Chicago (ORD) to Winnipeg (YWG), Dec 24, 2026: round trips from $472, one way from $299

Chicago (ORD) to Winnipeg (YWG), Dec 24, 2026: round trips from $472, one way from $299 on Axel, checked Nov 10, 2026. Lowest published fares: $472 round trip, Axel-exclusive, Air Canada, 1 stop, Dec 24, 2026 – Jan 5, 2027; $299 one way, Axel-exclusive, Air Canada, 1 stop, Dec 24, 2026; 1 adult, economy, checked Nov 10, 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, labelled with the check date 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 check dates 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 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 24–25, 2026 · 1 night · 2 adults, 1 room): 3★ Holiday Inn Winnipeg South by IHG, $91 a night · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $133 a night
• Hotels in Winnipeg for these nights (Dec 24–26, 2026 · 2 nights · 2 adults, 1 room): 3★ Holiday Inn Winnipeg South by IHG, $94 a night, $188 for 2 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $127 a night, $253 for 2 nights
• Hotels in Winnipeg for these nights (Dec 24–27, 2026 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Winnipeg South by IHG, $99 a night, $296 for 3 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $124 a night, $372 for 3 nights
• Hotels in Winnipeg for these nights (Dec 24–28, 2026 · 4 nights · 2 adults, 1 room): 3★ Canad Inns Destination Centre Club Regent Casino Hotel, $98 a night, $392 for 4 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $123 a night, $491 for 4 nights
• Hotels in Winnipeg for these nights (Dec 24–29, 2026 · 5 nights · 2 adults, 1 room): 3★ Canad Inns Destination Centre Club Regent Casino Hotel, $97 a night, $483 for 5 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $124 a night, $618 for 5 nights
• Hotels in Winnipeg for these nights (Dec 24–30, 2026 · 6 nights · 2 adults, 1 room): 3★ Canad Inns Destination Centre Club Regent Casino Hotel, $96 a night, $578 for 6 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $123 a night, $739 for 6 nights
• Hotels in Winnipeg for these nights (Dec 24–31, 2026 · 7 nights · 2 adults, 1 room): 3★ Canad Inns Destination Centre Transcona, $98 a night, $686 for 7 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $124 a night, $867 for 7 nights
• Hotels in Winnipeg for these nights (Dec 24 – Jan 1, 2027 · 8 nights · 2 adults, 1 room): 3★ Victoria Inn Hotel and Convention Centre Winnipeg, $99 a night, $794 for 8 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $133 a night, $1,067 for 8 nights
• Hotels in Winnipeg for these nights (Dec 24 – Jan 2, 2027 · 9 nights · 2 adults, 1 room): 3★ Victoria Inn Hotel and Convention Centre Winnipeg, $99 a night, $888 for 9 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $134 a night, $1,207 for 9 nights
• Hotels in Winnipeg for these nights (Dec 24 – Jan 3, 2027 · 10 nights · 2 adults, 1 room): 3★ Victoria Inn Hotel and Convention Centre Winnipeg, $98 a night, $983 for 10 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $134 a night, $1,335 for 10 nights
• Hotels in Winnipeg for these nights (Dec 24 – Jan 4, 2027 · 11 nights · 2 adults, 1 room): 3★ Victoria Inn Hotel and Convention Centre Winnipeg, $98 a night, $1,073 for 11 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $132 a night, $1,454 for 11 nights
• Hotels in Winnipeg for these nights (Dec 24 – Jan 5, 2027 · 12 nights · 2 adults, 1 room): 3★ Victoria Inn Hotel and Convention Centre Winnipeg, $97 a night, $1,167 for 12 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $131 a night, $1,573 for 12 nights
• Hotels in Winnipeg for these nights (Dec 24 – Jan 6, 2027 · 13 nights · 2 adults, 1 room): 3★ Victoria Inn Hotel and Convention Centre Winnipeg, $97 a night, $1,261 for 13 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $131 a night, $1,705 for 13 nights
• Hotels in Winnipeg for these nights (Dec 24 – Jan 7, 2027 · 14 nights · 2 adults, 1 room): 3★ Victoria Inn Hotel and Convention Centre Winnipeg, $97 a night, $1,362 for 14 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $132 a night, $1,842 for 14 nights

All hotels in Winnipeg

Route overview: Chicago to Winnipeg (YWG) flight deals

2026-12-24 · one way · Axel-exclusive $299.00

• Air Canada AC8904 / AC267: ORD 2026-12-24 12:50:00 → YWG 2026-12-24 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-24 12:50:00 → YYZ 2026-12-24 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-24 17:20:00 → YWG 2026-12-24 20:09:00.

