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Cheap flights from Massachusetts to Chicago from $49

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Massachusetts to Chicago departing on 12/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Massachusetts to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Massachusetts to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Massachusetts to Chicago.

Cheap last minute flights

Planning a quick getaway from Massachusetts to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Massachusetts to Chicago

Find recent round-trip train or bus tickets from Massachusetts to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
6:00 am - 11:42 amBOS-MDW
6h 42m1 stop
12:57 pm - 12:30 amMDW-BOS
10h 33m1 stop
$100Frontier
Find Deal
Tue, Dec 10 - Wed, Dec 11
6:00 am - 11:42 amBOS-MDW
6h 42m1 stop
12:57 pm - 12:30 amMDW-BOS
10h 33m1 stop
$104Frontier
Find Deal
Wed, Dec 4 - Tue, Dec 10
8:54 am - 3:43 pmBOS-ORD
7h 49m1 stop
9:58 am - 12:38 amORD-BOS
13h 40m1 stop
Mon, Dec 9 - Tue, Dec 10
8:54 am - 3:43 pmBOS-ORD
7h 49m1 stop
9:58 am - 12:38 amORD-BOS
13h 40m1 stop
Mon, Dec 9 - Tue, Dec 10
5:00 am - 4:06 pmBOS-ORD
12h 06m1 stop
8:14 pm - 9:58 amORD-BOS
12h 44m1 stop
$117Spirit Airlines
Find Deal
Wed, Dec 11 - Wed, Dec 18
5:00 am - 4:06 pmBOS-ORD
12h 06m1 stop
9:58 am - 12:38 amORD-BOS
13h 40m1 stop
$132Spirit Airlines
Find Deal
Sat, Dec 7 - Tue, Dec 10
6:00 am - 8:05 amBOS-ORD
3h 05mnonstop
4:40 pm - 8:02 pmORD-BOS
2h 22mnonstop
$157JetBlue
Find Deal
Thu, Dec 5 - Tue, Dec 10
3:52 pm - 5:59 pmBOS-ORD
3h 07mnonstop
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
$158JetBlue
Find Deal
Thu, Jan 9 - Sun, Jan 12
6:00 pm - 7:45 pmBOS-MDW
2h 45mnonstop
8:05 am - 11:20 amMDW-BOS
2h 15mnonstop
$158Southwest
Find Deal
Wed, Dec 4 - Sat, Dec 7
6:25 am - 8:15 amBOS-MDW
2h 50mnonstop
9:00 am - 12:15 pmMDW-BOS
2h 15mnonstop
$179Southwest
Find Deal
Thu, Jan 2 - Sat, Jan 25
6:00 am - 11:42 amBOS-MDW
6h 42m1 stop
$49Frontier
Find Deal
Tue, Dec 10
6:00 am - 11:42 amBOS-MDW
6h 42m1 stop
$51Frontier
Find Deal
Tue, Dec 10
5:00 am - 4:06 pmBOS-ORD
12h 06m1 stop
$58Spirit Airlines
Find Deal
Tue, Dec 10
5:00 am - 4:06 pmBOS-ORD
12h 06m1 stop
$59Spirit Airlines
Find Deal
Tue, Dec 10
5:40 pm - 7:30 pmBOS-MDW
2h 50mnonstop
$79Southwest
Find Deal
Wed, Feb 5
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
$79JetBlue
Find Deal
Tue, Dec 10
8:20 pm - 10:23 pmBOS-ORD
3h 03mnonstop
$84Delta
Find Deal
Tue, Jan 7
11:28 am - 3:44 pmBOS-ORD
5h 16m1 stop
$88JetBlue
Find Deal
Sun, Jan 19
7:00 am - 8:45 amBOS-MDW
2h 45mnonstop
$95Southwest
Find Deal
Wed, Jan 1
