Route overview: Toronto to Chicago (ORD) flight deals

Toronto (YYZ) to Chicago (ORD), Nov 29, 2026: round trips from $369, one way from $240

Toronto (YYZ) to Chicago (ORD), Nov 29, 2026: round trips from $369, one way from $240 on Axel, checked Oct 29, 2026. Lowest published fares: $369 round trip, Axel-exclusive, Delta Air Lines, 1 stop, Nov 29, 2026 – Dec 1, 2026; $240 one way, Axel-exclusive, Delta Air Lines, 1 stop, Nov 29, 2026; 1 adult, economy, checked Oct 29, 2026.

YYZ → ORD1 adulteconomyOne way and round trips

30 flight options · 2 airlines

Choose your return date

One-way flights and round trips by duration. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

November 2026

Nov 29, 2026 · One wayDelta Air LinesUp to 1 stop each way$240.00

Nov 29, 2026 · One wayAmerican AirlinesNonstop$246.00

Nov 29, 2026 – Nov 30, 2026 · 1 nightDelta Air LinesUp to 1 stop each way$402.00

Nov 29, 2026 – Nov 30, 2026 · 1 nightAmerican AirlinesNonstop$414.00

Hotels for these nights (Nov 29–30, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey $101 · 4★ Warwick Allerton - Chicago $122 · 5★ Sofitel Chicago Magnificent Mile $309

Nov 29, 2026 – Dec 1, 2026 · 2 nightsDelta Air LinesUp to 1 stop each way$368.50

Nov 29, 2026 – Dec 1, 2026 · 2 nightsAmerican AirlinesNonstop$379.50

Hotels for these nights (Nov 29 – Dec 1, 2026 · 2 nights · 2 adults, 1 room): 3★ Hotel Versey $188 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $268 · 5★ Sofitel Chicago Magnificent Mile $626

Nov 29, 2026 – Dec 2, 2026 · 3 nightsDelta Air LinesUp to 1 stop each way$368.50

Nov 29, 2026 – Dec 2, 2026 · 3 nightsAmerican AirlinesNonstop$379.50

Hotels for these nights (Nov 29 – Dec 2, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey $289 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $402 · 5★ Sofitel Chicago Magnificent Mile $935

Nov 29, 2026 – Dec 3, 2026 · 4 nightsDelta Air LinesUp to 1 stop each way$368.50

Nov 29, 2026 – Dec 3, 2026 · 4 nightsAmerican AirlinesNonstop$379.50

Hotels for these nights (Nov 29 – Dec 3, 2026 · 4 nights · 2 adults, 1 room): 3★ Hotel Versey $389 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $537 · 5★ Sofitel Chicago Magnificent Mile $1,232

Nov 29, 2026 – Dec 4, 2026 · 5 nightsDelta Air LinesUp to 1 stop each way$368.50

Nov 29, 2026 – Dec 4, 2026 · 5 nightsAmerican AirlinesNonstop$379.50

Hotels for these nights (Nov 29 – Dec 4, 2026 · 5 nights · 2 adults, 1 room): 3★ The Willows Hotel $495 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $671 · 5★ Sofitel Chicago Magnificent Mile $1,466

Nov 29, 2026 – Dec 5, 2026 · 6 nightsDelta Air LinesUp to 1 stop each way$368.50

Nov 29, 2026 – Dec 5, 2026 · 6 nightsAmerican AirlinesNonstop$379.50

Hotels for these nights (Nov 29 – Dec 5, 2026 · 6 nights · 2 adults, 1 room): 3★ The Willows Hotel $698 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $846 · 5★ Sofitel Chicago Magnificent Mile $1,763

Nov 29, 2026 – Dec 6, 2026 · 7 nightsDelta Air LinesUp to 1 stop each way$368.50

Nov 29, 2026 – Dec 6, 2026 · 7 nightsAmerican AirlinesNonstop$379.50

Hotels for these nights (Nov 29 – Dec 6, 2026 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $927 · 4★ Warwick Allerton - Chicago $985 · 5★ Sofitel Chicago Magnificent Mile $2,072

Nov 29, 2026 – Dec 7, 2026 · 8 nightsDelta Air LinesUp to 1 stop each way$368.50

Nov 29, 2026 – Dec 7, 2026 · 8 nightsAmerican AirlinesNonstop$379.50

Hotels for these nights (Nov 29 – Dec 7, 2026 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $1,031 · 4★ Warwick Allerton - Chicago $1,079 · 5★ Sofitel Chicago Magnificent Mile $2,278

Nov 29, 2026 – Dec 8, 2026 · 9 nightsDelta Air LinesUp to 1 stop each way$368.50

Nov 29, 2026 – Dec 8, 2026 · 9 nightsAmerican AirlinesNonstop$379.50

Hotels for these nights (Nov 29 – Dec 8, 2026 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $1,135 · 4★ Warwick Allerton - Chicago $1,164 · 5★ Sofitel Chicago Magnificent Mile $2,492

Nov 29, 2026 – Dec 9, 2026 · 10 nightsDelta Air LinesUp to 1 stop each way$368.50