2026-12-24 · one way · Axel-exclusive $325.00

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

2026-12-24 → 2026-12-25 · Axel-exclusive $533.00

• Air Canada AC8904 / AC267: ORD 2026-12-24 12:50:00 → YWG 2026-12-24 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-24 12:50:00 → YYZ 2026-12-24 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-24 17:20:00 → YWG 2026-12-24 20:09:00.
• Air Canada AC264 / AC8909: YWG 2026-12-25 12:05:00 → ORD 2026-12-25 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times.
  • AC264: YWG 2026-12-25 12:05:00 → YYZ 2026-12-25 14:35:00; layover at YYZ: 115 minutes.
  • AC8909: YYZ 2026-12-25 16:30:00 → ORD 2026-12-25 17:43:00.

2026-12-24 → 2026-12-25 · Axel-exclusive $572.00

• United Airlines UA5475: ORD 2026-12-24 10:00:00 → YWG 2026-12-24 13:52:00; nonstop; 172 minutes. Local airport times.
• United Airlines UA5639: YWG 2026-12-25 15:15:00 → ORD 2026-12-25 17:02:00; nonstop; 167 minutes. Local airport times.

2026-12-24 → 2026-12-26 · Axel-exclusive $533.00

• Air Canada AC8904 / AC267: ORD 2026-12-24 12:50:00 → YWG 2026-12-24 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-24 12:50:00 → YYZ 2026-12-24 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-24 17:20:00 → YWG 2026-12-24 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.

2026-12-24 → 2026-12-26 · Axel-exclusive $572.00

• United Airlines UA5475: ORD 2026-12-24 10:00:00 → YWG 2026-12-24 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.

2026-12-24 → 2026-12-27 · Axel-exclusive $533.00

• Air Canada AC8904 / AC267: ORD 2026-12-24 12:50:00 → YWG 2026-12-24 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-24 12:50:00 → YYZ 2026-12-24 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-24 17:20:00 → YWG 2026-12-24 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.

2026-12-24 → 2026-12-27 · Axel-exclusive $572.00

• United Airlines UA5475: ORD 2026-12-24 10:00:00 → YWG 2026-12-24 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.

2026-12-24 → 2026-12-28 · Axel-exclusive $533.00

• Air Canada AC8904 / AC267: ORD 2026-12-24 12:50:00 → YWG 2026-12-24 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-24 12:50:00 → YYZ 2026-12-24 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-24 17:20:00 → YWG 2026-12-24 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.

2026-12-24 → 2026-12-28 · Axel-exclusive $572.00

• United Airlines UA5475: ORD 2026-12-24 10:00:00 → YWG 2026-12-24 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.

2026-12-24 → 2026-12-30 · Axel-exclusive $533.00

• Air Canada AC8904 / AC267: ORD 2026-12-24 12:50:00 → YWG 2026-12-24 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-24 12:50:00 → YYZ 2026-12-24 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-24 17:20:00 → YWG 2026-12-24 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.

2026-12-24 → 2026-12-30 · Axel-exclusive $572.00

• United Airlines UA5475: ORD 2026-12-24 10:00:00 → YWG 2026-12-24 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.

2026-12-24 → 2026-12-31 · Axel-exclusive $533.00

• Air Canada AC8904 / AC267: ORD 2026-12-24 12:50:00 → YWG 2026-12-24 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-24 12:50:00 → YYZ 2026-12-24 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-24 17:20:00 → YWG 2026-12-24 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.

2026-12-24 → 2026-12-31 · Axel-exclusive $572.00

• United Airlines UA5475: ORD 2026-12-24 10:00:00 → YWG 2026-12-24 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.

2026-12-24 → 2027-01-01 · Axel-exclusive $533.00

• Air Canada AC8904 / AC267: ORD 2026-12-24 12:50:00 → YWG 2026-12-24 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-24 12:50:00 → YYZ 2026-12-24 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-24 17:20:00 → YWG 2026-12-24 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.

