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.
Round-trip
1 adult
Economy
0 bags
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One-way
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Cheap round-trip flights
KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to Massachusetts.
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.
JetBlue flights from Chicago to Massachusetts
Our best JetBlue deals on Chicago to Massachusetts flight tickets
JetBlue![JetBlue]()
Apr 12![JetBlue]()
Apr 14
ORD10:42 amChicago O'Hare Intl
2h 30m
BOS2:12 pmBoston Logan Intl
BOS5:15 pmBoston Logan Intl
3h 12m
ORD7:27 pmChicago O'Hare Intl
JetBlue![JetBlue]()
May 7![JetBlue]()
May 13
ORD7:31 pmChicago O'Hare Intl
2h 29m
BOS11:00 pmBoston Logan Intl
BOS4:30 pmBoston Logan Intl
3h 06m
ORD6:36 pmChicago O'Hare Intl
Southwest flights from Chicago to Massachusetts
Our best Southwest deals on Chicago to Massachusetts flight tickets
Southwest![Southwest]()
Apr 12![Southwest]()
Apr 14
MDW3:00 pmChicago Midway
2h 20m
BOS6:20 pmBoston Logan Intl
BOS9:35 amBoston Logan Intl
2h 35m
MDW11:10 amChicago Midway
Southwest![Southwest]()
Apr 12![Southwest]()
Apr 14
MDW4:35 pmChicago Midway
4h 40m
1 stop
BOS10:15 pmBoston Logan Intl
BOS9:35 amBoston Logan Intl
2h 35m
MDW11:10 amChicago 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
Prices
Airlines
Other information
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.
What is the cheapest airline that flies from Chicago to Massachusetts?
JetBlue, Southwest, and Delta are the most popular carriers operating from Chicago to Massachusetts
What airlines fly to Massachusetts?
American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Massachusetts from Chicago according to our data. American Airlines is the first choice among our users, with 35% of people opting to fly with this airline when traveling to Massachusetts. Keep in mind that there are 7 different airlines that fly to Massachusetts on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to Massachusetts on average per day?
As of April 2025, there are 58 flights per day flying from Chicago to Massachusetts. The most common time of day flights depart is 6:00PM, with 40% of flights taking off at noon.
How many flights depart from Chicago to Massachusetts on average per week?
406 flights are operational weekly from Chicago to Massachusetts as of April 2025. The most popular departure day for this route is Thu, with 27% of flights per week taking off on this day.
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 |
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?
The number of operators available for flights from Chicago to Massachusetts is 7 as of April 2025.
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?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Massachusetts is Boeing 737-800 (22.15% of total bookings). The next most popular plane models are Embraer 175 (17.02%), Boeing 737 MAX 8 (11.76%), and Boeing 737-900 (8.23%).
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 | ||
|---|---|---|---|---|---|
| PriceFrom $38 | Free Cancellation | Rating 6.3 7,888 reviews | |||
| PriceFrom $63 | Free Cancellation | Rating 8.0 7,897 reviews | |||
| PriceFrom $69 | Free Cancellation | Rating 5.9 3,277 reviews | |||
| PriceFrom $82 | Free Cancellation | Rating 7.3 2,922 reviews | |||
| PriceFrom $140 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $153 | Free Cancellation | Rating 7.4 8,616 reviews | |||
| PriceFrom $157 | Free Cancellation | Rating 8.0 4,274 reviews |
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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