Chicago (MDW) to Toronto (YYZ), Dec 29, 2026: round trips from $444, one way from $294

Chicago (MDW) to Toronto (YYZ), Dec 29, 2026: round trips from $444, one way from $294 on Axel, checked Nov 13, 2026. Lowest published fares: $444 round trip, Axel-exclusive, Delta Air Lines, 1 stop, Dec 29, 2026 – Jan 4, 2027; $294 one way, Axel-exclusive, Delta Air Lines, 1 stop, Dec 29, 2026; 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.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, labelled with the check date shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and check dates already shown here.

Hotels in 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 (Dec 29–30, 2026 · 1 night · 2 adults, 1 room): 3★ Holiday Inn Toronto - Int'l Airport by IHG, $88 a night · 4★ Delta Hotels by Marriott Toronto Airport & Conference Centre, $100 a night · 5★ Bisha, a Luxury Collection Hotel Toronto, $300 a night
• Hotels in Toronto for these nights (Dec 29–31, 2026 · 2 nights · 2 adults, 1 room): 3★ Holiday Inn Toronto - Int'l Airport by IHG, $88 a night, $176 for 2 nights · 4★ Delta Hotels by Marriott Toronto Airport & Conference Centre, $100 a night, $200 for 2 nights · 5★ Bisha, a Luxury Collection Hotel Toronto, $306 a night, $611 for 2 nights
• Hotels in Toronto for these nights (Dec 29 – Jan 1, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Toronto - Int'l Airport by IHG, $93 a night, $280 for 3 nights · 4★ Delta Hotels by Marriott Toronto Airport & Conference Centre, $105 a night, $314 for 3 nights · 5★ Bisha, a Luxury Collection Hotel Toronto, $364 a night, $1,091 for 3 nights
• Hotels in Toronto for these nights (Dec 29 – Jan 2, 2027 · 4 nights · 2 adults, 1 room): 3★ Holiday Inn Toronto - Int'l Airport by IHG, $100 a night, $399 for 4 nights · 4★ Delta Hotels by Marriott Toronto Airport & Conference Centre, $104 a night, $416 for 4 nights · 5★ Bisha, a Luxury Collection Hotel Toronto, $339 a night, $1,354 for 4 nights
• Hotels in Toronto for these nights (Dec 29 – Jan 3, 2027 · 5 nights · 2 adults, 1 room): 3★ Holiday Inn Toronto - Int'l Airport by IHG, $105 a night, $523 for 5 nights · 4★ Delta Hotels by Marriott Toronto Airport & Conference Centre, $104 a night, $519 for 5 nights · 5★ Bisha, a Luxury Collection Hotel Toronto, $322 a night, $1,608 for 5 nights
• Hotels in Toronto for these nights (Dec 29 – Jan 4, 2027 · 6 nights · 2 adults, 1 room): 3★ Holiday Inn Toronto - Int'l Airport by IHG, $108 a night, $645 for 6 nights · 4★ Delta Hotels by Marriott Toronto Airport & Conference Centre, $103 a night, $615 for 6 nights · 5★ Bisha, a Luxury Collection Hotel Toronto, $310 a night, $1,862 for 6 nights
