Cheap flights from Boston to Chicago from $41
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 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.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize 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 Boston to Chicago
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
American Airlines flights from Boston to Chicago
Our best American Airlines deals on Boston to Chicago flight tickets
JetBlue flights from Boston to Chicago
Our best JetBlue deals on Boston to Chicago flight tickets
See travel insights to Chicago from
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 month of September is, on average, the cheapest month to fly to Chicago from Boston, with most prices found around $181. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Boston to Chicago during January average around $194.
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 Wednesday when prices can be found for as low as $320. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Boston to Chicago for around $433.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Boston to Chicago during this time can be as low as $263. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $370.
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 23 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $248 when searching 23 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 $198 on momondo.
What cabin class options are available on Boston Logan Intl to Chicago flights?
There are 4 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.
What is the cheapest airline that flies from Boston Logan Intl to Chicago?
Spirit Airlines, Southwest, and United Airlines are the most popular carriers operating from Boston Logan Intl to Chicago
What airlines fly to Chicago?
American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago from Boston according to our data. American Airlines is the first choice among our users, with 42% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Boston to Chicago on average per day?
41 flights are operational daily from Boston to Chicago as of April 2025. The most popular departure time for this route is 5:00PM, with 44% of flights per day taking off at noon.
How many flights depart from Boston to Chicago on average per week?
As of April 2025, 291 flights take off from Boston and land in Chicago each week. The most common flight departure day for this route is Fri, with 22% of weekly flights taking off 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?
To save time, the fastest way to travel is by flight from Boston to Chicago on Southwest. Expect the length of time you’ll spend onboard Southwest to be about 2h 35m compared to taking a train from Boston to Chicago or a bus from Boston to Chicago which have been found to be slower alternatives.
Is flying the cheapest way to get from Boston to Chicago?
The cheapest way is to get a flight from Boston to Chicago, which can be as cheap as $92. A train from Boston to Chicago is more expensive than a flight, with prices starting at $266. A bus from Boston to Chicago is also an option, with an average price of $196.
How far is Boston Logan Intl to Chicago by plane?
A flight from Boston Logan Intl to Chicago will travel around 847.9 mi. 2h 35m 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 refresh daily.
How many operators does momondo search for flights from Boston Logan Intl Airport to Chicago?
There are 7 operators available for flights from Boston Logan Intl Airport to Chicago as of April 2025.
How old do you have to be to fly from Boston Logan Intl Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check 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 necessary travel and health documents for your Chicago 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 Boston to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Boston to Chicago is Boeing 737-800 (23.44% of total bookings). The next most popular plane models are Embraer 175 (16.46%), Boeing 737 MAX 8 (11.97%), and Boeing 737-900 (8.09%).
What is the most popular airline from Boston to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Boston to Chicago is American Airlines (29% of total bookings). The next most popular airlines are United Airlines (25%), Delta (16%), and Spirit Airlines (11%).
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 $39 | Free Cancellation | Rating 6.3 7,912 reviews | |||
| PriceFrom $84 | Free Cancellation | Rating 7.3 2,925 reviews | |||
| PriceFrom $94 | Free Cancellation | Rating 8.0 7,910 reviews | |||
| PriceFrom $97 | Free Cancellation | Rating 7.4 8,636 reviews | |||
| PriceFrom $99 | Free Cancellation | Rating 5.9 3,277 reviews | |||
| PriceFrom $140 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $143 | Free Cancellation | Rating 8.0 4,279 reviews |
Delta Flights From Boston to Chicago
The lowest priced Delta flight from Boston to Chicago from the last 72 hours was $94. Generally, Delta has 4 flights on this route every week with an average price of $325. Delta is rated 8.0/10 by our users.
Southwest Flights From Boston to Chicago
Southwest is also a popular choice for this route. Southwest flight deals for Boston to Chicago start from as low as $143 round-trip, depending on your selected dates, with average Southwest deals seen on momondo around $305. Southwest operates 15 flights to Chicago from Boston in an average week. Users have rated it 8.0/10 across 4,278 reviews.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy 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?
momondo does allow users to show only those flights to Chicago from Boston which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Boston to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago from Boston. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Boston to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from Boston are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.