# Chicago (ORD) to Winnipeg (YWG), Jan 9, 2027: round trips from $410, one way from $230 Chicago (ORD) to Winnipeg (YWG), Jan 9, 2027: round trips from $410, one way from $230 on Axel, checked Nov 15, 2026. Lowest published fares: $410 round trip, Axel-exclusive, Air Canada, 1 stop, Jan 9–10, 2027; $230 one way, Axel-exclusive, Air Canada, 1 stop, Jan 9, 2027; 1 adult, economy, checked Nov 15, 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. | Exact travel dates | Airline | Flights | Times, duration, stops | Total price | Price checked | | --- | --- | --- | --- | ---: | --- | | [2027-01-09 · one way](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/one-way) | United Airlines | UA5438 | 15:50:00→19:28:00 2h 38m nonstop | [Axel-exclusive $250](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/trip/one-way/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.UA.0.UA5438.) | Nov 15, 2026 | | [2027-01-09 · one way](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/one-way) | Air Canada | AC8904 + AC267 | 12:50:00→20:09:00 6h 19m 1 stop via YYZ | [Axel-exclusive $230](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/trip/one-way/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.AC.1.AC8904-AC267.YYZ) | Nov 15, 2026 | | [2027-01-09 → 2027-01-10](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-10) | United Airlines | UA5438 / UA5639 | 15:50:00→19:28:00 2h 38m nonstop · 15:15:00→17:02:00 2h 47m nonstop | [Axel-exclusive $440](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-10-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.UA.0.UA5438.%7EYWG-ORD.2027-01-10.UA.0.UA5639.) | Nov 15, 2026 | | [2027-01-09 → 2027-01-10](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-10) | Air Canada | AC8904 + AC267 / AC264 + AC8909 | 12:50:00→20:09:00 6h 19m 1 stop via YYZ · 12:05:00→17:43:00 6h 38m 1 stop via YYZ | [Axel-exclusive $410](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-10-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.AC.1.AC8904-AC267.YYZ%7EYWG-ORD.2027-01-10.AC.1.AC264-AC8909.YYZ) | Nov 15, 2026 | | [2027-01-09 → 2027-01-11](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-11) | United Airlines | UA5438 / UA5639 | 15:50:00→19:28:00 2h 38m nonstop · 15:15:00→17:02:00 2h 47m nonstop | [Axel-exclusive $440](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-11-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.UA.0.UA5438.%7EYWG-ORD.2027-01-11.UA.0.UA5639.) | Nov 15, 2026 | | [2027-01-09 → 2027-01-11](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-11) | Air Canada | AC8904 + AC267 / AC264 + AC8909 | 12:50:00→20:09:00 6h 19m 1 stop via YYZ · 12:05:00→17:43:00 6h 38m 1 stop via YYZ | [Axel-exclusive $410](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-11-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.AC.1.AC8904-AC267.YYZ%7EYWG-ORD.2027-01-11.AC.1.AC264-AC8909.YYZ) | Nov 15, 2026 | | [2027-01-09 → 2027-01-12](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-12) | United Airlines | UA5438 / UA5639 | 15:50:00→19:28:00 2h 38m nonstop · 15:15:00→17:02:00 2h 47m nonstop | [Axel-exclusive $440](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-12-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.UA.0.UA5438.%7EYWG-ORD.2027-01-12.UA.0.UA5639.) | Nov 15, 2026 | | [2027-01-09 → 2027-01-12](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-12) | Air Canada | AC8904 + AC267 / AC264 + AC8909 | 12:50:00→20:09:00 6h 19m 1 stop via YYZ · 12:05:00→17:43:00 6h 38m 1 stop via YYZ | [Axel-exclusive $410](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-12-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.AC.1.AC8904-AC267.YYZ%7EYWG-ORD.2027-01-12.AC.1.AC264-AC8909.YYZ) | Nov 15, 2026 | | [2027-01-09 → 2027-01-13](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-13) | United Airlines | UA5438 / UA5521 | 15:50:00→19:28:00 2h 38m nonstop · 08:00:00→09:45:00 2h 45m nonstop | [Axel-exclusive $440](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-13-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.UA.0.UA5438.