
Southwest Side Holidays
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Our guide on where to stay in Southwest Side
Find the best Southwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Side

Back of the Yards
2 out of top 10 points of interest in this area
While there might not be top attractions in Back of the Yards, you can explore the larger area and discover places like Bridgeport Art Center and Zhou B Art Center.
Southwest Side Holiday
Our pick of the best Southwest Side Hotel Deals

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$393 per night from 15 Sept to 16 Sept
NZ$393
15 Sept - 16 Sept
includes taxes & fees

Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$335 per night from 3 Sept to 4 Sept
NZ$335
3 Sept - 4 Sept
includes taxes & fees

The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$333 per night from 22 Sept to 23 Sept
NZ$333
22 Sept - 23 Sept
includes taxes & fees
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.
Discover the most popular places to visit in Southwest Side

Wrigley Field
A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Navy Pier
One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

McCormick Place
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
What to do in Southwest Side

Wendella's 90-min Chicago River Architecture Tour
NZ$68
per adult
94% of travellers recommend

Chicago By Night River & Lake Cruise
NZ$75
per adult
96% of travellers recommend
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