Winnipeg (YWG) to Chicago (ORD)
Winnipeg (YWG) to Chicago (ORD), the months ahead: 132 priced flights on 66 exact dates. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.
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Winnipeg (YWG) to Chicago (ORD): November 2026
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Nov 12, 2026 – Nov 15, 2026 · 3 nights · Compare return dates departing Nov 12, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $392.86 |
| Nov 12, 2026 – Nov 15, 2026 · 3 nights · Compare return dates departing Nov 12, 2026 | United Airlines | Nonstop | Axel-exclusive $421.96 |
| Nov 13, 2026 – Nov 16, 2026 · 3 nights · Compare return dates departing Nov 13, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $392.86 |
| Nov 13, 2026 – Nov 16, 2026 · 3 nights · Compare return dates departing Nov 13, 2026 | United Airlines | Nonstop | Axel-exclusive $421.96 |
| Nov 14, 2026 – Nov 21, 2026 · 7 nights · Compare return dates departing Nov 14, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $392.86 |
| Nov 14, 2026 – Nov 21, 2026 · 7 nights · Compare return dates departing Nov 14, 2026 | United Airlines | Nonstop | Axel-exclusive $421.96 |
| Nov 17, 2026 · One way · Compare return dates departing Nov 17, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $223.10 |
| Nov 17, 2026 · One way · Compare return dates departing Nov 17, 2026 | United Airlines | Nonstop | Axel-exclusive $242.50 |
| Nov 19, 2026 – Nov 22, 2026 · 3 nights · Compare return dates departing Nov 19, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $392.86 |
| Nov 19, 2026 – Nov 22, 2026 · 3 nights · Compare return dates departing Nov 19, 2026 | United Airlines | Nonstop | Axel-exclusive $421.96 |
| Nov 20, 2026 – Nov 23, 2026 · 3 nights · Compare return dates departing Nov 20, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $392.86 |
| Nov 20, 2026 – Nov 23, 2026 · 3 nights · Compare return dates departing Nov 20, 2026 | United Airlines | Nonstop | Axel-exclusive $421.96 |
| Nov 21, 2026 – Nov 28, 2026 · 7 nights · Compare return dates departing Nov 21, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $427.28 |
| Nov 21, 2026 – Nov 28, 2026 · 7 nights · Compare return dates departing Nov 21, 2026 | United Airlines | Nonstop | Axel-exclusive $458.93 |
| Nov 24, 2026 · One way · Compare return dates departing Nov 24, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $262.20 |
| Nov 24, 2026 · One way · Compare return dates departing Nov 24, 2026 | United Airlines | Nonstop | Axel-exclusive $285.00 |
| Nov 26, 2026 – Nov 29, 2026 · 3 nights · Compare return dates departing Nov 26, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $461.70 |
| Nov 26, 2026 – Nov 29, 2026 · 3 nights · Compare return dates departing Nov 26, 2026 | United Airlines | Nonstop | Axel-exclusive $495.90 |
| Nov 27, 2026 – Nov 30, 2026 · 3 nights · Compare return dates departing Nov 27, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $461.70 |
| Nov 27, 2026 – Nov 30, 2026 · 3 nights · Compare return dates departing Nov 27, 2026 | United Airlines | Nonstop | Axel-exclusive $495.90 |
| Nov 28, 2026 – Dec 5, 2026 · 7 nights · Compare return dates departing Nov 28, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $433.35 |
| Nov 28, 2026 – Dec 5, 2026 · 7 nights · Compare return dates departing Nov 28, 2026 | United Airlines | Nonstop | Axel-exclusive $465.45 |
Winnipeg (YWG) to Chicago (ORD): December 2026
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Dec 1, 2026 · One way · Compare return dates departing Dec 1, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $230.00 |
| Dec 1, 2026 · One way · Compare return dates departing Dec 1, 2026 | United Airlines | Nonstop | Axel-exclusive $250.00 |
| Dec 3, 2026 – Dec 6, 2026 · 3 nights · Compare return dates departing Dec 3, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $405.00 |
| Dec 3, 2026 – Dec 6, 2026 · 3 nights · Compare return dates departing Dec 3, 2026 | United Airlines | Nonstop | Axel-exclusive $435.00 |
| Dec 4, 2026 – Dec 7, 2026 · 3 nights · Compare return dates departing Dec 4, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $405.00 |
| Dec 4, 2026 – Dec 7, 2026 · 3 nights · Compare return dates departing Dec 4, 2026 | United Airlines | Nonstop | Axel-exclusive $435.00 |
