$62 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 1/14. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$120
Overall average: $212
JetBlue
Thu 1/15Sun 1/18
BOS - ORD • Non-stop
Cheapest one-way
$62
Typical prices: $88-$198
Frontier
Wed 1/14
BOS - ORD • 1 stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Useful Info
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

Thu, Jan 15 - Sun, Jan 18
JetBlue Logo
3:35 pm - 5:43 pm
BOS
-
ORD
3h 08mnonstop
JetBlue Logo
7:45 am - 11:10 am
ORD
-
BOS
2h 25mnonstop
$120JetBlue
Sat, Jan 17 - Sun, Jan 18
Southwest Logo
4:55 pm - 6:45 pm
BOS
-
MDW
2h 50mnonstop
Southwest Logo
5:35 pm - 8:50 pm
MDW
-
BOS
2h 15mnonstop
$127Southwest
Sat, Jan 17 - Tue, Jan 20
Delta Logo
5:15 pm - 7:26 pm
BOS
-
ORD
3h 11mnonstop
Delta Logo
10:40 am - 2:13 pm
ORD
-
BOS
2h 33mnonstop
$127Delta
Wed, Jan 21 - Mon, Jan 26
Frontier Logo
6:00 am - 12:05 pm
BOS
-
MDW
7h 05m1 stop
Frontier Logo
5:01 pm - 1:13 am
MDW
-
BOS
7h 12m1 stop
$128Frontier
Thu, Jan 22 - Sun, Jan 25
Frontier Logo
6:00 am - 1:37 pm
BOS
-
ORD
8h 37m1 stop
Frontier Logo
2:42 pm - 1:13 am
ORD
-
BOS
9h 31m1 stop
$128Frontier
Sat, Jan 24 - Sat, Jan 31
Frontier Logo
6:00 am - 10:44 pm
BOS
-
ORD
17h 44m1 stop
Frontier Logo
6:03 am - 1:13 am
ORD
-
BOS
18h 10m1 stop
$129Frontier
Sat, Jan 24 - Sat, Jan 31
Spirit Airlines Logo
7:00 am - 7:41 pm
BOS
-
ORD
13h 41m1 stop
Spirit Airlines Logo
5:15 am - 4:28 pm
ORD
-
BOS
10h 13m1 stop
$130Spirit Airlines
Sat, Jan 17 - Fri, Jan 23
Delta Logo
5:15 pm - 7:26 pm
BOS
-
ORD
3h 11mnonstop
Delta Logo
6:59 pm - 10:31 pm
ORD
-
BOS
2h 32mnonstop
$132Delta
Wed, Jan 14 - Wed, Jan 21
Multiple Airlines Logo
6:00 am - 4:52 pm
BOS
-
ORD
11h 52m1 stop
Multiple Airlines Logo
6:05 am - 2:38 pm
ORD
-
BOS
7h 33m1 stop
$135Multiple Airlines
Fri, Jan 9 - Mon, Jan 12
Multiple Airlines Logo
3:43 pm - 11:09 pm
BOS
-
MDW
8h 26m1 stop
Multiple Airlines Logo
3:01 pm - 4:19 pm
MDW
-
BOS
24h 18m1 stop
$143Multiple Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$62
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 2% 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
Lansing
Valparaiso
Chesterton
Schererville
Munster
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 $474
Business Class flights to Chicagofrom $505
Prem Econ Class flights to Chicagofrom $128
Economy Class flights to Chicagofrom $117