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Get Price Alerts - $9.99/monthBook 5-8 weeks in advance for this business route. Tuesday and Wednesday departures offer 20-30% savings over Monday morning flights.
January-February and November offer the best deals. Avoid summer months and major conference seasons when business demand peaks.
United dominates O'Hare routes. Southwest serves Midway with competitive prices. Alaska, American, and Delta also compete on this route.
Great deals start around $200 roundtrip. Under $280 is good value. Regular prices range from $320-500 depending on timing.
O'Hare (ORD) has more flight options and better connections, but Midway (MDW) often offers cheaper Southwest flights. Consider ground transport costs to your final destination.
Yes! United, American, Alaska, and Southwest all offer direct flights. Flight time is approximately 4 hours and 15 minutes.
Avoid summer months (June-August) and major business conference periods. Monday morning and Friday evening flights can cost 40-60% more.
Chicago is 2 hours ahead of Seattle. A 7 AM departure from Seattle arrives around 1 PM Chicago time, perfect for afternoon meetings.
Don't overpay for this popular business route. Get alerts when Seattle to Chicago deals drop to your target price.
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