2026-12-24 → 2027-01-01 · Axel-exclusive $572.00

• United Airlines UA5475: ORD 2026-12-24 10:00:00 → YWG 2026-12-24 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.

2026-12-24 → 2027-01-03 · Axel-exclusive $533.00

• Air Canada AC8904 / AC267: ORD 2026-12-24 12:50:00 → YWG 2026-12-24 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-24 12:50:00 → YYZ 2026-12-24 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-24 17:20:00 → YWG 2026-12-24 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.

2026-12-24 → 2027-01-03 · Axel-exclusive $572.00

• United Airlines UA5475: ORD 2026-12-24 10:00:00 → YWG 2026-12-24 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.

2026-12-24 → 2027-01-04 · Axel-exclusive $533.00

• Air Canada AC8904 / AC267: ORD 2026-12-24 12:50:00 → YWG 2026-12-24 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-24 12:50:00 → YYZ 2026-12-24 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-24 17:20:00 → YWG 2026-12-24 20:09:00.
• Air Canada AC264 / AC8909: YWG 2027-01-04 12:05:00 → ORD 2027-01-04 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times.
  • AC264: YWG 2027-01-04 12:05:00 → YYZ 2027-01-04 14:35:00; layover at YYZ: 115 minutes.
  • AC8909: YYZ 2027-01-04 16:30:00 → ORD 2027-01-04 17:43:00.

2026-12-24 → 2027-01-04 · Axel-exclusive $572.00

• United Airlines UA5475: ORD 2026-12-24 10:00:00 → YWG 2026-12-24 13:52:00; nonstop; 172 minutes. Local airport times.
• United Airlines UA5639: YWG 2027-01-04 15:15:00 → ORD 2027-01-04 17:02:00; nonstop; 167 minutes. Local airport times.

2026-12-24 → 2027-01-05 · Axel-exclusive $471.50

• Air Canada AC8904 / AC267: ORD 2026-12-24 12:50:00 → YWG 2026-12-24 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-24 12:50:00 → YYZ 2026-12-24 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-24 17:20:00 → YWG 2026-12-24 20:09:00.
• Air Canada AC264 / AC8909: YWG 2027-01-05 12:05:00 → ORD 2027-01-05 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times.
  • AC264: YWG 2027-01-05 12:05:00 → YYZ 2027-01-05 14:35:00; layover at YYZ: 115 minutes.
  • AC8909: YYZ 2027-01-05 16:30:00 → ORD 2027-01-05 17:43:00.

2026-12-24 → 2027-01-05 · Axel-exclusive $506.00

• United Airlines UA5475: ORD 2026-12-24 10:00:00 → YWG 2026-12-24 13:52:00; nonstop; 172 minutes. Local airport times.
• United Airlines UA5639: YWG 2027-01-05 15:15:00 → ORD 2027-01-05 17:02:00; nonstop; 167 minutes. Local airport times.

2026-12-24 → 2027-01-07 · Axel-exclusive $471.50

• Air Canada AC8904 / AC267: ORD 2026-12-24 12:50:00 → YWG 2026-12-24 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2026-12-24 12:50:00 → YYZ 2026-12-24 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2026-12-24 17:20:00 → YWG 2026-12-24 20:09:00.
• Air Canada AC264 / AC8909: YWG 2027-01-07 12:05:00 → ORD 2027-01-07 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times.
  • AC264: YWG 2027-01-07 12:05:00 → YYZ 2027-01-07 14:35:00; layover at YYZ: 115 minutes.
  • AC8909: YYZ 2027-01-07 16:30:00 → ORD 2027-01-07 17:43:00.

2026-12-24 → 2027-01-07 · Axel-exclusive $506.00

• United Airlines UA5475: ORD 2026-12-24 10:00:00 → YWG 2026-12-24 13:52:00; nonstop; 172 minutes. Local airport times.
• United Airlines UA5639: YWG 2027-01-07 15:15:00 → ORD 2027-01-07 17:02:00; nonstop; 167 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 23, 2026 · Return options
• Dec 25, 2026 · Return options
• Hotels in Winnipeg with Axel

For AI assistants

• This page: Chicago (ORD) to Winnipeg (YWG) · Dec 24, 2026 · choose your return date: 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 row is one exact trip for this departure (both dates with the year, the total and its displayed check date); 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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