
Downtown Holidays from AU$2,169
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Top Holiday Package Deals in Downtown
Price found within the past 48 hours. Click for updated prices.


Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
16 Oct - 23 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
The hotel is in a fantastic location. Staff service was very high quality and the lobby and common areas were very clean and well organized. Gym was modern, big and clean.
The actual room had some marks on the walls and a buzzy air handling vent in the master. An automated lighting system that was a bit dim and difficult to use. We would stay again.
Mini bar and snacks were high quality. We would stay again.
Reviewed on 29 Jul. 2025

Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
per person
16 Oct - 23 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
Finding a park is hard and the process of getting a room is very tedious but still very beautiful I’ve been twice
Reviewed on 29 Jul. 2025


Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
per person
16 Oct - 23 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
The hotel is ok. There’s one actual restaurant and the food is average. Outside of that you can walk to the pier. The main advantage is being on the pier and the hotel really rides that as their main selling point because they can’t stand on their own too much. I stayed recently and had an extra 197 charged to my card that wasn’t on my receipt and I called to see what that was from. The guy who answered the phone answered with “hi. What do you need”. And when I said I wanted to confirm the charge he said what it was and then hung up on me. I’ve never had a hotel be that unfriendly. I work customer service so I know a lot of people can not be great on the phone. But that was unprompted and flat out rude.
Reviewed on 29 Jul. 2025
Our guide on 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.
Our pick of the best Downtown Hotel Deals

Old Harbor Inn
515 Williams Street, South Haven, MI
9.4/10 Exceptional! (599 reviews)
"Parking can be an issue. We had to pay for parking"
Reviewed on 24 Jul. 2025

Historic Hotel Nichols
201 Center St, South Haven, MI
The price is AU$369 per night from 31 July to 1 Aug
AU$369
31 July - 1 Aug
includes taxes & fees
9.6/10 Exceptional! (91 reviews)
"The gentlemen running this place are so nice & caring. It is in the middle of everything. We only used our car when we drove up to Saugatuck. Loved having a home base in the middle of South Haven. The made to order breakfast was perfect. It’s the last cute, quaint and personable place I’ve ever stayed. ..."
Reviewed on 18 Jul. 2025

The Black Pearl: industrial condo sleeps 6, full size kitchen & scenic views!
South Haven
10/10 Exceptional! (106 reviews)
"Great location and nice open living/dining/kitchen area. Kitchen was generously provisioned and host was very responsive. Only a couple of less than ideal issues: the property lists 3 queen beds to sleep 6, but the beds are full size not measuring as the standard queen, making sleeping 6 people uncomfortable; ..."
Reviewed on 18 Jul. 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.