BOS

$88 Find Cheap Flights from Illinois to Boston - Compare and Save

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 10/2. 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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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

Thu, Aug 20 - Wed, Aug 26
Southwest Logo
7:55 pm - 8:00 am
MDW
-
BOS
11h 05m
1 stop
Southwest Logo
5:45 pm - 9:50 pm
BOS
-
MDW
5h 05m
1 stop
$167Southwest
Thu, Aug 20 - Sun, Aug 23
United Airlines Logo
9:40 pm - 1:11 am
ORD
-
BOS
2h 31mnonstop
United Airlines Logo
5:45 am - 9:38 am
BOS
-
ORD
4h 53m
1 stop
$168United Airlines
Thu, Aug 20 - Sun, Aug 23
JetBlue Logo
8:20 pm - 11:51 pm
ORD
-
BOS
2h 31mnonstop
JetBlue Logo
5:01 am - 8:52 am
BOS
-
ORD
4h 51m
1 stop
$169JetBlue
Wed, Sep 16 - Sun, Sep 20
Multiple Airlines Logo
7:30 pm - 11:09 pm
ORD
-
BOS
2h 39mnonstop
Multiple Airlines Logo
6:55 am - 11:47 am
BOS
-
ORD
5h 52m
1 stop
$170Multiple Airlines
Tue, Sep 29 - Wed, Oct 7
JetBlue Logo
9:38 am - 1:06 pm
ORD
-
BOS
2h 28mnonstop
JetBlue Logo
6:55 am - 11:47 am
BOS
-
ORD
5h 52m
1 stop
$171JetBlue
Wed, Sep 16 - Sun, Sep 20
American Airlines Logo
8:50 am - 12:29 pm
ORD
-
BOS
2h 39mnonstop
American Airlines Logo
8:33 am - 10:35 am
BOS
-
ORD
3h 02mnonstop
$177American Airlines
Sat, Oct 3 - Wed, Oct 7
American Airlines Logo
4:57 pm - 11:59 pm
MLI
-
BOS
6h 02m
1 stop
American Airlines Logo
10:29 am - 4:32 pm
BOS
-
MLI
7h 03m
1 stop
$319American Airlines
Thu, Aug 20 - Sun, Aug 23
Delta Logo
4:24 pm - 11:41 pm
BMI
-
BOS
6h 17m
1 stop
Delta Logo
5:30 am - 11:27 am
BOS
-
BMI
6h 57m
1 stop
$319Delta
Sat, Aug 8 - Sat, Aug 15
Delta Logo
12:09 pm - 7:35 pm
BMI
-
BOS
6h 26m
1 stop
Delta Logo
6:50 am - 11:27 am
BOS
-
BMI
5h 37m
1 stop
$320Delta
Sat, Aug 15 - Thu, Aug 20
Multiple Airlines Logo
1:25 pm - 7:46 am
PIA
-
BOS
41h 21m
2 stops
Multiple Airlines Logo
10:04 am - 8:30 am
BOS
-
PIA
23h 26m
1 stop
$357Multiple Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$88
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 7% lower on average.
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.

Everything you need to know for your flight to Boston

Information on the airport you'll fly into in Boston

Boston (BOS)