Chicago Beach Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to €185 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.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was €1,004, price is now €870 per person
€870
per person
25 Jan - 30 Jan
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (3,098 reviews)
staff was very helpful & friendly, hotel was clean.

Reviewed on 14 Dec 2025

Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
Downtown Chicago
Price was €1,242, price is now €1,080 per person
€1,080
per person
25 Jan - 30 Jan
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,386 reviews)
Went there for a conf

Reviewed on 16 Dec 2025

The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was €926, price is now €874 per person
€874
per person
25 Jan - 30 Jan
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very Good! (1,444 reviews)
I loved the location near to everything but not surrounded by just buildings which was what I was looking for a great pier view, the size of the rooms were perfect and the staff were amazing. I will be staying here again!

Reviewed on 16 Dec 2025

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was €978, price is now €978 per person
€978
per person
25 Jan - 30 Jan
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
Great! Staff was friendly and helpful

Reviewed on 16 Dec 2025

Don't see what you're looking for?
See all available trips from Dublin to Chicago
View all trips
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

4 out of 5
163 East Walton Place Chicago IL
  • 11 min walk from Michigan Avenue
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, a 24-hour fitness centre and valet parking (surcharge). Our guests praise the helpful staff ...
8.4/10 Very Good! (2,004 reviews)
Room was great people weee wonderful. Glad to see they had restaurant opened as using closed in winter months.

Reviewed on 9 Dec 2025

Millennium Knickerbocker Chicago
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
105 E Delaware Pl Chicago IL
  • 10 min walk from Michigan Avenue
Stay at this boutique hotel in Chicago. Enjoy free breakfast, free Wi-Fi and a fitness centre. Our guests praise the restaurant and the helpful staff in their ...
8.2/10 Very Good! (3,790 reviews)
Clean, great staff

Reviewed on 15 Dec 2025

The Whitehall Hotel, BW Premier Collection
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

3 out of 5
4900 S Lake Shore Dr Chicago IL
  • 15 min drive from Michigan Avenue
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the overall ...
hotel was about what we expected. Nice breakfast and staff was kind

Reviewed on 8 Nov 2023

Chicago Lake Shore Hotel
See all 5,610 properties in Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.