Cheap flights from Chicago Midway Airport to Massachusetts from $59
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 Midway Airport to Massachusetts departing on 6/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Chicago Midway Airport to Massachusetts
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Southwest flights from Chicago Midway Airport to Massachusetts
Our best Southwest deals on Chicago Midway Airport to Massachusetts flight tickets
Frontier flights from Chicago Midway Airport to Massachusetts
Our best Frontier deals on Chicago Midway Airport to Massachusetts flight tickets
See travel insights to Massachusetts from
How to get the cheapest flight ticket from Chicago Midway 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
What is the cheapest month to fly to Massachusetts?
In general, January is the cheapest month to fly from Chicago Midway Airport to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $185. If you aren’t able to travel to Massachusetts during the month of January, then flying in March is also cheap. Prices for this month can be found on momondo for an average of $237.
What is the cheapest day to depart on your flight to Massachusetts?
According to our data, Saturday is the cheapest day to fly to Massachusetts from Chicago Midway Airport. The lowest ticket price found for a Saturday departure recently was $231. 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 Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $299.
What is the cheapest time of day to depart on your flight to Massachusetts?
Our data shows that the cheapest Chicago Midway Airport to Massachusetts flights are usually those with departure times in the afternoon. Our users have found flights to Massachusetts in the afternoon for as low as $230. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $298 on average. Flights to Massachusetts from Chicago Midway Airport at noon are generally more expensive because this time of day is more convenient for travelers’ schedules.
What is the cheapest Chicago Midway to Massachusetts flight route?
Fly from Chicago Midway to Boston Logan Intl for the best Chicago Midway - 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 Midway Airport when booking 16 weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $278 when searching 16 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Chicago Midway Airport for as low as $193 on momondo.
What cabin class options are available on Chicago Midway to Massachusetts flights?
There are 1 cabin classes available to choose from on Chicago Midway 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 Midway to Massachusetts?
Southwest, Allegiant Air, and Delta are the most popular carriers operating from Chicago Midway to Massachusetts
What airlines fly to Massachusetts?
Southwest, Delta and United Airlines are the top three most popular airlines that fly to Massachusetts from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 85% of people opting to fly with this airline when traveling to Massachusetts. Keep in mind that there are 4 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 Midway Airport to Massachusetts on average per day?
As of May 2025, there are 4 flights per day flying from Chicago Midway Airport to Massachusetts. The most common time of day flights depart is 12:00PM, with 34% of flights taking off in the afternoon.
How many flights depart from Chicago Midway Airport to Massachusetts on average per week?
32 flights are operational weekly from Chicago Midway Airport to Massachusetts as of May 2025. The most popular departure day for this route is Sun, with 25% of flights per week taking off on this day.
Cheap Chicago Midway Airport to Massachusetts flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Massachusetts
Best Price Found | $59 |
|---|---|
Fastest flight time | 1h 55m |
Direct flights | Every day |
Airports in Massachusetts | 3 airports |
When did momondo last update prices for flights from Chicago Midway Airport to Massachusetts?
Prices for flights from Chicago Midway Airport to Massachusetts are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago Midway Airport to Massachusetts?
As of May 2025, there are 4 operators available to choose from for flights from Chicago Midway Airport to Massachusetts.
How old do you have to be to fly from Chicago Midway Airport 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 Midway Airport 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 Midway Airport to Massachusetts?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago Midway Airport to Massachusetts is Boeing 737-800 (17.76% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (15.30%), Embraer 175 (12.40%), and Airbus A220-300 (11.75%).
Best airlines flying from Chicago Midway Airport to Massachusetts
Compare and see reviews for airlines that fly from Chicago Midway Airport to Massachusetts with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $63 | Free Cancellation | Rating 8.0 7,940 reviews | |||
| PriceFrom $100 | Free Cancellation | Rating 5.9 3,288 reviews | |||
| PriceFrom $157 | Free Cancellation | Rating 7.4 8,701 reviews | |||
| PriceFrom $157 | 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?
Yes. All flights to Massachusetts from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.
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?
If you are not ready to book a flight from Chicago to Massachusetts now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Massachusetts and let you know when they change.