| Dec 5, 2026 – Dec 12, 2026 · 7 nights · Compare return dates departing Dec 5, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $405.00 |
| Dec 5, 2026 – Dec 12, 2026 · 7 nights · Compare return dates departing Dec 5, 2026 | United Airlines | Nonstop | Axel-exclusive $435.00 |
| Dec 8, 2026 · One way · Compare return dates departing Dec 8, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $230.00 |
| Dec 8, 2026 · One way · Compare return dates departing Dec 8, 2026 | United Airlines | Nonstop | Axel-exclusive $250.00 |
| Dec 10, 2026 – Dec 13, 2026 · 3 nights · Compare return dates departing Dec 10, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $405.00 |
| Dec 10, 2026 – Dec 13, 2026 · 3 nights · Compare return dates departing Dec 10, 2026 | United Airlines | Nonstop | Axel-exclusive $435.00 |
| Dec 11, 2026 – Dec 14, 2026 · 3 nights · Compare return dates departing Dec 11, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $405.00 |
| Dec 11, 2026 – Dec 14, 2026 · 3 nights · Compare return dates departing Dec 11, 2026 | United Airlines | Nonstop | Axel-exclusive $435.00 |
| Dec 12, 2026 – Dec 19, 2026 · 7 nights · Compare return dates departing Dec 12, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $465.75 |
| Dec 12, 2026 – Dec 19, 2026 · 7 nights · Compare return dates departing Dec 12, 2026 | United Airlines | Nonstop | Axel-exclusive $500.25 |
| Dec 15, 2026 · One way · Compare return dates departing Dec 15, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $230.00 |
| Dec 15, 2026 · One way · Compare return dates departing Dec 15, 2026 | United Airlines | Nonstop | Axel-exclusive $250.00 |
| Dec 17, 2026 – Dec 20, 2026 · 3 nights · Compare return dates departing Dec 17, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $465.75 |
| Dec 17, 2026 – Dec 20, 2026 · 3 nights · Compare return dates departing Dec 17, 2026 | United Airlines | Nonstop | Axel-exclusive $500.25 |
| Dec 18, 2026 – Dec 21, 2026 · 3 nights · Compare return dates departing Dec 18, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $465.75 |
| Dec 18, 2026 – Dec 21, 2026 · 3 nights · Compare return dates departing Dec 18, 2026 | United Airlines | Nonstop | Axel-exclusive $500.25 |
| Dec 19, 2026 – Dec 26, 2026 · 7 nights · Compare return dates departing Dec 19, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $526.50 |
| Dec 19, 2026 – Dec 26, 2026 · 7 nights · Compare return dates departing Dec 19, 2026 | United Airlines | Nonstop | Axel-exclusive $565.50 |
| Dec 22, 2026 · One way · Compare return dates departing Dec 22, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $299.00 |
| Dec 22, 2026 · One way · Compare return dates departing Dec 22, 2026 | United Airlines | Nonstop | Axel-exclusive $325.00 |
| Dec 24, 2026 – Dec 27, 2026 · 3 nights · Compare return dates departing Dec 24, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $526.50 |
| Dec 24, 2026 – Dec 27, 2026 · 3 nights · Compare return dates departing Dec 24, 2026 | United Airlines | Nonstop | Axel-exclusive $565.50 |
| Dec 25, 2026 – Dec 28, 2026 · 3 nights · Compare return dates departing Dec 25, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $526.50 |
| Dec 25, 2026 – Dec 28, 2026 · 3 nights · Compare return dates departing Dec 25, 2026 | United Airlines | Nonstop | Axel-exclusive $565.50 |
| Dec 26, 2026 – Jan 2, 2027 · 7 nights · Compare return dates departing Dec 26, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $512.33 |
| Dec 26, 2026 – Jan 2, 2027 · 7 nights · Compare return dates departing Dec 26, 2026 | United Airlines | Nonstop | Axel-exclusive $550.28 |
| Dec 29, 2026 · One way · Compare return dates departing Dec 29, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $299.00 |
| Dec 29, 2026 · One way · Compare return dates departing Dec 29, 2026 | United Airlines | Nonstop | Axel-exclusive $325.00 |
| Dec 31, 2026 – Jan 3, 2027 · 3 nights · Compare return dates departing Dec 31, 2026 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $512.33 |
| Dec 31, 2026 – Jan 3, 2027 · 3 nights · Compare return dates departing Dec 31, 2026 | United Airlines | Nonstop | Axel-exclusive $550.28 |
Winnipeg (YWG) to Chicago (ORD): January 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Jan 1, 2027 – Jan 4, 2027 · 3 nights · Compare return dates departing Jan 1, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $441.46 |
