
Great River Road All inclusive Holidays
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Price found within the past 48 hours. Click for updated prices.

Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was €826, price is now €493 per person
€493
per person
30 Oct - 2 Nov
found 1 day ago
Return flight included
New York (JFK) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
This is an exceptional hotel. The rooms are clean. The service is impeccable, and the products!! The signature scent is to die for. It is now a part of my life. I had to buy a candle on the way out and have already visited the online store for body wash and lotion. Well done. There are a lot of choices in Chicago, but this is now my go to. Will definitely be back!
Reviewed on 12 Sept 2025

Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was €1,324, price is now €897 per person
€897
per person
30 Oct - 2 Nov
found 1 day ago
Return flight included
New York (JFK) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
Got pick pocketed in the elevator. I really like this hotel. Plan to return.
Reviewed on 8 Sept 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,234, price is now €886 per person
€886
per person
31 Oct - 2 Nov
found 24 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
The hotel needs a facelift in its rooms. It’s a 5-star hotel, and you expect more. The restaurant was good, and the food was good. On our second day, my server told me a croissant came with my breakfast, but I got charged. I didn’t say anything. On the 20th floor, you can hear everything from outside, like you are on the second floor. No soundproofing? It's hard to sleep at night.
Reviewed on 17 Sept 2025

21c Museum Hotel Chicago
Downtown Chicago
Save 100% on your flight
Price was €742, price is now €575 per person
€575
per person
30 Oct - 2 Nov
found 1 day ago
Return flight included
New York (JFK) to Chicago (ORD)
8.8/10 Excellent! (1,626 reviews)
Nothing special. Lower floor rooms are loud. Not enough chargers and not TV in bedroom with suite option. Behind the times.
Reviewed on 19 Sept 2025

The Langham, Chicago
Downtown Chicago
Save 100% on your flight
Price was €1,412, price is now €1,100 per person
€1,100
per person
30 Oct - 2 Nov
found 1 day ago
Return flight included
New York (JFK) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on 12 Aug 2025
Don't see what you're looking for?
See all available trips from New York to Great River Road
View all tripsPrice found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,234, price is now €886 per person
€886
per person
31 Oct - 2 Nov
found 24 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
The hotel needs a facelift in its rooms. It’s a 5-star hotel, and you expect more. The restaurant was good, and the food was good. On our second day, my server told me a croissant came with my breakfast, but I got charged. I didn’t say anything. On the 20th floor, you can hear everything from outside, like you are on the second floor. No soundproofing? It's hard to sleep at night.
Reviewed on 17 Sept 2025

Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was €1,324, price is now €897 per person
€897
per person
30 Oct - 2 Nov
found 1 day ago
Return flight included
New York (JFK) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
Got pick pocketed in the elevator. I really like this hotel. Plan to return.
Reviewed on 8 Sept 2025

The Langham, Chicago
Downtown Chicago
Save 100% on your flight
Price was €1,412, price is now €1,100 per person
€1,100
per person
30 Oct - 2 Nov
found 1 day ago
Return flight included
New York (JFK) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on 12 Aug 2025
Don't see what you're looking for?
See all available trips from Dublin to Great River Road
View all tripsPrice found within the past 48 hours. Click for updated prices.

theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was €622, price is now €428 per person
€428
per person
30 Oct - 2 Nov
found 1 day ago
Return flight included
New York (JFK) to Chicago (ORD)
9/10 Wonderful! (1,014 reviews)
Convenient location for what we were doing. Highly suggested if you are going to a show at the Chicago Theater.
Reviewed on 17 Sept 2025

Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was €826, price is now €493 per person
€493
per person
30 Oct - 2 Nov
found 1 day ago
Return flight included
New York (JFK) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
This is an exceptional hotel. The rooms are clean. The service is impeccable, and the products!! The signature scent is to die for. It is now a part of my life. I had to buy a candle on the way out and have already visited the online store for body wash and lotion. Well done. There are a lot of choices in Chicago, but this is now my go to. Will definitely be back!
Reviewed on 12 Sept 2025

Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was €1,324, price is now €897 per person
€897
per person
30 Oct - 2 Nov
found 1 day ago
Return flight included
New York (JFK) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
Got pick pocketed in the elevator. I really like this hotel. Plan to return.
Reviewed on 8 Sept 2025
Don't see what you're looking for?
See all available trips from New York to Great River Road
View all tripsPrice found within the past 48 hours. Click for updated prices.

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was €940, price is now €718 per person
€718
per person
31 Oct - 4 Nov
found 16 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (2,027 reviews)
Loved the classic luxurious hip ambience of the hotel. We had a great time and everyone was very nice. The TV in our room was old tech. Would be nice to have a smart TV to stream shows. Everything else was great.
Reviewed on 20 Sept 2025

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was €1,035, price is now €768 per person
€768
per person
31 Oct - 4 Nov
found 16 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,014 reviews)
Convenient location for what we were doing. Highly suggested if you are going to a show at the Chicago Theater.
Reviewed on 17 Sept 2025

Don't see what you're looking for?
See all available trips from Dublin to Great River Road
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.