Southwest Side Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Save up to AU$703 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

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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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

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$295 per night from 29 June to 30 June
AU$295
29 June - 30 June
includes taxes & fees
8.4/10 Very Good! (4,263 reviews)
"Na"

Reviewed on 25 Jun. 2025

Embassy Suites by Hilton Chicago Downtown River North
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is AU$332 per night from 1 July to 2 July
AU$332
1 July - 2 July
includes taxes & fees
9/10 Wonderful! (1,920 reviews)
"Our favorite Chicago hotel. The location is perfect for exploring the city, dining, and walking. My only complaint is that the condition of the pool was not nearly as clean and clear as usual."

Reviewed on 24 Jun. 2025

InterContinental Chicago Magnificent Mile by IHG
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$221 per night from 29 June to 30 June
AU$221
29 June - 30 June
includes taxes & fees
9.2/10 Wonderful! (3,230 reviews)
Citizen M Chicago
"We were very comfortable and the location was FANTASTIC! The only downside was not being able to get out of bed on both sides. Needed to climb over my husband. The room was small but had most of what we needed. There was a great " Iron Heaven" station on each floor that offered iron and steamer. ..."

Reviewed on 25 Jun. 2025

citizenM Chicago Downtown
See all 4,829 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Southwest Side holiday package cost?
From as little as , 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

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
Six Flags Great America featuring rides

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America
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

What to do in Southwest Side

River tour boat in Chicago

Architecture River Tour

AU$75
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$69
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

AU$69
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Southwest Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.