Cheap Flights from Chicago to Boston — $101

The Chicago — Boston route is served by a wide range of airlines: 5 in total, including American Airlines, United Airlines, JetBlue Airways, Frontier Airlines, and Southwest Airlines. Competition among carriers gives passengers the opportunity to find tickets at attractive fares — with prices starting from $101. Our service helps compare all available offers within seconds and choose the most convenient option. You can filter flights by price, departure time, or baggage rules to make your trip as comfortable as possible. With so many airlines, there’s always a chance to catch special promotions and save.

The minimum one-way ticket price from Chicago to Boston is $103 (September 2026), while the maximum is $121 (August 2026). On average, a ticket costs $111–$228.

Chicago is served by two main airports with different roles. O’Hare International (ORD) is the city’s major international and connecting hub, handling a wide mix of legacy and global carriers and often used for long-haul and business routes; fares there can be competitive on hub-to-hub itineraries. It sits about 17–20 miles northwest of downtown; travellers typically take the CTA Blue Line train (around 45–55 minutes, modest fare), taxis or rideshares (35–60 minutes depending on traffic, higher cost), and airport shuttles. Pros: extensive flight choices and frequent services; cons: busy terminals and potential for delays. Midway (MDW) is a smaller, more budget-leaning airport to the southwest, favored by low-cost carriers and for regional flights. It’s roughly 10–12 miles from the Loop and usually quicker to reach—CTA Orange Line trains take about 20–30 minutes for a low fare, while rideshares and taxis are faster but can be pricier during peak times. Pros: compact terminals and shorter walking times; cons: fewer international connections and limited late-night amenities compared with the larger hub.

Boston Logan International (BOS) is New England’s main international gateway and a full-service hub for several legacy carriers, while smaller suburban airports like Manchester‑Boston (MHT) and Providence‑TF Green (PVD) can be used for low‑cost or regional options. Logan sits just across Boston Harbor, typically 3–5 miles (10–20 minutes by car without heavy traffic) from downtown; the MBTA Silver Line, subway connections and taxis/shuttles offer links taking roughly 20–40 minutes with fares usually ranging from free (some airport rides) up to about $3–15 for transit and $25–50+ for taxis/rideshares. Pros: frequent flights, extensive international routes and good public transit; cons: peak‑time congestion and parking costs can be higher, while suburban airports may be cheaper but add ground transport time.