Southwest Side Holidays from AU$2,541

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The Latest Southwest Side Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Weston RFD

Hotel Weston RFD

2.5 out of 5
Price was AU$2,571, price is now AU$2,541 per person
AU$2,541
per person
21 Sept - 23 Sept
found 20 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
5.4/10 (180 reviews)
Property did not have a secure lock, the room was not clean and people were fixing cars on the property.

Reviewed on 13 July 2026

White Pines Lodge

White Pines Lodge

2 out of 5
Price was AU$2,714, price is now AU$2,647 per person
AU$2,647
per person
21 Sept - 23 Sept
found 20 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (53 reviews)
Definitely rustic. Cozy cabin that was outdated, but generally clean. If you’re looking for an outdoor experience, this is a good place. Two issues stand out for us: 1) the “queen” bed was horrible. It seemed it was for Lilliputians. My wife and I are practically beat each other all night. All things considered, sleeping should be comfortable. For this reason alone we would not sleep here again. 2) the air conditioning vent blew right on us. It was either hot or freezing. Nice park to visit, but wouldn’t stay here.

Reviewed on 9 July 2026

Riverview Inn & Suites, an Ascend Collection Hotel

Riverview Inn & Suites, an Ascend Collection Hotel

3 out of 5
Price was AU$2,644, price is now AU$2,603 per person
AU$2,603
per person
21 Sept - 23 Sept
found 20 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
8.4/10 Very good! (1,005 reviews)
Bathroom in Shower was slippery no Matt or Gran bars, food was warm, there was only Sausage, can not eat sausage, eggs was real eggs, only had donuts on weekend.

Reviewed on 13 July 2026

Motel 6 Rockford, IL

Motel 6 Rockford, IL

2 out of 5
Price was AU$2,573, price is now AU$2,543 per person
AU$2,543
per person
21 Sept - 23 Sept
found 20 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
6.6/10 (467 reviews)
This was just a stop over less than 12 hours. The room only appeared clean to the eye. Hair in shower so I didn’t use it and when I left in morning saw a few bugs. Heavy musty moldy smell and the ac smelled like cigarette smoke.

Reviewed on 8 July 2026

Clayton House Motel

Clayton House Motel

2.5 out of 5
Price was AU$2,586, price is now AU$2,560 per person
AU$2,560
per person
21 Sept - 23 Sept
found 20 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
5.8/10 (29 reviews)
The facility could be functional if it was maintained better 1) the air conditioner didn’t work 2) the tub drain was plugged we stood in water over our ankles while showering 3) the floor was dirty 4 ) the light bulb burnt out first night we was there 5 ) no comfort in the beds well worn out mattress

Reviewed on 3 July 2026

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
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Clearing

Visitors to Clearing appreciate its restaurants. A visit to Wintrust Sports Complex and SeatGeek Stadium might round out your trip if you're looking to see more of the area.

Find hotels in Clearing

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

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is AU$278 per night from 3 Aug to 4 Aug
AU$278
3 Aug - 4 Aug
includes taxes & fees
8.8/10 Excellent! (2,839 reviews)
"Clean rooms nice hotel"

Reviewed on 14 July 2026

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$282 per night from 27 July to 28 July
AU$282
27 July - 28 July
includes taxes & fees
8.2/10 Very good! (1,746 reviews)
"The property is located near the beach and restaurants. It’s ideal for accessibility. Unfortunately our hotel room shower was broken. The bathroom was in poor condition and had not been maintained."

Reviewed on 13 July 2026

The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$452 per night from 26 July to 27 July
AU$452
26 July - 27 July
includes taxes & fees
9.2/10 Wonderful! (1,917 reviews)
"While amenities and being up to date are important, my main focus for a hotel is it’s cleanliness and how comfortable is the bed since I’ve stayed many places that while nice, if the bed is uncomfortable can ruin your stay. Our room at Omni was clean and comfortable. There were a few things that ..."

Reviewed on 13 July 2026

Omni Chicago Hotel
See all 4,828 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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Stay near popular Southwest Side attractions

Marquette Park

9.4/10 (3 reviews)
After visiting Marquette Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.
See properties

What to do in 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: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$36
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Southwest Side

Frequently asked questions

How much does a Southwest Side holiday package cost?
From as little as AU$2,541, 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.

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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.