Cheap flights from Massachusetts to Chicago 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 Massachusetts to Chicago departing on 5/11. 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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Southwest flights from Massachusetts to Chicago Midway Airport
Our best Southwest deals on Massachusetts to Chicago Midway Airport flight tickets
Delta flights from Massachusetts to Chicago Midway Airport
Our best Delta deals on Massachusetts to Chicago Midway Airport flight tickets
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How to get the cheapest flight ticket from Massachusetts to Chicago Midway Airport
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 Chicago Midway Airport?
The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Massachusetts, with most prices found around $200. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Massachusetts during the month September is also very affordable. Most momondo users find prices during this month for around $208.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Massachusetts. The lowest ticket price found for a Thursday departure recently was $324. 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 Massachusetts because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $461.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Massachusetts at noon is the least expensive time of day to depart. momondo users have found prices as low as $347 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $371. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Massachusetts to Chicago Midway flight route?
Fly from Boston Logan Intl to Chicago Midway for the best Massachusetts - Chicago Midway flight prices
How far in advance should I book a flight to Chicago Midway Airport?
You are more likely to see cheaper flights to Chicago Midway Airport from Massachusetts when booking 7 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $260 when searching 7 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Massachusetts for as low as $185 on momondo.
What cabin class options are available on Massachusetts to Chicago Midway flights?
There are 1 cabin classes available to choose from on Massachusetts to Chicago Midway 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 Massachusetts to Chicago Midway?
Southwest, Allegiant Air, and Delta are the most popular carriers operating from Massachusetts to Chicago Midway
What airlines fly to Chicago Midway Airport?
Southwest, Delta and Frontier are the top three most popular airlines that fly to Chicago Midway Airport from Massachusetts according to our data. Southwest is the first choice among our users, with 83% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 5 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Massachusetts to Chicago Midway Airport on average per day?
4 flights are operational daily from Massachusetts to Chicago Midway Airport as of May 2025. The most popular departure time for this route is 5:00AM, with 47% of flights per day taking off in the afternoon.
How many flights depart from Massachusetts to Chicago Midway Airport on average per week?
The number of flights available between Massachusetts and Chicago Midway Airport is 32 per week as of May 2025. The most frequent departure day is Sun, with 25% of weekly flights leaving on this day.
Cheap Massachusetts to Chicago Midway Airport flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Massachusetts to Chicago Midway Airport
When did momondo last update prices for flights from Massachusetts to Chicago Midway Airport?
Prices for flights from Massachusetts to Chicago Midway Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Massachusetts to Chicago Midway Airport?
There are 5 operators available for flights from Massachusetts to Chicago Midway Airport as of May 2025.
How old do you have to be to fly from Massachusetts to Chicago Midway Airport?
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 Massachusetts to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Massachusetts to Chicago Midway Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Massachusetts to Chicago Midway Airport is Boeing 737-800 (20.74% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (17.20%), Embraer 175 (11.11%), and Airbus A321neo (8.80%).
Best airlines flying from Massachusetts to Chicago Midway Airport
Compare and see reviews for airlines that fly from Massachusetts to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $76 | Free Cancellation | Rating 6.3 7,966 reviews | |||
| PriceFrom $97 | Free Cancellation | Rating 7.4 8,701 reviews | |||
| PriceFrom $100 | Free Cancellation | Rating 5.9 3,288 reviews | |||
| PriceFrom $139 | Free Cancellation | Rating 8.0 4,294 reviews | |||
| PriceFrom $237 | Free Cancellation | Rating 8.0 7,940 reviews |
Traveling to a place near Chicago?
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Why should I use momondo to find a flight deal from Massachusetts to Chicago?
It is quick and easy to find Massachusetts to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.
Can I find flights from Massachusetts to Chicago with flexible booking policies on momondo?
Yes. All flights to Chicago from Massachusetts on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Massachusetts to Chicago?
momondo helps you find the best flight between Massachusetts and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from Massachusetts to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from Massachusetts 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.