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Cheap flights from Chicago to Massachusetts from $45

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Massachusetts departing on 12/17. 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 Chicago to Massachusetts

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Massachusetts 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 Chicago to Massachusetts.

Cheap last minute flights

Planning a quick getaway from Chicago to Massachusetts? 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 Massachusetts, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Massachusetts

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

All round-trip flight deals to Massachusetts

The cheapest plane tickets to Massachusetts found on KAYAK recently.
9:58 am - 12:38 amORD-BOS
13h 40m1 stop
5:00 am - 4:06 pmBOS-ORD
12h 06m1 stop
$101Spirit Airlines
Find Deal
Tue, Dec 10 - Wed, Dec 11
12:57 pm - 12:30 amMDW-BOS
10h 33m1 stop
5:45 am - 1:24 pmBOS-MDW
8h 39m1 stop
$103Frontier
Find Deal
Wed, Dec 11 - Wed, Dec 18
2:05 pm - 5:34 pmORD-BOS
2h 29mnonstop
7:25 am - 9:28 amBOS-ORD
3h 03mnonstop
$155Delta
Find Deal
Tue, Dec 10 - Thu, Dec 12
8:30 pm - 11:40 pmMDW-BOS
2h 10mnonstop
6:40 am - 8:25 amBOS-MDW
2h 45mnonstop
$158Southwest
Find Deal
Fri, Dec 13 - Sun, Dec 15
1:55 pm - 5:16 pmORD-BOS
2h 21mnonstop
5:45 am - 9:34 amBOS-ORD
4h 49m1 stop
$167United Airlines
Find Deal
Thu, Dec 12 - Sun, Dec 15
7:35 am - 11:03 amORD-BOS
2h 28mnonstop
3:30 pm - 5:36 pmBOS-ORD
3h 06mnonstop
$173Delta
Find Deal
Wed, Dec 25 - Tue, Jan 7
8:30 pm - 11:40 pmMDW-BOS
2h 10mnonstop
8:15 pm - 10:00 pmBOS-MDW
2h 45mnonstop
$179Southwest
Find Deal
Fri, Dec 13 - Sat, Jan 4
8:30 pm - 12:15 amORD-BOS
2h 45mnonstop
6:00 am - 8:08 amBOS-ORD
3h 08mnonstop
$182American Airlines
Find Deal
Sun, Jan 5 - Fri, Jan 10
8:30 pm - 12:15 amORD-BOS
2h 45mnonstop
2:52 pm - 4:52 pmBOS-ORD
3h 00mnonstop
$183American Airlines
Find Deal
Sun, Jan 5 - Sun, Jan 12
10:55 am - 2:22 pmORD-BOS
2h 27mnonstop
6:02 am - 8:05 amBOS-ORD
3h 03mnonstop
$218United Airlines
Find Deal
Wed, Dec 25 - Sat, Dec 28
9:58 am - 12:38 amORD-BOS
13h 40m1 stop
$45Spirit Airlines
Find Deal
Tue, Dec 17
5:24 pm - 12:30 amMDW-BOS
6h 06m1 stop
$52Frontier
Find Deal
Tue, Jan 14
2:35 pm - 6:10 pmORD-BOS
2h 35mnonstop
$79Delta
Find Deal
Mon, Feb 3
10:05 am - 1:20 pmMDW-BOS
2h 15mnonstop
$79Southwest
Find Deal
Mon, Feb 3
11:53 am - 5:28 pmORD-BOS
4h 35m1 stop
$88United Airlines
Find Deal
Sun, Feb 16
9:30 pm - 12:54 amORD-BOS
2h 24mnonstop
$95United Airlines
Find Deal
Wed, Dec 25
5:40 am - 8:55 amMDW-BOS
2h 15mnonstop
$95Southwest
Find Deal
Thu, Nov 28
2:35 pm - 6:10 pmORD-BOS
2h 35mnonstop
$100Delta
Find Deal
Mon, Jan 6
1:39 pm - 8:32 pmORD-BOS
