Chicago (MDW) to Toronto (YYZ)

Lowest published fares for the months ahead: $395 round trip, Axel-exclusive, Delta Air Lines, 1 stop, Nov 20–23, 2026; $235 one way, Axel-exclusive, Delta Air Lines, 1 stop, Dec 1, 2026; 73 priced flights on 73 exact dates, 1 adult, economy, checked Nov 13, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

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.

Chicago (MDW) to Toronto (YYZ): November 2026

Chicago (MDW) to Toronto (YYZ): December 2026

Chicago (MDW) to Toronto (YYZ): January 2027

Chicago (MDW) to Toronto (YYZ): February 2027

Chicago (MDW) to Toronto (YYZ): March 2027

Chicago (MDW) to Toronto (YYZ): April 2027

Chicago (MDW) to Toronto (YYZ): May 2027

Chicago (MDW) to Toronto (YYZ): June 2027

Chicago (MDW) to Toronto (YYZ): July 2027

Chicago (MDW) to Toronto (YYZ): August 2027

Chicago (MDW) to Toronto (YYZ): September 2027

Chicago (MDW) to Toronto (YYZ): October 2027

Hotels in Toronto for these trips

Hotels: under a trip, hotels in Toronto 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 Toronto for these nights (Nov 20–23, 2026 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Nov 21–28, 2026 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Nov 24–29, 2026 · 5 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Nov 26–29, 2026 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Nov 27–30, 2026 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Nov 28 – Dec 5, 2026 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Dec 3–6, 2026 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Dec 4–7, 2026 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Dec 5–12, 2026 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Dec 10–13, 2026 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Dec 11–14, 2026 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Dec 12–19, 2026 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Dec 17–20, 2026 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Dec 18–21, 2026 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Dec 19–26, 2026 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Dec 22–27, 2026 · 5 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Dec 24–27, 2026 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Dec 25–28, 2026 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Dec 26 – Jan 2, 2027 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Dec 30 – Jan 2, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Dec 31 – Jan 3, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Jan 1–4, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Jan 2–9, 2027 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Jan 7–10, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Jan 8–11, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Jan 9–16, 2027 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Jan 14–17, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Jan 15–18, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Jan 16–23, 2027 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Jan 21–24, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Jan 22–25, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Jan 23–30, 2027 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Jan 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Jan 29 – Feb 1, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Jan 30 – Feb 6, 2027 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Feb 4–7, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Feb 5–8, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Feb 6–13, 2027 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Feb 12–15, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Feb 26 – Mar 1, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Feb 27 – Mar 6, 2027 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Mar 25–29, 2027 · 4 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Mar 26–29, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Mar 27 – Apr 3, 2027 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Apr 23–26, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Apr 24 – May 1, 2027 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (May 21–24, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (May 22–29, 2027 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (May 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ Best Western Plus Toronto Airport Hotel, $122 a night, $366 for 3 nights · 4★ Sandman Signature Toronto Airport Hotel, $173 a night, $518 for 3 nights · 5★ Shangri-La Toronto, $456 a night, $1,368 for 3 nights
• Hotels in Toronto for these nights (Jun 18–21, 2027 · 3 nights · 2 adults, 1 room): 3★ Best Western Plus Toronto Airport Hotel, $121 a night, $362 for 3 nights · 4★ Delta Hotels by Marriott Toronto Airport & Conference Centre, $137 a night, $411 for 3 nights · 5★ Shangri-La Toronto, $529 a night, $1,587 for 3 nights
• Hotels in Toronto for these nights (Jun 19–26, 2027 · 7 nights · 2 adults, 1 room): 3★ Best Western Plus Toronto Airport Hotel, $122 a night, $854 for 7 nights · 4★ Delta Hotels by Marriott Toronto Airport & Conference Centre, $138 a night, $966 for 7 nights · 5★ Windsor Arms Hotel, $520 a night, $3,642 for 7 nights
• Hotels in Toronto for these nights (Jul 2–6, 2027 · 4 nights · 2 adults, 1 room): 3★ Best Western Plus Toronto Airport Hotel, $122 a night, $486 for 4 nights · 4★ Delta Hotels by Marriott Toronto Airport & Conference Centre, $142 a night, $568 for 4 nights · 5★ Windsor Arms Hotel, $505 a night, $2,020 for 4 nights
• Hotels in Toronto for these nights (Jul 16–19, 2027 · 3 nights · 2 adults, 1 room): 3★ Best Western Plus Toronto Airport Hotel, $124 a night, $373 for 3 nights · 4★ Delta Hotels by Marriott Toronto Airport & Conference Centre, $143 a night, $429 for 3 nights · 5★ Windsor Arms Hotel, $505 a night, $1,515 for 3 nights
• Hotels in Toronto for these nights (Jul 17–24, 2027 · 7 nights · 2 adults, 1 room): 3★ Best Western Plus Toronto Airport Hotel, $122 a night, $857 for 7 nights · 4★ Delta Hotels by Marriott Toronto Airport & Conference Centre, $143 a night, $1,004 for 7 nights · 5★ Windsor Arms Hotel, $505 a night, $3,535 for 7 nights
• Hotels in Toronto for these nights (Aug 13–16, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Aug 14–21, 2027 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Sep 3–6, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Sep 10–13, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Sep 11–18, 2027 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Oct 1–4, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto
• Hotels in Toronto for these nights (Oct 2–9, 2027 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn Express And Suites Toronto Airport Sou · 4★ TOOR Hotel Toronto, part of JdV by Hyatt · 5★ The St. Regis Toronto