Nov 29, 2026 – Dec 9, 2026 · 10 nightsAmerican AirlinesNonstop$379.50

Hotels for these nights (Nov 29 – Dec 9, 2026 · 10 nights · 2 adults, 1 room): 3★ The Willows Hotel $1,254 · 4★ Warwick Allerton - Chicago $1,253 · 5★ Waldorf Astoria Chicago $5,066

Nov 29, 2026 – Dec 10, 2026 · 11 nightsDelta Air LinesUp to 1 stop each way$368.50

Nov 29, 2026 – Dec 10, 2026 · 11 nightsAmerican AirlinesNonstop$379.50

Hotels for these nights (Nov 29 – Dec 10, 2026 · 11 nights · 2 adults, 1 room): 3★ The Willows Hotel $1,347 · 4★ Warwick Allerton - Chicago $1,342 · 5★ Waldorf Astoria Chicago $5,518

Nov 29, 2026 – Dec 11, 2026 · 12 nightsDelta Air LinesUp to 1 stop each way$368.50

Nov 29, 2026 – Dec 11, 2026 · 12 nightsAmerican AirlinesNonstop$379.50

Hotels for these nights (Nov 29 – Dec 11, 2026 · 12 nights · 2 adults, 1 room): 3★ The Willows Hotel $1,441 · 4★ Warwick Allerton - Chicago $1,431 · 5★ Waldorf Astoria Chicago $6,048

Nov 29, 2026 – Dec 12, 2026 · 13 nightsDelta Air LinesUp to 1 stop each way$368.50

Nov 29, 2026 – Dec 12, 2026 · 13 nightsAmerican AirlinesNonstop$379.50

Hotels for these nights (Nov 29 – Dec 12, 2026 · 13 nights · 2 adults, 1 room): 3★ Hotel Versey $1,590 · 4★ Warwick Allerton - Chicago $1,559 · 5★ Waldorf Astoria Chicago $6,924

Nov 29, 2026 – Dec 13, 2026 · 14 nightsDelta Air LinesUp to 1 stop each way$368.50

Nov 29, 2026 – Dec 13, 2026 · 14 nightsAmerican AirlinesNonstop$379.50

Hotels for these nights (Nov 29 – Dec 13, 2026 · 14 nights · 2 adults, 1 room): 3★ Hotel Versey $1,747 · 4★ Warwick Allerton - Chicago $1,691 · 5★ Waldorf Astoria Chicago $7,948