5h 53m1 stop
$128American Airlines
Find Deal
Fri, Feb 21
5:42 pm - 10:52 pmORD-BOS
4h 10m1 stop
$133American Airlines
Find Deal
Mon, Dec 23
11:51 am - 7:29 pmORD-BOS
6h 38m1 stop
8:54 am - 3:43 pmBOS-ORD
7h 49m1 stop
Tue, Nov 26 - Mon, Dec 9
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
8:54 am - 11:19 pmBOS-ORD
15h 25m1 stop
Mon, Nov 25 - Fri, Dec 6
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
8:10 am - 10:21 amBOS-ORD
3h 11mnonstop
$200Spirit Airlines
Find Deal
Mon, Nov 25 - Tue, Dec 3
11:51 am - 7:29 pmORD-BOS
6h 38m1 stop
8:10 am - 10:21 amBOS-ORD
3h 11mnonstop
$207Spirit Airlines
Find Deal
Tue, Nov 26 - Tue, Dec 3
6:48 pm - 12:31 amMDW-BOS
4h 43m1 stop
6:00 am - 11:42 amBOS-MDW
6h 42m1 stop
$208Frontier
Find Deal
Tue, Nov 26 - Tue, Dec 10
6:48 pm - 12:31 amMDW-BOS
4h 43m1 stop
12:38 pm - 9:02 pmBOS-MDW
9h 24m1 stop
$218Frontier
Find Deal
Tue, Nov 26 - Fri, Dec 6
9:45 am - 1:08 pmORD-BOS
2h 23mnonstop
6:45 am - 8:49 amBOS-ORD
3h 04mnonstop
$277American Airlines
Find Deal
Mon, Nov 25 - Mon, Dec 30
1:25 pm - 4:38 pmORD-BOS
2h 13mnonstop
8:00 am - 12:25 pmBOS-ORD
5h 25m1 stop
$307American Airlines
Find Deal
Sun, Nov 24 - Wed, Nov 27
10:35 am - 2:00 pmORD-BOS
2h 25mnonstop
10:45 am - 12:41 pmBOS-ORD
2h 56mnonstop
$318United Airlines
Find Deal
Tue, Nov 26 - Fri, Nov 29
10:35 am - 11:43 pmORD-ALB
12h 08m2 stops
6:00 am - 9:44 amALB-ORD
4h 44m1 stop
$633United Airlines
Find Deal
Sun, Nov 24 - Thu, Nov 28
6:30 am - 10:00 amORD-BOS
2h 30mnonstop
11:05 am - 1:00 pmBOS-ORD
2h 55mnonstop
$155Delta
Find Deal
Mon, Dec 9 - Wed, Dec 11
8:50 am - 12:12 pmORD-BOS
2h 22mnonstop
6:00 am - 8:06 amBOS-ORD
3h 06mnonstop
$157JetBlue
Find Deal
Thu, Dec 5 - Thu, Dec 12
8:05 am - 11:20 amMDW-BOS
2h 15mnonstop
7:00 am - 8:45 amBOS-MDW
2h 45mnonstop
$158Southwest
Find Deal
Sat, Dec 7 - Thu, Dec 12
6:40 am - 10:00 amORD-BOS
2h 20mnonstop
7:25 am - 9:28 amBOS-ORD
3h 03mnonstop
$158Delta
Find Deal
Thu, Dec 5 - Sun, Dec 8
8:30 pm - 11:40 pmMDW-BOS
2h 10mnonstop
8:15 pm - 10:00 pmBOS-MDW
2h 45mnonstop
$179Southwest
Find Deal
Fri, Dec 13 - Sat, Jan 4
8:30 pm - 12:15 amORD-BOS
2h 45mnonstop
2:52 pm - 4:52 pmBOS-ORD
3h 00mnonstop
$183American Airlines
Find Deal
Sun, Jan 5 - Sun, Jan 12
7:25 am - 10:59 amORD-BOS
2h 34mnonstop
6:45 am - 8:49 amBOS-ORD
3h 04mnonstop
$189American Airlines
Find Deal
Wed, Dec 25 - Wed, Jan 1
1:55 pm - 5:16 pmORD-BOS
2h 21mnonstop
6:02 am - 8:05 amBOS-ORD
3h 03mnonstop
$197United Airlines
Find Deal
Sat, Dec 14 - Sat, Jan 4
9:37 pm - 1:09 amORD-BOS
2h 32mnonstop
6:00 am - 7:50 amBOS-ORD
2h 50mnonstop
$207United Airlines
Find Deal
Mon, Mar 31 - Sun, Apr 6
4:45 pm - 8:04 pmORD-BOS
2h 19mnonstop
8:10 am - 10:21 amBOS-ORD
3h 11mnonstop
$284Spirit Airlines
Find Deal
Mon, Dec 2 - Tue, Dec 3

