Cheapest ski trips from Chicago this winter

Round-trip flights from Chicago (ORD) to airports near ski areas, 11-20 to 04-10: dates, drive times to the mountains, Ikon and Epic passes and snow.

• Los Angeles (Mountain High, Mt. Baldy): $195, 2026-12-17 to 2026-12-20
• Denver (Vail, Keystone, Copper Mountain): $219, 2026-11-23 to 2026-11-30
• Montréal (Mont Tremblant Resort, Station Mont Tremblant, Stowe Mountain Resort, Smugglers' Notch Resort): $365, 2026-12-01 to 2026-12-03
• Rome (Campo Felice, Ovindoli, Pescasseroli): $409, 2027-02-16 to 2027-02-19
• Anchorage (Alyeska Resort): $420, 2026-12-05 to 2026-12-12
• Santa Ana (Mountain High, Mt. Baldy): $426, 2026-12-05 to 2026-12-07
• Madrid (La Pinilla): $696, 2027-03-20 to 2027-03-30
• Orio al Serio (BG) (Ponte di Legno - Passo Tonale, Folgaria, Area sciistica Folgaria, Aprica): $734, 2027-02-14 to 2027-02-19
• Venezia (VE) (Dolomiti Superski, Alta Badia, Cortina d'Ampezzo): $738, 2026-11-30 to 2026-12-06
• Vienna (Stuhleck - Semmering, Aflenzer Bürgeralm): $806, 2026-11-24 to 2026-12-01
• Podgorica (Kolašin 1600, Kolašin 1450 ski resort, Колашин 1450 ски резорт): $866, 2026-12-29 to 2027-01-05
• Yerevan (Ծաղկաձոր լեռնադահուկային առողջարան, Tsaghkadzor Ski resort, Myler Mountain Resort): $875, 2027-01-27 to 2027-02-05