Find Cheap Flights from Boston to Chicago (BOS - Google
Use Google Flights to find cheap flights from Boston to Chicago, and book tickets for your next trip.
$64 CHEAP FLIGHTS from Boston to Chicago (BOS - KAYAK
Find flights to Chicago from $64. Fly from Boston on Southwest, United Airlines, Delta and more. Search for Chicago flights on KAYAK now to find the best deal.
$45 Flights from Boston (BOS) to Chicago (CHIA) | Skyscanner
Find the best deals on flights from Boston Logan International (BOS) to Chicago (CHIA). Compare prices from hundreds of major travel agents and airlines, all in one search.
$49 Cheap Flights from Boston (BOS) to Chicago (CHI) - Expedia
Today's featured flight deals from Logan International Airport (BOS) to Chicago Expedia compares millions of flights to find the best value deals for where you want to go.
Cheap Flights from Boston to Chicago | United Airlines
Find United Airlines cheap flights from Boston to Chicago. Enjoy a Boston to Chicago modern flight experience in premium cabins with Wi-Fi.
American Airlines flights from Boston to Chicago
Explore our latest deals on flights from Boston to Chicago. Book your next flight with American Airlines.
Book Flights from Boston to Chicago - JetBlue
Don’t just settle for cheap flights from Boston to Chicago. JetBlue raises the bars with free wi-fi for all, and live TV & movies at every seat. Book a low fare from BOS to ORD now.
Southwest® flights from Boston to Chicago (Midway) from
Find flights from Boston to Chicago (Midway). Bundle your Southwest Airlines flight with a hotel or rental car booking and find even more savings.
$68+ Flights from Boston to Chicago | Cheapflights
Feb 17, 2026 · Find airfare and ticket deals for cheap flights from Boston to Chicago. Search flight deals from various travel partners with one click at $68.
$68 Cheap Flights from Boston to Chicago in 2026 | momondo
Search and compare airfare from 1000+ airlines and travel sites to get the cheapest flights from Boston to Chicago with momondo.