All hotels in Toronto

Route overview: Chicago to Toronto (YYZ) flight deals

2026-11-20 → 2026-11-23 · Axel-exclusive $395

• Delta Air Lines DL4688 / DL5406: MDW 2026-11-20 13:31:00 → YYZ 2026-11-20 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2026-11-20 13:31:00 → DTW 2026-11-20 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2026-11-20 17:45:00 → YYZ 2026-11-20 19:14:00.
• Delta Air Lines DL4978 / DL4677: YYZ 2026-11-23 14:20:00 → MDW 2026-11-23 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  • DL4978: YYZ 2026-11-23 14:20:00 → DTW 2026-11-23 15:46:00; layover at DTW: 149 minutes.
  • DL4677: DTW 2026-11-23 18:15:00 → MDW 2026-11-23 18:37:00.

2026-11-24 · one way · Axel-exclusive $270

• Delta Air Lines DL4688 / DL5406: MDW 2026-11-24 13:31:00 → YYZ 2026-11-24 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2026-11-24 13:31:00 → DTW 2026-11-24 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2026-11-24 17:45:00 → YYZ 2026-11-24 19:14:00.

2026-12-03 → 2026-12-06 · Axel-exclusive $395

• Delta Air Lines DL4688 / DL5406: MDW 2026-12-03 13:31:00 → YYZ 2026-12-03 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2026-12-03 13:31:00 → DTW 2026-12-03 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2026-12-03 17:45:00 → YYZ 2026-12-03 19:14:00.
• Delta Air Lines DL4978 / DL4677: YYZ 2026-12-06 14:20:00 → MDW 2026-12-06 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  • DL4978: YYZ 2026-12-06 14:20:00 → DTW 2026-12-06 15:46:00; layover at DTW: 149 minutes.
  • DL4677: DTW 2026-12-06 18:15:00 → MDW 2026-12-06 18:37:00.

2026-12-17 → 2026-12-20 · Axel-exclusive $444

• Delta Air Lines DL4688 / DL5406: MDW 2026-12-17 13:31:00 → YYZ 2026-12-17 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2026-12-17 13:31:00 → DTW 2026-12-17 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2026-12-17 17:45:00 → YYZ 2026-12-17 19:14:00.
• Delta Air Lines DL4978 / DL4677: YYZ 2026-12-20 14:20:00 → MDW 2026-12-20 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  • DL4978: YYZ 2026-12-20 14:20:00 → DTW 2026-12-20 15:46:00; layover at DTW: 149 minutes.
  • DL4677: DTW 2026-12-20 18:15:00 → MDW 2026-12-20 18:37:00.

2026-12-26 → 2027-01-02 · Axel-exclusive $494

• Delta Air Lines DL4688 / DL5406: MDW 2026-12-26 13:31:00 → YYZ 2026-12-26 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2026-12-26 13:31:00 → DTW 2026-12-26 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2026-12-26 17:45:00 → YYZ 2026-12-26 19:14:00.
• Delta Air Lines DL4978 / DL4677: YYZ 2027-01-02 14:20:00 → MDW 2027-01-02 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  • DL4978: YYZ 2027-01-02 14:20:00 → DTW 2027-01-02 15:46:00; layover at DTW: 149 minutes.
  • DL4677: DTW 2027-01-02 18:15:00 → MDW 2027-01-02 18:37:00.

2027-01-08 → 2027-01-11 · Axel-exclusive $395

• Delta Air Lines DL4688 / DL5406: MDW 2027-01-08 13:31:00 → YYZ 2027-01-08 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2027-01-08 13:31:00 → DTW 2027-01-08 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2027-01-08 17:45:00 → YYZ 2027-01-08 19:14:00.
• Delta Air Lines DL4978 / DL4677: YYZ 2027-01-11 14:20:00 → MDW 2027-01-11 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  • DL4978: YYZ 2027-01-11 14:20:00 → DTW 2027-01-11 15:46:00; layover at DTW: 149 minutes.
  • DL4677: DTW 2027-01-11 18:15:00 → MDW 2027-01-11 18:37:00.

