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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United Airlines flights from Massachusetts to Chicago O'Hare Intl Airport
Our best United Airlines deals on Massachusetts to Chicago O'Hare Intl Airport flight tickets
JetBlue flights from Massachusetts to Chicago O'Hare Intl Airport
Our best JetBlue deals on Massachusetts to Chicago O'Hare Intl Airport flight tickets
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How to get the cheapest flight ticket from Massachusetts to Chicago O'Hare Intl 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 O'Hare Intl Airport?
The month of August is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Massachusetts averaging around $199.
What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?
The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $309. This is often the case because there is less demand to fly during this day of the week. 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 $413.
What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?
Flying to Chicago O'Hare Intl Airport from Massachusetts in the evening is the least expensive time of day to depart. momondo users have found prices as low as $251 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $350. 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 O'Hare Intl flight route?
Fly from Boston Logan Intl to Chicago O'Hare Intl for the best Massachusetts - Chicago O'Hare Intl flight prices
How far in advance should I book a flight to Chicago O'Hare Intl Airport?
You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $241 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Massachusetts for as low as $209 on momondo.
What cabin class options are available on Massachusetts to Chicago O'Hare Intl flights?
There are 4 cabin classes available to choose from on Massachusetts to Chicago O'Hare Intl 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 O'Hare Intl?
Spirit Airlines, United Airlines, and JetBlue are the most popular carriers operating from Massachusetts to Chicago O'Hare Intl
What airlines fly to Chicago O'Hare Intl Airport?
American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport. Keep in mind that there are 7 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Massachusetts to Chicago O'Hare Intl Airport on average per day?
As of June 2025, there are 95 flights per day flying from Massachusetts to Chicago O'Hare Intl Airport. The most common time of day flights depart is 6:00AM, with 41% of flights taking off at noon.
How many flights depart from Massachusetts to Chicago O'Hare Intl Airport on average per week?
As of June 2025, 668 flights take off from Massachusetts and land in Chicago O'Hare Intl Airport each week. The most common flight departure day for this route is Mon, with 18% of weekly flights taking off on this day.
Cheap Massachusetts to Chicago O'Hare Intl Airport flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Massachusetts to Chicago O'Hare Intl Airport
When did momondo last update prices for flights from Massachusetts to Chicago O'Hare Intl Airport?
Prices for flights from Massachusetts to Chicago O'Hare Intl Airport were last updated today.
How many operators does momondo search for flights from Massachusetts to Chicago O'Hare Intl Airport?
There are 7 operators available for flights from Massachusetts to Chicago O'Hare Intl Airport as of June 2025.
How old do you have to be to fly from Massachusetts to Chicago O'Hare Intl Airport?
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 O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The necessary travel and health documents for your Chicago O'Hare Intl 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 O'Hare Intl Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Massachusetts to Chicago O'Hare Intl Airport is Boeing 737-800 (25.87% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (12.93%), Boeing 737-900 (10.85%), and Embraer 175 (10.41%).
Best airlines flying from Massachusetts to Chicago O'Hare Intl Airport
Compare and see reviews for airlines that fly from Massachusetts to Chicago O'Hare Intl Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $39 | Free Cancellation | Rating 6.3 8,066 reviews | |||
| PriceFrom $79 | Free Cancellation | Rating 7.3 2,924 reviews | |||
| PriceFrom $93 | Free Cancellation | Rating 8.0 7,964 reviews | |||
| PriceFrom $100 | Free Cancellation | Rating 5.9 3,301 reviews | |||
| PriceFrom $137 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $138 | Free Cancellation | Rating 7.4 8,810 reviews | |||
| PriceFrom $156 | Free Cancellation | Rating 8.0 4,280 reviews |
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Why should I use momondo to find a flight deal from Massachusetts to Chicago?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Massachusetts to Chicago for you.
Can I find flights from Massachusetts to Chicago with flexible booking policies on momondo?
All flight searches from Massachusetts to Chicago on momondo can be filtered to show those which offer flexible booking policies.
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?
If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Massachusetts and alert you when they change.