Flights for your trip

Sun, Nov 29 · One way
Delta Air Lines
9:45 amYYZ
5h 14m
DTW · 2h 4m
1:59 pmORD
One-way total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sun, Nov 29 · One way
American Airlines
11:45 amYYZ
2h 30m
Nonstop
1:15 pmORD
One-way total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sun, Nov 29 – Mon, Nov 30
Delta Air Lines
9:45 amYYZ
5h 14m
DTW · 2h 4m
1:59 pmORD
Delta Air Lines
5:02 pmORD
5h 5m
DTW · 2h 11m
11:07 pmYYZ
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sun, Nov 29 – Mon, Nov 30
American Airlines
11:45 amYYZ
2h 30m
Nonstop
1:15 pmORD
American Airlines
2:50 pmORD
1h 53m
Nonstop
5:43 pmYYZ
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sun, Nov 29 – Tue, Dec 1
Delta Air Lines
9:45 amYYZ
5h 14m
DTW · 2h 4m
1:59 pmORD
Delta Air Lines
5:02 pmORD
5h 5m
DTW · 2h 11m
11:07 pmYYZ
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sun, Nov 29 – Tue, Dec 1
American Airlines
11:45 amYYZ
2h 30m
Nonstop
1:15 pmORD
American Airlines
8:45 pmORD
2h 14m
Nonstop
11:59 pmYYZ
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sun, Nov 29 – Wed, Dec 2
Delta Air Lines
9:45 amYYZ
5h 14m
DTW · 2h 4m
1:59 pmORD
Delta Air Lines
5:02 pmORD
5h 5m
DTW · 2h 11m
11:07 pmYYZ
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sun, Nov 29 – Wed, Dec 2
American Airlines
11:45 amYYZ
2h 30m
Nonstop
1:15 pmORD
American Airlines
9:42 amORD
1h 53m
Nonstop
12:35 pmYYZ
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sun, Nov 29 – Thu, Dec 3
Delta Air Lines
9:45 amYYZ
5h 14m
DTW · 2h 4m
1:59 pmORD
Delta Air Lines
5:02 pmORD
5h 5m
DTW · 2h 11m
11:07 pmYYZ
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sun, Nov 29 – Thu, Dec 3
American Airlines
11:45 amYYZ
2h 30m
Nonstop
1:15 pmORD
American Airlines
9:42 amORD
1h 53m
Nonstop
12:35 pmYYZ
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sun, Nov 29 – Sat, Dec 5
Delta Air Lines
9:45 amYYZ
5h 14m
DTW · 2h 4m
1:59 pmORD
Delta Air Lines
5:02 pmORD
5h 5m
DTW · 2h 11m
11:07 pmYYZ
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sun, Nov 29 – Sat, Dec 5
American Airlines
11:45 amYYZ
2h 30m
Nonstop
1:15 pmORD
American Airlines
11:45 amORD
1h 59m
Nonstop
2:44 pmYYZ
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sun, Nov 29 – Sun, Dec 6
Delta Air Lines
9:45 amYYZ
5h 14m
DTW · 2h 4m
1:59 pmORD
Delta Air Lines
5:02 pmORD
5h 5m
DTW · 2h 11m
11:07 pmYYZ
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sun, Nov 29 – Sun, Dec 6
American Airlines
11:45 amYYZ
2h 30m
Nonstop
1:15 pmORD
American Airlines
6:50 pmORD
1h 54m
Nonstop
9:44 pmYYZ
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sun, Nov 29 – Mon, Dec 7
Delta Air Lines
9:45 amYYZ
5h 14m
DTW · 2h 4m
1:59 pmORD
Delta Air Lines
5:02 pmORD
5h 5m
DTW · 2h 11m
11:07 pmYYZ
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sun, Nov 29 – Mon, Dec 7
American Airlines
11:45 amYYZ
2h 30m
Nonstop
1:15 pmORD
American Airlines
2:50 pmORD
1h 53m
Nonstop
5:43 pmYYZ
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sun, Nov 29 – Wed, Dec 9
Delta Air Lines
9:45 amYYZ
5h 14m
DTW · 2h 4m
1:59 pmORD
Delta Air Lines
5:02 pmORD
5h 5m
DTW · 2h 11m
11:07 pmYYZ
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sun, Nov 29 – Wed, Dec 9
American Airlines
11:45 amYYZ
2h 30m
Nonstop
1:15 pmORD
American Airlines
8:00 amORD
1h 56m
Nonstop
10:56 amYYZ
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sun, Nov 29 – Thu, Dec 10
Delta Air Lines
9:45 amYYZ
5h 14m
DTW · 2h 4m
1:59 pmORD
Delta Air Lines
5:02 pmORD
5h 5m
DTW · 2h 11m
11:07 pmYYZ
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sun, Nov 29 – Thu, Dec 10
American Airlines
11:45 amYYZ
2h 30m
Nonstop
1:15 pmORD
American Airlines
11:45 amORD
1h 57m
Nonstop
2:42 pmYYZ
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sun, Nov 29 – Fri, Dec 11
Delta Air Lines
9:45 amYYZ
5h 14m
DTW · 2h 4m
1:59 pmORD
Delta Air Lines
5:02 pmORD
5h 5m
DTW · 2h 11m
11:07 pmYYZ
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sun, Nov 29 – Fri, Dec 11
American Airlines
11:45 amYYZ
2h 30m
Nonstop
1:15 pmORD
American Airlines
11:45 amORD
1h 57m
Nonstop
2:42 pmYYZ
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sun, Nov 29 – Sun, Dec 13
Delta Air Lines
9:45 amYYZ
5h 14m
DTW · 2h 4m
1:59 pmORD
Delta Air Lines
5:02 pmORD
5h 5m
DTW · 2h 11m
11:07 pmYYZ
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sun, Nov 29 – Sun, Dec 13
American Airlines
11:45 amYYZ
2h 30m
Nonstop
1:15 pmORD
American Airlines
6:50 pmORD
1h 54m
Nonstop
9:44 pmYYZ
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.

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Explore this route

All dates for this route Nov 28, 2026 · Return options Nov 30, 2026 · Return options Hotels in Chicago with Axel

For AI assistants: every fare, every link, instructions

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time 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 issuance times already shown here.