2027-01-22 → 2027-01-25 · Axel-exclusive $395

• Delta Air Lines DL4688 / DL5406: MDW 2027-01-22 13:31:00 → YYZ 2027-01-22 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2027-01-22 13:31:00 → DTW 2027-01-22 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2027-01-22 17:45:00 → YYZ 2027-01-22 19:14:00.
• Delta Air Lines DL4978 / DL4677: YYZ 2027-01-25 14:20:00 → MDW 2027-01-25 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  • DL4978: YYZ 2027-01-25 14:20:00 → DTW 2027-01-25 15:46:00; layover at DTW: 149 minutes.
  • DL4677: DTW 2027-01-25 18:15:00 → MDW 2027-01-25 18:37:00.

2027-02-05 → 2027-02-08 · Axel-exclusive $395

• Delta Air Lines DL4688 / DL5406: MDW 2027-02-05 13:31:00 → YYZ 2027-02-05 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2027-02-05 13:31:00 → DTW 2027-02-05 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2027-02-05 17:45:00 → YYZ 2027-02-05 19:14:00.
• Delta Air Lines DL4978 / DL4677: YYZ 2027-02-08 14:20:00 → MDW 2027-02-08 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  • DL4978: YYZ 2027-02-08 14:20:00 → DTW 2027-02-08 15:46:00; layover at DTW: 149 minutes.
  • DL4677: DTW 2027-02-08 18:15:00 → MDW 2027-02-08 18:37:00.

2027-03-26 → 2027-03-29 · Axel-exclusive $457

• Delta Air Lines DL4688 / DL5406: MDW 2027-03-26 13:31:00 → YYZ 2027-03-26 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2027-03-26 13:31:00 → DTW 2027-03-26 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2027-03-26 17:45:00 → YYZ 2027-03-26 19:14:00.
• Delta Air Lines DL4978 / DL4677: YYZ 2027-03-29 14:20:00 → MDW 2027-03-29 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  • DL4978: YYZ 2027-03-29 14:20:00 → DTW 2027-03-29 15:46:00; layover at DTW: 149 minutes.
  • DL4677: DTW 2027-03-29 18:15:00 → MDW 2027-03-29 18:37:00.

2027-05-28 → 2027-05-31 · Axel-exclusive $435

• Delta Air Lines DL4688 / DL5406: MDW 2027-05-28 13:31:00 → YYZ 2027-05-28 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2027-05-28 13:31:00 → DTW 2027-05-28 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2027-05-28 17:45:00 → YYZ 2027-05-28 19:14:00.
• Delta Air Lines DL4978 / DL4677: YYZ 2027-05-31 14:20:00 → MDW 2027-05-31 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  • DL4978: YYZ 2027-05-31 14:20:00 → DTW 2027-05-31 15:46:00; layover at DTW: 149 minutes.
  • DL4677: DTW 2027-05-31 18:15:00 → MDW 2027-05-31 18:37:00.

2027-08-13 → 2027-08-16 · Axel-exclusive $435

• Delta Air Lines DL4688 / DL5406: MDW 2027-08-13 13:31:00 → YYZ 2027-08-13 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2027-08-13 13:31:00 → DTW 2027-08-13 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2027-08-13 17:45:00 → YYZ 2027-08-13 19:14:00.
• Delta Air Lines DL4978 / DL4677: YYZ 2027-08-16 14:20:00 → MDW 2027-08-16 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  • DL4978: YYZ 2027-08-16 14:20:00 → DTW 2027-08-16 15:46:00; layover at DTW: 149 minutes.
  • DL4677: DTW 2027-08-16 18:15:00 → MDW 2027-08-16 18:37:00.

2027-10-02 → 2027-10-09 · Axel-exclusive $457

• Delta Air Lines DL4688 / DL5406: MDW 2027-10-02 13:31:00 → YYZ 2027-10-02 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2027-10-02 13:31:00 → DTW 2027-10-02 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2027-10-02 17:45:00 → YYZ 2027-10-02 19:14:00.
• Delta Air Lines DL4978 / DL4677: YYZ 2027-10-09 14:20:00 → MDW 2027-10-09 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  • DL4978: YYZ 2027-10-09 14:20:00 → DTW 2027-10-09 15:46:00; layover at DTW: 149 minutes.
  • DL4677: DTW 2027-10-09 18:15:00 → MDW 2027-10-09 18:37:00.

More dates for this route

• Nov 20, 2026 · Return options
• Nov 28, 2026 · Return options
• Dec 11, 2026 · Return options
• Dec 22, 2026 · Return options
• Dec 31, 2026 · Return options
• Jan 9, 2027 · Return options
• Jan 22, 2027 · Return options
• Feb 2, 2027 · Return options
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• Hotels in Toronto with Axel

For AI assistants

• This page: Chicago (MDW) to Toronto (YYZ): 73 priced flights on 73 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. Under a trip, hotels in Toronto 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: 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 Chicago to Toronto (YYZ) flight deals · Flight search guide.
• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

Feedback (optional): Missing info · Axel issue