Cheap flights from Massachusetts to Chicago from $55
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 7/9. 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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How to get the cheapest flight ticket from Massachusetts to Chicago
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?
The month of September is, on average, the cheapest month to fly to Chicago from Massachusetts, with most prices found around $177. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Massachusetts to Chicago during January average around $194.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $310. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Massachusetts to Chicago for around $415.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Massachusetts to Chicago during this time can be as low as $261. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $351.
What is the cheapest Massachusetts to Chicago flight route?
Fly from Boston Logan Intl to Chicago Midway for the best Massachusetts - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Massachusetts when booking 5 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $241 when searching 5 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Massachusetts for as low as $209 on momondo.
What cabin class options are available on Massachusetts to Chicago flights?
There are 4 cabin classes available to choose from on Massachusetts to Chicago 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?
Spirit Airlines, Southwest, and JetBlue are the most popular carriers operating from Massachusetts to Chicago
What airlines fly to Chicago?
American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago from Massachusetts according to our data. American Airlines is the first choice among our users, with 38% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Massachusetts to Chicago on average per day?
121 flights are operational daily from Massachusetts to Chicago as of June 2025. The most popular departure time for this route is 6:00AM, with 41% of flights per day taking off in the afternoon.
How many flights depart from Massachusetts to Chicago on average per week?
847 flights are operational weekly from Massachusetts to Chicago as of June 2025. The most popular departure day for this route is Mon, with 16% of flights per week taking off on this day.
Cheap Massachusetts to Chicago flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Massachusetts to Chicago
When did momondo last update prices for flights from Massachusetts to Chicago?
Prices for flights from Massachusetts to Chicago are updated daily.
How many operators does momondo search for flights from Massachusetts to Chicago?
There are 7 operators available for flights from Massachusetts to Chicago as of June 2025.
How old do you have to be to fly from Massachusetts to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Massachusetts to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Massachusetts to Chicago?
Based on momondo bookings for flights between Massachusetts and Chicago, the leading plane model is Boeing 737-800, making up 25.23% of the total bookings. Other popular models include Boeing 737 MAX 8 with 13.91%, Boeing 737-900 with 10.56%, and Embraer 175 with 10.03%.
Best airlines flying from Massachusetts to Chicago
Compare and see reviews for airlines that fly from Massachusetts to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $39 | Free Cancellation | Rating 6.3 8,060 reviews | |||
| PriceFrom $79 | Free Cancellation | Rating 7.3 2,922 reviews | |||
| PriceFrom $93 | Free Cancellation | Rating 8.0 7,963 reviews | |||
| PriceFrom $97 | Free Cancellation | Rating 7.4 8,801 reviews | |||
| PriceFrom $100 | Free Cancellation | Rating 5.9 3,296 reviews | |||
| PriceFrom $126 | Free Cancellation | Rating 8.0 4,278 reviews | |||
| PriceFrom $137 | Free Cancellation | Rating 7.2 10,000 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
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?
momondo does allow users to show only those flights to Chicago from Massachusetts which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Massachusetts to Chicago?
Once all potential Massachusetts to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Massachusetts to Chicago right now. Can momondo alert me if prices change?
Of course. momondo tracks the price of Massachusetts to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.