Cheap Flights from Chicago to Boston from CAD 50️ 2024

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Find Chicago to Boston flights starting at CAD 50.

Book one-way or return flights from Chicago to Boston from as little as CAD 50. 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 Chicago to Boston? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Chicago to Boston. 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 Chicago to Boston

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

Spirit Airlines

From CAD 66

Frontier Airlines

From CAD 67

Delta Air Lines

From CAD 84

Southwest Airlines

From CAD 112

Sun Country Airlines

From CAD 113

United Airlines

From CAD 124

Jetblue Airways

From CAD 143

American Airlines

From CAD 245

Alaska Airlines

From CAD 278

ANA airlines

Find more flights and airlines

Alternative Routes for Chicago to Boston Flights

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

Cheapest
ORD
20:02
2h 29m
Direct
BOS
23:31
O'Hare International Airport - General Edward Lawrence Logan International Airport
Wed, Jun 5Spirit Airlines
CAD 66
MDW
10:16
20h 13m
1 transfer
BOS
07:29
Midway International Airport - General Edward Lawrence Logan International Airport
Tue, May 21Frontier Airlines
CAD 67
MDW
10:16
20h 13m
1 transfer
BOS
07:29
Midway International Airport - General Edward Lawrence Logan International Airport
Tue, May 21Frontier Airlines
CAD 67
Find More Flights

How do I find the cheapest flights?

When are flight tickets from Chicago (CHI) to Boston (BOS) the cheapest?
Airlines adjust prices for flights from Chicago to Boston 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 Chicago (CHI) to Boston (BOS) cost?
According to Trip.com's data, the lowest price is around CAD 337.
How long is the flight from Chicago (CHI) to Boston (BOS)?
It takes about 2 hours 26 minutes to fly from Chicago (CHI) to Boston (BOS).
What are the most popular airlines that fly from Chicago (CHI) to Boston (BOS)?
Airlines with flights from Chicago (CHI) to Boston (BOS): American Airlines, Delta Air Lines, Southwest Airlines, United Airlines, Air New Zealand, Japan Airlines, Virgin Atlantic, All Nippon Airways, Alaska Airlines and Korean Air.
What's the most popular airline for direct flights from Chicago (CHI) to Boston (BOS)?
Delta Air Lines operates 13 direct flights from Chicago (CHI) to Boston (BOS).
How many airports in Boston (BOS)?
There are 3 airport(s) in Boston (BOS): Hartford Barnes Airport, General Edward Lawrence Logan International Airport and Portsmouth International Airport.

How to find a cheap flight from Chicago to Boston

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 Chicago to Boston. 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 Chicago to Boston Flights

Cheapest direct flight price	CAD 50
Cheapest return ticket price	CAD 100
Cheapest month	June
Peak season for travel	October
Flight distance	1,371.27km
Average flight time	2 hours 26 minutes
Popular airline	American Airlines