Chicago (ORD) to Winnipeg (YWG), Jan 4, 2027: round trips from $472, one way from $299

Chicago (ORD) to Winnipeg (YWG), Jan 4, 2027: round trips from $472, one way from $299 on Axel, checked Nov 14, 2026. Lowest published fares: $472 round trip, Axel-exclusive, Air Canada, 1 stop, Jan 4–5, 2027; $299 one way, Axel-exclusive, Air Canada, 1 stop, Jan 4, 2027; 1 adult, economy, checked Nov 14, 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 (Jan 4–5, 2027 · 1 night · 2 adults, 1 room): 3★ Canad Inns Destination Centre Club Regent Casino Hotel, $85 a night · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $119 a night
• Hotels in Winnipeg for these nights (Jan 4–6, 2027 · 2 nights · 2 adults, 1 room): 3★ Canad Inns Destination Centre Transcona, $85 a night, $170 for 2 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $126 a night, $251 for 2 nights
• Hotels in Winnipeg for these nights (Jan 4–7, 2027 · 3 nights · 2 adults, 1 room): 3★ Canad Inns Destination Centre Club Regent Casino Hotel, $85 a night, $255 for 3 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $129 a night, $388 for 3 nights
• Hotels in Winnipeg for these nights (Jan 4–8, 2027 · 4 nights · 2 adults, 1 room): 3★ Canad Inns Destination Centre Club Regent Casino Hotel, $85 a night, $340 for 4 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $127 a night, $507 for 4 nights
• Hotels in Winnipeg for these nights (Jan 4–9, 2027 · 5 nights · 2 adults, 1 room): 3★ Canad Inns Destination Centre Transcona, $84 a night, $421 for 5 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $125 a night, $626 for 5 nights
• Hotels in Winnipeg for these nights (Jan 4–10, 2027 · 6 nights · 2 adults, 1 room): 3★ Canad Inns Destination Centre Transcona, $86 a night, $517 for 6 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $126 a night, $754 for 6 nights
• Hotels in Winnipeg for these nights (Jan 4–11, 2027 · 7 nights · 2 adults, 1 room): 3★ Canad Inns Destination Centre Transcona, $85 a night, $598 for 7 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $126 a night, $881 for 7 nights
• Hotels in Winnipeg for these nights (Jan 4–12, 2027 · 8 nights · 2 adults, 1 room): 3★ Canad Inns Destination Centre Transcona, $85 a night, $683 for 8 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $125 a night, $1,000 for 8 nights
• Hotels in Winnipeg for these nights (Jan 4–13, 2027 · 9 nights · 2 adults, 1 room): 3★ Canad Inns Destination Centre Transcona, $85 a night, $767 for 9 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $127 a night, $1,142 for 9 nights
• Hotels in Winnipeg for these nights (Jan 4–14, 2027 · 10 nights · 2 adults, 1 room): 3★ Canad Inns Destination Centre Transcona, $86 a night, $864 for 10 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $128 a night, $1,275 for 10 nights
• Hotels in Winnipeg for these nights (Jan 4–15, 2027 · 11 nights · 2 adults, 1 room): 3★ Canad Inns Destination Centre Transcona, $87 a night, $955 for 11 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $127 a night, $1,394 for 11 nights
• Hotels in Winnipeg for these nights (Jan 4–16, 2027 · 12 nights · 2 adults, 1 room): 3★ Canad Inns Destination Centre Transcona, $88 a night, $1,050 for 12 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $127 a night, $1,527 for 12 nights
• Hotels in Winnipeg for these nights (Jan 4–17, 2027 · 13 nights · 2 adults, 1 room): 3★ Canad Inns Destination Centre Transcona, $88 a night, $1,145 for 13 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $127 a night, $1,646 for 13 nights
• Hotels in Winnipeg for these nights (Jan 4–18, 2027 · 14 nights · 2 adults, 1 room): 3★ Canad Inns Destination Centre Transcona, $88 a night, $1,228 for 14 nights · 4★ The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $126 a night, $1,765 for 14 nights

All hotels in Winnipeg

Route overview: Chicago to Winnipeg (YWG) flight deals

2027-01-04 · one way · Axel-exclusive $299

• Air Canada AC8904 / AC267: ORD 2027-01-04 12:50:00 → YWG 2027-01-04 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2027-01-04 12:50:00 → YYZ 2027-01-04 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2027-01-04 17:20:00 → YWG 2027-01-04 20:09:00.

