$36 Find Cheap Flights from Boston to Chicago

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Find cheap flights from Boston to Chicago starting at $36.

Book one-way or return flights from Boston to Chicago from as little as $36. 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 cheap airlines flights 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.

Spirit Airlines

From $36

Delta Air Lines

From $42

American Airlines

From $46

Sun Country Airlines

From $84

Southwest Airlines

From $84

United Airlines

From $86

Jetblue Airways

From $103

Frontier Airlines

From $135

Alaska Airlines

From $381

ANA airlines

Find more flights and airlines

Find cheap flights from Boston to Chicago by different airports

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

Cheapest
BOS
07:00
2h 33m
Direct
ORD
08:33
General Edward Lawrence Logan International Airport - O'Hare International Airport
Wed, Jun 12Spirit Airlines
$37
BOS
12:41
11h 0m
1 transfer
MDW
22:41
General Edward Lawrence Logan International Airport - Midway International Airport
Sat, Apr 27Frontier Airlines
$135
BOS
12:41
11h 0m
1 transfer
MDW
22:41
General Edward Lawrence Logan International Airport - Midway International Airport
Sat, Apr 27Frontier Airlines
$135
Find More Flights

Frequently Asked Questions

When are flight tickets from Boston (BOS) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from Boston to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much do flights from Boston (BOS) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around $238.
How long does it take to fly from Boston (BOS) to Chicago (CHI) and what is the distance?
It takes around 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. It takes about 40 minutes by taxi.
- The distance from Midway International Airport to downtown is about 14km. It takes about 30 minutes by taxi.
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.

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

Boston to Chicago Flight Information

Cheapest nonstop flight price	$35
Cheapest round-trip ticket price	$73
Off-season for travel	December
Peak season for travel	October
Flight distance	1,371.27km
Average flight time	2 hours 52 minutes
Popular airline	American Airlines