Cheap flights from Chicago to Boston from $42
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 5/7. 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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Frontier flights from Chicago to Boston
Our best Frontier deals on Chicago to Boston flight tickets
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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, September 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 $191. If you aren’t able to travel during the month of September, then book flights to Boston from Chicago during August instead. Flights to Boston in August, while not as cheap as those in September, still average around $209.
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 $252. 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 $330.
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 $203. 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 $298 per ticket.
What is the cheapest Chicago to Boston Logan Intl flight route?
Fly from Chicago O'Hare Intl 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 6 weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $242 when searching 6 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 $206 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, Frontier, and Delta 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 37% 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 February 2025, there are 42 flights per day flying from Chicago to Boston. The most common time of day flights depart is 12:00PM, with 40% of flights taking off at noon.
How many flights depart from Chicago to Boston on average per week?
As of February 2025, 294 flights take off from Chicago and land in Boston each week. The most common flight departure day for this route is Thu, with 19% 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
Is flying the fastest way to get from Chicago to Boston?
The quickest way is to book a flight from Chicago to Boston, which can be as quick as 2h 10m onboard Southwest. You can also get a train from Chicago to Boston, or a bus from Chicago to Boston which can take you longer to arrive at your destination.
Is flying the cheapest way to get from Chicago to Boston?
A flight from Chicago to Boston is currently going to be the least expensive option currently available. You can also find deals for a train from Chicago to Boston starting at $291, or consider a bus from Chicago to Boston starting at $230. Both of these alternative options are worth considering when looking to reach your destination.
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 February 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 20.75% of all bookings. The subsequent popular models are Embraer 175 at 15.61%, Boeing 737 MAX 8 at 10.95%, and Boeing 737-900 at 7.16%.
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 28%, Delta with 17%, and JetBlue with 11%.
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 $38 | Free Cancellation | Rating 6.3 8,013 reviews | |||
| PriceFrom $63 | Free Cancellation | Rating 8.0 8,219 reviews | |||
| PriceFrom $85 | Free Cancellation | Rating 7.4 3,070 reviews | |||
| PriceFrom $86 | Free Cancellation | Rating 6.0 3,355 reviews | |||
| PriceFrom $139 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $156 | Free Cancellation | Rating 7.4 8,765 reviews | |||
| PriceFrom $157 | Free Cancellation | Rating 8.1 4,411 reviews |
Southwest Flights From Chicago to Boston
Southwest flight deals from Chicago to Boston start from $157 round-trip. Over the 8 Southwest flights for this route in a normal week, average airfare is usually $278 round-trip - but some users have found much cheaper deals with momondo.
Delta Flights From Chicago to Boston
Another popular option for Chicago to Boston flights is Delta (8.0/10, 8,220 ratings). Delta flies from Chicago to Boston around 17 times per week, with deals starting from $63 round-trip and rising to an average price of around $302.
Traveling to a place near Boston?
Book flights to Boston if you plan to visit one of these locationsWhy use momondo?
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.