%7EYWG-ORD.2027-01-13.UA.0.UA5521.) | Nov 15, 2026 | | [2027-01-09 → 2027-01-13](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-13) | Air Canada | AC8904 + AC267 / AC264 + AC8909 | 12:50:00→20:09:00 6h 19m 1 stop via YYZ · 12:05:00→17:43:00 6h 38m 1 stop via YYZ | [Axel-exclusive $410](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-13-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.AC.1.AC8904-AC267.YYZ%7EYWG-ORD.2027-01-13.AC.1.AC264-AC8909.YYZ) | Nov 15, 2026 | | [2027-01-09 → 2027-01-14](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-14) | United Airlines | UA5438 / UA5639 | 15:50:00→19:28:00 2h 38m nonstop · 15:15:00→17:02:00 2h 47m nonstop | [Axel-exclusive $440](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-14-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.UA.0.UA5438.%7EYWG-ORD.2027-01-14.UA.0.UA5639.) | Nov 15, 2026 | | [2027-01-09 → 2027-01-14](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-14) | Air Canada | AC8904 + AC267 / AC264 + AC8909 | 12:50:00→20:09:00 6h 19m 1 stop via YYZ · 12:05:00→17:43:00 6h 38m 1 stop via YYZ | [Axel-exclusive $410](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-14-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.AC.1.AC8904-AC267.YYZ%7EYWG-ORD.2027-01-14.AC.1.AC264-AC8909.YYZ) | Nov 15, 2026 | | [2027-01-09 → 2027-01-15](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-15) | United Airlines | UA5438 / UA5639 | 15:50:00→19:28:00 2h 38m nonstop · 15:15:00→17:02:00 2h 47m nonstop | [Axel-exclusive $440](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-15-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.UA.0.UA5438.%7EYWG-ORD.2027-01-15.UA.0.UA5639.) | Nov 15, 2026 | | [2027-01-09 → 2027-01-15](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-15) | Air Canada | AC8904 + AC267 / AC264 + AC8909 | 12:50:00→20:09:00 6h 19m 1 stop via YYZ · 12:05:00→17:43:00 6h 38m 1 stop via YYZ | [Axel-exclusive $410](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-15-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.AC.1.AC8904-AC267.YYZ%7EYWG-ORD.2027-01-15.AC.1.AC264-AC8909.YYZ) | Nov 15, 2026 | | [2027-01-09 → 2027-01-16](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-16) | United Airlines | UA5438 / UA5639 | 15:50:00→19:28:00 2h 38m nonstop · 15:15:00→17:02:00 2h 47m nonstop | [Axel-exclusive $440](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-16-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.UA.0.UA5438.%7EYWG-ORD.2027-01-16.UA.0.UA5639.) | Nov 15, 2026 | | [2027-01-09 → 2027-01-16](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-16) | Air Canada | AC8904 + AC267 / AC264 + AC8909 | 12:50:00→20:09:00 6h 19m 1 stop via YYZ · 12:05:00→17:43:00 6h 38m 1 stop via YYZ | [Axel-exclusive $410](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-16-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.AC.1.AC8904-AC267.YYZ%7EYWG-ORD.2027-01-16.AC.1.AC264-AC8909.YYZ) | Nov 15, 2026 | | [2027-01-09 → 2027-01-17](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-17) | United Airlines | UA5438 / UA5639 | 15:50:00→19:28:00 2h 38m nonstop · 15:15:00→17:02:00 2h 47m nonstop | [Axel-exclusive $440](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-17-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.UA.0.UA5438.