Cheap Flights from Seattle to Chicago — $50

The route Seattle — Chicago is served by many carriers — 5 in total, including United Airlines, Alaska Airlines, Southwest Airlines, Hawaiian Airlines, and Frontier Airlines. This gives passengers wide opportunities: from finding the lowest fare (from $50) 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.

Planning a trip from Seattle to Chicago? Our search scans over 700 airlines, 50+ agencies and 5+ top booking systems to uncover the best prices, schedules and flexible conditions so you can pick the flight that fits your timetable and budget. Start comparing now and lock in the option that suits your travel plans with confidence.

Seattle–Tacoma International Airport (SEA) is the region’s primary international hub, handling most long-haul and domestic flights and serving legacy carriers like Alaska Airlines and Delta alongside several international carriers; it can also be competitive on price for cross‑country routes. Located about 14 miles south of downtown Seattle, SEA is accessible by the Link light rail (roughly 35–40 minutes, fares typically in the low single digits), taxis or rideshares (25–45 minutes depending on traffic, fares vary), and airport shuttles. Pros: comprehensive amenities, frequent connections and good public‑transit links. Cons: can be busy at peak times and transfer walks can be lengthy.

Chicago is served by three main airports with distinct roles. O'Hare International (ORD) is the city's primary international hub and a major connecting point for legacy carriers and many global flights; it typically offers a wide range of long‑haul and domestic connections and can be perceived as mid‑to‑premium in price compared with budget-focused options. Located about 17–20 miles northwest of downtown, O'Hare is reachable by the CTA Blue Line in roughly 45–50 minutes, taxis or rideshares in 30–60 minutes depending on traffic (fares vary), and several shuttle and express services. Pros: extensive schedules and amenities; cons: busy terminals and occasional congestion. Midway Airport (MDW) functions more as a domestic and low‑cost carrier base, often used for short‑haul flights around the U.S. and by discount airlines; fares can feel more budget‑friendly on many routes, especially point‑to‑point. Midway sits roughly 10 miles southwest of the Loop and is typically a 20–35 minute drive in normal traffic. Public transit includes the CTA Orange Line, taking about 25–30 minutes to downtown with economical fares; shuttles and taxis are also common. Pros: compact layout and faster security lines; cons: fewer international options and smaller amenities than the larger hub. General travel notes: choose O'Hare when you need international connections or more flight options, and consider Midway for quicker domestic hops and potentially lower fares. Both airports have solid public transit links, although travel times and costs can vary with time of day and luggage needs.

Fly direct from Seattle to Chicago for the quickest, most convenient way to get between these two vibrant cities — fewer hassles, no long layovers, and more time to enjoy your visit. While some connecting options can be cheaper, a nonstop saves hours and delivers a more comfortable, reliable travel experience, perfect for business trips or weekend getaways.

In different months, ticket prices from Seattle to Chicago vary: minimum — $124 (March 2026), maximum — $162 (June 2026). Typically, the flight costs $139–$292.