| Jan 1, 2027 – Jan 4, 2027 · 3 nights · Compare return dates departing Jan 1, 2027 | United Airlines | Nonstop | Axel-exclusive $474.16 |
| Jan 2, 2027 – Jan 9, 2027 · 7 nights · Compare return dates departing Jan 2, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $441.46 |
| Jan 2, 2027 – Jan 9, 2027 · 7 nights · Compare return dates departing Jan 2, 2027 | United Airlines | Nonstop | Axel-exclusive $474.16 |
| Jan 5, 2027 · One way · Compare return dates departing Jan 5, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $218.50 |
| Jan 5, 2027 · One way · Compare return dates departing Jan 5, 2027 | United Airlines | Nonstop | Axel-exclusive $237.50 |
| Jan 7, 2027 – Jan 10, 2027 · 3 nights · Compare return dates departing Jan 7, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $384.76 |
| Jan 7, 2027 – Jan 10, 2027 · 3 nights · Compare return dates departing Jan 7, 2027 | United Airlines | Nonstop | Axel-exclusive $413.26 |
| Jan 8, 2027 – Jan 11, 2027 · 3 nights · Compare return dates departing Jan 8, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $384.76 |
| Jan 8, 2027 – Jan 11, 2027 · 3 nights · Compare return dates departing Jan 8, 2027 | United Airlines | Nonstop | Axel-exclusive $413.26 |
| Jan 9, 2027 – Jan 16, 2027 · 7 nights · Compare return dates departing Jan 9, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $384.76 |
| Jan 9, 2027 – Jan 16, 2027 · 7 nights · Compare return dates departing Jan 9, 2027 | United Airlines | Nonstop | Axel-exclusive $413.26 |
| Jan 12, 2027 · One way · Compare return dates departing Jan 12, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $218.50 |
| Jan 12, 2027 · One way · Compare return dates departing Jan 12, 2027 | United Airlines | Nonstop | Axel-exclusive $237.50 |
| Jan 14, 2027 – Jan 17, 2027 · 3 nights · Compare return dates departing Jan 14, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $384.76 |
| Jan 14, 2027 – Jan 17, 2027 · 3 nights · Compare return dates departing Jan 14, 2027 | United Airlines | Nonstop | Axel-exclusive $413.26 |
| Jan 15, 2027 – Jan 18, 2027 · 3 nights · Compare return dates departing Jan 15, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $384.76 |
| Jan 15, 2027 – Jan 18, 2027 · 3 nights · Compare return dates departing Jan 15, 2027 | United Airlines | Nonstop | Axel-exclusive $413.26 |
| Jan 16, 2027 – Jan 23, 2027 · 7 nights · Compare return dates departing Jan 16, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $384.76 |
| Jan 16, 2027 – Jan 23, 2027 · 7 nights · Compare return dates departing Jan 16, 2027 | United Airlines | Nonstop | Axel-exclusive $413.26 |
| Jan 19, 2027 · One way · Compare return dates departing Jan 19, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $218.50 |
| Jan 19, 2027 · One way · Compare return dates departing Jan 19, 2027 | United Airlines | Nonstop | Axel-exclusive $237.50 |
| Jan 21, 2027 – Jan 24, 2027 · 3 nights · Compare return dates departing Jan 21, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $384.76 |
| Jan 21, 2027 – Jan 24, 2027 · 3 nights · Compare return dates departing Jan 21, 2027 | United Airlines | Nonstop | Axel-exclusive $413.26 |
| Jan 22, 2027 – Jan 25, 2027 · 3 nights · Compare return dates departing Jan 22, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $384.76 |
| Jan 22, 2027 – Jan 25, 2027 · 3 nights · Compare return dates departing Jan 22, 2027 | United Airlines | Nonstop | Axel-exclusive $413.26 |
| Jan 23, 2027 – Jan 30, 2027 · 7 nights · Compare return dates departing Jan 23, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $384.76 |
| Jan 23, 2027 – Jan 30, 2027 · 7 nights · Compare return dates departing Jan 23, 2027 | United Airlines | Nonstop | Axel-exclusive $413.26 |
| Jan 26, 2027 · One way · Compare return dates departing Jan 26, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $218.50 |
| Jan 26, 2027 · One way · Compare return dates departing Jan 26, 2027 | United Airlines | Nonstop | Axel-exclusive $237.50 |
| Jan 28, 2027 – Jan 31, 2027 · 3 nights · Compare return dates departing Jan 28, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $384.76 |
| Jan 28, 2027 – Jan 31, 2027 · 3 nights · Compare return dates departing Jan 28, 2027 | United Airlines | Nonstop | Axel-exclusive $413.26 |
