Far Southwest Side Holidays from AU$2,499

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The Latest Far Southwest Side Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was AU$2,874, price is now AU$2,499 per person
AU$2,499
per person
2 Sept - 5 Sept
found 4 hours ago
Return direct flight included
Brisbane (BNE) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was AU$3,374, price is now AU$2,723 per person
AU$2,723
per person
2 Sept - 5 Sept
found 4 hours ago
Return direct flight included
Brisbane (BNE) to Chicago (ORD)
9.4/10 Exceptional! (4,714 reviews)
Excellent!!

Reviewed on 21 July 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was AU$3,445, price is now AU$2,787 per person
AU$2,787
per person
2 Sept - 5 Sept
found 4 hours ago
Return direct flight included
Brisbane (BNE) to Chicago (ORD)
9.2/10 Wonderful! (1,136 reviews)

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was AU$3,307, price is now AU$2,772 per person
AU$2,772
per person
2 Sept - 5 Sept
found 4 hours ago
Return direct flight included
Brisbane (BNE) to Chicago (ORD)
9.2/10 Wonderful! (1,035 reviews)
One of the best places we’ve ever stayed. We had an amazing view of downtown Chicago from our floor, and our executive suite was clean and comfortable. We thoroughly enjoyed our stay and would definitely come back. The customer service and our room were excellent.

Reviewed on 20 July 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was AU$3,810, price is now AU$3,251 per person
AU$3,251
per person
2 Sept - 5 Sept
found 4 hours ago
Return direct flight included
Brisbane (BNE) to Chicago (ORD)
9.6/10 Exceptional! (1,934 reviews)

Our guide on where to stay in Far Southwest Side

Find the best Far Southwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Far Southwest Side
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Ashburn

The restaurants and churches are a few reasons travellers visit Ashburn. Though there aren't many top sights in the neighbourhood, you can visit Ephraim Bajar Cultural Center and Childrens Museum of Oak Lawn, a few notable attractions nearby.

Find hotels in Ashburn

Far Southwest Side Holiday

Far Southwest Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)

Our pick of the best Far Southwest Side Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
The price is AU$308 per night from 6 Aug to 7 Aug
AU$308
6 Aug - 7 Aug
includes taxes & fees
Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$292 per night from 26 July to 27 July
AU$292
26 July - 27 July
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
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$505 per night from 26 July to 27 July
AU$505
26 July - 27 July
includes taxes & fees
8.6/10 Excellent! (1,941 reviews)
"There wasn’t any Clean linen available upon request. Sheets / Towels etc. The Breakfast Menu/ Bar was great."

Reviewed on 20 July 2026

The Wade
See all 4,639 properties in Far 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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Stay near popular Far Southwest Side attractions

Beverly Arts Center

Beverly Arts Center is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Make some time to visit the shops while you're in the area.
See properties

What to do in Far Southwest Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$39
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

AU$58
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago Architecture Center River Cruise aboard First Lady

Chicago Architecture Center River Cruise aboard First Lady

AU$82
per adult
98% of travellers recommend
Chicago Architecture Center River Cruise aboard First Lady
See all activities in Far Southwest Side

Frequently asked questions

How much does a Far Southwest Side holiday package cost?
Tailor make your Far Southwest Side holiday package from an affordable AU$2,499. Choose from any combination of rental cars, flights and hotels to craft the getaway you've been dreaming about. Remember to add on some activities and experiences!
How do I get a cheap travel package to Far Southwest Side?
Combining your flight and hotel with Expedia won't just save valuable time — it'll save you a nice amount too. A Far Southwest Side holiday package makes it a cinch to create your dream adventure. With more than 550 airlines all over the world to choose from, finding convenient flights that fit your schedule will be no sweat. On top of that, we have over 1 000 000 hotel options globally to pick from. Now that's what you call choice. Whatever your budget, Expedia can show you the world.
What are the top hotels in Far Southwest Side?
Check out the deals at Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton in Chester Highlands. Any good Far Southwest Side itinerary has to include a stop in this great city!
How far in advance should I book my Far Southwest Side holiday?
It can be hard to know when is the perfect time to book your Far Southwest Side trip. But typically the earlier you book, the more affordable the prices. In some cases, you can reserve your flights and hotels nearly a year prior to departure. If you're considering a last-minute getaway, no need to panic! There are incredible bargains posted on Expedia every single day.
What does an Expedia Far Southwest Side travel package include?
Flights, hotels and car rentals — we connect you to the best deals. All you'll have to do is select your favourite combination. Once you've made your booking, you can add on the fun stuff like day tours and sightseeing activities. Our travel packages make it easy to customize an awesome Far Southwest Side trip.
What should I know before booking a Far Southwest Side travel package?
Whether it's relaxation or adventure you're chasing, a Far Southwest Side holiday package lets you organise your escape your way. Plus, you'll get access to great discounts just for combining your hotel with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Far Southwest Side Expedia holiday package?
With a holiday package, you're the one in charge. Whether you want to fly to Far Southwest Side in business or coach, simply pick from the available airline options. Expedia has access to more than 550 partner airlines globally.
If I'm not able to travel, can I cancel my Far Southwest Side holiday package?
If your holiday plans in Far Southwest Side have been upended, it's good to know that it is possible to cancel your booking. If you booked less than 24 hours ago, you may be eligible to receive a refund. If your booking is older than that, your airline, hotel or car rental company may charge a fee. For more details, check our Customer Service Portal.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.