Chicago (ORD) to Winnipeg (YWG), Dec 20, 2026: round trips from $533, one way from $299

Chicago (ORD) to Winnipeg (YWG), Dec 20, 2026: round trips from $533, one way from $299 on Axel, checked Oct 29, 2026. Lowest published fares: $533 round trip, Axel-exclusive, Air Canada, 1 stop, Dec 20–21, 2026; $299 one way, Axel-exclusive, Air Canada, 1 stop, Dec 20, 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.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and issuance times already shown here.

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 lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Winnipeg for these nights (Dec 20–21, 2026 · 1 night · 2 adults, 1 room): 3★ Victoria Inn Hotel and Convention Centre Winnipeg, $90 total · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $119 total
• Hotels in Winnipeg for these nights (Dec 20–22, 2026 · 2 nights · 2 adults, 1 room): 3★ Holiday Inn & Suites Winnipeg Downtown by IHG, $185 total · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $238 total
• Hotels in Winnipeg for these nights (Dec 20–23, 2026 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn & Suites Winnipeg Downtown by IHG, $271 total · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $361 total
• Hotels in Winnipeg for these nights (Dec 20–24, 2026 · 4 nights · 2 adults, 1 room): 3★ Holiday Inn & Suites Winnipeg Downtown by IHG, $354 total · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $483 total
• Hotels in Winnipeg for these nights (Dec 20–25, 2026 · 5 nights · 2 adults, 1 room): 3★ Holiday Inn & Suites Winnipeg Downtown by IHG, $468 total · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $616 total
• Hotels in Winnipeg for these nights (Dec 20–26, 2026 · 6 nights · 2 adults, 1 room): 3★ Holiday Inn & Suites Winnipeg Downtown by IHG, $581 total · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $736 total
• Hotels in Winnipeg for these nights (Dec 20–27, 2026 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn & Suites Winnipeg Downtown by IHG, $680 total · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $855 total
• Hotels in Winnipeg for these nights (Dec 20–28, 2026 · 8 nights · 2 adults, 1 room): 3★ Holiday Inn & Suites Winnipeg Downtown by IHG, $771 total · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $974 total
• Hotels in Winnipeg for these nights (Dec 20–29, 2026 · 9 nights · 2 adults, 1 room): 3★ Holiday Inn & Suites Winnipeg Downtown by IHG, $868 total · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $1,101 total
• Hotels in Winnipeg for these nights (Dec 20–30, 2026 · 10 nights · 2 adults, 1 room): 3★ Holiday Inn & Suites Winnipeg Downtown by IHG, $954 total · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $1,222 total
• Hotels in Winnipeg for these nights (Dec 20–31, 2026 · 11 nights · 2 adults, 1 room): 3★ Holiday Inn & Suites Winnipeg Downtown by IHG, $1,053 total · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $1,350 total
• Hotels in Winnipeg for these nights (Dec 20 – Jan 1, 2027 · 12 nights · 2 adults, 1 room): 3★ Holiday Inn & Suites Winnipeg Downtown by IHG, $1,149 total · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $1,550 total
• Hotels in Winnipeg for these nights (Dec 20 – Jan 2, 2027 · 13 nights · 2 adults, 1 room): 3★ Holiday Inn & Suites Winnipeg Downtown by IHG, $1,256 total · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $1,690 total
• Hotels in Winnipeg for these nights (Dec 20 – Jan 3, 2027 · 14 nights · 2 adults, 1 room): 3★ Victoria Inn Hotel and Convention Centre Winnipeg, $1,353 total · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $1,818 total

All hotels in Winnipeg

Route overview: Chicago to Winnipeg (YWG) flight deals

2026-12-20 · one way · Axel-exclusive $299.00

• Air Canada AC8904 / AC267: ORD 2026-12-20 12:50:00 → YWG 2026-12-20 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-20 12:50:00 → YYZ 2026-12-20 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-20 17:20:00 → YWG 2026-12-20 20:09:00.

2026-12-20 · one way · Axel-exclusive $325.00

• United Airlines UA5475: ORD 2026-12-20 10:00:00 → YWG 2026-12-20 13:52:00; nonstop; 172 minutes. Local airport times.

2026-12-20 → 2026-12-21 · Axel-exclusive $533.00

• Air Canada AC8904 / AC267: ORD 2026-12-20 12:50:00 → YWG 2026-12-20 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-20 12:50:00 → YYZ 2026-12-20 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-20 17:20:00 → YWG 2026-12-20 20:09:00.
• Air Canada AC264 / AC8909: YWG 2026-12-21 12:05:00 → ORD 2026-12-21 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times.
  • AC264: YWG 2026-12-21 12:05:00 → YYZ 2026-12-21 14:35:00; layover at YYZ: 115 minutes.
  • AC8909: YYZ 2026-12-21 16:30:00 → ORD 2026-12-21 17:43:00.

