$67 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 2/18. 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

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Everything you should know

Cheapest round-trip
$132
Overall average: $262
Southwest
Wed 4/8Sat 4/11
BOS - MDW • Non-stop
Cheapest one-way
$67
Typical prices: $89-$198
JetBlue
Wed 2/18
BOS - ORD • Non-stop
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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

Wed, Apr 8 - Sat, Apr 11
Southwest Logo
10:45 am - 12:25 pm
BOS
-
MDW
2h 40mnonstop
Southwest Logo
7:45 am - 11:00 am
MDW
-
BOS
2h 15mnonstop
$132Southwest
Sat, Mar 28 - Mon, Mar 30
Southwest Logo
6:35 pm - 8:30 pm
BOS
-
MDW
2h 55mnonstop
Southwest Logo
7:00 pm - 10:15 pm
MDW
-
BOS
2h 15mnonstop
$133Southwest
Mon, Feb 23 - Thu, Feb 26
JetBlue Logo
7:00 am - 9:10 am
BOS
-
ORD
3h 10mnonstop
JetBlue Logo
10:00 am - 1:20 pm
ORD
-
BOS
2h 20mnonstop
$133JetBlue
Sat, May 2 - Tue, May 5
United Airlines Logo
6:00 am - 8:00 am
BOS
-
ORD
3h 00mnonstop
United Airlines Logo
7:00 am - 12:51 pm
ORD
-
BOS
4h 51m
1 stop
$134United Airlines
Sun, Feb 22 - Thu, Feb 26
JetBlue Logo
7:00 am - 9:10 am
BOS
-
ORD
3h 10mnonstop
JetBlue Logo
10:00 am - 1:20 pm
ORD
-
BOS
2h 20mnonstop
$135JetBlue
Sat, Feb 28 - Tue, Mar 3
American Airlines Logo
6:52 am - 9:03 am
BOS
-
ORD
3h 11mnonstop
American Airlines Logo
7:18 am - 10:46 am
ORD
-
BOS
2h 28mnonstop
$136American Airlines
Tue, Feb 24 - Tue, Feb 24
Delta Logo
7:15 am - 9:28 am
BOS
-
ORD
3h 13mnonstop
Delta Logo
2:25 pm - 5:51 pm
ORD
-
BOS
2h 26mnonstop
$137Delta
Thu, Apr 2 - Mon, Apr 6
American Airlines Logo
6:52 am - 9:03 am
BOS
-
ORD
3h 11mnonstop
American Airlines Logo
7:40 pm - 11:01 pm
ORD
-
BOS
2h 21mnonstop
$138American Airlines
Fri, Apr 24 - Mon, Apr 27
Delta Logo
5:24 pm - 10:15 pm
ORH
-
ORD
5h 51m
1 stop
Delta Logo
9:35 am - 4:43 pm
ORD
-
ORH
6h 08m
1 stop
$207Delta
Sat, Mar 21 - Sun, Mar 22
United Airlines Logo
6:00 am - 7:33 am
ALB
-
ORD
2h 33mnonstop
United Airlines Logo
9:19 pm - 12:30 am
ORD
-
ALB
2h 11mnonstop
$270United Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$67
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 9% 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
Griffith
Saint John

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 $398
Business Class flights to Chicagofrom $402
Premium Economy Class flights to Chicagofrom $322
Economy Class flights to Chicagofrom $135