Big names, great deals
Big names, great deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customise your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Chicago to Boston
Cheap return flights
Cheap one-way flights
Cheap last-minute flights
Cheap direct flights
JetBlue flights from Chicago to Boston
Our best JetBlue deals on Chicago to Boston flight tickets
Southwest flights from Chicago to Boston
Our best Southwest deals on Chicago to Boston flight tickets
See travel insights to Boston from
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 £148. The month of August is another great option to travel to Boston, with average flight prices from Chicago averaging around £161.
What is the cheapest day to depart on your flight to Boston?
The cheapest day to depart on your flight to Boston is on a Wednesday when prices can be found for as low as £148. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around £1,441. These prices are subject to change though, so be sure to set up a Price Alert for flights to Boston.
What is the cheapest time of day to depart on your flight to Boston?
Our most recent data shows that the best time of day to fly to Boston is in the evening. Flights from Chicago to Boston during this time can be as low as £143. In the afternoon is when there is more demand to fly to Boston, so prices are often more expensive at around £760 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 6 weeks ahead of your departure date. In general, you can expect to find flights to Boston for around £188 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 £156 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.
How many flights depart from Chicago to Boston on average per day?
As of March 2025, 22 flights take off from Chicago and land in Boston each day. The most common flight departure time for this route is 13:00, with 45% of daily flights taking off in the afternoon.
How many flights depart from Chicago to Boston on average per week?
159 flights are operational weekly from Chicago to Boston as of March 2025. The most popular departure day for this route is Thu, with 40% of flights per week 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
Best price found | £38 |
|---|---|
Fastest flight time | 2h 20m |
Direct flights | Mon, Tue, Thu, Fri, Sat and Sun |
Airports in Boston | 1 airport |
Is flying the fastest way to get from Chicago to Boston?
The quickest way to travel this route is to take a flight from Chicago to Boston, doing so can potentially save up to 23h 00m of travel time. While these options may take longer, booking a train from Chicago to Boston or a bus from Chicago to Boston may suit your needs if travel time is less of a factor in your decision making.
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 £206, or consider a bus from Chicago to Boston starting at £140. Both of these alternative options are worth considering when looking to reach your destination.
How far is Chicago to Boston Logan Intl by plane?
Chicago and Boston Logan Intl are 847.9 mi apart from one another. Flights usually cover this in 2h 20m, depending on flying conditions and air traffic around both airports.
What is the carbon footprint of flying from Chicago to Boston Logan Intl?
753lb is the expected carbon footprint of a flight from Chicago to Boston Logan Intl, though you can sort and filter momondo flight search results by CO2 to find the best option. By train, you could lower your emissions for this trip by about 75%. Emissions for travelling this route by bus are generally around 119lb.
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 were last updated today.
How old do you have to be to fly from Chicago to Boston Logan Intl 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 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 22.24% of all bookings. The subsequent popular models are Embraer 175 at 17.57%, Boeing 737 MAX 8 at 11.73%, and Boeing 737-900 at 7.85%.
Travelling 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?
Finding the right flight to Boston from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Boston quick and easy, saving you time and money.
Can I find flights from Chicago to Boston with flexible booking policies on momondo?
momondo does allow users to show only those flights to Boston from Chicago which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Chicago to Boston?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Boston.
I’m not ready to book a flight from Chicago to Boston right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Boston, momondo offers a useful price alert feature which will track prices for flights to Boston from Chicago and alert you when they change.