Cheap flights from Boston to Chicago from £44
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Boston to Chicago departing on 30/10. 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 Boston 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 cheapest month to fly to Chicago from Boston is in September. Flight prices, which tend to average around £130, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of September, then book flights to Chicago from Boston during January instead. Flights to Chicago in January, while not as cheap as those in September, still average around £143.
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 Thursday when prices can be found for as low as £123. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Friday, with ticket prices averaging around £374.
What is the cheapest time of day to depart on your flight to Chicago?
Flying to Chicago from Boston in the morning is the least expensive time of day to depart. momondo users have found prices as low as £127 when looking at flights departing in the morning. Flights in the afternoon are often more expensive, with an average ticket price of £374.
What is the cheapest Boston Logan Intl to Chicago flight route?
Fly from Boston Logan Intl to Chicago Midway for the best Boston Logan Intl - 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 Boston when booking 5 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around £178 when searching 5 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Boston for as low as £154 on momondo.
What cabin class options are available on Boston Logan Intl to Chicago flights?
There are 3 cabin classes available to choose from on Boston Logan Intl to Chicago 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 Boston to Chicago on average per day?
57 flights are operational daily from Boston to Chicago as of June 2025. The most popular departure time for this route is 06:00, with 43% of flights per day taking off in the afternoon.
How many flights depart from Boston to Chicago on average per week?
The number of flights available between Boston and Chicago is 405 per week as of June 2025. The most frequent departure day is Fri, with 19% of weekly flights leaving on this day.
When to book flights from Boston to Chicago
Cheap Boston to Chicago (BOS to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Boston to Chicago
Is flying the fastest way to get from Boston to Chicago?
The quickest way to travel this route is to take a flight from Boston to Chicago, doing so can potentially save up to 20h 20m of travel time. While these options may take longer, booking a train from Boston to Chicago or a bus from Boston to Chicago may suit your needs if travel time is less of a factor in your decision making.
Is flying the cheapest way to get from Boston to Chicago?
Expect a flight to be one of the cheapest options available to you for travel. Currently, a flight has deals available from £92. While they may not be the most cost-effective options currently available a train from Boston to Chicago or a bus from Boston to Chicago can also be options worth looking into if other factors outside of cost are a higher priority.
How far is Boston Logan Intl to Chicago by plane?
Chicago is 847.9 mi away from Boston Logan Intl. 2h 50m is a normal flight duration for this route.
When did momondo last update prices for flights from Boston Logan Intl Airport to Chicago?
Prices for flights from Boston Logan Intl Airport to Chicago were last updated today.
How many operators does momondo search for flights from Boston Logan Intl Airport to Chicago?
There is 1 operator available for flights from Boston Logan Intl Airport to Chicago as of June 2025.
How old do you have to be to fly from Boston Logan Intl Airport to Chicago?
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 Boston Logan Intl Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago 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 Chicago. 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 Boston to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Boston to Chicago is Boeing 737-800, representing 25.15% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 13.62%, Embraer 175 at 10.64%, and Boeing 737-900 at 10.52%.
Best airlines flying from Boston to Chicago
Compare and see reviews for airlines that fly from Boston to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom £72 | Free Cancellation | Rating 7.2 10,000 reviews |
American Airlines Flights From Boston to Chicago
American Airlines operates around 49 flights from Boston to Chicago every week. The average price of these flights found in the last 72 hours has been £155, but momondo users have found American Airlines deals from Boston to Chicago from as low as £98 round-trip. American Airlines has been scored 7.2/10 in 10,000 reviews.
Why use momondo?
Why should I use momondo to find a flight deal from Boston to Chicago?
It is quick and easy to find Boston 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 Boston to Chicago with flexible booking policies on momondo?
Flights from Boston to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Boston to Chicago?
momondo helps you find the best flight between Boston and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.
I’m not ready to book a flight from Boston 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 Boston and alert you when they change.