| Jan 29, 2027 – Feb 1, 2027 · 3 nights · Compare return dates departing Jan 29, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $388.81 |
| Jan 29, 2027 – Feb 1, 2027 · 3 nights · Compare return dates departing Jan 29, 2027 | United Airlines | Nonstop | Axel-exclusive $417.61 |
| Jan 30, 2027 – Feb 6, 2027 · 7 nights · Compare return dates departing Jan 30, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $388.81 |
| Jan 30, 2027 – Feb 6, 2027 · 7 nights · Compare return dates departing Jan 30, 2027 | United Airlines | Nonstop | Axel-exclusive $417.61 |
Winnipeg (YWG) to Chicago (ORD): February 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Feb 2, 2027 · One way · Compare return dates departing Feb 2, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $223.10 |
| Feb 2, 2027 · One way · Compare return dates departing Feb 2, 2027 | United Airlines | Nonstop | Axel-exclusive $242.50 |
| Feb 12, 2027 – Feb 15, 2027 · 3 nights · Compare return dates departing Feb 12, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $392.86 |
| Feb 12, 2027 – Feb 15, 2027 · 3 nights · Compare return dates departing Feb 12, 2027 | United Airlines | Nonstop | Axel-exclusive $421.96 |
| Feb 13, 2027 – Feb 20, 2027 · 7 nights · Compare return dates departing Feb 13, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $392.86 |
| Feb 13, 2027 – Feb 20, 2027 · 7 nights · Compare return dates departing Feb 13, 2027 | United Airlines | Nonstop | Axel-exclusive $421.96 |
Winnipeg (YWG) to Chicago (ORD): March 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Mar 12, 2027 – Mar 15, 2027 · 3 nights · Compare return dates departing Mar 12, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $405.00 |
| Mar 12, 2027 – Mar 15, 2027 · 3 nights · Compare return dates departing Mar 12, 2027 | United Airlines | Nonstop | Axel-exclusive $435.00 |
| Mar 13, 2027 – Mar 20, 2027 · 7 nights · Compare return dates departing Mar 13, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $435.38 |
| Mar 13, 2027 – Mar 20, 2027 · 7 nights · Compare return dates departing Mar 13, 2027 | United Airlines | Nonstop | Axel-exclusive $467.63 |
Winnipeg (YWG) to Chicago (ORD): April 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Apr 9, 2027 – Apr 12, 2027 · 3 nights · Compare return dates departing Apr 9, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $460.00 |
| Apr 9, 2027 – Apr 12, 2027 · 3 nights · Compare return dates departing Apr 9, 2027 | United Airlines | Nonstop | Axel-exclusive $490.00 |
| Apr 10, 2027 – Apr 17, 2027 · 7 nights · Compare return dates departing Apr 10, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $460.00 |
| Apr 10, 2027 – Apr 17, 2027 · 7 nights · Compare return dates departing Apr 10, 2027 | United Airlines | Nonstop | Axel-exclusive $490.00 |
Winnipeg (YWG) to Chicago (ORD): May 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| May 7, 2027 – May 10, 2027 · 3 nights · Compare return dates departing May 7, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $460.00 |
| May 7, 2027 – May 10, 2027 · 3 nights · Compare return dates departing May 7, 2027 | United Airlines | Nonstop | Axel-exclusive $490.00 |
| May 8, 2027 – May 15, 2027 · 7 nights · Compare return dates departing May 8, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $460.00 |
| May 8, 2027 – May 15, 2027 · 7 nights · Compare return dates departing May 8, 2027 | United Airlines | Nonstop | Axel-exclusive $490.00 |
Winnipeg (YWG) to Chicago (ORD): June 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Jun 4, 2027 – Jun 7, 2027 · 3 nights · Compare return dates departing Jun 4, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $460.00 |
| Jun 4, 2027 – Jun 7, 2027 · 3 nights · Compare return dates departing Jun 4, 2027 | United Airlines | Nonstop | Axel-exclusive $490.00 |
| Jun 5, 2027 – Jun 12, 2027 · 7 nights · Compare return dates departing Jun 5, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $460.00 |
| Jun 5, 2027 – Jun 12, 2027 · 7 nights · Compare return dates departing Jun 5, 2027 | United Airlines | Nonstop | Axel-exclusive $490.00 |
Winnipeg (YWG) to Chicago (ORD): July 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Jul 2, 2027 – Jul 5, 2027 · 3 nights · Compare return dates departing Jul 2, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $547.40 |
| Jul 2, 2027 – Jul 5, 2027 · 3 nights · Compare return dates departing Jul 2, 2027 | United Airlines | Nonstop | Axel-exclusive $583.10 |