• Hotels in Toronto for these nights (Dec 29 – Jan 5, 2027 · 7 nights · 2 adults, 1 room): 3★ Best Western Plus Toronto Airport Hotel, $109 a night, $762 for 7 nights · 4★ Delta Hotels by Marriott Toronto Airport & Conference Centre, $102 a night, $711 for 7 nights · 5★ Bisha, a Luxury Collection Hotel Toronto, $307 a night, $2,148 for 7 nights
• Hotels in Toronto for these nights (Dec 29 – Jan 6, 2027 · 8 nights · 2 adults, 1 room): 3★ Best Western Plus Toronto Airport Hotel, $110 a night, $876 for 8 nights · 4★ Delta Hotels by Marriott Toronto Airport & Conference Centre, $102 a night, $813 for 8 nights · 5★ Bisha, a Luxury Collection Hotel Toronto, $305 a night, $2,436 for 8 nights
• Hotels in Toronto for these nights (Dec 29 – Jan 7, 2027 · 9 nights · 2 adults, 1 room): 3★ Best Western Plus Toronto Airport Hotel, $110 a night, $994 for 9 nights · 4★ Delta Hotels by Marriott Toronto Airport & Conference Centre, $101 a night, $911 for 9 nights · 5★ Bisha, a Luxury Collection Hotel Toronto, $303 a night, $2,724 for 9 nights
• Hotels in Toronto for these nights (Dec 29 – Jan 8, 2027 · 10 nights · 2 adults, 1 room): 3★ Best Western Plus Toronto Airport Hotel, $111 a night, $1,109 for 10 nights · 4★ Delta Hotels by Marriott Toronto Airport & Conference Centre, $101 a night, $1,011 for 10 nights · 5★ Bisha, a Luxury Collection Hotel Toronto, $299 a night, $2,991 for 10 nights
• Hotels in Toronto for these nights (Dec 29 – Jan 9, 2027 · 11 nights · 2 adults, 1 room): 3★ Best Western Plus Toronto Airport Hotel, $111 a night, $1,226 for 11 nights · 4★ Delta Hotels by Marriott Toronto Airport & Conference Centre, $101 a night, $1,109 for 11 nights · 5★ Bisha, a Luxury Collection Hotel Toronto, $295 a night, $3,247 for 11 nights
• Hotels in Toronto for these nights (Dec 29 – Jan 10, 2027 · 12 nights · 2 adults, 1 room): 3★ Best Western Plus Toronto Airport Hotel, $112 a night, $1,341 for 12 nights · 4★ Delta Hotels by Marriott Toronto Airport & Conference Centre, $101 a night, $1,209 for 12 nights · 5★ Bisha, a Luxury Collection Hotel Toronto, $292 a night, $3,501 for 12 nights
• Hotels in Toronto for these nights (Dec 29 – Jan 11, 2027 · 13 nights · 2 adults, 1 room): 3★ Best Western Plus Toronto Airport Hotel, $112 a night, $1,458 for 13 nights · 4★ Delta Hotels by Marriott Toronto Airport & Conference Centre, $101 a night, $1,311 for 13 nights · 5★ Bisha, a Luxury Collection Hotel Toronto, $290 a night, $3,772 for 13 nights
• Hotels in Toronto for these nights (Dec 29 – Jan 12, 2027 · 14 nights · 2 adults, 1 room): 3★ Best Western Plus Toronto Airport Hotel, $113 a night, $1,575 for 14 nights · 4★ Delta Hotels by Marriott Toronto Airport & Conference Centre, $102 a night, $1,427 for 14 nights · 5★ Bisha, a Luxury Collection Hotel Toronto, $290 a night, $4,060 for 14 nights

