Downtown Holidays
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Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,945, price is now €1,237 per person
€1,237
per person
14 Feb - 20 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Loved it here and would stay again! Everything was perfect!
Reviewed on 21 Dec 2025
Waldorf Astoria Chicago
Downtown Chicago
Price was €2,145, price is now €1,512 per person
€1,512
per person
14 Feb - 20 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Absolutely fantastic hotel great service, you couldn’t ask for more.
Reviewed on 3 Dec 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was €1,529, price is now €1,083 per person
€1,083
per person
14 Mar - 20 Mar
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (326 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.
Reviewed on 18 Dec 2025
Where to stay in Downtown
Find the best Downtown areas and neighborhoods for the activities you enjoy most. Learn more about Downtown
North Side
1 out of top 10 points of interest in this area
While visiting North Side, you might make a stop by sights like North Beach and Michigan Maritime Museum.
Top hotels in Downtown
Old Harbor Inn
515 Williams Street South Haven MI
Fully refundableReserve now, pay when you stay
The price is €109 per night from 6 Jan to 7 Jan
€109
6 Jan - 7 Jan 2026
includes taxes & fees
9.4/10 Exceptional! (680 reviews)
Great location
Reviewed on 14 Dec 2025
Historic Hotel Nichols
201 Center St South Haven MI
The price is €133 per night from 27 Dec to 28 Dec
€133
27 Dec - 28 Dec
includes taxes & fees
9.6/10 Exceptional! (126 reviews)
Historic Hotel Nichols was a great experience for our small family. Nick (manager) was fantastic. If you are staying in town, you won't regret staying here. Location is excellent, walkable to all shops/restaurants.
Reviewed on 12 Dec 2025
New Home with swim spa, theatre & game room. 1 block to town & close to beach.
South Haven MI
10/10 Exceptional! (195 reviews)
I only gave this property and host 5 stars because there was not a higher rating. Susan was amazing very communicative and friendly. She made this stay very comfortable and one of the most amazing properties I have ever experienced. The house has enough entertainment options even if your not able ...
Reviewed on 23 Nov 2025
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.