Southwest Side Holidays from AU$1,876

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The Latest Southwest Side Holiday Deals

Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton
Waldorf Astoria Chicago
Virgin Hotels Chicago
Trump International Hotel & Tower Chicago
Hotel Riu Plaza Chicago

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

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

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$175 per night from 9 Jan to 10 Jan
AU$175
includes taxes & fees
9 Jan - 10 Jan
7.8/10 Good! (8,372 reviews)
"This is the second time booking here and I love it."

Reviewed on 4 Jan. 2025

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$181 per night from 16 Jan to 17 Jan
AU$181
includes taxes & fees
16 Jan - 17 Jan
8.6/10 Excellent! (3,689 reviews)
"Downtown"

Reviewed on 6 Jan. 2025

River Hotel
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 AU$184 per night from 26 Jan to 27 Jan
AU$184
includes taxes & fees
26 Jan - 27 Jan
8.2/10 Very Good! (3,457 reviews)
"Every thing was great"

Reviewed on 6 Jan. 2025

Embassy Suites by Hilton Chicago Downtown River North
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.

Frequently asked questions

How much does a Southwest Side holiday package cost?
From as little as AU$1,876, 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.

Discover the most popular places to visit in Southwest Side

What to do in Southwest Side

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