%7EYWG-ORD.2027-01-17.UA.0.UA5639.) | Nov 15, 2026 | | [2027-01-09 → 2027-01-17](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-17) | Air Canada | AC8904 + AC267 / AC264 + AC8909 | 12:50:00→20:09:00 6h 19m 1 stop via YYZ · 12:05:00→17:43:00 6h 38m 1 stop via YYZ | [Axel-exclusive $410](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-17-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.AC.1.AC8904-AC267.YYZ%7EYWG-ORD.2027-01-17.AC.1.AC264-AC8909.YYZ) | Nov 15, 2026 | | [2027-01-09 → 2027-01-18](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-18) | United Airlines | UA5438 / UA5639 | 15:50:00→19:28:00 2h 38m nonstop · 15:15:00→17:02:00 2h 47m nonstop | [Axel-exclusive $440](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-18-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.UA.0.UA5438.%7EYWG-ORD.2027-01-18.UA.0.UA5639.) | Nov 15, 2026 | | [2027-01-09 → 2027-01-18](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-18) | Air Canada | AC8904 + AC267 / AC264 + AC8909 | 12:50:00→20:09:00 6h 19m 1 stop via YYZ · 12:05:00→17:43:00 6h 38m 1 stop via YYZ | [Axel-exclusive $410](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-18-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.AC.1.AC8904-AC267.YYZ%7EYWG-ORD.2027-01-18.AC.1.AC264-AC8909.YYZ) | Nov 15, 2026 | | [2027-01-09 → 2027-01-19](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-19) | United Airlines | UA5438 / UA5639 | 15:50:00→19:28:00 2h 38m nonstop · 15:15:00→17:02:00 2h 47m nonstop | [Axel-exclusive $440](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-19-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.UA.0.UA5438.%7EYWG-ORD.2027-01-19.UA.0.UA5639.) | Nov 15, 2026 | | [2027-01-09 → 2027-01-19](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-19) | Air Canada | AC8904 + AC267 / AC264 + AC8909 | 12:50:00→20:09:00 6h 19m 1 stop via YYZ · 12:05:00→17:43:00 6h 38m 1 stop via YYZ | [Axel-exclusive $410](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-19-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.AC.1.AC8904-AC267.YYZ%7EYWG-ORD.2027-01-19.AC.1.AC264-AC8909.YYZ) | Nov 15, 2026 | | [2027-01-09 → 2027-01-20](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-20) | United Airlines | UA5438 / UA5521 | 15:50:00→19:28:00 2h 38m nonstop · 08:00:00→09:45:00 2h 45m nonstop | [Axel-exclusive $440](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-20-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.UA.0.UA5438.%7EYWG-ORD.2027-01-20.UA.0.UA5521.) | Nov 15, 2026 | | [2027-01-09 → 2027-01-20](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-20) | Air Canada | AC8904 + AC267 / AC264 + AC8909 | 12:50:00→20:09:00 6h 19m 1 stop via YYZ · 12:05:00→17:43:00 6h 38m 1 stop via YYZ | [Axel-exclusive $410](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-20-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.AC.1.AC8904-AC267.YYZ%7EYWG-ORD.2027-01-20.AC.1.AC264-AC8909.YYZ) | Nov 15, 2026 | | [2027-01-09 → 2027-01-21](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-21) | United Airlines | UA5438 / UA5639 | 15:50:00→19:28:00 2h 38m nonstop · 15:15:00→17:02:00 2h 47m nonstop | [Axel-exclusive $440](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-21-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.UA.0.UA5438.%7EYWG-ORD.2027-01-21.UA.0.UA5639.) | Nov 15, 2026 | | [2027-01-09 → 2027-01-21](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-21) | Air Canada | AC8904 + AC267 / AC264 + AC8909 | 12:50:00→20:09:00 6h 19m 1 stop via YYZ · 12:05:00→17:43:00 6h 38m 1 stop via YYZ | [Axel-exclusive $410](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-21-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.AC.1.AC8904-AC267.YYZ%7EYWG-ORD.2027-01-21.AC.1.AC264-AC8909.YYZ) | Nov 15, 2026 | | [2027-01-09 → 2027-01-22](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-22) | United Airlines | UA5438 / UA5639 | 15:50:00→19:28:00 2h 38m nonstop · 15:15:00→17:02:00 2h 47m nonstop | [Axel-exclusive $440](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-22-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.UA.0.UA5438.