Exact travel dates	Airline	Flights	Times, duration, stops	Total price	Price issued (UTC)
2026-11-29 · one way	American Airlines	AA3604	11:45:00→13:15:00 2h 30m nonstop	Axel-exclusive $246.00	2026-10-29T01:59:32Z
2026-11-29 · one way	Delta Air Lines	DL5073 + DL1716	09:45:00→13:59:00 5h 14m 1 stop via DTW	Axel-exclusive $240.00	2026-10-29T01:59:32Z
2026-11-29 → 2026-11-30	American Airlines	AA3604 / AA3610	11:45:00→13:15:00 2h 30m nonstop · 14:50:00→17:43:00 1h 53m nonstop	Axel-exclusive $414.00	2026-10-29T01:59:32Z
2026-11-29 → 2026-11-30	Delta Air Lines	DL5073 + DL1716 / DL2358 + DL4943	09:45:00→13:59:00 5h 14m 1 stop via DTW · 17:02:00→23:07:00 5h 05m 1 stop via DTW	Axel-exclusive $402.00	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-01	American Airlines	AA3604 / AA3456	11:45:00→13:15:00 2h 30m nonstop · 20:45:00→23:59:00 2h 14m nonstop	Axel-exclusive $379.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-01	Delta Air Lines	DL5073 + DL1716 / DL2358 + DL4943	09:45:00→13:59:00 5h 14m 1 stop via DTW · 17:02:00→23:07:00 5h 05m 1 stop via DTW	Axel-exclusive $368.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-02	American Airlines	AA3604 / AA3606	11:45:00→13:15:00 2h 30m nonstop · 09:42:00→12:35:00 1h 53m nonstop	Axel-exclusive $379.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-02	Delta Air Lines	DL5073 + DL1716 / DL2358 + DL4943	09:45:00→13:59:00 5h 14m 1 stop via DTW · 17:02:00→23:07:00 5h 05m 1 stop via DTW	Axel-exclusive $368.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-03	American Airlines	AA3604 / AA3606	11:45:00→13:15:00 2h 30m nonstop · 09:42:00→12:35:00 1h 53m nonstop	Axel-exclusive $379.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-03	Delta Air Lines	DL5073 + DL1716 / DL2358 + DL4943	09:45:00→13:59:00 5h 14m 1 stop via DTW · 17:02:00→23:07:00 5h 05m 1 stop via DTW	Axel-exclusive $368.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-04	American Airlines	AA3604 / AA3608	11:45:00→13:15:00 2h 30m nonstop · 11:45:00→14:42:00 1h 57m nonstop	Axel-exclusive $379.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-04	Delta Air Lines	DL5073 + DL1716 / DL2358 + DL4943	09:45:00→13:59:00 5h 14m 1 stop via DTW · 17:02:00→23:07:00 5h 05m 1 stop via DTW	Axel-exclusive $368.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-05	American Airlines	AA3604 / AA6211	11:45:00→13:15:00 2h 30m nonstop · 11:45:00→14:44:00 1h 59m nonstop	Axel-exclusive $379.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-05	Delta Air Lines	DL5073 + DL1716 / DL2358 + DL4943	09:45:00→13:59:00 5h 14m 1 stop via DTW · 17:02:00→23:07:00 5h 05m 1 stop via DTW	Axel-exclusive $368.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-06	American Airlines	AA3604 / AA3456	11:45:00→13:15:00 2h 30m nonstop · 18:50:00→21:44:00 1h 54m nonstop	Axel-exclusive $379.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-06	Delta Air Lines	DL5073 + DL1716 / DL2358 + DL4943	09:45:00→13:59:00 5h 14m 1 stop via DTW · 17:02:00→23:07:00 5h 05m 1 stop via DTW	Axel-exclusive $368.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-07	American Airlines	AA3604 / AA3610	11:45:00→13:15:00 2h 30m nonstop · 14:50:00→17:43:00 1h 53m nonstop	Axel-exclusive $379.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-07	Delta Air Lines	DL5073 + DL1716 / DL2358 + DL4943	09:45:00→13:59:00 5h 14m 1 stop via DTW · 17:02:00→23:07:00 5h 05m 1 stop via DTW	Axel-exclusive $368.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-08	American Airlines	AA3604 / AA6488	11:45:00→13:15:00 2h 30m nonstop · 08:00:00→10:56:00 1h 56m nonstop	Axel-exclusive $379.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-08	Delta Air Lines	DL5073 + DL1716 / DL2358 + DL4943	09:45:00→13:59:00 5h 14m 1 stop via DTW · 17:02:00→23:07:00 5h 05m 1 stop via DTW	Axel-exclusive $368.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-09	American Airlines	AA3604 / AA6488	11:45:00→13:15:00 2h 30m nonstop · 08:00:00→10:56:00 1h 56m nonstop	Axel-exclusive $379.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-09	Delta Air Lines	DL5073 + DL1716 / DL2358 + DL4943	09:45:00→13:59:00 5h 14m 1 stop via DTW · 17:02:00→23:07:00 5h 05m 1 stop via DTW	Axel-exclusive $368.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-10	American Airlines	AA3604 / AA3608	11:45:00→13:15:00 2h 30m nonstop · 11:45:00→14:42:00 1h 57m nonstop	Axel-exclusive $379.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-10	Delta Air Lines	DL5073 + DL1716 / DL2358 + DL4943	09:45:00→13:59:00 5h 14m 1 stop via DTW · 17:02:00→23:07:00 5h 05m 1 stop via DTW	Axel-exclusive $368.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-11	American Airlines	AA3604 / AA3608	11:45:00→13:15:00 2h 30m nonstop · 11:45:00→14:42:00 1h 57m nonstop	Axel-exclusive $379.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-11	Delta Air Lines	DL5073 + DL1716 / DL2358 + DL4943	09:45:00→13:59:00 5h 14m 1 stop via DTW · 17:02:00→23:07:00 5h 05m 1 stop via DTW	Axel-exclusive $368.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-12	American Airlines	AA3604 / AA6211	11:45:00→13:15:00 2h 30m nonstop · 11:45:00→14:44:00 1h 59m nonstop	Axel-exclusive $379.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-12	Delta Air Lines	DL5073 + DL1716 / DL2358 + DL4943	09:45:00→13:59:00 5h 14m 1 stop via DTW · 17:02:00→23:07:00 5h 05m 1 stop via DTW	Axel-exclusive $368.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-13	American Airlines	AA3604 / AA3456	11:45:00→13:15:00 2h 30m nonstop · 18:50:00→21:44:00 1h 54m nonstop	Axel-exclusive $379.50	2026-10-29T01:59:32Z
2026-11-29 → 2026-12-13	Delta Air Lines	DL5073 + DL1716 / DL2358 + DL4943	09:45:00→13:59:00 5h 14m 1 stop via DTW · 17:02:00→23:07:00 5h 05m 1 stop via DTW	Axel-exclusive $368.50	2026-10-29T01:59:32Z

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.