| Jul 3, 2027 – Jul 10, 2027 · 7 nights · Compare return dates departing Jul 3, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $512.90 |
| Jul 3, 2027 – Jul 10, 2027 · 7 nights · Compare return dates departing Jul 3, 2027 | United Airlines | Nonstop | Axel-exclusive $546.35 |
| Jul 30, 2027 – Aug 2, 2027 · 3 nights · Compare return dates departing Jul 30, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $476.10 |
| Jul 30, 2027 – Aug 2, 2027 · 3 nights · Compare return dates departing Jul 30, 2027 | United Airlines | Nonstop | Axel-exclusive $507.15 |
| Jul 31, 2027 – Aug 7, 2027 · 7 nights · Compare return dates departing Jul 31, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $476.10 |
| Jul 31, 2027 – Aug 7, 2027 · 7 nights · Compare return dates departing Jul 31, 2027 | United Airlines | Nonstop | Axel-exclusive $507.15 |
Winnipeg (YWG) to Chicago (ORD): August 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Aug 27, 2027 – Aug 30, 2027 · 3 nights · Compare return dates departing Aug 27, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $473.80 |
| Aug 27, 2027 – Aug 30, 2027 · 3 nights · Compare return dates departing Aug 27, 2027 | United Airlines | Nonstop | Axel-exclusive $504.70 |
| Aug 28, 2027 – Sep 4, 2027 · 7 nights · Compare return dates departing Aug 28, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $494.50 |
| Aug 28, 2027 – Sep 4, 2027 · 7 nights · Compare return dates departing Aug 28, 2027 | United Airlines | Nonstop | Axel-exclusive $526.75 |
Winnipeg (YWG) to Chicago (ORD): September 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Sep 17, 2027 – Sep 20, 2027 · 3 nights · Compare return dates departing Sep 17, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $460.00 |
| Sep 17, 2027 – Sep 20, 2027 · 3 nights · Compare return dates departing Sep 17, 2027 | United Airlines | Nonstop | Axel-exclusive $490.00 |
| Sep 18, 2027 – Sep 25, 2027 · 7 nights · Compare return dates departing Sep 18, 2027 | Delta Air Lines | Up to 1 stop each way | Axel-exclusive $460.00 |
| Sep 18, 2027 – Sep 25, 2027 · 7 nights · Compare return dates departing Sep 18, 2027 | United Airlines | Nonstop | Axel-exclusive $490.00 |
Route overview: Winnipeg to Chicago (ORD) flight deals
2026-11-12 → 2026-11-15 · Axel-exclusive $392.86
- Delta Air Lines DL3871 / DL1435: YWG 2026-11-12 13:38:00 → ORD 2026-11-12 19:45:00; 1 stop(s) via MSP; 427 minutes. Local airport times.
- DL3871: YWG 2026-11-12 13:38:00 → MSP 2026-11-12 14:10:00; layover at MSP: 225 minutes.
- DL1435: MSP 2026-11-12 17:55:00 → ORD 2026-11-12 19:45:00.
- Delta Air Lines DL1306 / DL3656: ORD 2026-11-15 17:42:00 → YWG 2026-11-16 00:33:00; 1 stop(s) via MSP; 351 minutes. Local airport times.
- DL1306: ORD 2026-11-15 17:42:00 → MSP 2026-11-15 19:14:00; layover at MSP: 155 minutes.
- DL3656: MSP 2026-11-15 21:49:00 → YWG 2026-11-16 00:33:00.
2026-11-12 → 2026-11-15 · Axel-exclusive $421.96
- United Airlines UA5639: YWG 2026-11-12 15:15:00 → ORD 2026-11-12 16:50:00; nonstop; 155 minutes. Local airport times.
- United Airlines UA5475: ORD 2026-11-15 09:35:00 → YWG 2026-11-15 13:23:00; nonstop; 168 minutes. Local airport times.
2026-11-17 · one way · Axel-exclusive $223.10
- Delta Air Lines DL3871 / DL1435: YWG 2026-11-17 13:38:00 → ORD 2026-11-17 19:45:00; 1 stop(s) via MSP; 427 minutes. Local airport times.
- DL3871: YWG 2026-11-17 13:38:00 → MSP 2026-11-17 14:10:00; layover at MSP: 225 minutes.
- DL1435: MSP 2026-11-17 17:55:00 → ORD 2026-11-17 19:45:00.
2026-11-17 · one way · Axel-exclusive $242.50
- United Airlines UA5639: YWG 2026-11-17 15:15:00 → ORD 2026-11-17 16:50:00; nonstop; 155 minutes. Local airport times.
2026-11-21 → 2026-11-28 · Axel-exclusive $427.28
- Delta Air Lines DL3871 / DL1435: YWG 2026-11-21 13:38:00 → ORD 2026-11-21 19:45:00; 1 stop(s) via MSP; 427 minutes. Local airport times.
- DL3871: YWG 2026-11-21 13:38:00 → MSP 2026-11-21 14:10:00; layover at MSP: 225 minutes.
- DL1435: MSP 2026-11-21 17:55:00 → ORD 2026-11-21 19:45:00.
- Delta Air Lines DL1306 / DL3656: ORD 2026-11-28 17:42:00 → YWG 2026-11-29 00:33:00; 1 stop(s) via MSP; 351 minutes. Local airport times.
- DL1306: ORD 2026-11-28 17:42:00 → MSP 2026-11-28 19:14:00; layover at MSP: 155 minutes.
- DL3656: MSP 2026-11-28 21:49:00 → YWG 2026-11-29 00:33:00.
