$59 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 1/6. 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
$117
Typical prices: $158-$389
Southwest
Sat 12/13Wed 12/17
BOS - MDW • Non-stop
Cheapest non-stop
$117
Typical prices: $158-$368
Southwest
Tue 12/9Tue 12/16
BOS - MDW • Non-stop
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Flight Deals
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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

Sat, Dec 13 - Wed, Dec 17
Southwest Logo
5:20 am - 7:05 amBOS-MDW
2h 45mnonstop
Southwest Logo
6:15 pm - 9:35 pmMDW-BOS
2h 20mnonstop
$117Southwest
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Sun, Dec 14 - Sat, Dec 20
JetBlue Logo
5:29 pm - 7:43 pmBOS-ORD
3h 14mnonstop
JetBlue Logo
8:15 pm - 11:44 pmORD-BOS
2h 29mnonstop
$117JetBlue
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Fri, Jan 9 - Thu, Jan 15
Frontier Logo
6:00 am - 11:35 amBOS-ORD
6h 35m1 stop
Frontier Logo
4:41 pm - 1:13 amORD-BOS
7h 32m1 stop
$124Frontier
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Thu, Jan 1 - Mon, Jan 5
American Airlines Logo
6:36 am - 8:47 amBOS-ORD
3h 11mnonstop
American Airlines Logo
8:20 pm - 11:51 pmORD-BOS
2h 31mnonstop
$125American Airlines
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Thu, Dec 11 - Sun, Dec 14
Frontier Logo
11:28 am - 5:27 pmBOS-ORD
6h 59m1 stop
Frontier Logo
6:00 am - 12:02 pmORD-BOS
5h 02m1 stop
$126Frontier
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Fri, Dec 5 - Sun, Dec 7
United Airlines Logo
6:23 pm - 8:23 pmBOS-ORD
3h 00mnonstop
United Airlines Logo
7:30 am - 10:49 amORD-BOS
2h 19mnonstop
$127United Airlines
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Sun, Dec 14 - Wed, Dec 17
Multiple Airlines Logo
8:11 pm - 9:48 amBOS-RFD
14h 37m1 stop
Multiple Airlines Logo
10:38 am - 9:52 amRFD-BOS
22h 14m1 stop
$217Multiple Airlines
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Sat, Dec 20 - Sun, Dec 21
American Airlines Logo
1:45 pm - 10:12 amORH-ORD
21h 27m1 stop
American Airlines Logo
8:45 pm - 1:17 pmORD-ORH
15h 32m1 stop
$224American Airlines
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Sun, Dec 14 - Wed, Dec 17
Multiple Airlines Logo
12:57 pm - 9:48 amBOS-RFD
21h 51m1 stop
Multiple Airlines Logo
10:38 am - 9:52 amRFD-BOS
22h 14m1 stop
$227Multiple Airlines
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Thu, Dec 11 - Sat, Dec 13
United Airlines Logo
6:10 am - 8:01 amBDL-ORD
2h 51mnonstop
United Airlines Logo
1:05 pm - 6:53 pmORD-BDL
4h 48m1 stop
$245United Airlines
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Useful Info

Good to know

Low seasonJanuary
Cheapest flight$59
Best time to beat the crowds with an average 12% 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 $360
Business Class flights to Chicagofrom $426
Prem Econ Class flights to Chicagofrom $324
Economy Class flights to Chicagofrom $117