4:51 pm - 10:44 pmORH-ORD
6h 53m1 stop
$104Delta
Find Deal
Tue, Dec 17
6:00 am - 1:10 pmBOS-ORD
8h 10m1 stop
11:51 am - 7:29 pmORD-BOS
6h 38m1 stop
Wed, Nov 20 - Thu, Nov 21
6:00 am - 1:10 pmBOS-ORD
8h 10m1 stop
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
Wed, Nov 20 - Mon, Nov 25
8:00 am - 8:15 pmBOS-ORD
13h 15m1 stop
11:45 am - 12:38 amORD-BOS
11h 53m1 stop
$139Spirit Airlines
Find Deal
Wed, Nov 20 - Wed, Dec 4
8:00 am - 8:15 pmBOS-ORD
13h 15m1 stop
11:51 am - 7:29 pmORD-BOS
6h 38m1 stop
$140Spirit Airlines
Find Deal
Wed, Nov 20 - Thu, Nov 21
6:00 am - 1:10 pmBOS-ORD
8h 10m1 stop
8:21 pm - 12:40 amORD-BOS
27h 19m1 stop
$149Frontier
Find Deal
Wed, Nov 20 - Mon, Nov 25
12:17 pm - 5:38 pmBOS-MDW
6h 21m1 stop
8:50 am - 12:40 amMDW-BOS
14h 50m1 stop
$177Frontier
Find Deal
Sat, Nov 23 - Tue, Nov 26
5:15 am - 7:17 amBOS-ORD
3h 02mnonstop
7:00 am - 10:19 amORD-BOS
2h 19mnonstop
$229American Airlines
Find Deal
Sun, Nov 24 - Tue, Nov 26
7:50 pm - 9:51 pmBOS-ORD
3h 01mnonstop
6:40 am - 10:00 amORD-BOS
2h 20mnonstop
$262Delta
Find Deal
Sat, Nov 23 - Wed, Dec 4
5:45 am - 11:40 amBOS-ORD
6h 55m1 stop
2:05 pm - 5:30 pmORD-BOS
2h 25mnonstop
$272Delta
Find Deal
Sun, Nov 24 - Wed, Dec 4
12:12 pm - 2:18 pmBOS-ORD
3h 06mnonstop
7:00 am - 10:19 amORD-BOS
2h 19mnonstop
$288American Airlines
Find Deal
Thu, Nov 21 - Tue, Nov 26
6:00 am - 8:05 amBOS-ORD
3h 05mnonstop
4:40 pm - 8:02 pmORD-BOS
2h 22mnonstop
$157JetBlue
Find Deal
Thu, Dec 5 - Tue, Dec 10
6:40 am - 8:25 amBOS-MDW
2h 45mnonstop
8:30 pm - 11:40 pmMDW-BOS
2h 10mnonstop
$158Southwest
Find Deal
Fri, Dec 13 - Sun, Dec 15
3:52 pm - 5:59 pmBOS-ORD
3h 07mnonstop
7:00 am - 10:15 amORD-BOS
2h 15mnonstop
$158JetBlue
Find Deal
Thu, Jan 9 - Sun, Jan 12
1:15 pm - 3:17 pmBOS-ORD
3h 02mnonstop
7:00 am - 10:20 amORD-BOS
2h 20mnonstop
$159American Airlines
Find Deal
Thu, Feb 13 - Sun, Feb 16
11:05 am - 1:00 pmBOS-ORD
2h 55mnonstop
6:30 am - 10:00 amORD-BOS
2h 30mnonstop
$165Delta
Find Deal
Thu, Dec 12 - Fri, Dec 13
7:45 pm - 9:43 pmBOS-ORD
2h 58mnonstop
7:15 am - 10:49 amORD-BOS
2h 34mnonstop
$168Delta
Find Deal
Fri, Dec 13 - Sat, Dec 14
2:15 pm - 4:00 pmBOS-MDW
2h 45mnonstop
8:05 am - 11:20 amMDW-BOS
2h 15mnonstop
$178Southwest
Find Deal
Sat, Feb 22 - Sun, Feb 23
8:45 am - 10:49 amBOS-ORD
3h 04mnonstop
12:30 pm - 3:49 pmORD-BOS
2h 19mnonstop
$193American Airlines
Find Deal
Wed, Dec 25 - Wed, Jan 29
6:02 am - 8:05 amBOS-ORD
3h 03mnonstop
10:55 am - 2:22 pmORD-BOS
2h 27mnonstop
$198United Airlines
Find Deal
Tue, Dec 31 - Thu, Jan 2
9:30 am - 11:26 amBOS-ORD
2h 56mnonstop
9:30 pm - 12:54 amORD-BOS
2h 24mnonstop
$201United Airlines
Find Deal
Mon, Dec 9 - Sat, Dec 21

