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$114 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

Wed, Dec 9 - Sun, Dec 13
Frontier Logo
5:35 am - 10:13 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
27h 38m1 stop Orlando
Frontier Logo
11:34 am - 9:29 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
10h 55m1 stop Atlanta Hartsfield-Jackson
$226Frontier
Wed, Dec 16 - Thu, Dec 31
Frontier Logo
5:24 pm - 9:30 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
15h 06m1 stop Orlando
Frontier Logo
10:25 am - 12:56 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
15h 31m1 stop Orlando
$227Frontier
Tue, Jan 19 - Tue, Jan 19
American Airlines Logo
8:30 am - 3:04 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
5h 34m1 stop Philadelphia
American Airlines Logo
5:54 pm - 8:14 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 20mnonstop
$243American Airlines
Sat, Dec 5 - Sat, Dec 5
American Airlines Logo
6:00 am - 9:33 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 33mnonstop
American Airlines Logo
1:13 pm - 5:15 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
5h 02m1 stop Philadelphia
$243American Airlines
Sat, Nov 21 - Mon, Nov 23
JetBlue Logo
5:30 pm - 8:59 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 29mnonstop
JetBlue Logo
7:55 am - 9:59 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 04mnonstop
$245JetBlue
Mon, Dec 21 - Thu, Dec 31
JetBlue Logo
7:55 pm - 11:21 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 26mnonstop
JetBlue Logo
4:45 pm - 6:58 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 13mnonstop
$245JetBlue
Sun, Dec 20 - Mon, Dec 28
Southwest Logo
4:05 pm - 7:20 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 15mnonstop
Southwest Logo
10:25 pm - 12:25 amBOS  Boston Logan Intl-MDW Chicago Midway
3h 00mnonstop
$287Southwest
Thu, Nov 19 - Sun, Nov 22
Southwest Logo
8:30 am - 12:00 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 30mnonstop
Southwest Logo
4:20 pm - 6:05 pmBOS  Boston Logan Intl-MDW Chicago Midway
2h 45mnonstop
$287Southwest
Thu, Nov 19 - Sun, Nov 22
Delta Logo
3:05 pm - 6:29 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 24mnonstop
Delta Logo
7:30 am - 9:35 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 05mnonstop
$287Delta
Wed, Dec 23 - Sat, Jan 2
Delta Logo
5:45 pm - 9:14 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 29mnonstop
Delta Logo
6:15 pm - 8:26 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 11mnonstop
$287Delta
Useful Info

Good to know

Low season

January

Cheapest flight

$114
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly with an average 9% 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
Revere
Warwick
South Portland
Hampton
Middletown
Wells
Waltham
Plymouth
Brookline
Woburn
Concord
Gloucester
Burlington
Seekonk
Danvers
York Beach
West Yarmouth
Somerville

More options for your flight to Boston