Hotels in Chicago for these nights (Nov 29–30, 2026 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $101 total · 4★ Warwick Allerton - Chicago, $122 total · 5★ Sofitel Chicago Magnificent Mile, $309 total
Hotels in Chicago for these nights (Nov 29 – Dec 1, 2026 · 2 nights · 2 adults, 1 room): 3★ Hotel Versey, $188 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $268 total · 5★ Sofitel Chicago Magnificent Mile, $626 total
Hotels in Chicago for these nights (Nov 29 – Dec 2, 2026 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $289 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $402 total · 5★ Sofitel Chicago Magnificent Mile, $935 total
Hotels in Chicago for these nights (Nov 29 – Dec 3, 2026 · 4 nights · 2 adults, 1 room): 3★ Hotel Versey, $389 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $537 total · 5★ Sofitel Chicago Magnificent Mile, $1,232 total
Hotels in Chicago for these nights (Nov 29 – Dec 4, 2026 · 5 nights · 2 adults, 1 room): 3★ The Willows Hotel, $495 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $671 total · 5★ Sofitel Chicago Magnificent Mile, $1,466 total
Hotels in Chicago for these nights (Nov 29 – Dec 5, 2026 · 6 nights · 2 adults, 1 room): 3★ The Willows Hotel, $698 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $846 total · 5★ Sofitel Chicago Magnificent Mile, $1,763 total
Hotels in Chicago for these nights (Nov 29 – Dec 6, 2026 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $927 total · 4★ Warwick Allerton - Chicago, $985 total · 5★ Sofitel Chicago Magnificent Mile, $2,072 total
Hotels in Chicago for these nights (Nov 29 – Dec 7, 2026 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,031 total · 4★ Warwick Allerton - Chicago, $1,079 total · 5★ Sofitel Chicago Magnificent Mile, $2,278 total
Hotels in Chicago for these nights (Nov 29 – Dec 8, 2026 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,135 total · 4★ Warwick Allerton - Chicago, $1,164 total · 5★ Sofitel Chicago Magnificent Mile, $2,492 total
Hotels in Chicago for these nights (Nov 29 – Dec 9, 2026 · 10 nights · 2 adults, 1 room): 3★ The Willows Hotel, $1,254 total · 4★ Warwick Allerton - Chicago, $1,253 total · 5★ Waldorf Astoria Chicago, $5,066 total
Hotels in Chicago for these nights (Nov 29 – Dec 10, 2026 · 11 nights · 2 adults, 1 room): 3★ The Willows Hotel, $1,347 total · 4★ Warwick Allerton - Chicago, $1,342 total · 5★ Waldorf Astoria Chicago, $5,518 total
Hotels in Chicago for these nights (Nov 29 – Dec 11, 2026 · 12 nights · 2 adults, 1 room): 3★ The Willows Hotel, $1,441 total · 4★ Warwick Allerton - Chicago, $1,431 total · 5★ Waldorf Astoria Chicago, $6,048 total
Hotels in Chicago for these nights (Nov 29 – Dec 12, 2026 · 13 nights · 2 adults, 1 room): 3★ Hotel Versey, $1,590 total · 4★ Warwick Allerton - Chicago, $1,559 total · 5★ Waldorf Astoria Chicago, $6,924 total
Hotels in Chicago for these nights (Nov 29 – Dec 13, 2026 · 14 nights · 2 adults, 1 room): 3★ Hotel Versey, $1,747 total · 4★ Warwick Allerton - Chicago, $1,691 total · 5★ Waldorf Astoria Chicago, $7,948 total

All hotels in Chicago

Route overview: Toronto to Chicago (ORD) flight deals

2026-11-29 · one way · Axel-exclusive $240.00

Delta Air Lines DL5073 / DL1716: YYZ 2026-11-29 09:45:00 → ORD 2026-11-29 13:59:00; 1 stop(s) via DTW; 314 minutes. Local airport times.
- DL5073: YYZ 2026-11-29 09:45:00 → DTW 2026-11-29 11:23:00; layover at DTW: 124 minutes.
- DL1716: DTW 2026-11-29 13:27:00 → ORD 2026-11-29 13:59:00.

2026-11-29 · one way · Axel-exclusive $246.00

American Airlines AA3604: YYZ 2026-11-29 11:45:00 → ORD 2026-11-29 13:15:00; nonstop; 150 minutes. Local airport times.