2026-11-21 → 2026-11-28 · Axel-exclusive $458.93
- United Airlines UA5639: YWG 2026-11-21 15:15:00 → ORD 2026-11-21 16:50:00; nonstop; 155 minutes. Local airport times.
- United Airlines UA5475: ORD 2026-11-28 10:00:00 → YWG 2026-11-28 13:52:00; nonstop; 172 minutes. Local airport times.
2026-12-04 → 2026-12-07 · Axel-exclusive $405.00
- Delta Air Lines DL3871 / DL1435: YWG 2026-12-04 13:38:00 → ORD 2026-12-04 19:45:00; 1 stop(s) via MSP; 427 minutes. Local airport times.
- DL3871: YWG 2026-12-04 13:38:00 → MSP 2026-12-04 14:10:00; layover at MSP: 225 minutes.
- DL1435: MSP 2026-12-04 17:55:00 → ORD 2026-12-04 19:45:00.
- Delta Air Lines DL1306 / DL3656: ORD 2026-12-07 17:42:00 → YWG 2026-12-08 00:33:00; 1 stop(s) via MSP; 351 minutes. Local airport times.
- DL1306: ORD 2026-12-07 17:42:00 → MSP 2026-12-07 19:14:00; layover at MSP: 155 minutes.
- DL3656: MSP 2026-12-07 21:49:00 → YWG 2026-12-08 00:33:00.
2026-12-04 → 2026-12-07 · Axel-exclusive $435.00
- United Airlines UA5639: YWG 2026-12-04 15:15:00 → ORD 2026-12-04 17:00:00; nonstop; 165 minutes. Local airport times.
- United Airlines UA5475: ORD 2026-12-07 10:00:00 → YWG 2026-12-07 13:52:00; nonstop; 172 minutes. Local airport times.
2026-12-17 → 2026-12-20 · Axel-exclusive $465.75
- Delta Air Lines DL3871 / DL1435: YWG 2026-12-17 13:38:00 → ORD 2026-12-17 19:45:00; 1 stop(s) via MSP; 427 minutes. Local airport times.
- DL3871: YWG 2026-12-17 13:38:00 → MSP 2026-12-17 14:10:00; layover at MSP: 225 minutes.
- DL1435: MSP 2026-12-17 17:55:00 → ORD 2026-12-17 19:45:00.
- Delta Air Lines DL1306 / DL3656: ORD 2026-12-20 17:42:00 → YWG 2026-12-21 00:33:00; 1 stop(s) via MSP; 351 minutes. Local airport times.
- DL1306: ORD 2026-12-20 17:42:00 → MSP 2026-12-20 19:14:00; layover at MSP: 155 minutes.
- DL3656: MSP 2026-12-20 21:49:00 → YWG 2026-12-21 00:33:00.
2026-12-17 → 2026-12-20 · Axel-exclusive $500.25
- United Airlines UA5639: YWG 2026-12-17 15:15:00 → ORD 2026-12-17 17:02:00; nonstop; 167 minutes. Local airport times.
- United Airlines UA5475: ORD 2026-12-20 10:00:00 → YWG 2026-12-20 13:52:00; nonstop; 172 minutes. Local airport times.
2026-12-31 → 2027-01-03 · Axel-exclusive $512.33
- Delta Air Lines DL3871 / DL1435: YWG 2026-12-31 13:38:00 → ORD 2026-12-31 19:45:00; 1 stop(s) via MSP; 427 minutes. Local airport times.
- DL3871: YWG 2026-12-31 13:38:00 → MSP 2026-12-31 14:10:00; layover at MSP: 225 minutes.
- DL1435: MSP 2026-12-31 17:55:00 → ORD 2026-12-31 19:45:00.
- Delta Air Lines DL1306 / DL3656: ORD 2027-01-03 17:42:00 → YWG 2027-01-04 00:33:00; 1 stop(s) via MSP; 351 minutes. Local airport times.
- DL1306: ORD 2027-01-03 17:42:00 → MSP 2027-01-03 19:14:00; layover at MSP: 155 minutes.
- DL3656: MSP 2027-01-03 21:49:00 → YWG 2027-01-04 00:33:00.
2026-12-31 → 2027-01-03 · Axel-exclusive $550.28
- United Airlines UA5639: YWG 2026-12-31 15:15:00 → ORD 2026-12-31 17:02:00; nonstop; 167 minutes. Local airport times.
- United Airlines UA5438: ORD 2027-01-03 15:50:00 → YWG 2027-01-03 19:28:00; nonstop; 158 minutes. Local airport times.
2027-01-09 → 2027-01-16 · Axel-exclusive $384.76
- Delta Air Lines DL3871 / DL1435: YWG 2027-01-09 13:38:00 → ORD 2027-01-09 19:45:00; 1 stop(s) via MSP; 427 minutes. Local airport times.
