$66 Find Cheap Flights from Massachusetts to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 9/27. 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

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Flight Deals

Cheap Flights from Massachusetts to Chicago

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

lø., sep. 13 - on., sep. 17
Logo
8:38 am - 4:45 pmBOS-ORD
9h 07m1 stop
Logo
11:57 am - 11:57 pmORD-BOS
11h 00m1 stop
$129
Find Deal
on., sep. 17 - on., sep. 24
Spirit Airlines Logo
3:00 pm - 10:48 pmBOS-ORD
8h 48m1 stop
Spirit Airlines Logo
11:57 am - 11:57 pmORD-BOS
11h 00m1 stop
$135Spirit Airlines
Find Deal
to., okt. 2 - sø., okt. 5
Southwest Logo
5:15 am - 6:55 amBOS-MDW
2h 40mnonstop
Southwest Logo
6:05 am - 9:20 amMDW-BOS
2h 15mnonstop
$137Southwest
Find Deal
fr., sep. 5 - sø., sep. 7
Delta Logo
7:20 am - 9:15 amBOS-ORD
2h 55mnonstop
Delta Logo
7:00 am - 10:30 amORD-BOS
2h 30mnonstop
$137Delta
Find Deal
on., okt. 8 - on., okt. 15
American Airlines Logo
5:24 am - 7:25 amBOS-ORD
3h 01mnonstop
American Airlines Logo
7:32 pm - 11:02 pmORD-BOS
2h 30mnonstop
$139American Airlines
Find Deal
on., nov. 12 - ti., nov. 18
Southwest Logo
5:35 pm - 9:05 pmBOS-MDW
4h 30m1 stop
Southwest Logo
6:15 pm - 9:35 pmMDW-BOS
2h 20mnonstop
$143Southwest
Find Deal
to., okt. 23 - sø., okt. 26
Frontier Logo
9:50 am - 8:21 pmBOS-MDW
11h 31m1 stop
Frontier Logo
9:26 pm - 8:55 amMDW-BOS
10h 29m1 stop
$144Frontier
Find Deal
ma., sep. 8 - fr., sep. 12
Frontier Logo
8:47 am - 4:51 pmBOS-ORD
9h 04m1 stop
Frontier Logo
6:21 pm - 7:43 amORD-BOS
12h 22m1 stop
$144Frontier
Find Deal
fr., jan. 23 - sø., jan. 25
American Airlines Logo
3:25 pm - 10:51 amORH-ORD
20h 26m1 stop
American Airlines Logo
5:20 pm - 2:53 pmORD-ORH
20h 33m1 stop
$154American Airlines
Find Deal
fr., sep. 5 - ma., sep. 15
Delta Logo
7:20 am - 9:15 amBOS-ORD
2h 55mnonstop
Delta Logo
6:59 pm - 10:40 pmORD-BOS
2h 41mnonstop
$158Delta
Find Deal
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$66
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Boston to Chicago O'Hare Airport

FAQs for booking flights from Massachusetts to Chicago

  • How does KAYAK find such low prices on flights from Massachusetts to Chicago?

    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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago 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?

    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 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?

    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 from Massachusetts up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Valparaiso
Lansing
Chesterton
Munster
Schererville
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Massachusetts

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Chicagofrom $478
Business Class flights to Chicagofrom $271
Prem Econ Class flights to Chicagofrom $318
Economy Class flights to Chicagofrom $95

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