2026-11-29 → 2026-11-30 · Axel-exclusive $402.00

Delta Air Lines DL5073 / DL1716: YYZ 2026-11-29 09:45:00 → ORD 2026-11-29 13:59:00; 1 stop(s) via DTW; 314 minutes. Local airport times.
- DL5073: YYZ 2026-11-29 09:45:00 → DTW 2026-11-29 11:23:00; layover at DTW: 124 minutes.
- DL1716: DTW 2026-11-29 13:27:00 → ORD 2026-11-29 13:59:00.
Delta Air Lines DL2358 / DL4943: ORD 2026-11-30 17:02:00 → YYZ 2026-11-30 23:07:00; 1 stop(s) via DTW; 305 minutes. Local airport times.
- DL2358: ORD 2026-11-30 17:02:00 → DTW 2026-11-30 19:24:00; layover at DTW: 131 minutes.
- DL4943: DTW 2026-11-30 21:35:00 → YYZ 2026-11-30 23:07:00.

2026-11-29 → 2026-11-30 · Axel-exclusive $414.00

American Airlines AA3604: YYZ 2026-11-29 11:45:00 → ORD 2026-11-29 13:15:00; nonstop; 150 minutes. Local airport times.
American Airlines AA3610: ORD 2026-11-30 14:50:00 → YYZ 2026-11-30 17:43:00; nonstop; 113 minutes. Local airport times.

2026-11-29 → 2026-12-01 · Axel-exclusive $368.50

Delta Air Lines DL5073 / DL1716: YYZ 2026-11-29 09:45:00 → ORD 2026-11-29 13:59:00; 1 stop(s) via DTW; 314 minutes. Local airport times.
- DL5073: YYZ 2026-11-29 09:45:00 → DTW 2026-11-29 11:23:00; layover at DTW: 124 minutes.
- DL1716: DTW 2026-11-29 13:27:00 → ORD 2026-11-29 13:59:00.
Delta Air Lines DL2358 / DL4943: ORD 2026-12-01 17:02:00 → YYZ 2026-12-01 23:07:00; 1 stop(s) via DTW; 305 minutes. Local airport times.
- DL2358: ORD 2026-12-01 17:02:00 → DTW 2026-12-01 19:24:00; layover at DTW: 131 minutes.
- DL4943: DTW 2026-12-01 21:35:00 → YYZ 2026-12-01 23:07:00.

2026-11-29 → 2026-12-01 · Axel-exclusive $379.50

American Airlines AA3604: YYZ 2026-11-29 11:45:00 → ORD 2026-11-29 13:15:00; nonstop; 150 minutes. Local airport times.
American Airlines AA3456: ORD 2026-12-01 20:45:00 → YYZ 2026-12-01 23:59:00; nonstop; 134 minutes. Local airport times.

2026-11-29 → 2026-12-02 · Axel-exclusive $368.50

Delta Air Lines DL5073 / DL1716: YYZ 2026-11-29 09:45:00 → ORD 2026-11-29 13:59:00; 1 stop(s) via DTW; 314 minutes. Local airport times.
- DL5073: YYZ 2026-11-29 09:45:00 → DTW 2026-11-29 11:23:00; layover at DTW: 124 minutes.
- DL1716: DTW 2026-11-29 13:27:00 → ORD 2026-11-29 13:59:00.
Delta Air Lines DL2358 / DL4943: ORD 2026-12-02 17:02:00 → YYZ 2026-12-02 23:07:00; 1 stop(s) via DTW; 305 minutes. Local airport times.
- DL2358: ORD 2026-12-02 17:02:00 → DTW 2026-12-02 19:24:00; layover at DTW: 131 minutes.
- DL4943: DTW 2026-12-02 21:35:00 → YYZ 2026-12-02 23:07:00.

2026-11-29 → 2026-12-02 · Axel-exclusive $379.50

American Airlines AA3604: YYZ 2026-11-29 11:45:00 → ORD 2026-11-29 13:15:00; nonstop; 150 minutes. Local airport times.
American Airlines AA3606: ORD 2026-12-02 09:42:00 → YYZ 2026-12-02 12:35:00; nonstop; 113 minutes. Local airport times.

2026-11-29 → 2026-12-03 · Axel-exclusive $368.50

Delta Air Lines DL5073 / DL1716: YYZ 2026-11-29 09:45:00 → ORD 2026-11-29 13:59:00; 1 stop(s) via DTW; 314 minutes. Local airport times.
- DL5073: YYZ 2026-11-29 09:45:00 → DTW 2026-11-29 11:23:00; layover at DTW: 124 minutes.
- DL1716: DTW 2026-11-29 13:27:00 → ORD 2026-11-29 13:59:00.
Delta Air Lines DL2358 / DL4943: ORD 2026-12-03 17:02:00 → YYZ 2026-12-03 23:07:00; 1 stop(s) via DTW; 305 minutes. Local airport times.
- DL2358: ORD 2026-12-03 17:02:00 → DTW 2026-12-03 19:24:00; layover at DTW: 131 minutes.
- DL4943: DTW 2026-12-03 21:35:00 → YYZ 2026-12-03 23:07:00.

