Book United Toronto to Chicago flight deals from CA $289

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Search flights from Toronto to Chicago (YYZ - ORD)

October

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Tuesday 16th

Return Wednesday 31st
fromCA $289*Viewed: 3 hours ago

Thursday 18th

Return Friday 2nd
fromCA $289*Viewed: 3 hours ago

Tuesday 23rd

Return Wednesday 7th
fromCA $289*Viewed: 3 hours ago

November

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Saturday 24th

Return Sunday 9th
fromCA $289*Viewed: 3 hours ago

Wednesday 28th

Return Thursday 13th
fromCA $289*Viewed: 3 hours ago

Thursday 29th

Return Friday 14th
fromCA $289*Viewed: 3 hours ago

December

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Sunday 2nd

Return Monday 17th
fromCA $289*Viewed: 3 hours ago

Monday 3rd

Return Tuesday 18th
fromCA $289*Viewed: 3 hours ago

Tuesday 4th

Return Wednesday 19th
fromCA $289*Viewed: 3 hours ago
**Prices have been available for round trips within the last 48 hours and may not be currently available. Fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply..
Cruise ships and tour boats docked by a ferris wheel and urban buildings at Navy Pier in Chicago

Plan ahead for flights from Toronto to Chicago

from
to
Type
Dates
Price*
Toronto (YYZ)
to Chicago (ORD)
Roundtrip
Depart Sat 13 Oct 2018
Return Sun 28 Oct 2018
fromCA $ 289*Viewed: 3 hours ago
Toronto (YYZ)
to Chicago (ORD)
Roundtrip
Depart Mon 15 Oct 2018
Return Tue 30 Oct 2018
fromCA $ 289*Viewed: 3 hours ago
Toronto (YYZ)
to Chicago (ORD)
Roundtrip
Depart Tue 16 Oct 2018
Return Wed 31 Oct 2018
fromCA $ 289*Viewed: 3 hours ago
Toronto (YYZ)
to Chicago (ORD)
Roundtrip
Depart Wed 17 Oct 2018
Return Thu 1 Nov 2018
fromCA $ 289*Viewed: 3 hours ago
Toronto (YYZ)
to Chicago (ORD)
Roundtrip
Depart Thu 18 Oct 2018
Return Fri 2 Nov 2018
fromCA $ 289*Viewed: 3 hours ago
Toronto (YYZ)
to Chicago (ORD)
Roundtrip
Depart Mon 22 Oct 2018
Return Tue 6 Nov 2018
fromCA $ 289*Viewed: 3 hours ago
Toronto (YYZ)
to Chicago (ORD)
Roundtrip
Depart Tue 23 Oct 2018
Return Wed 7 Nov 2018
fromCA $ 289*Viewed: 3 hours ago
Toronto (YYZ)
to Chicago (ORD)
Roundtrip
Depart Wed 24 Oct 2018
Return Thu 8 Nov 2018
fromCA $ 289*Viewed: 3 hours ago
Toronto (YYZ)
to Chicago (ORD)
Roundtrip
Depart Thu 25 Oct 2018
Return Fri 9 Nov 2018
fromCA $ 289*Viewed: 3 hours ago
Toronto (YYZ)
to Chicago (ORD)
Roundtrip
Depart Wed 31 Oct 2018
Return Thu 15 Nov 2018
fromCA $ 289*Viewed: 3 hours ago
*Prices have been available for round trips within the last 48 hours and may not be currently available. Fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply.