Chicago splits traffic between O'Hare and Midway, giving budget and full-service travelers different ways to save.
O'Hare (ORD) is the main international gateway, with United and American running massive hub operations that cover every continent. Midway (MDW) is Southwest's Chicago fortress, offering lower domestic fares but very limited international service. Picking the right airport often matters more than picking the right airline — ground transport from Midway to the Loop takes about 25 minutes on the Orange Line, while O'Hare adds another 20 minutes via the Blue Line.
Fare seasonality in Chicago follows the Midwest weather cycle. January and February are brutally cold, so leisure demand craters and transatlantic fares drop 30-40% below summer peaks. The sweet spot for both weather and pricing is May through mid-June — warm enough for sightseeing, but before family holiday demand inflates everything. Thanksgiving week and Christmas are the worst for domestic pricing, with some routes doubling in cost.
O'Hare's Terminal 5 handles most international departures and has improved significantly since its 2019 expansion. If you are connecting between domestic and international in Chicago, allow at least 90 minutes — the inter-terminal tram is reliable but the security re-screening can queue. Southwest passengers at Midway benefit from free checked bags, which can shift the total cost equation meaningfully on domestic routes.
Midway is usually cheaper for domestic routes thanks to Southwest's low base fares and free bags. For international flights, O'Hare dominates with more carrier competition — compare both before booking.
January through February offers the steepest discounts as cold weather drives down leisure travel demand. May to mid-June is the best balance of pleasant weather and reasonable pricing.
The Blue Line train from O'Hare to the Loop takes about 45 minutes and costs just $5. Taxis and rideshares run 30-60 minutes depending on traffic and cost $40-60.
