Southwest Side Holidays

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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
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Garfield Ridge

Be sure to check out the restaurants and churches while you're strolling through Garfield Ridge, and hop on the metro at Midway Station to see more of the surrounding area.

Find hotels in Garfield Ridge

Top hotels in Southwest Side

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$265 per night from 22 Sept to 23 Sept
S$265
22 Sept - 23 Sept
includes taxes & fees
8.4/10 Very Good! (4,927 reviews)
First time exploring
"To start this hotel is extraordinary, the location is key if you want to explore Chicago. There is a Starbucks conveniently located outside and the grocery store across the street as well as multiple restaurants down the block. I would definitely rebook and consider this hotel as my first pick any ..."

Reviewed on 15 Sept, 2025

Embassy Suites by Hilton Chicago Downtown River North
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
7.8/10 Good! (9,188 reviews)
"Clean room, Confortable bed"

Reviewed on 16 Sept, 2025

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Congress Plaza Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
The price is S$275 per night from 22 Sept to 23 Sept
S$275
22 Sept - 23 Sept
includes taxes & fees
8.4/10 Very Good! (3,898 reviews)
"There were fees that were not disclosed on the website until you got to the hotel to check in."

Reviewed on 16 Sept, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,930 properties in Southwest Side
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.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place

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.

McCormick Place
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

What to do in Southwest Side

River tour boat in Chicago

Architecture River Tour

S$63
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$58
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

S$58
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Southwest Side

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.