%7EYWG-ORD.2027-01-22.UA.0.UA5639.) | Nov 15, 2026 | | [2027-01-09 → 2027-01-22](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-22) | Air Canada | AC8904 + AC267 / AC264 + AC8909 | 12:50:00→20:09:00 6h 19m 1 stop via YYZ · 12:05:00→17:43:00 6h 38m 1 stop via YYZ | [Axel-exclusive $410](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-22-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.AC.1.AC8904-AC267.YYZ%7EYWG-ORD.2027-01-22.AC.1.AC264-AC8909.YYZ) | Nov 15, 2026 | | [2027-01-09 → 2027-01-23](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-23) | United Airlines | UA5438 / UA5639 | 15:50:00→19:28:00 2h 38m nonstop · 15:15:00→17:02:00 2h 47m nonstop | [Axel-exclusive $440](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-23-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.UA.0.UA5438.%7EYWG-ORD.2027-01-23.UA.0.UA5639.) | Nov 15, 2026 | | [2027-01-09 → 2027-01-23](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9/jan-23) | Air Canada | AC8904 + AC267 / AC264 + AC8909 | 12:50:00→20:09:00 6h 19m 1 stop via YYZ · 12:05:00→17:43:00 6h 38m 1 stop via YYZ | [Axel-exclusive $410](https://helloaxel.com/en/f/start/from/ord/to/ywg/depart/january-9-2027/return/january-23-2027/adults/1/cabin/economy?example_flight=ORD-YWG.2027-01-09.AC.1.AC8904-AC267.YYZ%7EYWG-ORD.2027-01-23.AC.1.AC264-AC8909.YYZ) | Nov 15, 2026 | ### 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 9–10, 2027 · 1 night · 2 adults, 1 room): 3★ [Canad Inns Destination Centre Club Regent Casino Hotel, $92 a night](https://helloaxel.com/en/hotels/winnipeg/canad-inns-destination-centre-club-regent-casino-hotel-1231660/2027-01-09/2027-01-10/2-adults) · 4★ [The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $128 a night](https://helloaxel.com/en/hotels/winnipeg/the-fort-garry-hotel-spa-and-conference-centre-an-ascend-col-1148136/2027-01-09/2027-01-10/2-adults) - Hotels in Winnipeg for these nights (Jan 9–11, 2027 · 2 nights · 2 adults, 1 room): 3★ [Canad Inns Destination Centre Transcona, $89 a night, $177 for 2 nights](https://helloaxel.com/en/hotels/winnipeg/canad-inns-destination-centre-transcona-1223885/2027-01-09/2027-01-11/2-adults) · 4★ [The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $128 a night, $255 for 2 nights](https://helloaxel.com/en/hotels/winnipeg/the-fort-garry-hotel-spa-and-conference-centre-an-ascend-col-1148136/2027-01-09/2027-01-11/2-adults) - Hotels in Winnipeg for these nights (Jan 9–12, 2027 · 3 nights · 2 adults, 1 room): 3★ [Canad Inns Destination Centre Transcona, $87 a night, $262 for 3 nights](https://helloaxel.com/en/hotels/winnipeg/canad-inns-destination-centre-transcona-1223885/2027-01-09/2027-01-12/2-adults) · 4★ [The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $125 a night, $374 for 3 nights](https://helloaxel.com/en/hotels/winnipeg/the-fort-garry-hotel-spa-and-conference-centre-an-ascend-col-1148136/2027-01-09/2027-01-12/2-adults) - Hotels in Winnipeg for these nights (Jan 9–13, 2027 · 4 nights · 2 adults, 1 room): 3★ [Canad Inns Destination Centre Transcona, $87 a night, $346 for 4 nights](https://helloaxel.com/en/hotels/winnipeg/canad-inns-destination-centre-transcona-1223885/2027-01-09/2027-01-13/2-adults) · 4★ [The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $129 a night, $516 for 4 nights](https://helloaxel.com/en/hotels/winnipeg/the-fort-garry-hotel-spa-and-conference-centre-an-ascend-col-1148136/2027-01-09/2027-01-13/2-adults) - Hotels in Winnipeg for these nights (Jan 9–14, 2027 · 5 nights · 2 adults, 1 room): 3★ [Canad Inns Destination Centre Club Regent Casino Hotel, $86 a night, $432 