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.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
NZ$1,333
per person
24 Nov - 29 Nov
found 9 hours ago
Return flight included
Pittsburgh (PIT) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
NZ$1,540
per person
24 Nov - 29 Nov
found 9 hours ago
Return flight included
Pittsburgh (PIT) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Great location. So much to do in walking distance and hotel was great.

Reviewed on 16 Sept 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
NZ$1,365
per person
24 Nov - 29 Nov
found 9 hours ago
Return flight included
Pittsburgh (PIT) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
Comfortable room with a great view and luxuriously soft bed!

Reviewed on 13 Sept 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
NZ$1,408
per person
24 Nov - 29 Nov
found 9 hours ago
Return flight included
Pittsburgh (PIT) to Chicago (ORD)
9.4/10 Exceptional! (1,010 reviews)
Clean room, nice location

Reviewed on 15 Sept 2026

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Downtown Chicago
NZ$1,472
per person
24 Nov - 29 Nov
found 9 hours ago
Return flight included
Pittsburgh (PIT) to Chicago (ORD)
9.2/10 Wonderful! (2,381 reviews)
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Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$45
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

NZ$67
per adult
92% of travellers recommend
Art Institute of Chicago
Flyover in Chicago

Flyover in Chicago

NZ$47
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Far Southwest Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.