Downtown 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 €640, price is now €468 per person
€468
per person
31 Oct - 2 Nov
found 14 hours ago
Return flight included
New York (NYC) 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
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was €984, price is now €635 per person
€635
per person
31 Oct - 2 Nov
found 14 hours ago
Return flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
This property is fabulous in every aspect. Huge rooms, modern and fresh. The spa and workout facilities are amazing. I loved everything about this hotel. Location is perfect to explore the river walk, shopping and best dining options. Only small critique is only one person at the front and if they are busy with a guest, can be a long wait to check in or out.
Reviewed on 21 Sept 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was €954, price is now €672 per person
€672
per person
31 Oct - 2 Nov
found 14 hours ago
Return flight included
New York (NYC) 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
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 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,014 reviews)
The room was perfect and the front staff were exceptional. Our stay was amazing!
Reviewed on 21 Sept 2025
The Emily Hotel
Downtown Chicago
Price was €1,194, price is now €903 per person
€903
per person
31 Oct - 4 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
Great area ! Great food ! Easily walkable but be prepared to find parking. The hotel was amazing and staff was friendly. The coffee is room is great, the shampoo/conditioner/body wash provided I really liked
. Extra star of the hotel - the adjacent coffee shop!!!!!
Reviewed on 21 Sept 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 Michigan Maritime Museum and North Beach.
Top hotels in Downtown
Old Harbor Inn
515 Williams Street, South Haven, MI
Fully refundableReserve now, pay when you stay
The price is €115 per night from 23 Sept to 24 Sept
€115
23 Sept - 24 Sept
includes taxes & fees
9.4/10 Exceptional! (627 reviews)
"We had an excellent time. Jake at the front counter was awesome"
Reviewed on 15 Sept 2025
Historic Hotel Nichols
201 Center St, South Haven, MI
The price is €129 per night from 1 Oct to 2 Oct
€129
1 Oct - 2 Oct
includes taxes & fees
9.6/10 Exceptional! (111 reviews)
"Lovely hotel with lots of character The gentleman who booked us in and served breakfast was extremely helpful and polite The breakfast was delicious"
Reviewed on 16 Sept 2025
New Home with swim spa, theatre & game room. 1 block to town & close to beach.
South Haven
10/10 Exceptional! (190 reviews)
"The house was perfect for our family of 10. Plenty of space and amenities were all we needed."
Reviewed on 2 Sept 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.