West Side Holidays from AU$872

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The Latest West 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$1,248, price is now AU$872 per person
AU$872
per person
12 Oct - 15 Oct
found 1 day ago
Return flight included
Albuquerque (ABQ) to Chicago (ORD)
8.2/10 Very good! (2,854 reviews)
Bar be open more Have more things for breakfast

Reviewed on 26 July 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$1,644, price is now AU$1,035 per person
AU$1,035
per person
12 Oct - 15 Oct
found 1 day ago
Return flight included
Albuquerque (ABQ) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)
Convenient location.

Reviewed on 26 July 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$2,642, price is now AU$1,786 per person
AU$1,786
per person
12 Oct - 15 Oct
found 1 day ago
Return flight included
Albuquerque (ABQ) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Superb customer service! Above and beyond!

Reviewed on 23 July 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$1,963, price is now AU$1,378 per person
AU$1,378
per person
12 Oct - 15 Oct
found 1 day ago
Return flight included
Albuquerque (ABQ) to Chicago (ORD)
9.4/10 Exceptional! (2,606 reviews)
Nice Stay

Reviewed on 26 July 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was AU$1,421, price is now AU$1,015 per person
AU$1,015
per person
12 Oct - 15 Oct
found 1 day ago
Return flight included
Albuquerque (ABQ) to Chicago (ORD)
8.4/10 Very good! (2,054 reviews)
Nice place to stay, great location for general sightseeing. Room was spotless, the only negative was the coffee machine in room makes lousy coffee!

Reviewed on 26 July 2026

Our guide on where to stay in West Side

Find the best West Side areas and neighborhoods for the activities you enjoy most. Learn more about West Side
A cityscape with modern skyscrapers and a curved highway.

West Loop

1 out of top 10 points of interest in this area

Consider a visit to Milwaukee Avenue and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center.

Find hotels in West Loop

West Side Holiday

West Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Top Sights
Anna and Frederick Douglass Park, Humboldt Park and Garfield Park

Our pick of the best West Side Hotel Deals

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$301 per night from 20 Aug to 21 Aug
AU$301
20 Aug - 21 Aug
includes taxes & fees
Crowne Plaza Chicago West Loop by IHG
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$299 per night from 20 Aug to 21 Aug
AU$299
20 Aug - 21 Aug
includes taxes & fees
Holiday Inn & Suites Chicago - Downtown by IHG
The Emily Hotel

The Emily Hotel

4 out of 5
311 North Morgan Street Chicago IL
The price is AU$425 per night from 9 Aug to 10 Aug
AU$425
9 Aug - 10 Aug
includes taxes & fees
9.2/10 Wonderful! (1,317 reviews)
"Given the 4-star hotel status and high-cost /high-end location, I expected more. No place to fill up water bottles (except in the basement with water cooler). The rooms were very bare, carpet felt a bit old/unclean, and there were no drawers/dressers for clothing. WiFi wasn’t great and required continually ..."

Reviewed on 26 July 2026

The Emily Hotel
See all 799 properties in West 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

Stay near popular West Side attractions

A large, modern building with a curved facade and multiple vertical windows.

United Center

8.8/10 (4,269 reviews)
Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.
See properties

What to do in West Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

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

Art Institute of Chicago

AU$58
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in West Side

Frequently asked questions

How much does a West Side holiday package cost?
Be ready to book, because a trip to West Side starts from an affordable AU$872. When you combine your flights, hotels and car rentals into a travel package, you'll score the best prices.
How do I get a cheap travel package to West Side?
It's easy. Just bundle. Flights, rental cars and hotels — combine whatever you need into a West Side holiday package to save a pile of cash. Score even better deals when you include extras such as activities or tours to your booking. But that's not the only good part. You have the flexibility to put together your holiday your own way. We offer more than 550 airlines and 1 000 000 hotels across the world, so that everyone has an opportunity to travel and live out those holiday fantasies.
What are the top hotels in West Side?
Grace Abbott Homes is one place that most travellers to West Side include in their itinerary. For a memorable stay here, take a look at Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton.
How far in advance should I book my West Side holiday?
It can be tricky to know exactly when the best time is to book your West Side holiday. But generally the earlier you book, the cheaper the prices. Sometimes, you can lock in your flights and hotels nearly 12 months before departure. If you're thinking of a last-minute getaway, no need to worry! There are terrific deals popping up on Expedia every single day.
What does an Expedia West Side travel package include?
That depends on what you're after. If you're travelling alone, you might decide to bundle flights and hotels. Taking the whole crew to West Side? A travel package that includes rental cars, flights and hotels might suit you better. Expedia gives you the flexibility and freedom to tailor your travel package.
What should I know before booking a West Side travel package?
So many places to travel to, so many things to experience. With a travel package, you can cross more of them off your list. Bundle your flights, hotels and rental cars and get ready to save.
Can I choose my airline with a West Side Expedia holiday package?
Most definitely. Expedia has more than 550 airline partners to select from all over the world. With so much choice, finding the right carrier to get you to West Side shouldn't be hard.
If I'm not able to travel, can I cancel my West Side holiday package?
Don't worry if you're rethinking your West Side holiday package — you can cancel or change your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We understand life can sometimes throw a spanner in the works, so make your way to our Customer Service Portal if that happens. When you're ready to make changes, we'll take care of it.

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.