Northwest Side Luxury Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place
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)
The property waa clean and spacious Staff were very nice and helpful. The location was perfect a short walk or drive to alot of places ans the best of all was that A Garrett's popcorn shop waa right across the street!

Reviewed on 11 Aug 2026

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)
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)
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)
Don't see what you're looking for?
See all available trips from Dublin to Northwest Side
View all trips
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)
Great hotel in an awesome location!

Reviewed on 10 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)
The property waa clean and spacious Staff were very nice and helpful. The location was perfect a short walk or drive to alot of places ans the best of all was that A Garrett's popcorn shop waa right across the street!

Reviewed on 11 Aug 2026

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)
Don't see what you're looking for?
See all available trips from Dublin to Northwest Side
View all trips

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.