Northwest Side Luxury Holidays

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Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
€1,090
per person
17 Sept - 21 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very good! (2,879 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
€1,406
per person
17 Sept - 21 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
€1,216
per person
17 Sept - 21 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
Overall the views were wonderful. The proximity was great. The room wasn’t clean. Bedding had stains on it. No one cleaned our room. No towels. Front desk was definitely not friendly. The elevator stopped working.

Reviewed on 11 Aug 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
€1,194
per person
17 Sept - 21 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,808 reviews)
Loved the hotel, loved the restaurants and room service Staff was very kind. Perfect location

Reviewed on 11 Aug 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
€1,650
per person
17 Sept - 21 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Beautiful stay along the riverwalk. Pretty easy to get to public transportation as well as much to do within walking distance. The hotel was clean and well taken care of. We enjoyed to larger gym hotel with plenty of equipment.

Reviewed on 11 Aug 2026

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Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

Downtown Chicago
€974
per person
17 Sept - 21 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very good! (3,933 reviews)
The Hotel is located in a great area. Unfortunately it’s an older hotel and you can hear others through the wall with the rooms next to yours. If your room is facing the street there is street noise. The room was clean a little dated as it’s an older hotel. The staff were super friendly and helpful. I would probably only stay here again if the other hotels in the area I normally stay at are not available which is why I ended up at the hotel.The bakery coffee place in the lobby was good. I didn’t utilize the restaurant.

Reviewed on 11 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
€1,406
per person
17 Sept - 21 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
€1,216
per person
17 Sept - 21 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
Overall the views were wonderful. The proximity was great. The room wasn’t clean. Bedding had stains on it. No one cleaned our room. No towels. Front desk was definitely not friendly. The elevator stopped working.

Reviewed on 11 Aug 2026

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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€24
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

€21
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

€35
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Northwest Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.