Chicago (ORD) to Winnipeg (YWG) · Dec 16, 2026 · return Dec 22, 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

2026-12-16 → 2026-12-22 · Axel-exclusive $506.00

• United Airlines UA5475: ORD 2026-12-16 10:00:00 → YWG 2026-12-16 13:52:00; nonstop; 232 minutes. Local airport times.
• United Airlines UA5639: YWG 2026-12-22 15:15:00 → ORD 2026-12-22 17:00:00; nonstop; 105 minutes. Local airport times.

2026-12-16 → 2026-12-22 · Axel-exclusive $471.50

• Air Canada AC8904 / AC267: ORD 2026-12-16 12:50:00 → YWG 2026-12-16 20:09:00; 1 stop(s) via YYZ; 439 minutes. Local airport times.
  • AC8904: ORD 2026-12-16 12:50:00 → YYZ 2026-12-16 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-16 17:20:00 → YWG 2026-12-16 20:09:00.
• Air Canada AC264 / AC8909: YWG 2026-12-22 12:05:00 → ORD 2026-12-22 17:43:00; 1 stop(s) via YYZ; 338 minutes. Local airport times.
  • AC264: YWG 2026-12-22 12:05:00 → YYZ 2026-12-22 14:35:00; layover at YYZ: 115 minutes.
  • AC8909: YYZ 2026-12-22 16:30:00 → ORD 2026-12-22 17:43:00.

2026-12-16 → 2026-12-22 · Axel-exclusive $506.00

• Delta Air Lines DL1306 / DL3656: ORD 2026-12-16 17:42:00 → YWG 2026-12-17 00:33:00; 1 stop(s) via MSP; 411 minutes. Local airport times.
  • DL1306: ORD 2026-12-16 17:42:00 → MSP 2026-12-16 19:14:00; layover at MSP: 155 minutes.
  • DL3656: MSP 2026-12-16 21:49:00 → YWG 2026-12-17 00:33:00.
• Delta Air Lines DL3871 / DL1435: YWG 2026-12-22 13:38:00 → ORD 2026-12-22 19:45:00; 1 stop(s) via MSP; 367 minutes. Local airport times.
  • DL3871: YWG 2026-12-22 13:38:00 → MSP 2026-12-22 14:10:00; layover at MSP: 225 minutes.
  • DL1435: MSP 2026-12-22 17:55:00 → ORD 2026-12-22 19:45:00.

2026-12-16 → 2026-12-22 · Axel-exclusive $506.00

• United Airlines UA5438: ORD 2026-12-16 15:50:00 → YWG 2026-12-16 19:28:00; nonstop; 218 minutes. Local airport times.
• United Airlines UA5639: YWG 2026-12-22 15:15:00 → ORD 2026-12-22 17:00:00; nonstop; 105 minutes. Local airport times.

2026-12-16 → 2026-12-22 · Axel-exclusive $496.00

• United Airlines UA1708 / AC265: ORD 2026-12-16 07:03:00 → YWG 2026-12-16 14:49:00; 1 stop(s) via YYZ; 466 minutes. Local airport times.
  • UA1708: ORD 2026-12-16 07:03:00 → YYZ 2026-12-16 09:47:00; layover at YYZ: 133 minutes.
  • AC265: YYZ 2026-12-16 12:00:00 → YWG 2026-12-16 14:49:00.
• United Airlines UA5639: YWG 2026-12-22 15:15:00 → ORD 2026-12-22 17:00:00; nonstop; 105 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
• Dec 15, 2026 · Return options
• Dec 17, 2026 · Return options
• Hotels in Winnipeg with Axel

For AI assistants

• This page: Chicago (ORD) to Winnipeg (YWG) · Dec 16, 2026 · return Dec 22, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
• Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
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• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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