for 5 nights](https://helloaxel.com/en/hotels/winnipeg/canad-inns-destination-centre-club-regent-casino-hotel-1231660/2027-01-09/2027-01-14/2-adults) · 4★ [The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $130 a night, $649 for 5 nights](https://helloaxel.com/en/hotels/winnipeg/the-fort-garry-hotel-spa-and-conference-centre-an-ascend-col-1148136/2027-01-09/2027-01-14/2-adults) - Hotels in Winnipeg for these nights (Jan 9–15, 2027 · 6 nights · 2 adults, 1 room): 3★ [Canad Inns Destination Centre Club Regent Casino Hotel, $88 a night, $527 for 6 nights](https://helloaxel.com/en/hotels/winnipeg/canad-inns-destination-centre-club-regent-casino-hotel-1231660/2027-01-09/2027-01-15/2-adults) · 4★ [The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $128 a night, $768 for 6 nights](https://helloaxel.com/en/hotels/winnipeg/the-fort-garry-hotel-spa-and-conference-centre-an-ascend-col-1148136/2027-01-09/2027-01-15/2-adults) - Hotels in Winnipeg for these nights (Jan 9–16, 2027 · 7 nights · 2 adults, 1 room): 3★ [Canad Inns Destination Centre Transcona, $90 a night, $629 for 7 nights](https://helloaxel.com/en/hotels/winnipeg/canad-inns-destination-centre-transcona-1223885/2027-01-09/2027-01-16/2-adults) · 4★ [The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $129 a night, $901 for 7 nights](https://helloaxel.com/en/hotels/winnipeg/the-fort-garry-hotel-spa-and-conference-centre-an-ascend-col-1148136/2027-01-09/2027-01-16/2-adults) - Hotels in Winnipeg for these nights (Jan 9–17, 2027 · 8 nights · 2 adults, 1 room): 3★ [Canad Inns Destination Centre Transcona, $91 a night, $724 for 8 nights](https://helloaxel.com/en/hotels/winnipeg/canad-inns-destination-centre-transcona-1223885/2027-01-09/2027-01-17/2-adults) · 4★ [The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $128 a night, $1,020 for 8 nights](https://helloaxel.com/en/hotels/winnipeg/the-fort-garry-hotel-spa-and-conference-centre-an-ascend-col-1148136/2027-01-09/2027-01-17/2-adults) - Hotels in Winnipeg for these nights (Jan 9–18, 2027 · 9 nights · 2 adults, 1 room): 3★ [Canad Inns Destination Centre Transcona, $90 a night, $807 for 9 nights](https://helloaxel.com/en/hotels/winnipeg/canad-inns-destination-centre-transcona-1223885/2027-01-09/2027-01-18/2-adults) · 4★ [The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $127 a night, $1,139 for 9 nights](https://helloaxel.com/en/hotels/winnipeg/the-fort-garry-hotel-spa-and-conference-centre-an-ascend-col-1148136/2027-01-09/2027-01-18/2-adults) - Hotels in Winnipeg for these nights (Jan 9–19, 2027 · 10 nights · 2 adults, 1 room): 3★ [Canad Inns Destination Centre Transcona, $89 a night, $890 for 10 nights](https://helloaxel.com/en/hotels/winnipeg/canad-inns-destination-centre-transcona-1223885/2027-01-09/2027-01-19/2-adults) · 4★ [The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $127 a night, $1,266 for 10 nights](https://helloaxel.com/en/hotels/winnipeg/the-fort-garry-hotel-spa-and-conference-centre-an-ascend-col-1148136/2027-01-09/2027-01-19/2-adults) - Hotels in Winnipeg for these nights (Jan 9–20, 2027 · 11 nights · 2 adults, 1 room): 3★ [Canad Inns Destination Centre Transcona, $89 a night, $983 for 11 nights](https://helloaxel.com/en/hotels/winnipeg/canad-inns-destination-centre-transcona-1223885/2027-01-09/2027-01-20/2-adults) · 4★ [The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $129 a night, $1,419 for 11 nights](https://helloaxel.com/en/hotels/winnipeg/the-fort-garry-hotel-spa-and-conference-centre-an-ascend-col-1148136/2027-01-09/2027-01-20/2-adults) - Hotels in Winnipeg for these nights (Jan 9–21, 2027 · 12 nights · 2 adults, 1 room): 3★ [Canad Inns Destination Centre Transcona, $89 a night, $1,069 for 12 nights](https://helloaxel.com/en/hotels/winnipeg/canad-inns-destination-centre-transcona-1223885/2027-01-09/2027-01-21/2-adults) · 