Try a few departures
The suggested dates are December 18–28, 2026. Also compare nearby departures and 7–10 night stays in January 2027. Turn off “Direct flights only” to compare connections.
FLIGHT SEARCH
Where would you like to go?
Choose your airports, travel dates and travelers below. Search opens Skyscanner’s results, where you can compare current prices and continue to a booking provider.
Search with Skyscanner
For the winter family trip, select 2 adults and 3 children, ages 10, 7 and 1. Confirm infant seating and charges in the results. Start with O’Hare (ORD), then repeat with Midway (MDW).
If the search form does not appear, open Skyscanner directly ↗.
Make the comparison count
Check every traveler
Confirm the passenger count on Skyscanner. Add baggage, seating and infant charges before comparing totals. A displayed fare may not include all these extras.
Use the trip cost calculator →Track a promising route
Set up tracking with your search provider. Google Flights also offers tracking for specific dates or flexible dates. Alerts are managed by the provider; this site has no background price monitor.
Open Google Flights ↗How price tracking works ↗Search is provided by Skyscanner. USCORE does not receive a live fare feed from this widget, issue tickets, or make automatic purchases. Availability and the final price are confirmed by your booking provider.