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Cheap flights from Chicago to Massachusetts 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 Chicago to Massachusetts departing on 4/9. 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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0 bags

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Find the cheapest flights from Chicago to Massachusetts

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Massachusetts.
JetBlue Logo
10:42 am - 2:12 pmORD-BOS
2h 30mnonstop
JetBlue Logo
5:15 pm - 7:27 pmBOS-ORD
3h 12mnonstop
$97JetBlue
Find Deal
Sat, Apr 12 - Mon, Apr 14
Southwest Logo
3:00 pm - 6:20 pmMDW-BOS
2h 20mnonstop
Southwest Logo
5:45 am - 7:20 amBOS-MDW
2h 35mnonstop
$97Southwest
Find Deal
Sat, Apr 12 - Mon, Apr 14
Spirit Airlines Logo
7:47 pm - 10:22 amORD-BOS
13h 35m1 stop
Spirit Airlines Logo
3:49 pm - 11:04 pmBOS-ORD
8h 15m1 stop
$105Spirit Airlines
Find Deal
Wed, Apr 30 - Wed, May 7
American Airlines Logo
11:50 am - 3:22 pmORD-BOS
2h 32mnonstop
American Airlines Logo
5:38 pm - 7:36 pmBOS-ORD
2h 58mnonstop
$113American Airlines
Find Deal
Sat, May 10 - Sat, May 10
Spirit Airlines Logo
5:05 am - 2:44 pmORD-BOS
8h 39m1 stop
Spirit Airlines Logo
3:49 pm - 11:04 pmBOS-ORD
8h 15m1 stop
$118Spirit Airlines
Find Deal
Tue, May 13 - Tue, May 13
American Airlines Logo
4:40 pm - 8:01 pmORD-BOS
2h 21mnonstop
American Airlines Logo
6:35 am - 8:31 amBOS-ORD
2h 56mnonstop
$119American Airlines
Find Deal
Tue, May 13 - Wed, May 14
United Airlines Logo
6:30 am - 9:56 amORD-BOS
2h 26mnonstop
United Airlines Logo
7:30 pm - 11:42 pmBOS-ORD
5h 12m1 stop
$123United Airlines
Find Deal
Fri, Aug 22 - Sun, Aug 31
United Airlines Logo
9:20 pm - 12:45 amORD-BOS
2h 25mnonstop
United Airlines Logo
6:00 am - 7:57 amBOS-ORD
2h 57mnonstop
$143United Airlines
Find Deal
Thu, May 1 - Sun, May 4
Delta Logo
7:00 am - 10:25 amORD-BOS
2h 25mnonstop
Delta Logo
7:15 am - 9:09 amBOS-ORD
2h 54mnonstop
$210Delta
Find Deal
Mon, Jun 2 - Wed, Jun 4
Delta Logo
7:10 am - 3:11 pmORD-ORH
7h 01m1 stop
Delta Logo
3:55 pm - 10:19 pmORH-ORD
7h 24m1 stop
$212Delta
Find Deal
Tue, Jun 24 - Tue, Jul 1

JetBlue flights from Chicago to Massachusetts

Our best JetBlue deals on Chicago to Massachusetts flight tickets
JetBlue
Apr 12
ORD10:42 amChicago O'Hare Intl
2h 30m
BOS2:12 pmBoston Logan Intl
Apr 14
BOS5:15 pmBoston Logan Intl
3h 12m
ORD7:27 pmChicago O'Hare Intl
JetBlue
May 7
ORD7:31 pmChicago O'Hare Intl
2h 29m
BOS11:00 pmBoston Logan Intl
May 13
BOS4:30 pmBoston Logan Intl
3h 06m
ORD6:36 pmChicago O'Hare Intl
JetBlue
Apr 12
ORD8:29 pmChicago O'Hare Intl
2h 29m
BOS11:58 pmBoston Logan Intl
Apr 14
BOS5:15 pmBoston Logan Intl
3h 12m
ORD7:27 pmChicago O'Hare Intl

Southwest flights from Chicago to Massachusetts

Our best Southwest deals on Chicago to Massachusetts flight tickets
Southwest
Apr 12
MDW3:00 pmChicago Midway
2h 20m
BOS6:20 pmBoston Logan Intl
Apr 14
BOS9:35 amBoston Logan Intl
2h 35m
MDW11:10 amChicago Midway
Southwest
Apr 12
MDW4:35 pmChicago Midway
4h 40m
1 stop
BOS10:15 pmBoston Logan Intl
Apr 14
BOS9:35 amBoston Logan Intl
2h 35m
MDW11:10 amChicago Midway
Southwest
May 13
MDW6:25 pmChicago Midway
2h 20m
BOS9:45 pmBoston Logan Intl
May 14
BOS1:30 pmBoston Logan Intl
6h 40m
2 stops
MDW7:10 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 month to fly to Massachusetts?

In general, September is the cheapest month to fly from Chicago to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $191. If you aren’t able to travel to Massachusetts during the month of September, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $208.

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 $250. 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 $329.

What is the cheapest time of day to depart on your flight to Massachusetts?

Our data shows that the cheapest Chicago to Massachusetts flights are usually those with departure times in the evening. Our users have found flights to Massachusetts in the evening for as low as $194. If you have a flexible travel schedule, then try to avoid flying in the afternoon when prices are $300 on average. Flights to Massachusetts from Chicago in the afternoon are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Chicago to Massachusetts flight route?

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

How far in advance should I book a flight to Massachusetts?

You are more likely to see cheaper flights to Massachusetts from Chicago when booking 6 weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $242 when searching 6 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Chicago for as low as $200 on momondo.

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.

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

$49

Fastest flight time

1h 50m

Direct flights

Every day

Airports in Massachusetts

4 airports
The best one-way flight to Massachusetts from Chicago in the past 72 hours is $49. The best round-trip flight deal from Chicago to Massachusetts found on momondo in the last 72 hours is $97.
The fastest flight from Chicago to Massachusetts takes 1h 50m
Direct flights go from Chicago to Massachusetts every day.
There are 4 airports near Massachusetts: Worcester (ORH), 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
7,888 reviews
Search Spirit Airlines flights
DeltaPriceFrom $63Free CancellationRating
8.0
7,897 reviews
Search Delta flights
FrontierPriceFrom $69Free CancellationRating
5.9
3,277 reviews
Search Frontier flights
JetBluePriceFrom $82Free CancellationRating
7.3
2,922 reviews
Search JetBlue flights
American AirlinesPriceFrom $140Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $153Free CancellationRating
7.4
8,616 reviews
Search United Airlines flights
SouthwestPriceFrom $157Free CancellationRating
8.0
4,274 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.


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Popular cities in Massachusetts

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