ORD

$98 Find Cheap Flights from Massachusetts to Chicago O'Hare Airport - 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 O'Hare Intl departing on 9/25. 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

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Useful Info
Flight Deals

Cheap Flights from Massachusetts to O'Hare Intl

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Massachusetts to O'Hare Intl 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 Massachusetts to O'Hare Intl

Wed, Aug 26 - Sat, Sep 5
Frontier Logo
12:45 pm - 8:08 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
8h 23m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
7:44 pm - 9:09 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
12h 25m1 stop Orlando
$166Frontier
Sat, Aug 29 - Wed, Sep 2
Frontier Logo
12:45 pm - 8:08 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
8h 23m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
7:44 pm - 9:09 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
12h 25m1 stop Orlando
$166Frontier
Tue, Oct 20 - Sat, Oct 24
JetBlue Logo
6:55 am - 8:46 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 51mnonstop
JetBlue Logo
8:24 pm - 11:58 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 34mnonstop
$201JetBlue
Sat, Oct 3 - Tue, Oct 6
JetBlue Logo
5:00 pm - 7:01 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 01mnonstop
JetBlue Logo
8:24 pm - 12:23 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 59mnonstop
$202JetBlue
Sat, Oct 10 - Sat, Oct 17
Delta Logo
7:40 pm - 9:31 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 51mnonstop
Delta Logo
12:00 pm - 3:32 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 32mnonstop
$207Delta
Wed, Sep 9 - Sat, Sep 12
Delta Logo
7:30 am - 9:24 amBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 54mnonstop
Delta Logo
4:35 pm - 8:20 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 45mnonstop
$207Delta
Tue, Sep 15 - Wed, Sep 16
United Airlines Logo
5:01 pm - 7:00 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 59mnonstop
United Airlines Logo
6:10 am - 9:33 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 23mnonstop
$207United Airlines
Wed, Sep 30 - Tue, Nov 3
United Airlines Logo
5:01 pm - 7:00 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
2h 59mnonstop
United Airlines Logo
2:01 pm - 5:26 pmORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 25mnonstop
$217United Airlines
Sat, Oct 24 - Sat, Oct 31
American Airlines Logo
12:00 pm - 2:02 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 02mnonstop
American Airlines Logo
7:00 am - 10:33 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 33mnonstop
$217American Airlines
Sat, Oct 10 - Tue, Oct 13
American Airlines Logo
6:00 pm - 8:12 pmBOS  Boston Logan Intl-ORD Chicago O'Hare Intl
3h 12mnonstop
American Airlines Logo
7:00 am - 10:33 amORD  Chicago O'Hare Intl-BOS Boston Logan Intl
2h 33mnonstop
$217American Airlines
Useful Info

Good to know

Low season

January

Cheapest flight

$98
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from Boston to Chicago O'Hare Airport

FAQs for booking Massachusetts to Chicago O'Hare Airport flights

  • How does KAYAK find such low prices on flights from Massachusetts to Chicago O'Hare Airport?

    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 Massachusetts to Chicago O'Hare Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Massachusetts to Chicago O'Hare Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport from Massachusetts 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 Massachusetts to Chicago O'Hare Airport?

    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 Chicago O'Hare Airport with an airline and back to Massachusetts with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Massachusetts to Chicago O'Hare Airport?

    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 Chicago O'Hare Airport from Massachusetts 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 O'Hare Intl

Information on your arrival and departure airports

Chicago O'Hare Airport (ORD)