2027-01-04 · one way · Axel-exclusive $325

• United Airlines UA5475: ORD 2027-01-04 10:00:00 → YWG 2027-01-04 13:52:00; nonstop; 172 minutes. Local airport times.

2027-01-04 → 2027-01-05 · Axel-exclusive $472

• Air Canada AC8904 / AC267: ORD 2027-01-04 12:50:00 → YWG 2027-01-04 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2027-01-04 12:50:00 → YYZ 2027-01-04 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2027-01-04 17:20:00 → YWG 2027-01-04 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.

2027-01-04 → 2027-01-05 · Axel-exclusive $506

• United Airlines UA5475: ORD 2027-01-04 10:00:00 → YWG 2027-01-04 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.

2027-01-04 → 2027-01-06 · Axel-exclusive $472

• Air Canada AC8904 / AC267: ORD 2027-01-04 12:50:00 → YWG 2027-01-04 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2027-01-04 12:50:00 → YYZ 2027-01-04 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2027-01-04 17:20:00 → YWG 2027-01-04 20:09:00.
• Air Canada AC264 / AC8909: YWG 2027-01-06 12:05:00 → ORD 2027-01-06 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times.
  • AC264: YWG 2027-01-06 12:05:00 → YYZ 2027-01-06 14:35:00; layover at YYZ: 115 minutes.
  • AC8909: YYZ 2027-01-06 16:30:00 → ORD 2027-01-06 17:43:00.

2027-01-04 → 2027-01-06 · Axel-exclusive $506

• United Airlines UA5475: ORD 2027-01-04 10:00:00 → YWG 2027-01-04 13:52:00; nonstop; 172 minutes. Local airport times.
• United Airlines UA5521: YWG 2027-01-06 08:00:00 → ORD 2027-01-06 09:45:00; nonstop; 165 minutes. Local airport times.

2027-01-04 → 2027-01-07 · Axel-exclusive $472

• Air Canada AC8904 / AC267: ORD 2027-01-04 12:50:00 → YWG 2027-01-04 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2027-01-04 12:50:00 → YYZ 2027-01-04 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2027-01-04 17:20:00 → YWG 2027-01-04 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.

2027-01-04 → 2027-01-07 · Axel-exclusive $506

• United Airlines UA5475: ORD 2027-01-04 10:00:00 → YWG 2027-01-04 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.

2027-01-04 → 2027-01-08 · Axel-exclusive $472

• Air Canada AC8904 / AC267: ORD 2027-01-04 12:50:00 → YWG 2027-01-04 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2027-01-04 12:50:00 → YYZ 2027-01-04 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2027-01-04 17:20:00 → YWG 2027-01-04 20:09:00.
• Air Canada AC264 / AC8909: YWG 2027-01-08 12:05:00 → ORD 2027-01-08 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times.
  • AC264: YWG 2027-01-08 12:05:00 → YYZ 2027-01-08 14:35:00; layover at YYZ: 115 minutes.
  • AC8909: YYZ 2027-01-08 16:30:00 → ORD 2027-01-08 17:43:00.

2027-01-04 → 2027-01-08 · Axel-exclusive $506

• United Airlines UA5475: ORD 2027-01-04 10:00:00 → YWG 2027-01-04 13:52:00; nonstop; 172 minutes. Local airport times.
• United Airlines UA5639: YWG 2027-01-08 15:15:00 → ORD 2027-01-08 17:02:00; nonstop; 167 minutes. Local airport times.

2027-01-04 → 2027-01-10 · Axel-exclusive $472

• Air Canada AC8904 / AC267: ORD 2027-01-04 12:50:00 → YWG 2027-01-04 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2027-01-04 12:50:00 → YYZ 2027-01-04 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2027-01-04 17:20:00 → YWG 2027-01-04 20:09:00.
• Air Canada AC264 / AC8909: YWG 2027-01-10 12:05:00 → ORD 2027-01-10 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times.
  • AC264: YWG 2027-01-10 12:05:00 → YYZ 2027-01-10 14:35:00; layover at YYZ: 115 minutes.
  • AC8909: YYZ 2027-01-10 16:30:00 → ORD 2027-01-10 17:43:00.