2026-11-29 → 2026-12-03 · Axel-exclusive $379.50

American Airlines AA3604: YYZ 2026-11-29 11:45:00 → ORD 2026-11-29 13:15:00; nonstop; 150 minutes. Local airport times.
American Airlines AA3606: ORD 2026-12-03 09:42:00 → YYZ 2026-12-03 12:35:00; nonstop; 113 minutes. Local airport times.

2026-11-29 → 2026-12-05 · Axel-exclusive $368.50

Delta Air Lines DL5073 / DL1716: YYZ 2026-11-29 09:45:00 → ORD 2026-11-29 13:59:00; 1 stop(s) via DTW; 314 minutes. Local airport times.
- DL5073: YYZ 2026-11-29 09:45:00 → DTW 2026-11-29 11:23:00; layover at DTW: 124 minutes.
- DL1716: DTW 2026-11-29 13:27:00 → ORD 2026-11-29 13:59:00.
Delta Air Lines DL2358 / DL4943: ORD 2026-12-05 17:02:00 → YYZ 2026-12-05 23:07:00; 1 stop(s) via DTW; 305 minutes. Local airport times.
- DL2358: ORD 2026-12-05 17:02:00 → DTW 2026-12-05 19:24:00; layover at DTW: 131 minutes.
- DL4943: DTW 2026-12-05 21:35:00 → YYZ 2026-12-05 23:07:00.

2026-11-29 → 2026-12-05 · Axel-exclusive $379.50

American Airlines AA3604: YYZ 2026-11-29 11:45:00 → ORD 2026-11-29 13:15:00; nonstop; 150 minutes. Local airport times.
American Airlines AA6211: ORD 2026-12-05 11:45:00 → YYZ 2026-12-05 14:44:00; nonstop; 119 minutes. Local airport times.

2026-11-29 → 2026-12-06 · Axel-exclusive $368.50

Delta Air Lines DL5073 / DL1716: YYZ 2026-11-29 09:45:00 → ORD 2026-11-29 13:59:00; 1 stop(s) via DTW; 314 minutes. Local airport times.
- DL5073: YYZ 2026-11-29 09:45:00 → DTW 2026-11-29 11:23:00; layover at DTW: 124 minutes.
- DL1716: DTW 2026-11-29 13:27:00 → ORD 2026-11-29 13:59:00.
Delta Air Lines DL2358 / DL4943: ORD 2026-12-06 17:02:00 → YYZ 2026-12-06 23:07:00; 1 stop(s) via DTW; 305 minutes. Local airport times.
- DL2358: ORD 2026-12-06 17:02:00 → DTW 2026-12-06 19:24:00; layover at DTW: 131 minutes.
- DL4943: DTW 2026-12-06 21:35:00 → YYZ 2026-12-06 23:07:00.

2026-11-29 → 2026-12-06 · Axel-exclusive $379.50

American Airlines AA3604: YYZ 2026-11-29 11:45:00 → ORD 2026-11-29 13:15:00; nonstop; 150 minutes. Local airport times.
American Airlines AA3456: ORD 2026-12-06 18:50:00 → YYZ 2026-12-06 21:44:00; nonstop; 114 minutes. Local airport times.

2026-11-29 → 2026-12-07 · Axel-exclusive $368.50

Delta Air Lines DL5073 / DL1716: YYZ 2026-11-29 09:45:00 → ORD 2026-11-29 13:59:00; 1 stop(s) via DTW; 314 minutes. Local airport times.
- DL5073: YYZ 2026-11-29 09:45:00 → DTW 2026-11-29 11:23:00; layover at DTW: 124 minutes.
- DL1716: DTW 2026-11-29 13:27:00 → ORD 2026-11-29 13:59:00.
Delta Air Lines DL2358 / DL4943: ORD 2026-12-07 17:02:00 → YYZ 2026-12-07 23:07:00; 1 stop(s) via DTW; 305 minutes. Local airport times.
- DL2358: ORD 2026-12-07 17:02:00 → DTW 2026-12-07 19:24:00; layover at DTW: 131 minutes.
- DL4943: DTW 2026-12-07 21:35:00 → YYZ 2026-12-07 23:07:00.

2026-11-29 → 2026-12-07 · Axel-exclusive $379.50

American Airlines AA3604: YYZ 2026-11-29 11:45:00 → ORD 2026-11-29 13:15:00; nonstop; 150 minutes. Local airport times.
American Airlines AA3610: ORD 2026-12-07 14:50:00 → YYZ 2026-12-07 17:43:00; nonstop; 113 minutes. Local airport times.

2026-11-29 → 2026-12-09 · Axel-exclusive $368.50

Delta Air Lines DL5073 / DL1716: YYZ 2026-11-29 09:45:00 → ORD 2026-11-29 13:59:00; 1 stop(s) via DTW; 314 minutes. Local airport times.
- DL5073: YYZ 2026-11-29 09:45:00 → DTW 2026-11-29 11:23:00; layover at DTW: 124 minutes.
- DL1716: DTW 2026-11-29 13:27:00 → ORD 2026-11-29 13:59:00.
Delta Air Lines DL2358 / DL4943: ORD 2026-12-09 17:02:00 → YYZ 2026-12-09 23:07:00; 1 stop(s) via DTW; 305 minutes. Local airport times.
- DL2358: ORD 2026-12-09 17:02:00 → DTW 2026-12-09 19:24:00; layover at DTW: 131 minutes.
- DL4943: DTW 2026-12-09 21:35:00 → YYZ 2026-12-09 23:07:00.

