Southwest Side Holidays from AU$1,198

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The Latest Southwest Side Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
Price was AU$1,419, price is now AU$1,198 per person
AU$1,198
per person
26 Sept - 28 Sept
found 4 hours ago
Return direct flight included
Orlando (MCO) to Chicago (ORD)
8.4/10 Very Good! (3,738 reviews)
It was nice and comfortable.

Reviewed on 22 Aug. 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was AU$2,088, price is now AU$1,566 per person
AU$1,566
per person
26 Sept - 28 Sept
found 4 hours ago
Return direct flight included
Orlando (MCO) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug. 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was AU$1,744, price is now AU$1,421 per person
AU$1,421
per person
26 Sept - 28 Sept
found 4 hours ago
Return direct flight included
Orlando (MCO) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Loved the atmosphere and friendly atmosphere

Reviewed on 18 Aug. 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was AU$1,835, price is now AU$1,498 per person
AU$1,498
per person
26 Sept - 28 Sept
found 4 hours ago
Return direct flight included
Orlando (MCO) to Chicago (ORD)
9.2/10 Wonderful! (1,159 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

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was AU$1,744, price is now AU$1,501 per person
AU$1,501
per person
26 Sept - 28 Sept
found 4 hours ago
Return direct flight included
Orlando (MCO) to Chicago (ORD)
9.4/10 Exceptional! (3,344 reviews)
I enjoyed the total experience of staying at this facility.

Reviewed on 22 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
Default Image

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.

Find hotels in Back of the Yards

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

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$273 per night from 1 Sept to 2 Sept
AU$273
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,210 reviews)
"The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude ..."

Reviewed on 20 Aug. 2025

The Wade
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$344 per night from 14 Sept to 15 Sept
AU$344
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (9,014 reviews)
"Great hotel"

Reviewed on 20 Aug. 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$352 per night from 3 Sept to 4 Sept
AU$352
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (1,873 reviews)
"Nice clean room."

Reviewed on 19 Aug. 2025

Palmer House a Hilton Hotel
See all 5,044 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.
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beach holidays
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Discover the most popular places to visit in Southwest Side

Navy Pier

Navy Pier

4.5/5(64 reviews)

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

4.5/5(73 reviews)

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

Millennium Park
Grant Park

Grant Park

4.5/5(47 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

What to do in Southwest Side

River tour boat in Chicago

Architecture River Tour

AU$63
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

AU$69
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Southwest Side

Frequently asked questions

How much does a Southwest Side holiday package cost?
From as little as AU$1,198, you can tailor make your Southwest Side holiday package. Simply bundle hotels, flights and rental cars and we'll reward you with discounts.
How do I get a cheap travel package to Southwest Side?
You'll save loads of cash if you combine your car rentals, flights and hotels into a Southwest Side travel package. Sometimes cheap packages mean fewer options. But that's not the case with Expedia. We offer over 550 air carriers and 1 000 000 hotels across the globe, which means you'll always have plenty of options to choose from. Want to save even more? Add some exciting activities to your package deal to unlock even more bargains! After all, travel is about more than just getting to your destination.
What are the top hotels in Southwest Side?
Check out the deals at Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton in Glendale. Any good Southwest Side itinerary should include this city!
How far in advance should I book my Southwest Side holiday?
You'll be rewarded with the widest variety at the cheapest prices by booking your adventure to Southwest Side early. Air carriers generally publish flights around a year in advance, so start your planning as soon as possible. Having said that, Expedia is constantly working to give you the best deals around, so it's never a bad time to book your dream holiday!
What does an Expedia Southwest Side travel package include?
With Expedia, you can select any combination of hotels, flights and car rentals to create your perfect Southwest Side package. Once you've made your booking, you can add on fun stuff like tours and activities. Remember, the more you bundle, the more dollars you'll save!
What should I know before booking a Southwest Side travel package?
Our prices are always low. However, you'll snap up an even better deal when you book your hotels, flights and car rentals together. With an Expedia package, you'll always get transparent pricing and lots of choice.
Can I choose my airline with a Southwest Side Expedia holiday package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines globally. Our packages give you the freedom to take your pick of available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Southwest Side holiday package?
Yes you can, and we'll help you every step of the way. You may be able to amend or cancel your Southwest Side holiday package at no cost within 24 hours of booking. However, you may be charged a fee by your airline, hotel or car rental company for older bookings. If your travel plans suddenly change, visit our Customer Service Portal for more information.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.