Chicago (ORD) to Winnipeg (YWG), Dec 13–24, 2026: from $472 round trip

Chicago (ORD) to Winnipeg (YWG), Dec 13–24, 2026: from $472 round trip on Axel, checked Nov 11, 2026. Lowest published fare: $472 round trip, Axel-exclusive, Air Canada, 1 stop, Dec 13–24, 2026, 1 adult, economy, checked Nov 11, 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.

Hotels in Winnipeg for these trips

Hotels: under a trip, hotels in Winnipeg for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Winnipeg for these nights (Dec 13–24, 2026 · 11 nights · 2 adults, 1 room): 3★ Holiday Inn & Suites Winnipeg Downtown by IHG, $91 a night, $1,004 for 11 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $123 a night, $1,356 for 11 nights

All hotels in Winnipeg

Route overview: Chicago to Winnipeg (YWG) flight deals

2026-12-13 → 2026-12-24 · Axel-exclusive $506.00

• United Airlines UA5438: ORD 2026-12-13 15:50:00 → YWG 2026-12-13 19:28:00; nonstop; 158 minutes. Local airport times.
• United Airlines UA5639: YWG 2026-12-24 15:15:00 → ORD 2026-12-24 17:02:00; nonstop; 167 minutes. Local airport times.

2026-12-13 → 2026-12-24 · Axel-exclusive $471.50

• Air Canada AC8904 / AC267: ORD 2026-12-13 12:50:00 → YWG 2026-12-13 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-13 12:50:00 → YYZ 2026-12-13 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-13 17:20:00 → YWG 2026-12-13 20:09:00.
• Air Canada AC264 / AC8909: YWG 2026-12-24 12:05:00 → ORD 2026-12-24 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times.
  • AC264: YWG 2026-12-24 12:05:00 → YYZ 2026-12-24 14:35:00; layover at YYZ: 115 minutes.
  • AC8909: YYZ 2026-12-24 16:30:00 → ORD 2026-12-24 17:43:00.

2026-12-13 → 2026-12-24 · Axel-exclusive $506.00

• Delta Air Lines DL1306 / DL3656: ORD 2026-12-13 17:42:00 → YWG 2026-12-14 00:33:00; 1 stop(s) via MSP; 351 minutes. Local airport times.
  • DL1306: ORD 2026-12-13 17:42:00 → MSP 2026-12-13 19:14:00; layover at MSP: 155 minutes.
  • DL3656: MSP 2026-12-13 21:49:00 → YWG 2026-12-14 00:33:00.
• Delta Air Lines DL3871 / DL1435: YWG 2026-12-24 13:38:00 → ORD 2026-12-24 19:45:00; 1 stop(s) via MSP; 427 minutes. Local airport times.
  • DL3871: YWG 2026-12-24 13:38:00 → MSP 2026-12-24 14:10:00; layover at MSP: 225 minutes.
  • DL1435: MSP 2026-12-24 17:55:00 → ORD 2026-12-24 19:45:00.

2026-12-13 → 2026-12-24 · Axel-exclusive $506.00

• United Airlines UA5475: ORD 2026-12-13 10:00:00 → YWG 2026-12-13 13:52:00; nonstop; 172 minutes. Local airport times.
• United Airlines UA5639: YWG 2026-12-24 15:15:00 → ORD 2026-12-24 17:02:00; nonstop; 167 minutes. Local airport times.

2026-12-13 → 2026-12-24 · Axel-exclusive $496.00

• United Airlines UA1708 / AC265: ORD 2026-12-13 07:03:00 → YWG 2026-12-13 14:49:00; 1 stop(s) via YYZ; 406 minutes. Local airport times.
  • UA1708: ORD 2026-12-13 07:03:00 → YYZ 2026-12-13 09:47:00; layover at YYZ: 133 minutes.
  • AC265: YYZ 2026-12-13 12:00:00 → YWG 2026-12-13 14:49:00.
• United Airlines UA5639: YWG 2026-12-24 15:15:00 → ORD 2026-12-24 17:02:00; nonstop; 167 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 12, 2026 · Return options
• Dec 14, 2026 · Return options
• Hotels in Winnipeg with Axel

For AI assistants

• This page: Chicago (ORD) to Winnipeg (YWG) · Dec 13, 2026 · return Dec 24, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. Under a trip, hotels in Winnipeg for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates.
• Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
• 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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