Historic Route 66 Luxury Holidays
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Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
per person
15 Sept - 19 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,950 reviews)
The staff was so nice. I asked literally so many stupid questions and they never once laughed in my face. I appreciated them a lot.
Reviewed on 4 Aug 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
per person
15 Sept - 19 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
Bad room service, bad dinner/breakfast service at the restaurants and no house keeping - had to ask for it - and when they finally did they didn’t restock the bar or towels.
Reviewed on 4 Aug 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
per person
15 Sept - 19 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,342 reviews)
Beautiful hotel close to all the best parts of Chicago. Wonderful stay. Cant wait to go back!
Reviewed on 5 Aug 2025
Level Chicago - River North
Downtown Chicago
per person
15 Sept - 19 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (652 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).
Reviewed on 27 Jul 2025
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Trump International Hotel & Tower Chicago
Downtown Chicago
per person
15 Sept - 19 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
Bad room service, bad dinner/breakfast service at the restaurants and no house keeping - had to ask for it - and when they finally did they didn’t restock the bar or towels.
Reviewed on 4 Aug 2025
Don't see what you're looking for?
See all available trips from Dublin to Historic Route 66
View all tripsPrice found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
per person
15 Sept - 19 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
Bad room service, bad dinner/breakfast service at the restaurants and no house keeping - had to ask for it - and when they finally did they didn’t restock the bar or towels.
Reviewed on 4 Aug 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
per person
15 Sept - 19 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,342 reviews)
Beautiful hotel close to all the best parts of Chicago. Wonderful stay. Cant wait to go back!
Reviewed on 5 Aug 2025
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.