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$113 Find Cheap Flights from Illinois to Boston - Compare and Save

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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.

Recent round-trip flight deals from Illinois to Boston

Sat, Oct 10 - Mon, Oct 12
JetBlue Logo
8:04 pm - 11:59 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 55mnonstop
JetBlue Logo
6:55 am - 8:47 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 52mnonstop
$218JetBlue
Thu, Nov 5 - Mon, Nov 9
JetBlue Logo
1:00 pm - 4:48 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 48mnonstop
JetBlue Logo
5:05 pm - 7:17 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 12mnonstop
$219JetBlue
Tue, Oct 27 - Tue, Nov 3
Southwest Logo
1:40 pm - 9:20 pmMDW  Chicago Midway-BOS Boston Logan Intl
6h 40m2 stops Cincinnati Cinci./N. Kentucky Baltimore/Washington
Southwest Logo
1:20 pm - 7:45 pmBOS  Boston Logan Intl-MDW Chicago Midway
7h 25m2 stops Baltimore/Washington Buffalo
$219Southwest
Sat, Oct 17 - Wed, Oct 21
Multiple Airlines Logo
9:38 am - 1:06 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 28mnonstop
Multiple Airlines Logo
12:57 pm - 6:31 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
6h 34m1 stop Atlanta Hartsfield-Jackson
$220Multiple Airlines
Wed, Nov 11 - Sat, Nov 14
Multiple Airlines Logo
8:15 pm - 11:59 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 44mnonstop
Multiple Airlines Logo
11:27 am - 6:16 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
7h 49m1 stop Atlanta Hartsfield-Jackson
$220Multiple Airlines
Sat, Oct 3 - Wed, Oct 7
Southwest Logo
8:25 am - 2:45 pmMDW  Chicago Midway-BOS Boston Logan Intl
5h 20m1 stop Kansas City
Southwest Logo
6:45 am - 11:20 amBOS  Boston Logan Intl-MDW Chicago Midway
5h 35m1 stop Baltimore/Washington
$222Southwest
Sun, Oct 11 - Tue, Oct 13
United Airlines Logo
6:10 am - 9:33 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 23mnonstop
United Airlines Logo
5:45 am - 9:38 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
4h 53m1 stop Washington, D.C. Dulles Intl
$222United Airlines
Sun, Nov 1 - Mon, Nov 2
United Airlines Logo
5:55 am - 11:07 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
4h 12m1 stop Newark
United Airlines Logo
8:25 pm - 10:29 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 04mnonstop
$222United Airlines
Tue, Oct 20 - Thu, Oct 22
Delta Logo
10:24 am - 1:54 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 30mnonstop
Delta Logo
7:40 pm - 9:31 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 51mnonstop
$223Delta
Wed, Oct 21 - Thu, Oct 22
Delta Logo
10:24 am - 1:54 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 30mnonstop
Delta Logo
7:40 pm - 9:31 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 51mnonstop
$223Delta
Useful Info

Good to know

Low season

January

Cheapest flight

$113
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly with an average 13% 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
Everett
Hampton
Warwick
Wells
Middletown
Revere
South Portland
Waltham
Plymouth
Brookline
Woburn
Concord
Gloucester
Burlington
York Beach
West Yarmouth
Danvers
Seekonk
Somerville

More options for your flight to Boston