Spirit Airlines flights from Chicago to Massachusetts

Our best Spirit Airlines deals on Chicago to Massachusetts flight tickets
Spirit Airlines
Dec 10
ORD9:58 amChicago O'Hare Intl
13h 40m
1 stop
BOS12:38 amBoston Logan Intl
Dec 11
BOS5:00 amBoston Logan Intl
12h 06m
1 stop
ORD4:06 pmChicago O'Hare Intl
Spirit Airlines
Dec 10
ORD9:58 amChicago O'Hare Intl
13h 40m
1 stop
BOS12:38 amBoston Logan Intl
Dec 17
BOS9:57 amBoston Logan Intl
11h 18m
1 stop
ORD8:15 pmChicago O'Hare Intl
Spirit Airlines
Dec 6
ORD11:45 amChicago O'Hare Intl
11h 53m
1 stop
BOS12:38 amBoston Logan Intl
Dec 10
BOS5:00 amBoston Logan Intl
12h 06m
1 stop
ORD4:06 pmChicago O'Hare Intl

Frontier flights from Chicago to Massachusetts

Our best Frontier deals on Chicago to Massachusetts flight tickets
Frontier
Dec 11
MDW12:57 pmChicago Midway
10h 33m
1 stop
BOS12:30 amBoston Logan Intl
Dec 18
BOS5:45 amBoston Logan Intl
8h 39m
1 stop
MDW1:24 pmChicago Midway
Frontier
Dec 10
MDW12:57 pmChicago Midway
10h 33m
1 stop
BOS12:30 amBoston Logan Intl
Dec 11
BOS6:00 amBoston Logan Intl
6h 42m
1 stop
MDW11:42 amChicago Midway
Frontier
Jan 21
MDW5:31 pmChicago Midway
6h 08m
1 stop
BOS12:39 amBoston Logan Intl
Jan 28
BOS6:00 amBoston Logan Intl
11h 16m
1 stop
MDW4:16 pmChicago Midway

See travel insights to Massachusetts from

How to get the cheapest flight ticket from Chicago to Massachusetts

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 day to depart on your flight to Massachusetts?

According to our data, Wednesday is the cheapest day to fly to Massachusetts from Chicago. The lowest ticket price found for a Wednesday departure recently was $227. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $290.

What is the cheapest Chicago to Massachusetts flight route?

Fly from Chicago Midway to Boston Logan Intl for the best Chicago - Massachusetts flight prices

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

There are 4 cabin classes available to choose from on Chicago to Massachusetts 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 Chicago to Massachusetts flights?

You could potentially save up to 38% on your flight if you consider stops on a Chicago to Massachusetts flight.

Cheap Chicago to Massachusetts flight deals and tips

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

Best Price Found

$45

Fastest flight time

1h 50m

Direct flights

Every day

Airports in Massachusetts

3 airports
The best one-way flight to Massachusetts from Chicago in the past 72 hours is $45. The best round-trip flight deal from Chicago to Massachusetts found on momondo in the last 72 hours is $101.
The fastest flight from Chicago to Massachusetts takes 1h 50m
Direct flights go from Chicago to Massachusetts every day.
There are 3 airports near Massachusetts: Boston Logan Intl (BOS), Albany Intl (ALB), Hartford Bradley Intl (BDL)

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

    Prices for flights from Chicago to Massachusetts were last updated today.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Massachusetts.

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

    The travel and health documents required for your trip to Massachusetts can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Massachusetts. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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


Best airlines flying from Chicago to Massachusetts

Compare and see reviews for airlines that fly from Chicago to Massachusetts with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $38Free CancellationRating
6.3
8,169 reviews
Search Spirit Airlines flights
DeltaPriceFrom $63Free CancellationRating
8.0
8,755 reviews
Search Delta flights
FrontierPriceFrom $69Free CancellationRating
6.1
3,536 reviews
Search Frontier flights
JetBluePriceFrom $83Free CancellationRating
7.4
3,389 reviews
Search JetBlue flights
American AirlinesPriceFrom $137Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $148Free CancellationRating
7.4
9,172 reviews
Search United Airlines flights
SouthwestPriceFrom $153Free CancellationRating
8.1
5,005 reviews
Search Southwest flights

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Massachusetts from Chicago.

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

Yes. momondo enables you to select and highlight flights to Massachusetts from Chicago with this policy.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Massachusetts.

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

Price alerts on flights to Massachusetts from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.


An easier way to manage your Massachusetts trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Popular cities in Massachusetts

Popular flights according to clicks in the last 7 days on momondo