
Historic Route 66 Beach Holidays
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Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was HK$8,188, price is now HK$5,135 per person
HK$5,135
per person
4 Sept - 7 Sept
found 16 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Clean, cozy, and updated. The shampoo and conditioner was amazing!! Consider selling it to guests!
Reviewed on 12 Jul 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was HK$10,436, price is now HK$6,562 per person
HK$6,562
per person
4 Sept - 7 Sept
found 16 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
The floor in the room was not clean. The shower gel was empty. The bed was comfortable and the breakfast buffet was good
Reviewed on 11 Jul 2026

Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was HK$11,047, price is now HK$7,137 per person
HK$7,137
per person
4 Sept - 7 Sept
found 16 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.
Reviewed on 9 Jul 2026

Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was HK$9,649, price is now HK$6,461 per person
HK$6,461
per person
4 Sept - 7 Sept
found 16 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!
Reviewed on 8 Jul 2026

Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
Price was HK$8,076, price is now HK$5,426 per person
HK$5,426
per person
4 Sept - 7 Sept
found 16 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Staff was amazing, we had a single king bed corner suite with a separate room that has a pull out bed from the couch. It was a perfect setup for us because the kids had their own little room with their own tv and everything. The pullout couch bed was very uncomfortable, but we kinda figured it wouldn't be the best in the first place so that was alright. The king bed was pretty good, no complaints there... What we disliked was that the room was not properly cleaned before us. They didn't vacuum, there were beer caps and change on the floor. The toilet was for sure not cleaned after the last guests in the room because it was pretty bad. There were only two bath towels which wasn't a big deal cause they brought us more and they also brought us a microwave after asking, that was pretty nice. The really stupid thing with the king bed room was that the TV is literally all the way over to the left mounted on the wall where you couldn't see it very well while laying in bed... It is really really stupid if you see what im talking about here. Imagine laying in bed at a $300 a night hotel and you and your wife are trying to watch a TV thats WAY over on the left side of the room... Its actually comical how the set up is... Valet parking is insane at $90 a night so I would recommend finding parking elsewhere around the hotel if you can. Overall it was a OK stay, nothing incredible and definitely not worth the $300 plus $90 parking...
Reviewed on 12 Jul 2026
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Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was HK$11,678, price is now HK$8,214 per person
HK$8,214
per person
4 Sept - 7 Sept
found 16 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
I love Trump hotels the absolute BEST
Reviewed on 10 Jul 2026

Nobu Hotel Chicago
Downtown Chicago
Save 100% on your flight
Price was HK$12,293, price is now HK$9,298 per person
HK$9,298
per person
4 Sept - 7 Sept
found 16 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (879 reviews)
Stunning hotel with really attentive staff, located in the heart of Chicago's West Loop neighborhood. You are surrounded by a ton of award-winning restaurants, shopping and also close to public transit. Rooms are spacious and are themed in a minimalistic Japanese onsen-style esthetic. We loved our stay here, though there are a few things to mention that made our stay less than a perfect 10. The bathroom is fully painted in black. Looks great, but terrible for styling your hair, if you have dark colored hair. Poor lighting concepts throughout the room and bathroom in general, which made it terrible for getting ready any time of the day. Closet area was dark, not great for getting dressed. Bedroom area was dark, not great for reading a book. Desk area is dark, not great for working remotely. Bathroom lighting is dark, not great if you are a woman trying to put on makeup. Housekeeping was fantastic and really knew how to personalize your stay, but they still knocked on the door when we had the "do not disturb" light on, which was very bothersome and woke us up a couple of times.
Reviewed on 6 Jul 2026
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See all available trips from Columbus to Historic Route 66
View all tripsPrice found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was HK$8,188, price is now HK$5,135 per person
HK$5,135
per person
4 Sept - 7 Sept
found 16 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Clean, cozy, and updated. The shampoo and conditioner was amazing!! Consider selling it to guests!
Reviewed on 12 Jul 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was HK$10,436, price is now HK$6,562 per person
HK$6,562
per person
4 Sept - 7 Sept
found 16 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
The floor in the room was not clean. The shower gel was empty. The bed was comfortable and the breakfast buffet was good
Reviewed on 11 Jul 2026

Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was HK$11,047, price is now HK$7,137 per person
HK$7,137
per person
4 Sept - 7 Sept
found 16 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.
Reviewed on 9 Jul 2026
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See all available trips from Columbus 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.
