Southwest Side Holidays from AU$2,747

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The Latest 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
per person
4 May - 10 May
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
8/10 Very Good! (1,433 reviews)
Staff are very nice and helpful. The rooms are good size.

Reviewed on 16 Feb. 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
4 May - 10 May
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (1,550 reviews)
Wonderful check-in experience, slow weekend in Chicago I guess because I was given a wonderful upgrade. My room is as big as an apartment

Reviewed on 12 Feb. 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
4 May - 10 May
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (287 reviews)
Amazing stay ! Love this property every time I’m in Chicago.

Reviewed on 20 Jan. 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
4 May - 10 May
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (998 reviews)
Staff were so friendly and nice. Room was perfect and we loved the snacks and options in our room mini bar. Selva, the rooftop bar, was also very fun and a must visit.

Reviewed on 16 Feb. 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
per person
4 May - 10 May
found 1 day ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
I was upset that the elevators were not working and it took a long to get to my room and the lobby. I would have appreciated communication about this ahead of time and would have switched hotels. Apparently it had been an issue for at least two weeks. The staff were amazing. The rooms were dark and small.

Reviewed on 14 Feb. 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

New City

2 out of top 10 points of interest in this area

Beaches and mountain views are just a few things travellers like about New City. A stop by Union Stock Yard Gate is also recommended if you've got time to explore the area.

Find hotels in New City

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$158 per night from 18 Feb to 19 Feb
AU$158
includes taxes & fees
18 Feb - 19 Feb
7.8/10 Good! (8,491 reviews)
"It was lovely"

Reviewed on 16 Feb. 2025

Congress Plaza Hotel
L7 Chicago by LOTTE
L7 Chicago by LOTTE
4.5 out of 5
225 N Wabash Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$238 per night from 23 Feb to 24 Feb
AU$238
includes taxes & fees
23 Feb - 24 Feb
9.6/10 Exceptional! (1,627 reviews)
"all good"

Reviewed on 14 Feb. 2025

L7 Chicago by LOTTE
Hilton Chicago
Hilton Chicago
4 out of 5
720 S Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$359 per night from 22 Feb to 23 Feb
AU$359
includes taxes & fees
22 Feb - 23 Feb
8.2/10 Very Good! (1,643 reviews)
"I look forward to staying again!"

Reviewed on 3 Feb. 2025

Hilton Chicago
See all 4,628 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 AU$2,747, 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

Wrigley Field which includes a city, central business district and a sporting event

Wrigley Field

4.5/5(21 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place

McCormick Place

4.5/5(21 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
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

What to do in Southwest Side

Flyover in Chicago

Flyover in Chicago

AU$61
per adult
96% of travellers recommend
Flyover in Chicago
Color Factory Chicago Ticket

Color Factory Chicago Ticket

AU$55
per adult
100% of travellers recommend
Color Factory Chicago Ticket
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

AU$72
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
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.