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$115 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 17 - Mon, Oct 19
JetBlue Logo
12:38 pm - 9:06 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
7h 28m1 stop New York John F Kennedy Intl
JetBlue Logo
3:41 pm - 10:10 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
7h 29m1 stop New York John F Kennedy Intl
$223JetBlue
Sat, Oct 17 - Sat, Oct 24
JetBlue Logo
12:38 pm - 9:06 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
7h 28m1 stop New York John F Kennedy Intl
JetBlue Logo
6:55 am - 11:24 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
5h 29m1 stop New York John F Kennedy Intl
$223JetBlue
Wed, Sep 23 - Tue, Sep 29
Frontier Logo
3:50 pm - 10:22 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
17h 32m1 stop Orlando
Frontier Logo
12:52 pm - 6:23 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
6h 31m1 stop Atlanta Hartsfield-Jackson
$228Frontier
Fri, Nov 20 - Sun, Nov 22
Frontier Logo
8:42 pm - 10:11 amMDW  Chicago Midway-BOS Boston Logan Intl
12h 29m1 stop Orlando
Frontier Logo
11:06 am - 7:47 pmBOS  Boston Logan Intl-MDW Chicago Midway
9h 41m1 stop Orlando
$236Frontier
Thu, Oct 15 - Mon, Oct 19
Southwest Logo
5:30 am - 8:55 amMDW  Chicago Midway-BOS Boston Logan Intl
2h 25mnonstop
Southwest Logo
10:00 pm - 11:40 pmBOS  Boston Logan Intl-MDW Chicago Midway
2h 40mnonstop
$249Southwest
Tue, Nov 3 - Fri, Nov 6
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
$249Southwest
Sat, Oct 24 - Tue, Oct 27
Delta Logo
7:25 am - 11:00 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 35mnonstop
Delta Logo
4:25 pm - 6:20 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 55mnonstop
$249Delta
Fri, Oct 30 - Sun, Nov 1
Delta Logo
10:24 am - 1:54 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 30mnonstop
Delta Logo
7:30 am - 9:24 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 54mnonstop
$249Delta
Thu, Oct 1 - Mon, Oct 5
United Airlines Logo
9:24 pm - 12:54 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 30mnonstop
United Airlines Logo
8:05 am - 10:00 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 55mnonstop
$249United Airlines
Fri, Nov 6 - Mon, Nov 9
United Airlines Logo
9:20 pm - 12:46 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 26mnonstop
United Airlines Logo
7:31 am - 9:34 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 03mnonstop
$249United Airlines
Useful Info

Good to know

Low season

January

Cheapest flight

$115
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Chicago Midway 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
Revere
Brookline
Concord
Woburn
Gloucester
Burlington
York Beach
West Yarmouth
Danvers
Seekonk
Quincy

More options for your flight to Boston