Cheap flights from Chicago to Boston 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 Chicago to Boston 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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Spirit Airlines flights from Chicago to Boston
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United Airlines flights from Chicago to Boston
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How to get the cheapest flight ticket from Chicago to Boston
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 typical price of a round-trip flight between Chicago and Boston?
What is the cheapest month to fly to Boston?
In general, August is the cheapest month to fly from Chicago to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $187. If you aren’t able to travel during the month of August, then book flights to Boston from Chicago during September instead. Flights to Boston in September, while not as cheap as those in August, still average around $189.
What is the cheapest day to depart on your flight to Boston?
The cheapest day to depart from Chicago to Boston is on a Wednesday when prices can be found for as low as $234. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Sunday is $303.
What is the cheapest time of day to depart on your flight to Boston?
According to our data, the cheapest time of day to fly to Boston is in the evening. momondo users have found flights departing from Chicago to Boston in the evening for as low as $199. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the afternoon is when there is more demand to fly to Boston, so prices are often more expensive at around $286 per ticket.
What is the cheapest Chicago to Boston Logan Intl flight route?
Fly from Chicago Midway to Boston Logan Intl for the best Chicago - Boston Logan Intl flight prices
How far in advance should I book a flight to Boston?
You are more likely to see cheaper flights to Boston from Chicago when booking 13 weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $229 when searching 13 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Chicago for as low as $191 on momondo.
What cabin class options are available on Chicago to Boston Logan Intl flights?
There are 4 cabin classes available to choose from on Chicago to Boston Logan 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 Chicago to Boston Logan Intl?
Spirit Airlines, JetBlue, and United Airlines are the most popular carriers operating from Chicago to Boston Logan Intl
What airlines fly to Boston?
American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Boston from Chicago according to our data. American Airlines is the first choice among our users, with 40% of people opting to fly with this airline when traveling to Boston. Keep in mind that there are 7 different airlines that fly to Boston on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to Boston on average per day?
As of June 2025, there are 52 flights per day flying from Chicago to Boston. The most common time of day flights depart is 7:00PM, with 44% of flights taking off at noon.
How many flights depart from Chicago to Boston on average per week?
As of June 2025, 368 flights take off from Chicago and land in Boston each week. The most common flight departure day for this route is Thu, with 22% of weekly flights taking off on this day.
When to book flights from Chicago to Boston
Cheap Chicago to Boston (CHI to BOS) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Boston
How far is Chicago to Boston Logan Intl by plane?
The distance between Chicago and Boston Logan Intl is about 847.9 mi. 2h 10m is a normal flight duration for this route.
When did momondo last update prices for flights from Chicago to Boston Logan Intl Airport?
Prices for flights from Chicago to Boston Logan Intl Airport are updated daily.
How many operators does momondo search for flights from Chicago to Boston Logan Intl Airport?
The number of operators available for flights from Chicago to Boston Logan Intl Airport is 7 as of June 2025.
How old do you have to be to fly from Chicago to Boston Logan 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 Chicago to Boston Logan Intl Airport.
What documentation or ID do you need to fly to Boston Logan Intl Airport?
The travel and health documents you'll need for your trip to Boston Logan Intl Airport 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 Boston Logan Intl Airport. 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 to Boston?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Boston is Boeing 737-800, representing 22.22% of all bookings. The subsequent popular models are Embraer 175 at 12.70%, Boeing 737 MAX 8 at 11.09%, and Airbus A220-300 at 9.70%.
What is the most popular airline from Chicago to Boston?
Based on momondo bookings for flights between Chicago and Boston, the leading airline is American Airlines, making up 29% of the total bookings. Other popular airlines include United Airlines with 27%, Delta with 16%, and Southwest with 10%.
Best airlines flying from Chicago to Boston
Compare and see reviews for airlines that fly from Chicago to Boston with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $36 | Free Cancellation | Rating 6.3 8,052 reviews | |||
| PriceFrom $69 | Free Cancellation | Rating 5.9 3,295 reviews | |||
| PriceFrom $79 | Free Cancellation | Rating 7.3 2,925 reviews | |||
| PriceFrom $89 | Free Cancellation | Rating 8.0 7,946 reviews | |||
| PriceFrom $127 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $131 | Free Cancellation | Rating 7.4 8,790 reviews | |||
| PriceFrom $156 | Free Cancellation | Rating 8.0 4,287 reviews |
Delta Flights From Chicago to Boston
Delta flight deals from Chicago to Boston start from $89 round-trip. Over the 16 Delta flights for this route in a normal week, average airfare is usually $223 round-trip - but some users have found much cheaper deals with momondo.
Southwest Flights From Chicago to Boston
Another popular option for Chicago to Boston flights is Southwest (8.0/10, 4,287 ratings). Southwest flies from Chicago to Boston around 30 times per week, with deals starting from $156 round-trip and rising to an average price of around $291.
Traveling to a place near Boston?
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Why should I use momondo to find a flight deal from Chicago to Boston?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Boston. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from Chicago to Boston with flexible booking policies on momondo?
All flight searches from Chicago to Boston on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Chicago to Boston?
momondo provides multiple filters to help you find the best flight to Boston 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 Boston right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Chicago to Boston flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.