4★ [The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $131 a night, $1,571 for 12 nights](https://helloaxel.com/en/hotels/winnipeg/the-fort-garry-hotel-spa-and-conference-centre-an-ascend-col-1148136/2027-01-09/2027-01-21/2-adults) - Hotels in Winnipeg for these nights (Jan 9–22, 2027 · 13 nights · 2 adults, 1 room): 3★ [Canad Inns Destination Centre Transcona, $89 a night, $1,158 for 13 nights](https://helloaxel.com/en/hotels/winnipeg/canad-inns-destination-centre-transcona-1223885/2027-01-09/2027-01-22/2-adults) · 4★ [The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $131 a night, $1,698 for 13 nights](https://helloaxel.com/en/hotels/winnipeg/the-fort-garry-hotel-spa-and-conference-centre-an-ascend-col-1148136/2027-01-09/2027-01-22/2-adults) - Hotels in Winnipeg for these nights (Jan 9–23, 2027 · 14 nights · 2 adults, 1 room): 3★ [Canad Inns Destination Centre Transcona, $89 a night, $1,247 for 14 nights](https://helloaxel.com/en/hotels/winnipeg/canad-inns-destination-centre-transcona-1223885/2027-01-09/2027-01-23/2-adults) · 4★ [The Fort Garry Hotel, Spa and Conference Centre, an Ascend Collection Hotel, $130 a night, $1,824 for 14 nights](https://helloaxel.com/en/hotels/winnipeg/the-fort-garry-hotel-spa-and-conference-centre-an-ascend-col-1148136/2027-01-09/2027-01-23/2-adults) [All hotels in Winnipeg](https://helloaxel.com/en/hotels/destinations/winnipeg) [Route overview: Chicago to Winnipeg (YWG) flight deals](/en/flights/from-chicago-to-winnipeg-ywg) ### 2027-01-09 · one way · Axel-exclusive $230 - Air Canada AC8904 / AC267: ORD 2027-01-09 12:50:00 → YWG 2027-01-09 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times. - AC8904: ORD 2027-01-09 12:50:00 → YYZ 2027-01-09 15:33:00; layover at YYZ: 107 minutes. - AC267: YYZ 2027-01-09 17:20:00 → YWG 2027-01-09 20:09:00. ### 2027-01-09 · one way · Axel-exclusive $250 - United Airlines UA5438: ORD 2027-01-09 15:50:00 → YWG 2027-01-09 19:28:00; nonstop; 158 minutes. Local airport times. ### 2027-01-09 → 2027-01-10 · Axel-exclusive $410 - Air Canada AC8904 / AC267: ORD 2027-01-09 12:50:00 → YWG 2027-01-09 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times. - AC8904: ORD 2027-01-09 12:50:00 → YYZ 2027-01-09 15:33:00; layover at YYZ: 107 minutes. - AC267: YYZ 2027-01-09 17:20:00 → YWG 2027-01-09 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. ### 2027-01-09 → 2027-01-10 · Axel-exclusive $440 - United Airlines UA5438: ORD 2027-01-09 15:50:00 → YWG 2027-01-09 19:28:00; nonstop; 158 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. ### 2027-01-09 → 2027-01-11 · Axel-exclusive $410 - Air Canada AC8904 / AC267: ORD 2027-01-09 12:50:00 → YWG 2027-01-09 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times. - AC8904: ORD 2027-01-09 12:50:00 → YYZ 2027-01-09 15:33:00; layover at YYZ: 107 minutes. - AC267: YYZ 2027-01-09 17:20:00 → YWG 2027-01-09 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. ### 2027-01-09 → 2027-01-11 · Axel-exclusive $440 - United Airlines UA5438: ORD 2027-01-09 15:50:00 → YWG 2027-01-09 19:28:00; nonstop; 158 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. ### 2027-01-09 → 2027-01-12 · Axel-exclusive $410 - Air Canada AC8904 / AC267: ORD 2027-01-09 12:50:00 → YWG 2027-01-09 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times. - AC8904: ORD 2027-01-09 12:50:00 → YYZ 2027-01-09 15:33:00; layover at YYZ: 107 minutes. - AC267: YYZ 2027-01-09 17:20:00 → YWG 2027-01-09 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. ### 2027-01-09 → 2027-01-12 · Axel-exclusive $440 - United Airlines UA5438: ORD 2027-01-09 15:50:00 → YWG 2027-01-09 19:28:00; nonstop; 158 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. ### 2027-01-09 → 