Northwest Chicago Mountain Vacations
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Flight and Mountain hotel deals in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,289, price is now CA $978 per person
CA $978
per person
May 8 - May 11
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
The rooms are extremely clean and have everything you need. The staff is so accommodating and friendly. The view is amazing
Reviewed on Mar 27, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,927, price is now CA $1,298 per person
CA $1,298
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Great location. Clean, comfortable, friendly staff.
Reviewed on Mar 30, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,444, price is now CA $1,054 per person
CA $1,054
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Amazing experience will be back soon
Reviewed on Mar 29, 2026
Warwick Allerton - Chicago
Downtown Chicago
Price was CA $1,422, price is now CA $1,094 per person
CA $1,094
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (3,039 reviews)
Requested additional towels, never came. Luggage racks were difficult to obtain. Rooms are small. Bring your own hairdryer. Water pressure in shower is minimal.
Reviewed on Mar 27, 2026
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View all trips5* Mountain holidays in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,012, price is now CA $1,637 per person
CA $1,637
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Quality staff and the property was well appointed
Reviewed on Mar 30, 2026
The Peninsula Chicago
Downtown Chicago
Price was CA $3,526, price is now CA $2,853 per person
CA $2,853
per person
May 26 - May 30
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
Excellent room and facilities. Helpfull staff and amazing locstion.
Reviewed on Mar 27, 2026
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View all trips3 Night Mountain holidays in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,496, price is now CA $958 per person
CA $958
per person
Jun 20 - Jun 23
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Great location. Clean, comfortable, friendly staff.
Reviewed on Mar 30, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,444, price is now CA $1,054 per person
CA $1,054
per person
May 21 - May 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Amazing experience will be back soon
Reviewed on Mar 29, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,418, price is now CA $1,058 per person
CA $1,058
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Great place to stay the young lady checking us in was not very friendly. Never received my complimentary drinks. There was never anyone at the bar. Valet guy was very helpful!!! Other than the small things it was a good stay!!!
Reviewed on Mar 29, 2026
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View all trips4 Night Mountain holidays in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,803, price is now CA $1,346 per person
CA $1,346
per person
Apr 30 - May 4
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
The rooms are extremely clean and have everything you need. The staff is so accommodating and friendly. The view is amazing
Reviewed on Mar 27, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,771, price is now CA $1,375 per person
CA $1,375
per person
May 6 - May 10
found 11 hours ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.4/10 Exceptional! (3,646 reviews)
Super clean, super friendly staff.
Reviewed on Mar 29, 2026
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