Historic Route 66 Kid friendly Vacations
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Top Kid friendly vacation packages in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ₩1,147,684, price is now ₩776,348 per person
₩776,348
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.2/10 Very Good! (2,797 reviews)
Rooms were small, but for the price it was good. The valet was expensive and took a while to get our car, but I don't think they are associated with the hotel, just use their lobby.
Reviewed on Jul 3, 2026
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩1,812,060, price is now ₩1,101,252 per person
₩1,101,252
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,128 reviews)
Great property in the heart of the city
Reviewed on Jul 1, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩1,540,960, price is now ₩988,158 per person
₩988,158
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
Hotel is very nice - rooms are quiet and clean, staff is helpful, breakfast is free (and very popular). I’m very happy with our stay, we’ll be back
Reviewed on Jul 3, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was ₩1,676,603, price is now ₩1,175,544 per person
₩1,175,544
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
stay away, no one told us it had been damage and under repair, staff could not even help get me bording pass, room service sub par. We got a notice from Expedia after we checked in saying we could cancil, a bit to late.
Reviewed on Jul 3, 2026
Omni Chicago Hotel
Downtown Chicago
Price was ₩1,261,054, price is now ₩884,314 per person
₩884,314
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
Exceptional hotel with even better service and accommodations! The location can’t be beat. We had a really great experience with Keith at the front desk. He went above and beyond to make sure we were comfortable and taken care of. We went with our two children and found it to be a more upscale hotel while still being family friendly. Hot tip/ if you show your room key at the Harry Potter store, you get a discount! Cannot recommend enough. We will be back!
Reviewed on Jul 3, 2026
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View all trips5* Kid friendly vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Nobu Hotel Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩2,132,728, price is now ₩1,612,792 per person
₩1,612,792
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (873 reviews)
The staff was friendly and helpful. They let us check in early, and I got an upgraded room. Very nice property, I would stay here again.
Reviewed on Jul 2, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩2,254,361, price is now ₩1,617,928 per person
₩1,617,928
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
The shower temp was about on the hot side no matter how low you had it. The bed& room were overall great
Reviewed on Jul 3, 2026
The Langham, Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩2,268,322, price is now ₩1,696,016 per person
₩1,696,016
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Everything was mostly great. Except it was a bit overpriced (especially the spa) and minibar person kept adding stuff I didn't use to my bill. Also they don't tell you what perks you have depending on your reservation. You have to ask. Also I stayed in a junior suite for 8 days and they wouldn't give me a late check out. Finally, they begrudgingly have me an hour after I reminded them I spent almost $9,000 dollars there. Gee, thanks. Front desk guy at check in was mostly unhelpful although he was friendly and polite. Tons of great stuff.
Reviewed on Jul 2, 2026
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See all available trips from Toronto to Historic Route 66
View all trips3 Night Kid friendly vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ₩1,147,684, price is now ₩776,348 per person
₩776,348
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.2/10 Very Good! (2,797 reviews)
Rooms were small, but for the price it was good. The valet was expensive and took a while to get our car, but I don't think they are associated with the hotel, just use their lobby.
Reviewed on Jul 3, 2026
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩1,812,060, price is now ₩1,101,252 per person
₩1,101,252
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,128 reviews)
Great property in the heart of the city
Reviewed on Jul 1, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩1,540,960, price is now ₩988,158 per person
₩988,158
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
Hotel is very nice - rooms are quiet and clean, staff is helpful, breakfast is free (and very popular). I’m very happy with our stay, we’ll be back
Reviewed on Jul 3, 2026
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See all available trips from Toronto to Historic Route 66
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