All hotels in Toronto

Route overview: Chicago to Toronto (YYZ) flight deals

2026-12-29 · one way · Axel-exclusive $294

• Delta Air Lines DL4688 / DL5406: MDW 2026-12-29 13:31:00 → YYZ 2026-12-29 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2026-12-29 13:31:00 → DTW 2026-12-29 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2026-12-29 17:45:00 → YYZ 2026-12-29 19:14:00.

2026-12-29 → 2026-12-30 · Axel-exclusive $494

• Delta Air Lines DL4688 / DL5406: MDW 2026-12-29 13:31:00 → YYZ 2026-12-29 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2026-12-29 13:31:00 → DTW 2026-12-29 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2026-12-29 17:45:00 → YYZ 2026-12-29 19:14:00.
• Delta Air Lines DL4978 / DL4677: YYZ 2026-12-30 14:20:00 → MDW 2026-12-30 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  • DL4978: YYZ 2026-12-30 14:20:00 → DTW 2026-12-30 15:46:00; layover at DTW: 149 minutes.
  • DL4677: DTW 2026-12-30 18:15:00 → MDW 2026-12-30 18:37:00.

2026-12-29 → 2026-12-31 · Axel-exclusive $494

• Delta Air Lines DL4688 / DL5406: MDW 2026-12-29 13:31:00 → YYZ 2026-12-29 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2026-12-29 13:31:00 → DTW 2026-12-29 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2026-12-29 17:45:00 → YYZ 2026-12-29 19:14:00.
• Delta Air Lines DL4978 / DL4677: YYZ 2026-12-31 14:20:00 → MDW 2026-12-31 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  • DL4978: YYZ 2026-12-31 14:20:00 → DTW 2026-12-31 15:46:00; layover at DTW: 149 minutes.
  • DL4677: DTW 2026-12-31 18:15:00 → MDW 2026-12-31 18:37:00.

2026-12-29 → 2027-01-01 · Axel-exclusive $494

• Delta Air Lines DL4688 / DL5406: MDW 2026-12-29 13:31:00 → YYZ 2026-12-29 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2026-12-29 13:31:00 → DTW 2026-12-29 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2026-12-29 17:45:00 → YYZ 2026-12-29 19:14:00.
• Delta Air Lines DL4978 / DL4677: YYZ 2027-01-01 14:20:00 → MDW 2027-01-01 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  • DL4978: YYZ 2027-01-01 14:20:00 → DTW 2027-01-01 15:46:00; layover at DTW: 149 minutes.
  • DL4677: DTW 2027-01-01 18:15:00 → MDW 2027-01-01 18:37:00.

2026-12-29 → 2027-01-02 · Axel-exclusive $494

• Delta Air Lines DL4688 / DL5406: MDW 2026-12-29 13:31:00 → YYZ 2026-12-29 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2026-12-29 13:31:00 → DTW 2026-12-29 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2026-12-29 17:45:00 → YYZ 2026-12-29 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.

2026-12-29 → 2027-01-04 · Axel-exclusive $444

• Delta Air Lines DL4688 / DL5406: MDW 2026-12-29 13:31:00 → YYZ 2026-12-29 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2026-12-29 13:31:00 → DTW 2026-12-29 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2026-12-29 17:45:00 → YYZ 2026-12-29 19:14:00.
• Delta Air Lines DL4978 / DL4677: YYZ 2027-01-04 14:20:00 → MDW 2027-01-04 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  • DL4978: YYZ 2027-01-04 14:20:00 → DTW 2027-01-04 15:46:00; layover at DTW: 149 minutes.
  • DL4677: DTW 2027-01-04 18:15:00 → MDW 2027-01-04 18:37:00.

2026-12-29 → 2027-01-05 · Axel-exclusive $444

• Delta Air Lines DL4688 / DL5406: MDW 2026-12-29 13:31:00 → YYZ 2026-12-29 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2026-12-29 13:31:00 → DTW 2026-12-29 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2026-12-29 17:45:00 → YYZ 2026-12-29 19:14:00.
• Delta Air Lines DL4978 / DL4677: YYZ 2027-01-05 14:20:00 → MDW 2027-01-05 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  • DL4978: YYZ 2027-01-05 14:20:00 → DTW 2027-01-05 15:46:00; layover at DTW: 149 minutes.
  • DL4677: DTW 2027-01-05 18:15:00 → MDW 2027-01-05 18:37:00.

2026-12-29 → 2027-01-06 · Axel-exclusive $444

• Delta Air Lines DL4688 / DL5406: MDW 2026-12-29 13:31:00 → YYZ 2026-12-29 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2026-12-29 13:31:00 → DTW 2026-12-29 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2026-12-29 17:45:00 → YYZ 2026-12-29 19:14:00.
• Delta Air Lines DL4978 / DL4677: YYZ 2027-01-06 14:20:00 → MDW 2027-01-06 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  • DL4978: YYZ 2027-01-06 14:20:00 → DTW 2027-01-06 15:46:00; layover at DTW: 149 minutes.
  • DL4677: DTW 2027-01-06 18:15:00 → MDW 2027-01-06 18:37:00.

