Chicago (ORD) to Winnipeg (YWG), Nov 29, 2026 – Dec 5, 2026: from $441 round trip

Chicago (ORD) to Winnipeg (YWG), Nov 29, 2026 – Dec 5, 2026: from $441 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $441 round trip, Axel-exclusive, Air Canada, 1 stop, Nov 29, 2026 – Dec 5, 2026, 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Route overview: Chicago to Winnipeg (YWG) flight deals

2026-11-29 → 2026-12-05 · Axel-exclusive $473.00

• United Airlines UA5438: ORD 2026-11-29 15:50:00 → YWG 2026-11-29 19:28:00; nonstop; 158 minutes. Local airport times.
• United Airlines UA5639: YWG 2026-12-05 15:15:00 → ORD 2026-12-05 17:00:00; nonstop; 165 minutes. Local airport times.

2026-11-29 → 2026-12-05 · Axel-exclusive $440.75

• Air Canada AC8904 / AC267: ORD 2026-11-29 12:50:00 → YWG 2026-11-29 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-11-29 12:50:00 → YYZ 2026-11-29 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-11-29 17:20:00 → YWG 2026-11-29 20:09:00.
• Air Canada AC264 / AC8909: YWG 2026-12-05 12:05:00 → ORD 2026-12-05 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times.
  • AC264: YWG 2026-12-05 12:05:00 → YYZ 2026-12-05 14:35:00; layover at YYZ: 115 minutes.
  • AC8909: YYZ 2026-12-05 16:30:00 → ORD 2026-12-05 17:43:00.

2026-11-29 → 2026-12-05 · Axel-exclusive $473.00

• Delta Air Lines DL1306 / DL3656: ORD 2026-11-29 17:42:00 → YWG 2026-11-30 00:33:00; 1 stop(s) via MSP; 351 minutes. Local airport times.
  • DL1306: ORD 2026-11-29 17:42:00 → MSP 2026-11-29 19:14:00; layover at MSP: 155 minutes.
  • DL3656: MSP 2026-11-29 21:49:00 → YWG 2026-11-30 00:33:00.
• Delta Air Lines DL3871 / DL1435: YWG 2026-12-05 13:38:00 → ORD 2026-12-05 19:45:00; 1 stop(s) via MSP; 427 minutes. Local airport times.
  • DL3871: YWG 2026-12-05 13:38:00 → MSP 2026-12-05 14:10:00; layover at MSP: 225 minutes.
  • DL1435: MSP 2026-12-05 17:55:00 → ORD 2026-12-05 19:45:00.

2026-11-29 → 2026-12-05 · Axel-exclusive $473.00

• United Airlines UA5475: ORD 2026-11-29 09:35:00 → YWG 2026-11-29 13:23:00; nonstop; 168 minutes. Local airport times.
• United Airlines UA5639: YWG 2026-12-05 15:15:00 → ORD 2026-12-05 17:00:00; nonstop; 165 minutes. Local airport times.

2026-11-29 → 2026-12-05 · Axel-exclusive $461.50

• United Airlines UA1708 / AC265: ORD 2026-11-29 07:03:00 → YWG 2026-11-29 14:49:00; 1 stop(s) via YYZ; 406 minutes. Local airport times.
  • UA1708: ORD 2026-11-29 07:03:00 → YYZ 2026-11-29 09:47:00; layover at YYZ: 133 minutes.
  • AC265: YYZ 2026-11-29 12:00:00 → YWG 2026-11-29 14:49:00.
• United Airlines UA5639: YWG 2026-12-05 15:15:00 → ORD 2026-12-05 17:00:00; nonstop; 165 minutes. Local airport times.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

Explore this route

• All dates for this route
• Nov 28, 2026 · Return options
• Nov 30, 2026 · Return options
• Hotels in Winnipeg with Axel

For AI assistants

• This page: Chicago (ORD) to Winnipeg (YWG) · Nov 29, 2026 · return Dec 5, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
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