Spirit Airlines flights from Massachusetts to Chicago

Our best Spirit Airlines deals on Massachusetts to Chicago flight tickets
Spirit Airlines
Dec 11
BOS5:00 amBoston Logan Intl
12h 06m
1 stop
ORD4:06 pmChicago O'Hare Intl
Dec 18
ORD8:14 pmChicago O'Hare Intl
12h 44m
1 stop
BOS9:58 amBoston Logan Intl
Spirit Airlines
Dec 7
BOS5:00 amBoston Logan Intl
12h 06m
1 stop
ORD4:06 pmChicago O'Hare Intl
Dec 10
ORD9:58 amChicago O'Hare Intl
13h 40m
1 stop
BOS12:38 amBoston Logan Intl
Spirit Airlines
Dec 7
BOS9:00 amBoston Logan Intl
16h 33m
2 stops
ORD12:33 amChicago O'Hare Intl
Dec 10
ORD9:58 amChicago O'Hare Intl
13h 40m
1 stop
BOS12:38 amBoston Logan Intl

JetBlue flights from Massachusetts to Chicago

Our best JetBlue deals on Massachusetts to Chicago flight tickets
JetBlue
Dec 5
BOS6:00 amBoston Logan Intl
3h 05m
ORD8:05 amChicago O'Hare Intl
Dec 10
ORD4:40 pmChicago O'Hare Intl
2h 22m
BOS8:02 pmBoston Logan Intl
JetBlue
Jan 9
BOS3:52 pmBoston Logan Intl
3h 07m
ORD5:59 pmChicago O'Hare Intl
Jan 12
ORD7:00 amChicago O'Hare Intl
2h 15m
BOS10:15 amBoston Logan Intl
JetBlue
Dec 10
BOS6:00 amBoston Logan Intl
3h 06m
ORD8:06 amChicago O'Hare Intl
Dec 10
ORD10:14 amChicago O'Hare Intl
7h 31m
1 stop
BOS6:45 pmBoston Logan Intl

How to get the cheapest flight ticket from Massachusetts to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies to Chicago from Massachusetts?

Spirit Airlines. Spirit Airlines, Frontier, and Southwest are the most popular carriers operating from Massachusetts to Chicago

What is the cheapest Massachusetts to Chicago flight route?

Boston Logan Intl - Chicago O'Hare Intl. Fly from Boston Logan Intl to Chicago O'Hare Intl for the best Massachusetts - Chicago flight prices

How many flights depart from Massachusetts to Chicago on average per day?

76 flights are operational weekly from Massachusetts to Chicago as of November 2024. The most popular departure time for this route is 2:00PM, with 43% of flights per day taking off in the afternoon.

What cabin class options are available on Massachusetts to Chicago flights?

There are 4 cabin classes available to choose from on Massachusetts to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Massachusetts to Chicago flights?

You could potentially save up to 31% on your flight if you consider stops on a Massachusetts to Chicago flight.

Cheap Massachusetts to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Massachusetts to Chicago

Best Price Found

$49

Fastest flight time

2h 15m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Massachusetts in the past 72 hours is $49. The best round-trip flight deal from Massachusetts to Chicago found on momondo in the last 72 hours is $100.
The fastest flight from Massachusetts to Chicago takes 2h 15m
Direct flights go from Massachusetts to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • When did momondo last update prices for flights from Massachusetts to Chicago?

    Prices for flights from Massachusetts to Chicago are updated daily.

  • How many operators does momondo search for flights from Massachusetts to Chicago?

  • How old do you have to be to fly from Massachusetts to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Massachusetts to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Massachusetts to Chicago?


Best airlines flying from Massachusetts to Chicago

Compare and see reviews for airlines that fly from Massachusetts to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $39Free CancellationRating
6.3
8,176 reviews
Search Spirit Airlines flights
JetBluePriceFrom $83Free CancellationRating
7.5
3,407 reviews
Search JetBlue flights
DeltaPriceFrom $94Free CancellationRating
8.0
8,766 reviews
Search Delta flights
FrontierPriceFrom $98Free CancellationRating
6.1
3,542 reviews
Search Frontier flights
American AirlinesPriceFrom $135Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $145Free CancellationRating
8.1
5,022 reviews
Search Southwest flights
United AirlinesPriceFrom $147Free CancellationRating
7.4
9,168 reviews
Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Massachusetts to Chicago?

It is quick and easy to find Massachusetts to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Massachusetts to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Massachusetts which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Massachusetts to Chicago?

Once all potential Massachusetts to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Massachusetts to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Massachusetts to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.


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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago