Cheapest ski trips from Chicago this winter

Round-trip flights from Chicago (MDW) 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): $392, 2026-12-24 to 2026-12-28
• Newburgh (Hunter Mountain): $409, 2027-01-21 to 2027-01-24
• Rome (Campo Felice, Ovindoli, Pescasseroli): $409, 2027-02-16 to 2027-02-19
• Anchorage (Alyeska Resort): $439, 2027-01-10 to 2027-01-16
• 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
• Podgorica (Kolašin 1600, Kolašin 1450 ski resort, Колашин 1450 ски резорт): $866, 2026-12-29 to 2027-01-05
• Tashkent ("Амирсай" Горнолыжный курорт, "Amirsay" Mountain Resort): $905, 2027-03-18 to 2027-03-25
• Almaty (Шымбұлақ, Shymbulak, Шымбулак, AK Bulak): $1045, 2027-02-10 to 2027-02-18
• Bishkek (Горнолыжная база Политех, Polytech ski resort): $1320, 2026-11-29 to 2026-12-05