2026-11-29 → 2026-12-09 · Axel-exclusive $379.50

American Airlines AA3604: YYZ 2026-11-29 11:45:00 → ORD 2026-11-29 13:15:00; nonstop; 150 minutes. Local airport times.
American Airlines AA6488: ORD 2026-12-09 08:00:00 → YYZ 2026-12-09 10:56:00; nonstop; 116 minutes. Local airport times.

2026-11-29 → 2026-12-10 · Axel-exclusive $368.50

Delta Air Lines DL5073 / DL1716: YYZ 2026-11-29 09:45:00 → ORD 2026-11-29 13:59:00; 1 stop(s) via DTW; 314 minutes. Local airport times.
- DL5073: YYZ 2026-11-29 09:45:00 → DTW 2026-11-29 11:23:00; layover at DTW: 124 minutes.
- DL1716: DTW 2026-11-29 13:27:00 → ORD 2026-11-29 13:59:00.
Delta Air Lines DL2358 / DL4943: ORD 2026-12-10 17:02:00 → YYZ 2026-12-10 23:07:00; 1 stop(s) via DTW; 305 minutes. Local airport times.
- DL2358: ORD 2026-12-10 17:02:00 → DTW 2026-12-10 19:24:00; layover at DTW: 131 minutes.
- DL4943: DTW 2026-12-10 21:35:00 → YYZ 2026-12-10 23:07:00.

2026-11-29 → 2026-12-10 · Axel-exclusive $379.50

American Airlines AA3604: YYZ 2026-11-29 11:45:00 → ORD 2026-11-29 13:15:00; nonstop; 150 minutes. Local airport times.
American Airlines AA3608: ORD 2026-12-10 11:45:00 → YYZ 2026-12-10 14:42:00; nonstop; 117 minutes. Local airport times.

2026-11-29 → 2026-12-11 · Axel-exclusive $368.50

Delta Air Lines DL5073 / DL1716: YYZ 2026-11-29 09:45:00 → ORD 2026-11-29 13:59:00; 1 stop(s) via DTW; 314 minutes. Local airport times.
- DL5073: YYZ 2026-11-29 09:45:00 → DTW 2026-11-29 11:23:00; layover at DTW: 124 minutes.
- DL1716: DTW 2026-11-29 13:27:00 → ORD 2026-11-29 13:59:00.
Delta Air Lines DL2358 / DL4943: ORD 2026-12-11 17:02:00 → YYZ 2026-12-11 23:07:00; 1 stop(s) via DTW; 305 minutes. Local airport times.
- DL2358: ORD 2026-12-11 17:02:00 → DTW 2026-12-11 19:24:00; layover at DTW: 131 minutes.
- DL4943: DTW 2026-12-11 21:35:00 → YYZ 2026-12-11 23:07:00.

2026-11-29 → 2026-12-11 · Axel-exclusive $379.50

American Airlines AA3604: YYZ 2026-11-29 11:45:00 → ORD 2026-11-29 13:15:00; nonstop; 150 minutes. Local airport times.
American Airlines AA3608: ORD 2026-12-11 11:45:00 → YYZ 2026-12-11 14:42:00; nonstop; 117 minutes. Local airport times.

2026-11-29 → 2026-12-13 · Axel-exclusive $368.50

Delta Air Lines DL5073 / DL1716: YYZ 2026-11-29 09:45:00 → ORD 2026-11-29 13:59:00; 1 stop(s) via DTW; 314 minutes. Local airport times.
- DL5073: YYZ 2026-11-29 09:45:00 → DTW 2026-11-29 11:23:00; layover at DTW: 124 minutes.
- DL1716: DTW 2026-11-29 13:27:00 → ORD 2026-11-29 13:59:00.
Delta Air Lines DL2358 / DL4943: ORD 2026-12-13 17:02:00 → YYZ 2026-12-13 23:07:00; 1 stop(s) via DTW; 305 minutes. Local airport times.
- DL2358: ORD 2026-12-13 17:02:00 → DTW 2026-12-13 19:24:00; layover at DTW: 131 minutes.
- DL4943: DTW 2026-12-13 21:35:00 → YYZ 2026-12-13 23:07:00.

2026-11-29 → 2026-12-13 · Axel-exclusive $379.50

American Airlines AA3604: YYZ 2026-11-29 11:45:00 → ORD 2026-11-29 13:15:00; nonstop; 150 minutes. Local airport times.
American Airlines AA3456: ORD 2026-12-13 18:50:00 → YYZ 2026-12-13 21:44:00; nonstop; 114 minutes. Local airport times.

Explore this route

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This page: Toronto (YYZ) to Chicago (ORD) · Nov 29, 2026 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals 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 the time its price was issued); 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.
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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 Toronto 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_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.