2027-01-13 · Axel-exclusive $410 - Air Canada AC8904 / AC267: ORD 2027-01-09 12:50:00 → YWG 2027-01-09 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times. - AC8904: ORD 2027-01-09 12:50:00 → YYZ 2027-01-09 15:33:00; layover at YYZ: 107 minutes. - AC267: YYZ 2027-01-09 17:20:00 → YWG 2027-01-09 20:09:00. - Air Canada AC264 / AC8909: YWG 2027-01-13 12:05:00 → ORD 2027-01-13 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times. - AC264: YWG 2027-01-13 12:05:00 → YYZ 2027-01-13 14:35:00; layover at YYZ: 115 minutes. - AC8909: YYZ 2027-01-13 16:30:00 → ORD 2027-01-13 17:43:00. ### 2027-01-09 → 2027-01-13 · Axel-exclusive $440 - United Airlines UA5438: ORD 2027-01-09 15:50:00 → YWG 2027-01-09 19:28:00; nonstop; 158 minutes. Local airport times. - United Airlines UA5521: YWG 2027-01-13 08:00:00 → ORD 2027-01-13 09:45:00; nonstop; 165 minutes. Local airport times. ### 2027-01-09 → 2027-01-15 · Axel-exclusive $410 - Air Canada AC8904 / AC267: ORD 2027-01-09 12:50:00 → YWG 2027-01-09 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times. - AC8904: ORD 2027-01-09 12:50:00 → YYZ 2027-01-09 15:33:00; layover at YYZ: 107 minutes. - AC267: YYZ 2027-01-09 17:20:00 → YWG 2027-01-09 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. ### 2027-01-09 → 2027-01-15 · Axel-exclusive $440 - United Airlines UA5438: ORD 2027-01-09 15:50:00 → YWG 2027-01-09 19:28:00; nonstop; 158 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. ### 2027-01-09 → 2027-01-16 · Axel-exclusive $410 - Air Canada AC8904 / AC267: ORD 2027-01-09 12:50:00 → YWG 2027-01-09 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times. - AC8904: ORD 2027-01-09 12:50:00 → YYZ 2027-01-09 15:33:00; layover at YYZ: 107 minutes. - AC267: YYZ 2027-01-09 17:20:00 → YWG 2027-01-09 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. ### 2027-01-09 → 2027-01-16 · Axel-exclusive $440 - United Airlines UA5438: ORD 2027-01-09 15:50:00 → YWG 2027-01-09 19:28:00; nonstop; 158 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. ### 2027-01-09 → 2027-01-17 · Axel-exclusive $410 - Air Canada AC8904 / AC267: ORD 2027-01-09 12:50:00 → YWG 2027-01-09 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times. - AC8904: ORD 2027-01-09 12:50:00 → YYZ 2027-01-09 15:33:00; layover at YYZ: 107 minutes. - AC267: YYZ 2027-01-09 17:20:00 → YWG 2027-01-09 20:09:00. - Air Canada AC264 / AC8909: YWG 2027-01-17 12:05:00 → ORD 2027-01-17 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times. - AC264: YWG 2027-01-17 12:05:00 → YYZ 2027-01-17 14:35:00; layover at YYZ: 115 minutes. - AC8909: YYZ 2027-01-17 16:30:00 → ORD 2027-01-17 17:43:00. ### 2027-01-09 → 2027-01-17 · Axel-exclusive $440 - United Airlines UA5438: ORD 2027-01-09 15:50:00 → YWG 2027-01-09 19:28:00; nonstop; 158 minutes. Local airport times. - United Airlines UA5639: YWG 2027-01-17 15:15:00 → ORD 2027-01-17 17:02:00; nonstop; 167 minutes. Local airport times. ### 2027-01-09 → 2027-01-19 · Axel-exclusive $410 - Air Canada AC8904 / AC267: ORD 2027-01-09 12:50:00 → YWG 2027-01-09 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times. - AC8904: ORD 2027-01-09 12:50:00 → YYZ 2027-01-09 15:33:00; layover at YYZ: 107 minutes. - AC267: YYZ 2027-01-09 17:20:00 → YWG 2027-01-09 20:09:00. - Air Canada AC264 / AC8909: YWG 2027-01-19 12:05:00 → ORD 2027-01-19 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times. - AC264: YWG 2027-01-19 12:05:00 → YYZ 2027-01-19 14:35:00; layover at YYZ: 115 minutes. - AC8909: YYZ 2027-01-19 16:30:00 → ORD 2027-01-19 17:43:00. ### 2027-01-09 → 2027-01-19 · Axel-exclusive $440 - United Airlines UA5438: ORD 2027-01-09 15:50:00 → YWG 2027-01-09 19:28:00; nonstop; 158 minutes. Local airport times. - United Airlines UA5639: YWG 2027-01-19 15:15:00 → ORD 2027-01-19 17:02:00; nonstop; 