2027-01-04 → 2027-01-10 · Axel-exclusive $506

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

2027-01-04 → 2027-01-11 · Axel-exclusive $472

• Air Canada AC8904 / AC267: ORD 2027-01-04 12:50:00 → YWG 2027-01-04 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2027-01-04 12:50:00 → YYZ 2027-01-04 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2027-01-04 17:20:00 → YWG 2027-01-04 20:09:00.
• Air Canada AC264 / AC8909: YWG 2027-01-11 12:05:00 → ORD 2027-01-11 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times.
  • AC264: YWG 2027-01-11 12:05:00 → YYZ 2027-01-11 14:35:00; layover at YYZ: 115 minutes.
  • AC8909: YYZ 2027-01-11 16:30:00 → ORD 2027-01-11 17:43:00.

2027-01-04 → 2027-01-11 · Axel-exclusive $506

• United Airlines UA5475: ORD 2027-01-04 10:00:00 → YWG 2027-01-04 13:52:00; nonstop; 172 minutes. Local airport times.
• United Airlines UA5639: YWG 2027-01-11 15:15:00 → ORD 2027-01-11 17:02:00; nonstop; 167 minutes. Local airport times.

2027-01-04 → 2027-01-12 · Axel-exclusive $472

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

2027-01-04 → 2027-01-12 · Axel-exclusive $506

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

2027-01-04 → 2027-01-14 · Axel-exclusive $472

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

2027-01-04 → 2027-01-14 · Axel-exclusive $506

• United Airlines UA5475: ORD 2027-01-04 10:00:00 → YWG 2027-01-04 13:52:00; nonstop; 172 minutes. Local airport times.
• United Airlines UA5639: YWG 2027-01-14 15:15:00 → ORD 2027-01-14 17:02:00; nonstop; 167 minutes. Local airport times.

2027-01-04 → 2027-01-15 · Axel-exclusive $472

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

2027-01-04 → 2027-01-15 · Axel-exclusive $506

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

2027-01-04 → 2027-01-16 · Axel-exclusive $472

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

2027-01-04 → 2027-01-16 · Axel-exclusive $506

• United Airlines UA5475: ORD 2027-01-04 10:00:00 → YWG 2027-01-04 13:52:00; nonstop; 172 minutes. Local airport times.
• United Airlines UA5639: YWG 2027-01-16 15:15:00 → ORD 2027-01-16 17:02:00; nonstop; 167 minutes. Local airport times.

2027-01-04 → 2027-01-18 · Axel-exclusive $472

• Air Canada AC8904 / AC267: ORD 2027-01-04 12:50:00 → YWG 2027-01-04 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
  • AC8904: ORD 2027-01-04 12:50:00 → YYZ 2027-01-04 15:33:00; layover at YYZ: 107 minutes.
  • AC267: YYZ 2027-01-04 17:20:00 → YWG 2027-01-04 20:09:00.
• Air Canada AC264 / AC8909: YWG 2027-01-18 12:05:00 → ORD 2027-01-18 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times.
  • AC264: YWG 2027-01-18 12:05:00 → YYZ 2027-01-18 14:35:00; layover at YYZ: 115 minutes.
  • AC8909: YYZ 2027-01-18 16:30:00 → ORD 2027-01-18 17:43:00.

2027-01-04 → 2027-01-18 · Axel-exclusive $506

• United Airlines UA5475: ORD 2027-01-04 10:00:00 → YWG 2027-01-04 13:52:00; nonstop; 172 minutes. Local airport times.
• United Airlines UA5639: YWG 2027-01-18 15:15:00 → ORD 2027-01-18 17:02:00; nonstop; 167 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 3, 2027 · Return options
• Jan 5, 2027 · Return options
• Hotels in Winnipeg with Axel

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• This page: Chicago (ORD) to Winnipeg (YWG) · Jan 4, 2027 · 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.
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