- DL3871: YWG 2027-01-09 13:38:00 → MSP 2027-01-09 14:10:00; layover at MSP: 225 minutes.
- DL1435: MSP 2027-01-09 17:55:00 → ORD 2027-01-09 19:45:00.
- Delta Air Lines DL1306 / DL3656: ORD 2027-01-16 17:42:00 → YWG 2027-01-17 00:33:00; 1 stop(s) via MSP; 351 minutes. Local airport times.
- DL1306: ORD 2027-01-16 17:42:00 → MSP 2027-01-16 19:14:00; layover at MSP: 155 minutes.
- DL3656: MSP 2027-01-16 21:49:00 → YWG 2027-01-17 00:33:00.
2027-01-09 → 2027-01-16 · Axel-exclusive $399.00
- Air Canada AC264 / AC8909: YWG 2027-01-09 12:05:00 → ORD 2027-01-09 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times.
- AC264: YWG 2027-01-09 12:05:00 → YYZ 2027-01-09 14:35:00; layover at YYZ: 115 minutes.
- AC8909: YYZ 2027-01-09 16:30:00 → ORD 2027-01-09 17:43:00.
- Air Canada AC8904 / AC267: ORD 2027-01-16 12:50:00 → YWG 2027-01-16 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
- AC8904: ORD 2027-01-16 12:50:00 → YYZ 2027-01-16 15:33:00; layover at YYZ: 107 minutes.
- AC267: YYZ 2027-01-16 17:20:00 → YWG 2027-01-16 20:09:00.
2027-01-22 → 2027-01-25 · Axel-exclusive $399.00
- Air Canada AC264 / AC8909: YWG 2027-01-22 12:05:00 → ORD 2027-01-22 17:43:00; 1 stop(s) via YYZ; 398 minutes. Local airport times.
- AC264: YWG 2027-01-22 12:05:00 → YYZ 2027-01-22 14:35:00; layover at YYZ: 115 minutes.
- AC8909: YYZ 2027-01-22 16:30:00 → ORD 2027-01-22 17:43:00.
- Air Canada AC8904 / AC267: ORD 2027-01-25 12:50:00 → YWG 2027-01-25 20:09:00; 1 stop(s) via YYZ; 379 minutes. Local airport times.
- AC8904: ORD 2027-01-25 12:50:00 → YYZ 2027-01-25 15:33:00; layover at YYZ: 107 minutes.
- AC267: YYZ 2027-01-25 17:20:00 → YWG 2027-01-25 20:09:00.
2027-01-22 → 2027-01-25 · Axel-exclusive $413.26
- United Airlines UA5639: YWG 2027-01-22 15:15:00 → ORD 2027-01-22 17:02:00; nonstop; 167 minutes. Local airport times.
- United Airlines UA5475: ORD 2027-01-25 10:00:00 → YWG 2027-01-25 13:52:00; nonstop; 172 minutes. Local airport times.
2027-02-13 → 2027-02-20 · Axel-exclusive $392.86
- Delta Air Lines DL3871 / DL1435: YWG 2027-02-13 13:38:00 → ORD 2027-02-13 19:45:00; 1 stop(s) via MSP; 427 minutes. Local airport times.
- DL3871: YWG 2027-02-13 13:38:00 → MSP 2027-02-13 14:10:00; layover at MSP: 225 minutes.
- DL1435: MSP 2027-02-13 17:55:00 → ORD 2027-02-13 19:45:00.
- Delta Air Lines DL1306 / DL3656: ORD 2027-02-20 17:42:00 → YWG 2027-02-21 00:33:00; 1 stop(s) via MSP; 351 minutes. Local airport times.
- DL1306: ORD 2027-02-20 17:42:00 → MSP 2027-02-20 19:14:00; layover at MSP: 155 minutes.
- DL3656: MSP 2027-02-20 21:49:00 → YWG 2027-02-21 00:33:00.
2027-02-13 → 2027-02-20 · Axel-exclusive $421.96
- United Airlines UA5639: YWG 2027-02-13 15:15:00 → ORD 2027-02-13 17:02:00; nonstop; 167 minutes. Local airport times.
- United Airlines UA5438: ORD 2027-02-20 15:50:00 → YWG 2027-02-20 19:28:00; nonstop; 158 minutes. Local airport times.
2027-05-07 → 2027-05-10 · Axel-exclusive $460.00
- Delta Air Lines DL3871 / DL1435: YWG 2027-05-07 13:38:00 → ORD 2027-05-07 20:45:00; 1 stop(s) via MSP; 427 minutes. Local airport times.
- DL3871: YWG 2027-05-07 13:38:00 → MSP 2027-05-07 15:10:00; layover at MSP: 225 minutes.
- DL1435: MSP 2027-05-07 18:55:00 → ORD 2027-05-07 20:45:00.