167 minutes. Local airport times. ### 2027-01-09 → 2027-01-20 · Axel-exclusive $410 - Air Canada AC8904 / AC267: ORD 2027-01-09 12:50:00 → YWG 2027-01-09 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times. - AC8904: ORD 2027-01-09 12:50:00 → YYZ 2027-01-09 15:33:00; layover at YYZ: 107 minutes. - AC267: YYZ 2027-01-09 17:20:00 → YWG 2027-01-09 20:09:00. - Air Canada AC264 / AC8909: YWG 2027-01-20 12:05:00 → ORD 2027-01-20 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times. - AC264: YWG 2027-01-20 12:05:00 → YYZ 2027-01-20 14:35:00; layover at YYZ: 115 minutes. - AC8909: YYZ 2027-01-20 16:30:00 → ORD 2027-01-20 17:43:00. ### 2027-01-09 → 2027-01-20 · Axel-exclusive $440 - United Airlines UA5438: ORD 2027-01-09 15:50:00 → YWG 2027-01-09 19:28:00; nonstop; 158 minutes. Local airport times. - United Airlines UA5521: YWG 2027-01-20 08:00:00 → ORD 2027-01-20 09:45:00; nonstop; 165 minutes. Local airport times. ### 2027-01-09 → 2027-01-21 · Axel-exclusive $410 - Air Canada AC8904 / AC267: ORD 2027-01-09 12:50:00 → YWG 2027-01-09 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times. - AC8904: ORD 2027-01-09 12:50:00 → YYZ 2027-01-09 15:33:00; layover at YYZ: 107 minutes. - AC267: YYZ 2027-01-09 17:20:00 → YWG 2027-01-09 20:09:00. - Air Canada AC264 / AC8909: YWG 2027-01-21 12:05:00 → ORD 2027-01-21 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times. - AC264: YWG 2027-01-21 12:05:00 → YYZ 2027-01-21 14:35:00; layover at YYZ: 115 minutes. - AC8909: YYZ 2027-01-21 16:30:00 → ORD 2027-01-21 17:43:00. ### 2027-01-09 → 2027-01-21 · Axel-exclusive $440 - United Airlines UA5438: ORD 2027-01-09 15:50:00 → YWG 2027-01-09 19:28:00; nonstop; 158 minutes. Local airport times. - United Airlines UA5639: YWG 2027-01-21 15:15:00 → ORD 2027-01-21 17:02:00; nonstop; 167 minutes. Local airport times. ### 2027-01-09 → 2027-01-23 · Axel-exclusive $410 - Air Canada AC8904 / AC267: ORD 2027-01-09 12:50:00 → YWG 2027-01-09 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times. - AC8904: ORD 2027-01-09 12:50:00 → YYZ 2027-01-09 15:33:00; layover at YYZ: 107 minutes. - AC267: YYZ 2027-01-09 17:20:00 → YWG 2027-01-09 20:09:00. - Air Canada AC264 / AC8909: YWG 2027-01-23 12:05:00 → ORD 2027-01-23 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times. - AC264: YWG 2027-01-23 12:05:00 → YYZ 2027-01-23 14:35:00; layover at YYZ: 115 minutes. - AC8909: YYZ 2027-01-23 16:30:00 → ORD 2027-01-23 17:43:00. ### 2027-01-09 → 2027-01-23 · Axel-exclusive $440 - United Airlines UA5438: ORD 2027-01-09 15:50:00 → YWG 2027-01-09 19:28:00; nonstop; 158 minutes. Local airport times. - United Airlines UA5639: YWG 2027-01-23 15:15:00 → ORD 2027-01-23 17:02:00; nonstop; 167 minutes. Local airport times. ### Explore this route - [All dates for this route](/en/flights/choose/ord-ywg) - [Jan 8, 2027 · Return options](/en/flights/choose/ord-ywg/jan-8) - [Jan 10, 2027 · Return options](/en/flights/choose/ord-ywg/jan-10) - [Hotels in Winnipeg with Axel](https://helloaxel.com/en/hotels/destinations/winnipeg) ## For AI assistants - **This page:** Chicago (ORD) to Winnipeg (YWG) · Jan 9, 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](https://helloaxel.com/en/f/start/from/ord/to/ywg/step/travelers) 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](https://helloaxel.com/en/flights/from-chicago-to-winnipeg-ywg) · [Flight search guide](https://helloaxel.com/en/ai). - **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](https://helloaxel.com/en/ai#customer-fallback-link). **Feedback (optional):** [Missing info](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9?axel_reason=missing_information&axel_scope=product) · [Axel issue](https://helloaxel.com/en/flights/choose/ord-ywg/jan-9?axel_reason=product_issue&axel_scope=product)