Far Southwest Side Romantic Holidays
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Top flight + Romantic hotel deals in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago O'Hare Airport
O'Hare
per person
15 Aug - 18 Aug
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
8.2/10 Very Good! (2,069 reviews)
Item was left in room. I tried for days to get contact with front desk and security will little to no luck. They say nothing reported so I consider that as theft by staff. Very disappointing.
Reviewed on 2 Jul. 2025
Silversmith Hotel Chicago Downtown
Downtown Chicago
per person
15 Aug - 18 Aug
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,840 reviews)
Absolutely loved the staff! The hotel was clean & quiet. I will definitely recommend it and I’ll be returning.
Reviewed on 4 Jul. 2025
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
per person
15 Aug - 18 Aug
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
8.4/10 Very Good! (4,263 reviews)
The room was very spacious and clean. We arrived late and the staff was not very helpful; just did the basics and left us to figure out the rest. The breakfast was good, but stressful because of the set up and amount of people. I think there may have been some sort of dinner option, but we were explained that at check-in, so I'm not too sure, but we saw people eating. The website says $79 valet available, but it's basically required because there is no option for street parking. The hotel is very close to everything and because of it, it's a very busy area. We stayed with children and would have preferred to stay in a more family friendly area.
Reviewed on 4 Jul. 2025
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View all trips4 Night Romantic holidays in Far Southwest Side
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Silversmith Hotel Chicago Downtown
Downtown Chicago
per person
15 Aug - 18 Aug
found 1 day ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,840 reviews)
Absolutely loved the staff! The hotel was clean & quiet. I will definitely recommend it and I’ll be returning.
Reviewed on 4 Jul. 2025
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.