOS Boston Logan Intl-MDW Chicago Midway

9h 34m1 stop Orlando

$228Frontier

Wed, Nov 25 - Sun, Dec 6

8:42 pm - 10:11 amMDW Chicago Midway-BOS Boston Logan Intl

12h 29m1 stop Orlando

11:08 am - 7:42 pmBOS Boston Logan Intl-MDW Chicago Midway

9h 34m1 stop Orlando

$228Frontier

Mon, Nov 2 - Fri, Nov 6

3:16 pm - 6:49 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 33mnonstop

4:41 pm - 6:55 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 14mnonstop

$229American Airlines

Fri, Nov 6 - Mon, Nov 9

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

2h 31mnonstop

5:43 am - 8:00 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 17mnonstop

$229American Airlines

Recent last minute flight deals from Illinois to Boston

Sun, Oct 25 - Wed, Oct 28

8:26 am - 11:02 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

25h 36m1 stop Orlando

12:39 pm - 6:16 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

6h 37m1 stop Atlanta Hartsfield-Jackson

$273Frontier

Fri, Oct 23 - Sat, Oct 31

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

13h 51m1 stop Orlando

11:27 am - 6:16 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

7h 49m1 stop Atlanta Hartsfield-Jackson

$303Frontier

Sat, Oct 24 - Thu, Nov 12

4:25 pm - 7:50 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 25mnonstop

12:45 pm - 2:30 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 45mnonstop

$315Southwest

Sat, Oct 24 - Thu, Nov 12

6:45 am - 2:00 pmMDW Chicago Midway-BOS Boston Logan Intl

6h 15m1 stop Nashville Intl

7:05 am - 8:50 amBOS Boston Logan Intl-MDW Chicago Midway

2h 45mnonstop

$325Southwest

Fri, Oct 23 - Sat, Nov 21

8:00 pm - 11:59 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 59mnonstop

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

3h 00mnonstop

$343JetBlue

Thu, Oct 22 - Sun, Nov 22

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

2h 55mnonstop

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

3h 00mnonstop

$343JetBlue

Sun, Oct 25 - Sat, Nov 21

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

2h 17mnonstop

7:31 am - 9:31 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 00mnonstop

$352United Airlines

Thu, Oct 22 - Sun, Nov 22

5:59 am - 12:14 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

5h 15m1 stop Washington, D.C. Reagan-National

6:50 am - 10:53 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

5h 03m1 stop New York LaGuardia

$372American Airlines

Wed, Oct 21 - Sun, Nov 1

10:25 am - 2:07 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 42mnonstop

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

3h 00mnonstop

$376United Airlines

Sun, Oct 25 - Thu, Oct 29

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

2h 37mnonstop

10:29 am - 12:33 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 04mnonstop

$376American Airlines

Recent direct flight deals from Illinois to Boston

Mon, Nov 2 - Fri, Nov 6

3:16 pm - 6:49 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 33mnonstop

4:41 pm - 6:55 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 14mnonstop

$229American Airlines

Fri, Nov 6 - Mon, Nov 9

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

2h 31mnonstop

5:43 am - 8:00 amBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 17mnonstop

$229American Airlines

Fri, Nov 13 - Sat, Nov 14

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

2h 24mnonstop

7:55 pm - 9:51 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

$229Delta

Fri, Nov 13 - Mon, Nov 16

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

2h 23mnonstop

8:40 pm - 10:36 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

2h 56mnonstop

$229Delta

Fri, Dec 11 - Tue, Dec 15

3:35 pm - 6:50 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 15mnonstop

12:50 pm - 2:40 pmBOS Boston Logan Intl-MDW Chicago Midway

2h 50mnonstop

$229Southwest

Fri, Nov 6 - Mon, Nov 9

6:45 pm - 10:05 pmMDW Chicago Midway-BOS Boston Logan Intl

2h 20mnonstop

7:05 am - 8:50 amBOS Boston Logan Intl-MDW Chicago Midway

2h 45mnonstop

$229Southwest

Thu, Nov 5 - Fri, Nov 6

8:15 pm - 11:59 pmORD 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

$234JetBlue

Fri, Feb 12 - Mon, Feb 15

1:55 pm - 5:22 pmORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 27mnonstop

11:00 am - 1:05 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 05mnonstop

$236JetBlue

Thu, Nov 12 - Sun, Nov 15

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

2h 29mnonstop

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

3h 04mnonstop

$268United Airlines

Sat, Dec 19 - Sat, Jan 2

9:49 pm - 1:18 amORD Chicago O'Hare Intl-BOS Boston Logan Intl

2h 29mnonstop

11:44 am - 1:51 pmBOS Boston Logan Intl-ORD Chicago O'Hare Intl

3h 07mnonstop

$274United Airlines

Useful Info

Low season	January
High season	July
Cheapest flight	$111

Best time to beat the crowds with an average 27% drop in price.

Most popular time to fly with an average 11% increase in price.

Flight from Chicago Midway 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

Revere

Warwick

Hampton

South Portland

Middletown

Wells

Waltham

Plymouth

Brookline

Woburn

Concord

Gloucester

Burlington

Seekonk

York Beach

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

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Find direct flights for Boston

Flights from domestic origins to Boston

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