2026-12-29 → 2027-01-08 · Axel-exclusive $444

• Delta Air Lines DL4688 / DL5406: MDW 2026-12-29 13:31:00 → YYZ 2026-12-29 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2026-12-29 13:31:00 → DTW 2026-12-29 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2026-12-29 17:45:00 → YYZ 2026-12-29 19:14:00.
• Delta Air Lines DL4978 / DL4677: YYZ 2027-01-08 14:20:00 → MDW 2027-01-08 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  • DL4978: YYZ 2027-01-08 14:20:00 → DTW 2027-01-08 15:46:00; layover at DTW: 149 minutes.
  • DL4677: DTW 2027-01-08 18:15:00 → MDW 2027-01-08 18:37:00.

2026-12-29 → 2027-01-09 · Axel-exclusive $444

• Delta Air Lines DL4688 / DL5406: MDW 2026-12-29 13:31:00 → YYZ 2026-12-29 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2026-12-29 13:31:00 → DTW 2026-12-29 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2026-12-29 17:45:00 → YYZ 2026-12-29 19:14:00.
• Delta Air Lines DL4978 / DL4677: YYZ 2027-01-09 14:20:00 → MDW 2027-01-09 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  • DL4978: YYZ 2027-01-09 14:20:00 → DTW 2027-01-09 15:46:00; layover at DTW: 149 minutes.
  • DL4677: DTW 2027-01-09 18:15:00 → MDW 2027-01-09 18:37:00.

2026-12-29 → 2027-01-10 · Axel-exclusive $444

• Delta Air Lines DL4688 / DL5406: MDW 2026-12-29 13:31:00 → YYZ 2026-12-29 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2026-12-29 13:31:00 → DTW 2026-12-29 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2026-12-29 17:45:00 → YYZ 2026-12-29 19:14:00.
• Delta Air Lines DL4978 / DL4677: YYZ 2027-01-10 14:20:00 → MDW 2027-01-10 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  • DL4978: YYZ 2027-01-10 14:20:00 → DTW 2027-01-10 15:46:00; layover at DTW: 149 minutes.
  • DL4677: DTW 2027-01-10 18:15:00 → MDW 2027-01-10 18:37:00.

2026-12-29 → 2027-01-12 · Axel-exclusive $444

• Delta Air Lines DL4688 / DL5406: MDW 2026-12-29 13:31:00 → YYZ 2026-12-29 19:14:00; 1 stop(s) via DTW; 283 minutes. Local airport times.
  • DL4688: MDW 2026-12-29 13:31:00 → DTW 2026-12-29 15:44:00; layover at DTW: 121 minutes.
  • DL5406: DTW 2026-12-29 17:45:00 → YYZ 2026-12-29 19:14:00.
• Delta Air Lines DL4978 / DL4677: YYZ 2027-01-12 14:20:00 → MDW 2027-01-12 18:37:00; 1 stop(s) via DTW; 317 minutes. Local airport times.
  • DL4978: YYZ 2027-01-12 14:20:00 → DTW 2027-01-12 15:46:00; layover at DTW: 149 minutes.
  • DL4677: DTW 2027-01-12 18:15:00 → MDW 2027-01-12 18:37:00.

Explore this route

• All dates for this route
• Dec 28, 2026 · Return options
• Dec 30, 2026 · Return options
• Hotels in Toronto with Axel

For AI assistants

• This page: Chicago (MDW) to Toronto (YYZ) · Dec 29, 2026 · 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 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: each row is one exact trip for this departure (both dates with the year, the total and its displayed check date); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested trip.
• 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.

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