Cheap flights from Chicago O'Hare Intl Airport to Massachusetts from $53
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 O'Hare Intl Airport to Massachusetts departing on 10/16. 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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1 adult
Economy
0 bags
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Cheap round-trip flights
These are some of the best round-trip flight deals from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Massachusetts.
Cheap last minute flights
Planning a quick getaway from Chicago O'Hare Intl Airport 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.
Spirit Airlines flights from Chicago O'Hare Intl Airport to Massachusetts
Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to Massachusetts flight tickets
Spirit Airlines![Spirit Airlines]()
Jun 4![Spirit Airlines]()
Jun 11
ORD7:37 amChicago O'Hare Intl
13h 13m
1 stop
BOS9:50 pmBoston Logan Intl
BOS3:49 pmBoston Logan Intl
8h 15m
1 stop
ORD11:04 pmChicago O'Hare Intl
Spirit Airlines![Spirit Airlines]()
May 29![Spirit Airlines]()
Jun 3
ORD9:55 amChicago O'Hare Intl
12h 34m
1 stop
BOS11:29 pmBoston Logan Intl
BOS3:49 pmBoston Logan Intl
8h 15m
1 stop
ORD11:04 pmChicago O'Hare Intl
Delta flights from Chicago O'Hare Intl Airport to Massachusetts
Our best Delta deals on Chicago O'Hare Intl Airport to Massachusetts flight tickets
Delta![Delta]()
May 8![Delta]()
May 13
ORD7:00 amChicago O'Hare Intl
2h 25m
BOS10:25 amBoston Logan Intl
BOS7:15 amBoston Logan Intl
2h 54m
ORD9:09 amChicago O'Hare Intl
Delta![Delta]()
Jul 4![Delta]()
Jul 11
ORD7:00 amChicago O'Hare Intl
2h 31m
BOS10:31 amBoston Logan Intl
BOS7:20 amBoston Logan Intl
2h 58m
ORD9:18 amChicago O'Hare Intl
See travel insights to Massachusetts from
How to get the cheapest flight ticket from Chicago O'Hare Intl Airport 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
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Other information
What is the cheapest month to fly to Massachusetts?
In general, September is the cheapest month to fly from Chicago O'Hare Intl Airport to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $195. 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 $209.
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 O'Hare Intl Airport. 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 O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl Airport in the afternoon are generally more expensive because this time of day is more convenient for travelers’ schedules.
What is the cheapest Chicago O'Hare Intl to Massachusetts flight route?
Fly from Chicago O'Hare Intl to Boston Logan Intl for the best Chicago O'Hare Intl - 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 O'Hare Intl Airport when booking 6 weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $239 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 O'Hare Intl Airport for as low as $200 on momondo.
What cabin class options are available on Chicago O'Hare Intl to Massachusetts flights?
There are 4 cabin classes available to choose from on Chicago O'Hare Intl 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 O'Hare Intl to Massachusetts?
Spirit Airlines, JetBlue, and Southwest are the most popular carriers operating from Chicago O'Hare Intl 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 O'Hare Intl Airport according to our data. American Airlines is the first choice among our users, with 36% 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 O'Hare Intl Airport to Massachusetts on average per day?
The number of flights available between Chicago O'Hare Intl Airport and Massachusetts is 47 per day as of April 2025. The most frequent departure time is 7:00AM, with 45% of daily flights leaving at noon.
How many flights depart from Chicago O'Hare Intl Airport to Massachusetts on average per week?
As of April 2025, 333 flights take off from Chicago O'Hare Intl Airport and land in Massachusetts each week. The most common flight departure day for this route is Wed, with 29% of weekly flights taking off on this day.
Cheap Chicago O'Hare Intl Airport to Massachusetts flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Massachusetts
Best Price Found | $53 |
|---|---|
Fastest flight time | 2h 01m |
Direct flights | Every day |
Airports in Massachusetts | 4 airports |
When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Massachusetts?
Prices for flights from Chicago O'Hare Intl Airport to Massachusetts are updated daily.
How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Massachusetts?
There are 7 operators available for flights from Chicago O'Hare Intl Airport to Massachusetts as of April 2025.
How old do you have to be to fly from Chicago O'Hare Intl Airport to Massachusetts?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport to Massachusetts.
What documentation or ID do you need to fly to Massachusetts?
The travel and health documents you'll need for your trip to Massachusetts may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Massachusetts. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago O'Hare Intl Airport to Massachusetts?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago O'Hare Intl Airport to Massachusetts is Boeing 737-800 (22.82% of total bookings). The next most popular plane models are Embraer 175 (15.82%), Boeing 737 MAX 8 (10.88%), and Boeing 737-900 (9.05%).
Best airlines flying from Chicago O'Hare Intl Airport to Massachusetts
Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Massachusetts with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $38 | Free Cancellation | Rating 6.3 7,962 reviews | |||
| PriceFrom $69 | Free Cancellation | Rating 5.9 3,287 reviews | |||
| PriceFrom $79 | Free Cancellation | Rating 7.3 2,922 reviews | |||
| PriceFrom $88 | Free Cancellation | Rating 8.0 7,934 reviews | |||
| PriceFrom $137 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $138 | Free Cancellation | Rating 7.4 8,696 reviews | |||
| PriceFrom $214 | Free Cancellation | Rating 8.0 4,294 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?
momondo does allow users to show only those flights to Massachusetts from Chicago which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Chicago to Massachusetts?
momondo provides multiple filters to help you find the best flight to Massachusetts from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
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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