- Delta Air Lines DL1306 / DL3656: ORD 2027-05-10 17:42:00 → YWG 2027-05-10 23:33:00; 1 stop(s) via MSP; 351 minutes. Local airport times.
- DL1306: ORD 2027-05-10 17:42:00 → MSP 2027-05-10 19:14:00; layover at MSP: 155 minutes.
- DL3656: MSP 2027-05-10 21:49:00 → YWG 2027-05-10 23:33:00.
2027-05-07 → 2027-05-10 · Axel-exclusive $490.00
- United Airlines UA5639: YWG 2027-05-07 15:15:00 → ORD 2027-05-07 18:02:00; nonstop; 167 minutes. Local airport times.
- United Airlines UA5475: ORD 2027-05-10 10:00:00 → YWG 2027-05-10 12:52:00; nonstop; 172 minutes. Local airport times.
2027-07-03 → 2027-07-10 · Axel-exclusive $512.90
- Delta Air Lines DL3871 / DL1435: YWG 2027-07-03 13:38:00 → ORD 2027-07-03 20:45:00; 1 stop(s) via MSP; 427 minutes. Local airport times.
- DL3871: YWG 2027-07-03 13:38:00 → MSP 2027-07-03 15:10:00; layover at MSP: 225 minutes.
- DL1435: MSP 2027-07-03 18:55:00 → ORD 2027-07-03 20:45:00.
- Delta Air Lines DL1306 / DL3656: ORD 2027-07-10 17:42:00 → YWG 2027-07-10 23:33:00; 1 stop(s) via MSP; 351 minutes. Local airport times.
- DL1306: ORD 2027-07-10 17:42:00 → MSP 2027-07-10 19:14:00; layover at MSP: 155 minutes.
- DL3656: MSP 2027-07-10 21:49:00 → YWG 2027-07-10 23:33:00.
2027-07-03 → 2027-07-10 · Axel-exclusive $546.35
- United Airlines UA5639: YWG 2027-07-03 15:15:00 → ORD 2027-07-03 18:02:00; nonstop; 167 minutes. Local airport times.
- United Airlines UA5438: ORD 2027-07-10 15:50:00 → YWG 2027-07-10 18:28:00; nonstop; 158 minutes. Local airport times.
2027-09-18 → 2027-09-25 · Axel-exclusive $460.00
- Delta Air Lines DL3871 / DL1435: YWG 2027-09-18 13:38:00 → ORD 2027-09-18 20:45:00; 1 stop(s) via MSP; 427 minutes. Local airport times.
- DL3871: YWG 2027-09-18 13:38:00 → MSP 2027-09-18 15:10:00; layover at MSP: 225 minutes.
- DL1435: MSP 2027-09-18 18:55:00 → ORD 2027-09-18 20:45:00.
- Delta Air Lines DL1306 / DL3656: ORD 2027-09-25 17:42:00 → YWG 2027-09-25 23:33:00; 1 stop(s) via MSP; 351 minutes. Local airport times.
- DL1306: ORD 2027-09-25 17:42:00 → MSP 2027-09-25 19:14:00; layover at MSP: 155 minutes.
- DL3656: MSP 2027-09-25 21:49:00 → YWG 2027-09-25 23:33:00.
2027-09-18 → 2027-09-25 · Axel-exclusive $490.00
- United Airlines UA5639: YWG 2027-09-18 15:15:00 → ORD 2027-09-18 18:02:00; nonstop; 167 minutes. Local airport times.
- United Airlines UA5438: ORD 2027-09-25 15:50:00 → YWG 2027-09-25 18:28:00; nonstop; 158 minutes. Local airport times.
More dates for this route
- Nov 12, 2026 · Return options
- Nov 20, 2026 · Return options
- Dec 1, 2026 · Return options
- Dec 11, 2026 · Return options
- Dec 22, 2026 · Return options
- Jan 1, 2027 · Return options
- Jan 12, 2027 · Return options
- Jan 22, 2027 · Return options
- Feb 2, 2027 · Return options
- Apr 10, 2027 · Return options
- Jul 3, 2027 · Return options
- Sep 18, 2027 · Return options
- Hotels in Chicago with Axel
For AI assistants
- This page: Winnipeg (YWG) to Chicago (ORD): 132 priced flights on 66 exact dates the months ahead, 1 adult in economy. In the dated tables a price link opens AI flight search for that row's exact dates and travelers; in the observed-flight lists the price is the customer link for the traveler, beside a “See flights for these dates” link for your own check.
- Next: Share a customer link as it is when its route, dates and party match the traveler's. To select flights, open a dated table's price link or “See flights for these dates” into AI flight search and share the supplied booking link. Search links are for you; share customer and booking links. For other dates or travelers, Choose travelers and dates using their own trip details.
- 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 Winnipeg to Chicago (ORD) 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_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.
Feedback (optional): Missing info · Axel issue