2026-12-20 → 2026-12-21 · Axel-exclusive $572.00

• United Airlines UA5475: ORD 2026-12-20 10:00:00 → YWG 2026-12-20 13:52:00; nonstop; 172 minutes. Local airport times.
• United Airlines UA5639: YWG 2026-12-21 15:15:00 → ORD 2026-12-21 17:02:00; nonstop; 167 minutes. Local airport times.

2026-12-20 → 2026-12-22 · Axel-exclusive $533.00

• Air Canada AC8904 / AC267: ORD 2026-12-20 12:50:00 → YWG 2026-12-20 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-20 12:50:00 → YYZ 2026-12-20 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-20 17:20:00 → YWG 2026-12-20 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; 398 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.

2026-12-20 → 2026-12-22 · Axel-exclusive $572.00

• United Airlines UA5475: ORD 2026-12-20 10:00:00 → YWG 2026-12-20 13:52:00; nonstop; 172 minutes. Local airport times.
• United Airlines UA5639: YWG 2026-12-22 15:15:00 → ORD 2026-12-22 17:00:00; nonstop; 165 minutes. Local airport times.

2026-12-20 → 2026-12-23 · Axel-exclusive $533.00

• Air Canada AC8904 / AC267: ORD 2026-12-20 12:50:00 → YWG 2026-12-20 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-20 12:50:00 → YYZ 2026-12-20 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-20 17:20:00 → YWG 2026-12-20 20:09:00.
• Air Canada AC264 / AC8909: YWG 2026-12-23 12:05:00 → ORD 2026-12-23 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times.
  • AC264: YWG 2026-12-23 12:05:00 → YYZ 2026-12-23 14:35:00; layover at YYZ: 115 minutes.
  • AC8909: YYZ 2026-12-23 16:30:00 → ORD 2026-12-23 17:43:00.

2026-12-20 → 2026-12-23 · Axel-exclusive $572.00

• United Airlines UA5475: ORD 2026-12-20 10:00:00 → YWG 2026-12-20 13:52:00; nonstop; 172 minutes. Local airport times.
• United Airlines UA5639: YWG 2026-12-23 15:15:00 → ORD 2026-12-23 17:02:00; nonstop; 167 minutes. Local airport times.

2026-12-20 → 2026-12-24 · Axel-exclusive $533.00

• Air Canada AC8904 / AC267: ORD 2026-12-20 12:50:00 → YWG 2026-12-20 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-20 12:50:00 → YYZ 2026-12-20 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-20 17:20:00 → YWG 2026-12-20 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.

2026-12-20 → 2026-12-24 · Axel-exclusive $572.00

• United Airlines UA5475: ORD 2026-12-20 10:00:00 → YWG 2026-12-20 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.

2026-12-20 → 2026-12-26 · Axel-exclusive $533.00

• Air Canada AC8904 / AC267: ORD 2026-12-20 12:50:00 → YWG 2026-12-20 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-20 12:50:00 → YYZ 2026-12-20 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-20 17:20:00 → YWG 2026-12-20 20:09:00.
• Air Canada AC264 / AC8909: YWG 2026-12-26 12:05:00 → ORD 2026-12-26 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times.
  • AC264: YWG 2026-12-26 12:05:00 → YYZ 2026-12-26 14:35:00; layover at YYZ: 115 minutes.
  • AC8909: YYZ 2026-12-26 16:30:00 → ORD 2026-12-26 17:43:00.

2026-12-20 → 2026-12-26 · Axel-exclusive $572.00

• United Airlines UA5475: ORD 2026-12-20 10:00:00 → YWG 2026-12-20 13:52:00; nonstop; 172 minutes. Local airport times.
• United Airlines UA5639: YWG 2026-12-26 15:15:00 → ORD 2026-12-26 17:02:00; nonstop; 167 minutes. Local airport times.

2026-12-20 → 2026-12-27 · Axel-exclusive $533.00

• Air Canada AC8904 / AC267: ORD 2026-12-20 12:50:00 → YWG 2026-12-20 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-20 12:50:00 → YYZ 2026-12-20 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-20 17:20:00 → YWG 2026-12-20 20:09:00.
• Air Canada AC264 / AC8909: YWG 2026-12-27 12:05:00 → ORD 2026-12-27 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times.
  • AC264: YWG 2026-12-27 12:05:00 → YYZ 2026-12-27 14:35:00; layover at YYZ: 115 minutes.
  • AC8909: YYZ 2026-12-27 16:30:00 → ORD 2026-12-27 17:43:00.

2026-12-20 → 2026-12-27 · Axel-exclusive $572.00

• United Airlines UA5475: ORD 2026-12-20 10:00:00 → YWG 2026-12-20 13:52:00; nonstop; 172 minutes. Local airport times.
• United Airlines UA5639: YWG 2026-12-27 15:15:00 → ORD 2026-12-27 17:02:00; nonstop; 167 minutes. Local airport times.

