BOS

$92 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, Sep 10 - Mon, Sep 14
Southwest Logo
5:45 am - 9:00 amMDW  Chicago Midway-BOS Boston Logan Intl
2h 15mnonstop
Southwest Logo
6:40 pm - 8:25 pmBOS  Boston Logan Intl-MDW Chicago Midway
2h 45mnonstop
$166Southwest
Wed, Oct 21 - Mon, Oct 26
Southwest Logo
1:10 pm - 4:30 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 20mnonstop
Southwest Logo
5:50 am - 7:25 amBOS  Boston Logan Intl-MDW Chicago Midway
2h 35mnonstop
$166Southwest
Sat, Sep 26 - Sat, Oct 3
JetBlue Logo
7:00 am - 2:26 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
6h 26m1 stop New York John F Kennedy Intl
JetBlue Logo
4:11 pm - 9:58 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
6h 47m1 stop New York John F Kennedy Intl
$171JetBlue
Thu, Sep 3 - Sun, Sep 6
Multiple Airlines Logo
8:45 pm - 12:21 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 36mnonstop
Multiple Airlines Logo
12:45 pm - 8:04 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
8h 19m1 stop Atlanta Hartsfield-Jackson
$171Multiple Airlines
Tue, Sep 8 - Tue, Sep 15
Multiple Airlines Logo
8:20 pm - 12:16 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 56mnonstop
Multiple Airlines Logo
12:52 pm - 6:23 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
6h 31m1 stop Atlanta Hartsfield-Jackson
$171Multiple Airlines
Sat, Sep 19 - Mon, Sep 21
JetBlue Logo
8:24 pm - 12:09 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 45mnonstop
JetBlue Logo
5:15 am - 9:58 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
5h 43m1 stop New York John F Kennedy Intl
$172JetBlue
Tue, Sep 8 - Sat, Oct 3
Delta Logo
3:05 pm - 6:52 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 47mnonstop
Delta Logo
7:55 am - 2:29 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
7h 34m1 stop Atlanta Hartsfield-Jackson
$175Delta
Thu, Sep 10 - Tue, Oct 6
Delta Logo
7:35 am - 11:08 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 33mnonstop
Delta Logo
9:15 am - 12:59 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
4h 44m1 stop Detroit Metropolitan Wayne County
$175Delta
Thu, Sep 17 - Sun, Sep 20
United Airlines Logo
6:10 am - 9:33 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 23mnonstop
United Airlines Logo
7:05 am - 9:03 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 58mnonstop
$179United Airlines
Fri, Jan 15 - Mon, Jan 18
United Airlines Logo
6:00 am - 9:24 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 24mnonstop
United Airlines Logo
7:10 am - 9:08 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 58mnonstop
$185United Airlines
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Good to know

Low season

January

Cheapest flight

$92
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 8% 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.

Traveling to a place near Boston?

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

Everything you need to know for your flight to Boston

Information on the airport you'll fly into in Boston

Boston (BOS)