Southwest Side Holidays from AU$2,184
Book a Hotel + Flight or Car together to unlock savings
The Latest Southwest Side Holiday Deals
Price found within the past 48 hours. Click for updated prices.
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was AU$4,113, price is now AU$2,534 per person
AU$2,534
per person
31 Oct - 7 Nov
found 3 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend.
Also the coffee bags ? PERFECTION. Just had to add that
Reviewed on 22 Aug. 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was AU$5,610, price is now AU$3,478 per person
AU$3,478
per person
31 Oct - 7 Nov
found 3 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump
Reviewed on 29 Aug. 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was AU$5,537, price is now AU$3,571 per person
AU$3,571
per person
20 Oct - 26 Oct
found 7 hours ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on 10 Aug. 2025
Level Chicago – Old Town
Downtown Chicago
Price was AU$3,524, price is now AU$2,340 per person
AU$2,340
per person
20 Oct - 26 Oct
found 7 hours ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.
Reviewed on 27 Aug. 2025
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
Southwest Side Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Our pick of the best Southwest Side Hotel Deals
The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$271 per night from 2 Sept to 3 Sept
AU$271
2 Sept - 3 Sept
includes taxes & fees
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$354 per night from 15 Sept to 16 Sept
AU$354
15 Sept - 16 Sept
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is AU$286 per night from 4 Sept to 5 Sept
AU$286
4 Sept - 5 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
Navy Pier
A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.
Millennium Park
One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.
Grant Park
Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.
What to do in Southwest Side
Wendella's 90-min Chicago River Architecture Tour
AU$62
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
AU$69
per adult
96% of travellers recommend
More holiday ideas
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Hotels
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.