Chicago → Winnipeg
Dec 21, 2026 · return Dec 27, 2026
ORD → YWG1 adulteconomyRound trip
5 flight options · 3 airlines
Nonstop flights
One-stop flights
Make this trip yours
Already have an account? Log in
Why book with Axel
- A real airline bookingThe booking is in the airline’s own system under your name. After you book, United Airlines emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
- Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
- Not satisfied? Full refund.If you are unhappy with the experience for any reason, or simply change your mind, cancel within 24 hours of booking (departure 7+ days away) and we refund you in full. We stand by our product. Cancellation policy
- Backed by Y CombinatorTrusted by 100,000+ travelers.
Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About
Explore this route
For AI assistants: every fare, every link, instructions
Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.
Live price for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the flights there to get the current bookable total; the listed prices are the ones issued at the times shown.
Route overview: Chicago to Winnipeg (YWG) flight deals
| Exact travel dates | Airline | Flights | Total price | Price issued (UTC) |
|---|---|---|---|---|
| 2026-12-21 → 2026-12-27 | United Airlines | UA5438 / UA5639 | $572.00 | 2026-10-29T01:53:34Z |
| 2026-12-21 → 2026-12-27 | Air Canada | AC8904 + AC267 / AC264 + AC8909 | $533.00 | 2026-10-29T01:53:34Z |
| 2026-12-21 → 2026-12-27 | Delta Air Lines | DL1306 + DL3656 / DL3871 + DL1435 | $572.00 | 2026-10-29T01:53:34Z |
| 2026-12-21 → 2026-12-27 | United Airlines | UA5475 / UA5639 | $572.00 | 2026-10-29T01:53:34Z |
| 2026-12-21 → 2026-12-27 | United Airlines | UA1708 + AC265 / UA5639 | $559.00 | 2026-10-29T01:53:34Z |
2026-12-21 → 2026-12-27 · $572.00
- United Airlines UA5438: ORD 2026-12-21 15:50:00 → YWG 2026-12-21 19:28:00; nonstop; 218 minutes. Local airport times.
- United Airlines UA5639: YWG 2026-12-27 15:15:00 → ORD 2026-12-27 16:50:00; nonstop; 95 minutes. Local airport times.
2026-12-21 → 2026-12-27 · $533.00
- Air Canada AC8904 / AC267: ORD 2026-12-21 12:50:00 → YWG 2026-12-21 20:09:00; 1 stop(s) via YYZ; 439 minutes. Local airport times.
- AC8904: ORD 2026-12-21 12:50:00 → YYZ 2026-12-21 15:33:00; layover at YYZ: 107 minutes.
- AC267: YYZ 2026-12-21 17:20:00 → YWG 2026-12-21 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; 338 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.
2026-12-21 → 2026-12-27 · $572.00
- Delta Air Lines DL1306 / DL3656: ORD 2026-12-21 17:42:00 → YWG 2026-12-22 00:33:00; 1 stop(s) via MSP; 411 minutes. Local airport times.
- DL1306: ORD 2026-12-21 17:42:00 → MSP 2026-12-21 19:14:00; layover at MSP: 155 minutes.
- DL3656: MSP 2026-12-21 21:49:00 → YWG 2026-12-22 00:33:00.
- Delta Air Lines DL3871 / DL1435: YWG 2026-12-27 13:38:00 → ORD 2026-12-27 19:45:00; 1 stop(s) via MSP; 367 minutes. Local airport times.
- DL3871: YWG 2026-12-27 13:38:00 → MSP 2026-12-27 14:10:00; layover at MSP: 225 minutes.
- DL1435: MSP 2026-12-27 17:55:00 → ORD 2026-12-27 19:45:00.
2026-12-21 → 2026-12-27 · $572.00
- United Airlines UA5475: ORD 2026-12-21 09:35:00 → YWG 2026-12-21 13:23:00; nonstop; 228 minutes. Local airport times.
- United Airlines UA5639: YWG 2026-12-27 15:15:00 → ORD 2026-12-27 16:50:00; nonstop; 95 minutes. Local airport times.
2026-12-21 → 2026-12-27 · $559.00
- United Airlines UA1708 / AC265: ORD 2026-12-21 07:03:00 → YWG 2026-12-21 14:49:00; 1 stop(s) via YYZ; 466 minutes. Local airport times.
- UA1708: ORD 2026-12-21 07:03:00 → YYZ 2026-12-21 09:47:00; layover at YYZ: 133 minutes.
- AC265: YYZ 2026-12-21 12:00:00 → YWG 2026-12-21 14:49:00.
- United Airlines UA5639: YWG 2026-12-27 15:15:00 → ORD 2026-12-27 16:50:00; nonstop; 95 minutes. Local airport times.
Explore this route
For AI assistants
- This page: Chicago (ORD) to Winnipeg (YWG) · Dec 21, 2026 · return Dec 27, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
- Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
- 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. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. 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_fallbackusing IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace/return/YYYY-MM-DDwith/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.