BOS

$64 Find Cheap Flights from Illinois to Boston

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Boston departing on 2/11. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$132
Overall average: $284
Southwest
Sat 2/7Mon 2/9
MDW - BOS • Non-stop
Cheapest non-stop
$135
Typical prices: $159-$339
United Airlines
Sat 1/31Fri 2/6
ORD - BOS • Non-stop
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Illinois to Boston

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Illinois to Boston that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Illinois to Boston

Sat, Feb 7 - Mon, Feb 9
Southwest Logo
10:15 am - 1:30 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:45 pm - 7:35 pm
BOS
-
MDW
2h 50mnonstop
$132Southwest
Wed, Mar 4 - Mon, Mar 9
Multiple Airlines Logo
6:02 pm - 1:13 am
ORD
-
BOS
6h 11m
1 stop
Multiple Airlines Logo
7:00 am - 9:09 am
BOS
-
ORD
3h 09mnonstop
$133Multiple Airlines
Sat, Feb 28 - Wed, Mar 4
Delta Logo
7:05 am - 10:37 am
ORD
-
BOS
2h 32mnonstop
Delta Logo
7:15 am - 9:28 am
BOS
-
ORD
3h 13mnonstop
$135Delta
Sat, Feb 14 - Mon, Mar 2
Delta Logo
7:05 am - 10:37 am
ORD
-
BOS
2h 32mnonstop
Delta Logo
7:45 pm - 9:48 pm
BOS
-
ORD
3h 03mnonstop
$136Delta
Thu, Feb 5 - Mon, Feb 9
JetBlue Logo
7:45 am - 11:10 am
ORD
-
BOS
2h 25mnonstop
JetBlue Logo
3:35 pm - 5:43 pm
BOS
-
ORD
3h 08mnonstop
$137JetBlue
Fri, Jan 30 - Sun, Feb 1
Southwest Logo
5:35 pm - 8:50 pm
MDW
-
BOS
2h 15mnonstop
Southwest Logo
5:20 am - 7:10 am
BOS
-
MDW
2h 50mnonstop
$137Southwest
Tue, Mar 24 - Wed, Mar 25
United Airlines Logo
4:20 pm - 7:42 pm
ORD
-
BOS
2h 22mnonstop
United Airlines Logo
12:07 pm - 5:01 pm
BOS
-
ORD
5h 54m
1 stop
$141United Airlines
Mon, Mar 2 - Mon, Mar 9
Frontier Logo
6:00 am - 1:13 am
MDW
-
BOS
18h 13m
1 stop
Frontier Logo
12:35 pm - 10:19 pm
BOS
-
MDW
10h 44m
1 stop
$146Frontier
Mon, Mar 2 - Mon, Mar 9
Frontier Logo
6:00 am - 1:13 am
MDW
-
BOS
18h 13m
1 stop
Frontier Logo
12:35 pm - 10:19 pm
BOS
-
MDW
10h 44m
1 stop
$149Frontier
Wed, Mar 25 - Mon, Mar 30
United Airlines Logo
6:35 am - 3:16 pm
PIA
-
BOS
7h 41m
2 stops
United Airlines Logo
7:15 am - 12:36 pm
BOS
-
PIA
6h 21m
1 stop
$284United Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$64
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Chicago O'Hare Airport to Boston

FAQs for booking flights from Illinois 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.

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Hampton Beach
Hampton
Waltham
Wells
Warwick
Plymouth
Middletown
Everett
Gloucester
Concord
Woburn
York Beach
Brookline
Revere
Burlington
West Yarmouth
Danvers
South Portland
Braintree
Quincy

Everything you need to know for your flight to Boston

Information on the airport you'll fly into in Boston

Boston (BOS)