Cheap Flights from Boston to Chicago from CAD 49️ 2024

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Find Boston to Chicago flights starting at CAD 49.

Book one-way or return flights from Boston to Chicago from as little as CAD 49. Choose from the popular airlines below and book your flight today!

One way
Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Searching for the best last minute flight from Boston to Chicago? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Boston to Chicago. Stay updated on price trends and snag the best deals for your upcoming trip.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Find Cheapest Airlines Flying from Boston to Chicago

View airlines operating flights from Boston to Chicago. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Frontier Airlines

From CAD 59

Spirit Airlines

From CAD 64

Delta Air Lines

From CAD 68

American Airlines

From CAD 69

Sun Country Airlines

From CAD 115

United Airlines

From CAD 122

Jetblue Airways

From CAD 141

Southwest Airlines

From CAD 207

Alaska Airlines

From CAD 663

ANA airlines

Find more flights and airlines

Alternative Routes for Boston to Chicago Flights

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Boston to Chicago.

Cheapest
BOS
10:01
9h 22m
1 transfer
MDW
18:23
General Edward Lawrence Logan International Airport - Midway International Airport
Tue, May 7Spirit Airlines
CAD 55
BOS
05:05
13h 41m
1 transfer
ORD
17:46
General Edward Lawrence Logan International Airport - O'Hare International Airport
Tue, May 7Spirit Airlines
CAD 82
BOS
05:05
13h 41m
1 transfer
ORD
17:46
General Edward Lawrence Logan International Airport - O'Hare International Airport
Tue, May 7Spirit Airlines
CAD 82
Find More Flights

How do I find the cheapest flights?

When are flight tickets from Boston (BOS) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from Boston to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much are flights from Boston (BOS) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around CAD 321.
How long is the flight from Boston (BOS) to Chicago (CHI)?
It takes about 2 hours 52 minutes to fly from Boston (BOS) to Chicago (CHI).
What is the transportation method from the main airport to downtown in Chicago?
- The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
- The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
What are the most popular airlines that fly from Boston (BOS) to Chicago (CHI)?
Airlines with flights from Boston (BOS) to Chicago (CHI): United Airlines, Southwest Airlines, Delta Air Lines, Qatar Airways, Icelandair, Alaska Airlines, Korean Air, American Airlines, Jetblue Airways, LATAM Airlines, Iberia and El Al.
What's the most popular airline for direct flights from Boston (BOS) to Chicago (CHI)?
Delta Air Lines operates 10 direct flights from Boston (BOS) to Chicago (CHI).
How many airports in Chicago (CHI)?
There are 5 airport(s) in Chicago (CHI): Chicago Du Page County Airport, Midway International Airport, O'Hare International Airport, Chicago Palwaukee Airport and Chicago Rockford International Airport.

How to find a cheap flight from Boston to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Boston to Chicago. Book your flights at the right time and save more.

Book Early

Once prices are gone, they're gone. Lock in deals while you can!

Compare Flight Prices

Compare prices on travel agency and airline websites.

Look Out for Deals

Check airline and travel agency websites for latest flight deals

Check One-way Fares

Buying two cheap one-way flights can sometimes be a better deal than a round-trip.

Try Different Dates

Flying during the week, early in the morning, or late at night can help save money.

Use the Trip.com App

Save up to £10 per person when booking your flights on Trip.com

Flight Information for Boston to Chicago Flights

Cheapest direct flight price	CAD 48
Cheapest return ticket price	CAD 100
Cheapest month	December
Peak season for travel	October
Flight distance	1,371.27km
Average flight time	2 hours 52 minutes
Popular airline	American Airlines