Cheap Flights from Boston to Chicago Starting at $59

The route Boston — Chicago is served by many carriers — 5 in total, including United Airlines, Southwest Airlines, American Airlines, JetBlue Airways, and Frontier Airlines. This gives passengers wide opportunities: from finding the lowest fare (from $59) to selecting flights by schedule or service class. Our service aggregates data from multiple booking systems so you can compare offers in one place. This saves time and money: no need to check dozens of sites — just pick the right option and book online.

Boston Logan International (BOS) is the city’s primary international gateway and a full-service hub for major carriers, while smaller regional airports (notably Worcester and Manchester-Boston nearby) tend to serve low-cost and regional flights. Logan sits on Boston Harbor about 3–5 miles from downtown — typically a 15–30 minute drive depending on traffic — with options including the MBTA Silver Line and Blue Line plus taxis and ride-shares; expect public-transit fares to be modest and road transfers to vary with peak congestion. Travelers usually find Logan convenient for frequent nonstop service and international connections, though terminals can be busy and transfers may take longer during peak hours.

Chicago is served by three main airports with distinct roles. O’Hare International (ORD) is the primary international hub and a major transfer point for both legacy and global carriers, typically offering the widest range of routes and frequent premium lounges; it sits about 17 miles northwest of downtown and can take roughly 30–60 minutes by car depending on traffic, with taxi or rideshare fares commonly ranging from moderate to higher during peak times. The Blue Line ‘L’ provides a direct and usually cost-effective express to the Loop in about 40–50 minutes. Midway (MDW) is a smaller, more budget-leaning airport to the southwest, often favored by low-cost and domestic carriers; it’s about 10 miles from downtown and reachable in 20–35 minutes by car or roughly 25–40 minutes via the Orange Line for a lower fare. Pros: ORD offers the most international connectivity and amenities; cons: it can be busy with longer transfer distances. MDW can be quicker for domestic travelers but has fewer long-haul options. Both airports provide shuttle, rental car, and public transit choices, so pick based on schedule, price sensitivity, and preferred balance of convenience versus route variety.

In different months, ticket prices from Boston to Chicago vary: minimum — $62 (October 2025), maximum — $62 (November 2025). Typically, the flight costs $62–$62.