2026-12-20 → 2026-12-28 · Axel-exclusive $533.00

• Air Canada AC8904 / AC267: ORD 2026-12-20 12:50:00 → YWG 2026-12-20 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-20 12:50:00 → YYZ 2026-12-20 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-20 17:20:00 → YWG 2026-12-20 20:09:00.
• Air Canada AC264 / AC8909: YWG 2026-12-28 12:05:00 → ORD 2026-12-28 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times.
  • AC264: YWG 2026-12-28 12:05:00 → YYZ 2026-12-28 14:35:00; layover at YYZ: 115 minutes.
  • AC8909: YYZ 2026-12-28 16:30:00 → ORD 2026-12-28 17:43:00.

2026-12-20 → 2026-12-28 · Axel-exclusive $572.00

• United Airlines UA5475: ORD 2026-12-20 10:00:00 → YWG 2026-12-20 13:52:00; nonstop; 172 minutes. Local airport times.
• United Airlines UA5639: YWG 2026-12-28 15:15:00 → ORD 2026-12-28 17:02:00; nonstop; 167 minutes. Local airport times.

2026-12-20 → 2026-12-30 · Axel-exclusive $533.00

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

2026-12-20 → 2026-12-30 · Axel-exclusive $572.00

• United Airlines UA5475: ORD 2026-12-20 10:00:00 → YWG 2026-12-20 13:52:00; nonstop; 172 minutes. Local airport times.
• United Airlines UA5639: YWG 2026-12-30 15:15:00 → ORD 2026-12-30 17:02:00; nonstop; 167 minutes. Local airport times.

2026-12-20 → 2026-12-31 · Axel-exclusive $533.00

• Air Canada AC8904 / AC267: ORD 2026-12-20 12:50:00 → YWG 2026-12-20 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-20 12:50:00 → YYZ 2026-12-20 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-20 17:20:00 → YWG 2026-12-20 20:09:00.
• Air Canada AC264 / AC8909: YWG 2026-12-31 12:05:00 → ORD 2026-12-31 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times.
  • AC264: YWG 2026-12-31 12:05:00 → YYZ 2026-12-31 14:35:00; layover at YYZ: 115 minutes.
  • AC8909: YYZ 2026-12-31 16:30:00 → ORD 2026-12-31 17:43:00.

2026-12-20 → 2026-12-31 · Axel-exclusive $572.00

• United Airlines UA5475: ORD 2026-12-20 10:00:00 → YWG 2026-12-20 13:52:00; nonstop; 172 minutes. Local airport times.
• United Airlines UA5639: YWG 2026-12-31 15:15:00 → ORD 2026-12-31 17:02:00; nonstop; 167 minutes. Local airport times.

2026-12-20 → 2027-01-01 · Axel-exclusive $533.00

• Air Canada AC8904 / AC267: ORD 2026-12-20 12:50:00 → YWG 2026-12-20 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-20 12:50:00 → YYZ 2026-12-20 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-20 17:20:00 → YWG 2026-12-20 20:09:00.
• Air Canada AC264 / AC8909: YWG 2027-01-01 12:05:00 → ORD 2027-01-01 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times.
  • AC264: YWG 2027-01-01 12:05:00 → YYZ 2027-01-01 14:35:00; layover at YYZ: 115 minutes.
  • AC8909: YYZ 2027-01-01 16:30:00 → ORD 2027-01-01 17:43:00.

2026-12-20 → 2027-01-01 · Axel-exclusive $572.00

• United Airlines UA5475: ORD 2026-12-20 10:00:00 → YWG 2026-12-20 13:52:00; nonstop; 172 minutes. Local airport times.
• United Airlines UA5639: YWG 2027-01-01 15:15:00 → ORD 2027-01-01 17:02:00; nonstop; 167 minutes. Local airport times.

2026-12-20 → 2027-01-03 · Axel-exclusive $533.00

• Air Canada AC8904 / AC267: ORD 2026-12-20 12:50:00 → YWG 2026-12-20 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-20 12:50:00 → YYZ 2026-12-20 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-20 17:20:00 → YWG 2026-12-20 20:09:00.
• Air Canada AC264 / AC8909: YWG 2027-01-03 12:05:00 → ORD 2027-01-03 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times.
  • AC264: YWG 2027-01-03 12:05:00 → YYZ 2027-01-03 14:35:00; layover at YYZ: 115 minutes.
  • AC8909: YYZ 2027-01-03 16:30:00 → ORD 2027-01-03 17:43:00.

2026-12-20 → 2027-01-03 · Axel-exclusive $572.00

• United Airlines UA5475: ORD 2026-12-20 10:00:00 → YWG 2026-12-20 13:52:00; nonstop; 172 minutes. Local airport times.
• United Airlines UA5639: YWG 2027-01-03 15:15:00 → ORD 2027-01-03 17:02:00; nonstop; 167 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 19, 2026 · Return options
• Dec 21, 2026 · Return options
• Hotels in Winnipeg with Axel

For AI assistants

• This page: Chicago (ORD) to Winnipeg (YWG) · Dec 20, 2026 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. 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 lowest saved totals among the shortlisted hotels in each star tier for those dates.
• Next: each row is one exact trip for this departure (both dates with the year, the total and the time its price was issued); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested 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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