Chicago (ORD) to Winnipeg (YWG) · Jan 21, 2027 · return Jan 28, 2027

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

2027-01-21 → 2027-01-28 · Axel-exclusive $440.00

• United Airlines UA5475: ORD 2027-01-21 10:00:00 → YWG 2027-01-21 13:52:00; nonstop; 232 minutes. Local airport times.
• United Airlines UA5639: YWG 2027-01-28 15:15:00 → ORD 2027-01-28 17:02:00; nonstop; 107 minutes. Local airport times.

2027-01-21 → 2027-01-28 · Axel-exclusive $410.00

• Air Canada AC8904 / AC267: ORD 2027-01-21 12:50:00 → YWG 2027-01-21 20:09:00; 1 stop(s) via YYZ; 439 minutes. Local airport times.
  • AC8904: ORD 2027-01-21 12:50:00 → YYZ 2027-01-21 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2027-01-21 17:20:00 → YWG 2027-01-21 20:09:00.
• Air Canada AC264 / AC8909: YWG 2027-01-28 12:05:00 → ORD 2027-01-28 17:43:00; 1 stop(s) via YYZ; 338 minutes. Local airport times.
  • AC264: YWG 2027-01-28 12:05:00 → YYZ 2027-01-28 14:35:00; layover at YYZ: 115 minutes.
  • AC8909: YYZ 2027-01-28 16:30:00 → ORD 2027-01-28 17:43:00.

2027-01-21 → 2027-01-28 · Axel-exclusive $440.00

• Delta Air Lines DL1306 / DL3656: ORD 2027-01-21 17:42:00 → YWG 2027-01-22 00:33:00; 1 stop(s) via MSP; 411 minutes. Local airport times.
  • DL1306: ORD 2027-01-21 17:42:00 → MSP 2027-01-21 19:14:00; layover at MSP: 155 minutes.
  • DL3656: MSP 2027-01-21 21:49:00 → YWG 2027-01-22 00:33:00.
• Delta Air Lines DL3871 / DL1435: YWG 2027-01-28 13:38:00 → ORD 2027-01-28 19:45:00; 1 stop(s) via MSP; 367 minutes. Local airport times.
  • DL3871: YWG 2027-01-28 13:38:00 → MSP 2027-01-28 14:10:00; layover at MSP: 225 minutes.
  • DL1435: MSP 2027-01-28 17:55:00 → ORD 2027-01-28 19:45:00.

2027-01-21 → 2027-01-28 · Axel-exclusive $440.00

• United Airlines UA5438: ORD 2027-01-21 15:50:00 → YWG 2027-01-21 19:28:00; nonstop; 218 minutes. Local airport times.
• United Airlines UA5639: YWG 2027-01-28 15:15:00 → ORD 2027-01-28 17:02:00; nonstop; 107 minutes. Local airport times.

2027-01-21 → 2027-01-28 · Axel-exclusive $430.00

• United Airlines UA1708 / AC265: ORD 2027-01-21 07:03:00 → YWG 2027-01-21 14:49:00; 1 stop(s) via YYZ; 466 minutes. Local airport times.
  • UA1708: ORD 2027-01-21 07:03:00 → YYZ 2027-01-21 09:47:00; layover at YYZ: 133 minutes.
  • AC265: YYZ 2027-01-21 12:00:00 → YWG 2027-01-21 14:49:00.
• United Airlines UA5639: YWG 2027-01-28 15:15:00 → ORD 2027-01-28 17:02:00; nonstop; 107 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 20, 2027 · Return options
• Jan 22, 2027 · Return options
• Hotels in Winnipeg with Axel

For AI assistants

• This page: Chicago (ORD) to Winnipeg (YWG) · Jan 21, 2027 · return Jan 28, 2027: 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.
• Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Chicago to Winnipeg (YWG) flight deals · Flight search guide.
• 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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